Joseph Tipa, licensed Realtor Search Results

Exceptional Winter Park Living! Discover this newer, two-story SMART corner townhome, ideally situated in a highly desirable Winter Park location. Showcasing attractive architectural details, a welcoming covered entry, and meticulously maintained tropical landscaping, this residence offers the perfect blend of modern sophistication, comfort, and convenience. Step inside to a spacious, light-filled open-concept living and dining area highlighted by soaring ceilings, attractive wood-look flooring, contemporary finishes, and an effortless transition into the stunning kitchen. Designed for both everyday living and entertaining, the kitchen showcases crisp white cabinetry, stainless steel appliances, an expansive quartz waterfall island with seating for four, designer pendant lighting, and sliding glass doors opening to the private courtyard. A versatile built-in serving area, ideal for a coffee bar or dry bar, adds both style and functionality. The inviting courtyard provides a seamless extension of the interior living space, creating an intimate setting for alfresco dining, entertaining, or simply unwinding. Accented by elegant travertine flooring, this charming outdoor retreat also offers covered access to the detached two-car garage. Upstairs, you will find three generously sized bedrooms, two tastefully updated baths, and a spacious laundry room. The serene primary suite offers a relaxing escape with sophisticated accent walls, oversized windows, and elegant trim details. The luxurious en-suite bath features dual vanities, sleek quartz countertops, modern lighting, and an oversized walk-in shower with a frameless glass enclosure and exquisite floor-to-ceiling tile. Two additional bedrooms are filled with natural light and offer flexible living arrangements, including the possibility of a home office or study. Connecting these bedrooms is a beautifully designed Jack-and-Jill bath featuring a double-sink vanity, quartz countertops, stylish lighting, and a tub/shower combination enhanced by floor-to-ceiling tile. Remote-controlled window shades throughout provide added privacy and convenience, while a central vacuum system offers another thoughtful feature. Completing the second floor is an oversized laundry room equipped with a full-size washer and dryer, extensive custom cabinetry, ample countertop space, and attractive wood-look flooring. Perfectly positioned near the exciting new Minnesota Row development, this residence enjoys convenient access to shopping, dining, and major roadways. Just minutes from the heart of downtown Winter Park and its renowned Park Avenue shopping district, residents can enjoy an exceptional selection of sidewalk cafés, fine dining, upscale boutiques, museums, and the picturesque beauty of Central Park. Combining sophisticated finishes, thoughtfully designed interiors, exceptional outdoor living, and the convenience of SMART home technology, this impressive corner townhome offers an outstanding opportunity to enjoy the very best of the Winter Park lifestyle. A must-see residence! Call today to schedule your private showing!

3 Beds ⋅ 3 Baths ⋅ Park Shore SubDv. ⋅ 32789 Zip Code

Exceptional Winter Park Living! Discover this newer, two-story SMART corner townhome, ideally situated in a highly desirable Winter Park location. Showcasing attractive architectural details, a welcoming covered entry, and meticulously maintained tropical landscaping, this residence offers the perfect blend of modern sophistication, comfort, and convenience. Step inside to a spacious, light-filled open-concept living and dining area highlighted by soaring ceilings, attractive wood-look flooring, contemporary finishes, and an effortless transition into the stunning kitchen. Designed for both everyday living and entertaining, the kitchen showcases crisp white cabinetry, stainless steel appliances, an expansive quartz waterfall island with seating for four, designer pendant lighting, and sliding glass doors opening to the private courtyard. A versatile built-in serving area, ideal for a coffee bar or dry bar, adds both style and functionality. The inviting courtyard provides a seamless extension of the interior living space, creating an intimate setting for alfresco dining, entertaining, or simply unwinding. Accented by elegant travertine flooring, this charming outdoor retreat also offers covered access to the detached two-car garage. Upstairs, you will find three generously sized bedrooms, two tastefully updated baths, and a spacious laundry room. The serene primary suite offers a relaxing escape with sophisticated accent walls, oversized windows, and elegant trim details. The luxurious en-suite bath features dual vanities, sleek quartz countertops, modern lighting, and an oversized walk-in shower with a frameless glass enclosure and exquisite floor-to-ceiling tile. Two additional bedrooms are filled with natural light and offer flexible living arrangements, including the possibility of a home office or study. Connecting these bedrooms is a beautifully designed Jack-and-Jill bath featuring a double-sink vanity, quartz countertops, stylish lighting, and a tub/shower combination enhanced by floor-to-ceiling tile. Remote-controlled window shades throughout provide added privacy and convenience, while a central vacuum system offers another thoughtful feature. Completing the second floor is an oversized laundry room equipped with a full-size washer and dryer, extensive custom cabinetry, ample countertop space, and attractive wood-look flooring. Perfectly positioned near the exciting new Minnesota Row development, this residence enjoys convenient access to shopping, dining, and major roadways. Just minutes from the heart of downtown Winter Park and its renowned Park Avenue shopping district, residents can enjoy an exceptional selection of sidewalk cafés, fine dining, upscale boutiques, museums, and the picturesque beauty of Central Park. Combining sophisticated finishes, thoughtfully designed interiors, exceptional outdoor living, and the convenience of SMART home technology, this impressive corner townhome offers an outstanding opportunity to enjoy the very best of the Winter Park lifestyle. A must-see residence! Call today to schedule your private showing!

1261 Michigan Avenue, Winter Park

700 Melrose Avenue Unit A22, Winter Park

$325,000

Discover the charm of Winter Park Gardens, a sought-after 55+ community nestled among more than 8 acres of lush landscaping, majestic live oak trees, winding walking paths, and tranquil pond views. This inviting 2-bedroom, 2-bathroom condo offers approximately 1,074 square feet of comfortable living space. One of its most special features is the enclosed, air-conditioned Florida room, where dramatic floor-to-ceiling windows frame beautiful pond and garden views, creating the perfect setting to enjoy your morning coffee, unwind with a good book, or simply take in the peaceful surroundings. Thoughtfully updated by the current owner within the past year, improvements include a new tankless water heater, new toilets, upgraded electrical panel, new primary bedroom window, new primary bathroom vanity, and new closet doors throughout the hallway and bedrooms. The kitchen features updated appliances, including a newer refrigerator, and washer/dryer hookups add everyday convenience. One assigned parking space is also included. Enjoy the community swimming pool and beautifully maintained grounds. Conveniently located within in a few short minutes of downtown Winter Park, Park Avenue, Rollins College, and Mead Botanical Garden, this residence offers the perfect blend of comfortable living, natural beauty, and the sought-after Winter Park lifestyle. Experience the convenience, peaceful surroundings, and unique appeal that make Winter Park Gardens such a special place to call home!

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Discover the charm of Winter Park Gardens, a sought-after 55+ community nestled among more than 8 acres of lush landscaping, majestic live oak trees, winding walking paths, and tranquil pond views. This inviting 2-bedroom, 2-bathroom condo offers approximately 1,074 square feet of comfortable living space. One of its most special features is the enclosed, air-conditioned Florida room, where dramatic floor-to-ceiling windows frame beautiful pond and garden views, creating the perfect setting to enjoy your morning coffee, unwind with a good book, or simply take in the peaceful surroundings. Thoughtfully updated by the current owner within the past year, improvements include a new tankless water heater, new toilets, upgraded electrical panel, new primary bedroom window, new primary bathroom vanity, and new closet doors throughout the hallway and bedrooms. The kitchen features updated appliances, including a newer refrigerator, and washer/dryer hookups add everyday convenience. One assigned parking space is also included. Enjoy the community swimming pool and beautifully maintained grounds. Conveniently located within in a few short minutes of downtown Winter Park, Park Avenue, Rollins College, and Mead Botanical Garden, this residence offers the perfect blend of comfortable living, natural beauty, and the sought-after Winter Park lifestyle. Experience the convenience, peaceful surroundings, and unique appeal that make Winter Park Gardens such a special place to call home!

700 Melrose Avenue Unit A22, Winter Park

220 Killarney Bay Court Unit 6-2, Winter Park

$335,000

LAKE KILLARNEY • WINTER PARK • CONDO DUES JUST $455 MONTHLY! • Enjoy exceptional value in Killarney Bay, a private lakefront community offering an oasis in the city! This second-floor, 2-bedroom, 2-bath corner condo features 1,140 square feet of comfortable, low-maintenance living with a BRAND-NEW HVAC SYSTEM INSTALLED IN MAY 2026 and a recently upgraded full-size washer and dryer. Community roof replacement is underway, with completion scheduled for November 2026, and this unit’s roof special assessment has already been PAID IN FULL by the sellers! Inside, an open floor plan, high ceilings and abundant natural light create a welcoming atmosphere. A corner electric fireplace anchors the living and dining area, while wood-look laminate flooring flows throughout the main living spaces. The kitchen offers upgraded cabinetry with decorative glass-front accents, generous counter space, a breakfast bar and a separate pantry. The primary suite includes a spacious walk-in closet and private bath with a glass-enclosed shower, decorative tilework and a furniture-style vanity. The second bedroom opens to its own covered, screened balcony—an inviting spot to unwind outdoors. A second bathroom features a tub with a glass enclosure, and the separate laundry room provides cabinetry, shelving and additional storage. Community amenities include a swimming pool, lakefront dock, fishing, a waterfront deck overlooking Lake Killarney, paddleboard and kayak storage, and assigned covered parking. Situated along a no-outlet road with limited traffic, this peaceful retreat is just minutes from Winter Park Village, Trader Joe’s and an array of restaurants, shops and entertainment. An appealing choice for a primary residence or seasonal getaway!

2 Beds ⋅ 2 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

LAKE KILLARNEY • WINTER PARK • CONDO DUES JUST $455 MONTHLY! • Enjoy exceptional value in Killarney Bay, a private lakefront community offering an oasis in the city! This second-floor, 2-bedroom, 2-bath corner condo features 1,140 square feet of comfortable, low-maintenance living with a BRAND-NEW HVAC SYSTEM INSTALLED IN MAY 2026 and a recently upgraded full-size washer and dryer. Community roof replacement is underway, with completion scheduled for November 2026, and this unit’s roof special assessment has already been PAID IN FULL by the sellers! Inside, an open floor plan, high ceilings and abundant natural light create a welcoming atmosphere. A corner electric fireplace anchors the living and dining area, while wood-look laminate flooring flows throughout the main living spaces. The kitchen offers upgraded cabinetry with decorative glass-front accents, generous counter space, a breakfast bar and a separate pantry. The primary suite includes a spacious walk-in closet and private bath with a glass-enclosed shower, decorative tilework and a furniture-style vanity. The second bedroom opens to its own covered, screened balcony—an inviting spot to unwind outdoors. A second bathroom features a tub with a glass enclosure, and the separate laundry room provides cabinetry, shelving and additional storage. Community amenities include a swimming pool, lakefront dock, fishing, a waterfront deck overlooking Lake Killarney, paddleboard and kayak storage, and assigned covered parking. Situated along a no-outlet road with limited traffic, this peaceful retreat is just minutes from Winter Park Village, Trader Joe’s and an array of restaurants, shops and entertainment. An appealing choice for a primary residence or seasonal getaway!

220 Killarney Bay Court Unit 6-2, Winter Park

$3,495,000

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

$575,000

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

700 Melrose Avenue Unit M23, Winter Park

$340,000

Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

$255,000

Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park

330 W Morse Boulevard Unit 104, Winter Park

$1,379,000

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The interior space is professionally decorated with high end finishes and highly aesthetic. The turnkey floorplan offers open reception/waiting, full kitchen, bathroom, operating and pre-op rooms plus up to five private office spaces. Adjacent Unit 105 (separately listed in MLS) can also be purchased. Reserved parking spaces plus a wealth of street and public parking available nearby.

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The interior space is professionally decorated with high end finishes and highly aesthetic. The turnkey floorplan offers open reception/waiting, full kitchen, bathroom, operating and pre-op rooms plus up to five private office spaces. Adjacent Unit 105 (separately listed in MLS) can also be purchased. Reserved parking spaces plus a wealth of street and public parking available nearby.

330 W Morse Boulevard Unit 104, Winter Park

328 W Morse Boulevard Unit 105, Winter Park

$1,420,000

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The turnkey space is professionally decorated with high end finishes and highly aesthetic.Floorplan offers five multi-purpose office, three patient rooms, open reception/waiting, lounge/kitchen area and common restrooms (secure lobby). The adjoining/adjacent unit 104 can be combined with this unit (see separate listing for Unit 104 in MLS) for a total of 3652 hsf. Reserved parking spaces plus a wealth of street and public parking available nearby.

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The turnkey space is professionally decorated with high end finishes and highly aesthetic.Floorplan offers five multi-purpose office, three patient rooms, open reception/waiting, lounge/kitchen area and common restrooms (secure lobby). The adjoining/adjacent unit 104 can be combined with this unit (see separate listing for Unit 104 in MLS) for a total of 3652 hsf. Reserved parking spaces plus a wealth of street and public parking available nearby.

328 W Morse Boulevard Unit 105, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park

$825,000

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

$290,000

Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code

Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park

100 S Virginia Avenue Unit 201, Winter Park

$1,450,000

Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

1602 Alabama Drive Unit 107, Winter Park

$1,150,000

Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park

$1,599,000

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park

1306 S Pennsylvania Avenue Unit 5, Winter Park

$347,500

NEW PRICE! Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

2 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code

NEW PRICE! Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

1306 S Pennsylvania Avenue Unit 5, Winter Park

250 Carolina Avenue Unit 202, Winter Park

$649,000

Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park

200 S Interlachen Avenue Unit 350, Winter Park

$2,350,000

Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

1250 S Denning Drive Unit 127, Winter Park

$245,000

Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to a screened-in porch overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to a screened-in porch overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

500 N Pennsylvania Avenue Unit G, Winter Park

$349,500

Virtually Staged. LOCATION, LOCATION, LOCATION in Winter Park!!! **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code

Virtually Staged. LOCATION, LOCATION, LOCATION in Winter Park!!! **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

$999,000

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

443 Broadview Avenue, Winter Park

151 N Orlando Avenue Unit 242, Winter Park

$269,000

Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park

$429,000

A rare opportunity in Winter Park's 32789: one of the most affordable single-family homes currently on the market! Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park's 32789: one of the most affordable single-family homes currently on the market! Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

125 S Interlachen Avenue Unit 1, Winter Park

$3,645,000

STEPS TO PARK AVE.! From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natural light. From the underground private two car garage through the three living levels and up to the roof top terrace, each floor is serviced by a window wrapped staircase and your own private elevator (new in Oct. 2026). Creature Comforts include: Lutron lighting system, programmable shades, home audio system, Control4 home automation system. Your Private, Gated Terrace leads to double entry doors. The main level offers spacious living and dining areas opening to a Chef’s Dream Kitchen. Here you find solid wood cabinetry, quartz countertops, custom backsplash, Wolf five-burner natural gas cooktop, integrated Sub Zero refrigerator, Wolf wall oven and microwave, Bosch dishwasher, Sub Zero full size, dual zone wine refrigerator and a large island with counter seating. The adjacent sitting room faces East for starting your day with morning light or winding down your day with your favorite beverage. The wall mounted television adds to the convenience of this versatile space where you can catch up on the morning or evening news. The main living level also offers your guests the convenience of a private powder room. The second level is dedicated to the generous Primary Suite. This level offers a spacious bedroom, a custom walk-in closet, a gracious primary bathroom with a walk-in shower, double sinks, a custom vanity/makeup area, and a private water closet with automatic Toto Washlet. The Primary Suite level also features a customized office/lounge area with built-in cabinetry and a refrigerator. Adding to the convenience, you’ll find the laundry area integrated into the Primary Suite level. You are greeted to the Third Level through an open media room. The media loft area is adjacent to the two spacious and private ensuite bedrooms. Both bedrooms 2 and 3 feature walk-in closets and private bathrooms. Wait, there’s more! Up one more level you will find the incredible rooftop terrace. This approx. 800 sq. ft. space, serviced by your private elevator, is perfect for entertaining family and friends – no matter the size of the party! An entertainer’s delight, you will enjoy the outdoor kitchen with stainless 36” DCS natural gas grill, exhaust hood, refrigerator and sink. Adding to the convenience of entertaining on your private rooftop, this terrace has its own powder room. Additionally, there is an air-conditioned storage closet perfect for keeping dry and safe items you want protected from the weather. Going back downstairs to the underground garage, you’ll enjoy the security of your own oversized two-car garage. Not only does this level of Residence #1 offer you a private garage, you’ll also love the convenience and security of your own air-conditioned 9x13 storage room and another private foyer. The building’s garage area is accessed through a separate gated entrance. This underground parking area includes guest parking spaces. This exquisite residence is mere steps from all the dining, shopping and community amenities along Park Avenue and the adjacent Boulevards that make downtown Winter Park so coveted. Residence 1 of 125 South Interlachen Place is that rare opportunity to own an exquisite and perfectly located home offering the lock and leave lifestyle. All measurements are approximate and Buyer is responsible for verifying all dimensions.

3 Beds ⋅ 5 Baths ⋅ South Interlachen Place SubDv. ⋅ 32789 Zip Code

STEPS TO PARK AVE.! From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natural light. From the underground private two car garage through the three living levels and up to the roof top terrace, each floor is serviced by a window wrapped staircase and your own private elevator (new in Oct. 2026). Creature Comforts include: Lutron lighting system, programmable shades, home audio system, Control4 home automation system. Your Private, Gated Terrace leads to double entry doors. The main level offers spacious living and dining areas opening to a Chef’s Dream Kitchen. Here you find solid wood cabinetry, quartz countertops, custom backsplash, Wolf five-burner natural gas cooktop, integrated Sub Zero refrigerator, Wolf wall oven and microwave, Bosch dishwasher, Sub Zero full size, dual zone wine refrigerator and a large island with counter seating. The adjacent sitting room faces East for starting your day with morning light or winding down your day with your favorite beverage. The wall mounted television adds to the convenience of this versatile space where you can catch up on the morning or evening news. The main living level also offers your guests the convenience of a private powder room. The second level is dedicated to the generous Primary Suite. This level offers a spacious bedroom, a custom walk-in closet, a gracious primary bathroom with a walk-in shower, double sinks, a custom vanity/makeup area, and a private water closet with automatic Toto Washlet. The Primary Suite level also features a customized office/lounge area with built-in cabinetry and a refrigerator. Adding to the convenience, you’ll find the laundry area integrated into the Primary Suite level. You are greeted to the Third Level through an open media room. The media loft area is adjacent to the two spacious and private ensuite bedrooms. Both bedrooms 2 and 3 feature walk-in closets and private bathrooms. Wait, there’s more! Up one more level you will find the incredible rooftop terrace. This approx. 800 sq. ft. space, serviced by your private elevator, is perfect for entertaining family and friends – no matter the size of the party! An entertainer’s delight, you will enjoy the outdoor kitchen with stainless 36” DCS natural gas grill, exhaust hood, refrigerator and sink. Adding to the convenience of entertaining on your private rooftop, this terrace has its own powder room. Additionally, there is an air-conditioned storage closet perfect for keeping dry and safe items you want protected from the weather. Going back downstairs to the underground garage, you’ll enjoy the security of your own oversized two-car garage. Not only does this level of Residence #1 offer you a private garage, you’ll also love the convenience and security of your own air-conditioned 9x13 storage room and another private foyer. The building’s garage area is accessed through a separate gated entrance. This underground parking area includes guest parking spaces. This exquisite residence is mere steps from all the dining, shopping and community amenities along Park Avenue and the adjacent Boulevards that make downtown Winter Park so coveted. Residence 1 of 125 South Interlachen Place is that rare opportunity to own an exquisite and perfectly located home offering the lock and leave lifestyle. All measurements are approximate and Buyer is responsible for verifying all dimensions.

125 S Interlachen Avenue Unit 1, Winter Park

$650,000

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon Avenue, Winter Park

$2,400,000

Prime Winter Park office opportunity with exceptional visibility and accessibility. This well-maintained two-story masonry office building offers approximately 6,049 square feet on a 0.31-acre corner lot with 112 feet of frontage on Fairbanks Avenue and 114 feet along Lakeview Avenue. Located just one mile from I-4, the property provides quick access to downtown Orlando and downtown Winter Park. Fairbanks Avenue has recently undergone a major streetscape transformation including underground utilities, decorative street lighting, and a new sewer system, enhancing the corridor's appeal and long-term value. The building was originally constructed in 1948 and expanded with a second story addition in 1985, creating a professional office environment with flexible layout options for investors or owner-users. The property features 18 parking spaces and is zoned O-1 Office District by the City of Winter Park. Ideally positioned in a vibrant and highly walkable area, the building is steps from premier dining and retail including Hillstone Restaurant, Superica, Sixty Vines, and Trader Joe's. Recent improvements include a new tile roof (2009), full window replacement (2012), parking lot resurfacing (2013) extensive interior renovations (2017 and 2022), exterior repainting (2021), termite tenting (2023), new perimeter wall construction (2025), and professionally landscaped (2026). The downstairs suite is leased, generating 7,521.75 per month with the tenant paying utilities, alarm, housekeeping, building taxes, and insurance. The upstairs suite is currently vacant, offering an excellent opportunity for an owner-occupant or additional income. A rare chance to acquire a well-located Winter Park asset with stable income and value-add potential in one of Central Florida's most desirable business corridors. Sellers will consider a credit towards an elevator if needed.

Killarney Estates SubDv. ⋅ 32789 Zip Code

Prime Winter Park office opportunity with exceptional visibility and accessibility. This well-maintained two-story masonry office building offers approximately 6,049 square feet on a 0.31-acre corner lot with 112 feet of frontage on Fairbanks Avenue and 114 feet along Lakeview Avenue. Located just one mile from I-4, the property provides quick access to downtown Orlando and downtown Winter Park. Fairbanks Avenue has recently undergone a major streetscape transformation including underground utilities, decorative street lighting, and a new sewer system, enhancing the corridor's appeal and long-term value. The building was originally constructed in 1948 and expanded with a second story addition in 1985, creating a professional office environment with flexible layout options for investors or owner-users. The property features 18 parking spaces and is zoned O-1 Office District by the City of Winter Park. Ideally positioned in a vibrant and highly walkable area, the building is steps from premier dining and retail including Hillstone Restaurant, Superica, Sixty Vines, and Trader Joe's. Recent improvements include a new tile roof (2009), full window replacement (2012), parking lot resurfacing (2013) extensive interior renovations (2017 and 2022), exterior repainting (2021), termite tenting (2023), new perimeter wall construction (2025), and professionally landscaped (2026). The downstairs suite is leased, generating 7,521.75 per month with the tenant paying utilities, alarm, housekeeping, building taxes, and insurance. The upstairs suite is currently vacant, offering an excellent opportunity for an owner-occupant or additional income. A rare chance to acquire a well-located Winter Park asset with stable income and value-add potential in one of Central Florida's most desirable business corridors. Sellers will consider a credit towards an elevator if needed.

1477 W Fairbanks Avenue, Winter Park

$474,999

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

981 Aragon Avenue, Winter Park

$2,695,000

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

3 Beds ⋅ 4 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park

101 S New York Avenue Unit 311, Winter Park

$1,775,000

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park

151 North Orlando Avenue Unit 142, Winter Park

$199,900

**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!

1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condominium Assn Inc. SubDv. ⋅ 32789 Zip Code

**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!

151 North Orlando Avenue Unit 142, Winter Park

$199,900

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park

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