Winter Park Homes with Sidewalk Exterior Features

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park

$1,775,000

4 Beds ⋅ 5 Baths ⋅ Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

890 N Phelps Avenue, Winter Park

$635,000

2 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Luxury Meets Timeless Design in the Heart of Winter Park. Welcome to this beautifully renovated 2-bedroom, 2-bath residence where thoughtful design and exceptional craftsmanship come together to create a truly move-in ready home. Located just minutes from the shops and restaurants of Park Avenue, this home offers a rare combination of modern luxury and classic Winter Park charm. The light-filled open floor plan is anchored by a stunning chef's kitchen featuring Taj Mahal quartz countertops, custom cabinetry, premium stainless steel appliances, and a dramatic waterfall island that serves as the centerpiece of the home. Wide-plank wood flooring flows throughout, while recessed lighting, designer fixtures, and carefully selected finishes add warmth and sophistication to every room. The spacious primary suite is designed as a private retreat with custom-built closet systems and a beautifully appointed en-suite bath showcasing dual vanities, designer tile, quartz countertops, and a custom frameless glass shower. The guest bedroom also features custom closet cabinetry and easy access to an equally impressive second bathroom finished with high-end materials and elegant fixtures. From the welcoming covered front porch to the abundance of natural light throughout the home, every detail has been carefully considered to create a space that is both inviting and functional. Whether you're looking for a full-time residence or a low-maintenance luxury home in one of Central Florida's premier communities, this exceptional Winter Park property delivers style, quality, and an unbeatable location.

531 W Swoope Avenue, Winter Park

$2,390,000

4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park

$4,750,000

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park

$510,000

3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code

Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park

$3,895,000

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

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. Creature comforts include a Lutron lighting system, home audio system and programmable shades, all set to your schedule by the Control4 home automation system. You approach the double entry doors via a gated, spacious terrace. 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

$2,299,000

5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bedrooms, 5 bathrooms, and 2,868 square feet of thoughtfully designed living space, this home showcases contemporary architecture, refined finishes, and a functional layout tailored to today's lifestyle. A light-filled open floor plan creates effortless flow between the living, dining, and kitchen spaces, making the home equally suited for everyday living and entertaining. Designer details and carefully selected finishes bring warmth and sophistication throughout, while expansive windows enhance the bright, inviting interiors. The private outdoor living area is designed to embrace Florida living, featuring a resort-style pool and spa with plenty of space to relax, dine, and entertain. Ideally situated near Park Avenue, residents will enjoy convenient access to boutique shopping, acclaimed restaurants, golf courses, parks, and Winter Park's renowned arts and cultural destinations, all while enjoying the comfort and quality of a brand-new luxury home.

1840 Laurel Road, Winter Park

$1,275,000

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

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park

$1,250,000

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

$169,900

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

Winter Park Homes with Sidewalk Exterior Features

Newest Winter Park Homes with Sidewalk Exterior Features