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623 Woodley Road, Maitland
$620,000
3 Beds ⋅ 2 Baths ⋅ Oakland Shores 1st Add SubDv. ⋅ 32751 Zip Code
Seller has received MULTIPLE OFFERS, and are accepting offers until 5pm on Saturday, JULY 11, 2026. Welcome to your own private resort in the heart of Maitland! Perfectly situated on a beautifully landscaped .27-acre lot in the established Oakland Shores neighborhood, this exceptional three-bedroom, two-bathroom home offers close to 1,800 square feet of thoughtfully updated living space designed for both everyday comfort and unforgettable entertaining. The backyard is truly the star of the show, featuring a spectacular saltwater pool and spa completed in 2023. Designed to impress, this outdoor oasis showcases a stunning Tahoe Blue pebble finish, expansive sun shelf, elegant waterfall and scupper features, dramatic integrated fire bowls, and a heater/chiller for year-round enjoyment. The surrounding travertine pool deck, professionally designed landscape lighting, mature landscaping, and fully fenced backyard create an incredibly private setting, while the Paradise Grill summer kitchen(negotiable with the sale) makes outdoor entertaining effortless. The lush, beautifully manicured landscaping is effortlessly maintained by a 10-zone irrigation system with spray heads, back-flow prevention, and convenient Wi-Fi connectivity, allowing you to monitor and control watering schedules from virtually anywhere. Additionally, a comprehensive underground gutter drainage system directs all roof water to the street, minimizing standing water and protecting the home's foundation and landscaping. Inside, the home is equally impressive with an open and inviting layout enhanced by wood laminate flooring installed in 2019, custom white oak interior doors, crown molding, and large picture windows that frame picturesque views of the backyard retreat. The spacious living room, expanded in 2018, features a beautiful wood-burning fireplace added in 2019 along with custom built-in cabinetry and a built-in desk, creating the perfect gathering space. A newly added laundry/utility room(2026) includes the washer and dryer for added convenience. The kitchen is designed for both function and style with custom wood cabinetry, granite countertops, stainless steel appliances, a pantry, and a center island with seating for three, all overlooking the pool through a large picture window. The private primary suite offers custom cabinetry designed for a king-sized bed, custom blackout shades, white oak closet doors, a ceiling fan, and a beautifully remodeled ensuite bathroom completed in 2026 featuring floor-to-ceiling tile, a custom wood vanity, and a spacious frameless glass walk-in shower. Additional highlights include an oversized paver driveway, two-car garage, and an unbeatable location just minutes from Lake Lily Park, the skiable Lake Orienta boat ramp, I-4, and the shopping, dining, and entertainment destinations of Maitland and Winter Park. This is a rare opportunity to own a home where every day feels like a vacation. ROOF - 2016 HVAC - 2018 ELECTRICAL - 2026 WATER HEATER - 2026

623 Woodley Road, Maitland

910 Gamewell Avenue, Maitland
$620,000
3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 02 Rep 01 SubDv. ⋅ 32751 Zip Code
Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of mind with a dedicated laundry room featuring a brand-new washer (2026) and newer dryer (2024). Major system updates have already been taken care of, including a new water heater (2025) and a recently installed HVAC system (April 2026), providing efficiency, reliability, and confidence from day one. Ideally located with close proximity to I-4 for easy commuting, and just a short walk to Maitland Community Park and Lake Lily, this home offers the perfect balance of convenience and lifestyle. A move-in-ready opportunity where the essential upgrades are already done for you.

910 Gamewell Avenue, Maitland

1933 South Boulevard, Maitland
$618,000
5 Beds ⋅ 3 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code
Perfectly positioned in the highly sought-after Maitland community, this beautifully updated home offers an exceptional blend of space, style, and functionality designed for everyday comfort and effortless entertaining. With 2,376 square feet of living space, the split-level floor plan provides flexibility and privacy, featuring five bedrooms, three full bathrooms, and multiple living areas that easily adapt to family life, work-from-home needs, or hosting guests. Wood laminate flooring flows through the main living areas and is complemented by recessed lighting, ceiling fans throughout, and blinds on all windows. The lower level of the home offers excellent separation of space, featuring a spacious family room or den, two additional bedrooms, and a brand-new full bathroom (2026). This level is ideal for guests, extended family, or a private home office setup, allowing everyone to enjoy their own comfortable living area. At the heart of the home, the open kitchen, dining, and living area creates a natural gathering place. Fully renovated in 2020, the kitchen showcases gray shaker-style cabinetry, quartz countertops, a white tile backsplash, and a large island with seating for three. Stainless steel appliances, a white ceramic farmhouse sink, and recessed lighting complete the space, making it equally suited for casual meals or larger-scale entertaining. The open layout allows the cook to stay connected with guests while enjoying views of the dining, living and outdoor living areas. Down the hall you will pass two bedrooms. The primary suite is located to the end of the hall and offers a peaceful retreat with a beautifully renovated ensuite bathroom completed in 2021. This bathroom features a striking royal blue double vanity topped with quartz countertops, a fully tiled wall and shower with a frameless glass enclosure, and upgraded gold-toned lighting and bath fixtures that add a refined touch of luxury. Step outside to a backyard designed for true Florida living and unforgettable entertaining. The salt-generated pool, resurfaced in 2022, features a new sun shelf, elegant fountains, and heating for year-round enjoyment. New pavers installed in 2022 surround the pool and connect the outdoor living spaces, including a recently extended screened deck and a covered patio ideal for outdoor dining or relaxing in the shade. The fully fenced yard is finished with low-maintenance artificial turf and a grand privacy hedge, creating a clean, polished look while maximizing usable outdoor space. The home’s prime location further enhances its appeal, just minutes from Maitland Community Park offering playgrounds, tennis, basketball and racquetball courts, walking trails, and picnic pavilions. The Lake Maitland Boat Ramp is 13 minutes away, and nearby restaurants and shopping provide everyday convenience. This is a rare opportunity to own a move-in-ready home with thoughtful updates, exceptional outdoor living, and a highly desirable Maitland address. ROOF - 2023 HVAC - 2010 Water Heater - 2025 Pool Pump - 2025

1933 South Boulevard, Maitland

2400 Deloraine Trail, Maitland
$614,900
4 Beds ⋅ 2 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
This 4-bedroom, 2-bath corner-lot home in the sought-after Dommerich neighborhood blends mid-century charm with thoughtful updates and room to grow. Set on a .27-acre lot with mature landscaping, a brick-paved walkway, and an oversized driveway, this home offers easy curb appeal and a warm welcome. Inside, vaulted ceilings, exposed beams, and large windows fill the living spaces with natural light. A cozy family room with a fireplace and built-ins opens to a flexible layout, perfect for both everyday living and entertaining. The kitchen features solid-wood Amish cabinetry, quartz countertops, a built-in island cooktop, and new kitchen appliances. Step through the screened-in porch into a private backyard retreat. You’ll find a large open-air pool, a covered patio for grilling and relaxing, and a concrete sports pad ideal for basketball, scooters, or even a future pickleball court. There’s space to stretch out, play, and host — whether it’s a quiet evening at home or a weekend gathering. Recent upgrades include a 2019 roof, PEX plumbing, newer AC, new pool equipment (2022), updated plank flooring, and fresh paint inside and out — the big-ticket items are already handled. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from parks, trails, and the dining and shops of Downtown Winter Park. This neighborhood is known for its friendly community, walkable streets, and long-term value. If you’re looking for a home where your family can settle in, grow up, and make memories — 2400 Deloraine Trail is ready to welcome you. Step outside through the screened sunroom to your private backyard oasis, complete with a sparkling swimming pool, expansive patio seating, and a large patio perfect for the grill and lounging, an entertainer’s delight. The home also includes a generous attached 2-car garage with laundry hookups and extra storage. Located just minutes from A-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and close to Downtown Winter Park’s shops, restaurants, and cultural attractions, this home offers an exceptional lifestyle in a coveted neighborhood.

2400 Deloraine Trail, Maitland

204 Quayside Circle Unit 202, Maitland
$613,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views, creating an atmosphere of both grace and tranquility. The gourmet kitchen is a study in elegance and function, featuring hand finished cabinetry, premium appliances, and stone surfaces. Gracious living room flows seamlessly into a charming sunroom, featuring French doors and classic brick flooring. The primary suite offers a peaceful, retreat with lake views, spa-inspired finishes and impeccable attention to detail. With rich textures, layered lighting, and designer finishes throughout, this home balances sophistication and warmth in perfect measure. Located in an exclusive building with exceptional amenities including pool, spa, clubhouse, a BOAT SLIP and 1 covered carport space. This residence embodies elevated lakefront living, with distinctive character. Call today for your private viewing of this exquisite condo. Please note there is a $640 transfer fee for boat slip paid at closing by Buyer.

204 Quayside Circle Unit 202, Maitland

204 Quayside Circle Unit 503, Maitland
$600,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
Step into this beautifully updated 2-bedroom, 2-bath residence at The Moorings on Lake Maitland — a sought-after waterfront community that rarely has units available. Perched on the 5th floor, the condo is wrapped in oversized windows and a double-glass slider that fill the space with sunlight and open water views clear to the horizon. The chef-inspired kitchen has been fully reimagined with glossy custom cabinetry, a generous island with seating for casual meals, quartz counters, an induction cooktop, and a matching stainless appliance suite — plus the convenience of a full-size in-unit washer and dryer. Herringbone tile flooring runs throughout, blending low-maintenance practicality with warm, modern texture. The thoughtful split-bedroom layout adds privacy, while an expansive 10x15 screened patio extends your living space outdoors, and a 5x6 storage closet keeps things organized. Smart-home upgrades include an app-controlled August lock and a Nest thermostat for effortless climate control. Residents enjoy a covered, reserved parking spot, a newly modernized elevator, and lushly maintained grounds. The community clubhouse is built for entertaining, featuring a full kitchen, fireplace, heated pool, and spa — or head down to the shaded neighborhood dock for an afternoon of fishing under the cypress trees. Please note: dogs are not permitted. Location is everything here — you're steps from Fort Maitland Park, directly across from Lake Lily, and right in the heart of Maitland's Cultural Arts corridor. The Enzian Theater, Whole Foods, Winter Park Village, and the boutiques of Park Avenue are all just minutes away, with easy access to I-4, downtown Orlando, area theme parks, and the coast.

204 Quayside Circle Unit 503, Maitland

2081 Mohican Trail, Maitland
$600,000
3 Beds ⋅ 2 Baths ⋅ Highland Park Estates SubDv. ⋅ 32751 Zip Code
Discover mid-century character and cozy comfort at 2081 Mohican Trail in Maitland, a distinctive three bedroom, two bath home with a two car garage on a generous pie-shaped homesite. Mid century touches shine through a striking brick accent wall and decorative brick planter that add warmth and architectural interest to the large family room, accented with plantation shutters, crown molding, and oversized windows flooding the room with sunlight. The flexible floor plan offers multiple living and dining areas, ideal for entertaining, working from home, or creating a play space. Enjoy morning coffee on the expansive front porch, then step into a private backyard that feels like your own retreat through the gated courtyard. Storage is plentiful throughout, helping keep life organized with numerous built-ins, expansive cabinetry, and an oversized garage. A newer roof provides peace of mind plus updates throughout incluidng newer windows/doors, remodeled bathrooms, a full replumb, newer kitchen appliances, recent electrical panel replacements, and water heater replacement just two years ago. Located in the sought-after Dommerich neighborhood of Maitland, enjoy a smooth walk or bike ride to Dommerich Elementary and Maitland Middle, and great community access to Maitland Community Park. This home blends location, function, and style!

2081 Mohican Trail, Maitland

2462 Markingham Road, Maitland
$600,000
4 Beds ⋅ 2 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code
Conveniently located in the established subdivision of English Estates, this updated and upgraded 4 bed, 2 Bath pool home is sure to please. From the moment you drive down the tree lined street you will sense the pride in this charming neighborhood. Come home and relax in the fully fenced in back yard that was transformed into a personal outdoor haven complete with a sparkling 33 x 13.5 ft pool, freshly painted pool deck, new pool pump, recently installed artificial green spaces/ dog run, stone pavers, fire pit, hot tub and golf putting green. Whether you're relaxing by yourself or entertaining guest for a BBQ this outdoor oasis is in a class above the rest. Inside you will immediately be greeted by a transitional modern foyer highlighted by exposed brick with visible mortar joints; stunning. New energy efficient windows were installed throughout as well as tasteful LVP flooring. The living floor-plan has very functional spaces, so no guessing where everything goes. Those rooms include a living room, family room, kitchen, and off kitchen dining area. The kitchen was fully renovated recently with plumbing, shaker style cabinets, quarts counter tops, appliances and a backsplash. The kitchen also boast a dry bar for versatility. The family room is highlighted by high ceilings, a custom wood accent wall that really draws all eyes to it, 2 ceiling fans, sky lights, and the perfect amount of natural light coming through the French doors leading to the patio. The living room is a perfect spot for some extra couches and chairs and a coffee table. Ideal for hosting additional guest, reading a book, etc. The master quarters is the largest bedroom in the home and has high ceilings, double French door to the Florida room, 2 closets (1 walk in and one built in), ensuite bathroom, dual sink stone counter top vanity, separate make-up vanity with stone countertop, and a walk in shower. Bedroom 2, 3, and 4 gives homeowners many possibilities of their choosing. Bathroom 2 boast a bath with shower head, dual sink vanity, and extra storage cabinets. Transitioning between the main home and the outdoor retreat you will find a long versatile 40 x 10 Florida room under air (wall unit) that is completely covered, enclosed, new luxury laminate flooring, and complete with all new windows. An additional storage area was built for the pool equipment and outdoor necessities. Major system updates are as follows: Roof: 2021. HVAC: 2015 Plumbing: Partially re-plumbed in 2022. Electrical: New panel added in 2022 (in addition to the older one). English Estates is a very popular and convenient location close to a lot of popular areas. Commute quickly to areas such as Winter Park, Baldwin Park, Audubon Park, Oviedo, Casselberry, Altamonte Springs, Full Sail University, UCF, I-4, 417, 429, Shopping, restaurants, and more. A hidden gem in the area is Kewannee Park; home to Kewannee trail a 1.9 mile paved 2 lane loop. Amenities include a basketball court, pond, pier, and playground. Schedule your showing today before it's too late. Don't let this home pass you by.

2462 Markingham Road, Maitland

2167 Mohawk Trail, Maitland
$600,000
3 Beds ⋅ 2 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Celebrate the holidays in this charming 3 bedroom, 2 bath home nestled in one of Maitland’s most sought-after communities. As you step onto the inviting front porch and enter the foyer, you’re greeted by a sense of home, a perfect ambiance for festive celebrations and cherished family moments. This traditional residence features a spacious kitchen adorned with solid wood cabinetry, complemented by a cozy dining area that seamlessly opens to the inviting family room with a classic brick wood-burning fireplace–perfect for creating warm memories. The layout includes both a formal dining room and a formal living room, providing ample space for entertaining and family gatherings. The original fourth bedroom of the home was transformed into a generous master suite, featuring an en suite bath for added privacy and comfort. The two additional bedrooms share a conveniently located hallway bath, making this home ideal for families. Step outside to the screened porch, where you can relax and enjoy views of the fenced yard, offering plenty of space for gardening or play–design it to your liking! Recent updates include a new roof (2025), freshly painted interior walls (2025), public sewer upgrade (2025), a hot water heater (2024), ensuring peace of mind for years to come. Location is key, and this home is just a short walk away from the highly-rated Dommerich Elementary School. Transferable roof warranty and termite bond! No HOA fees! Don’t miss your chance to make this lovely home yours and create lasting holiday memories!

2167 Mohawk Trail, Maitland

751 Sequoia Trail, Maitland
$595,000
5 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
Virtually Staged. Located in one of Maitland’s established and tree-lined communities, this distinctive Mid-Century Inspired Chalet residence offers exceptional space, dramatic design elements, and endless potential for modern transformation. Positioned within sought-after school district the home benefits from access to some of the area’s most well-regarded schools. The home’s impressive pavered approach sets the stage for its chalet-inspired architecture, where soaring A-frame rooflines, dramatic window walls, and natural stone detailing create an unforgettable presence beneath a canopy of mature trees — where “Colorado ski chalet meets Old Florida.” With 5 bedrooms and 3.5 bathrooms, the home is filled with high ceilings, expansive windows, and retro-inspired details that create character throughout. A striking open staircase with vintage styling showcases craftsmanship and design elements rarely found in today’s construction, while a massive paver courtyard welcomes guests and enhances the home’s unique indoor-outdoor lifestyle. Inside, the formal dining and sunken living room feature coffered ceilings and a dramatic circular brick fireplace centerpiece, while walls of windows flood the interiors with natural light. The spacious kitchen includes a cooking island, double wall ovens, closet pantry, breakfast nook, and an abundance of windows overlooking the private backyard area. Adding exceptional flexibility, the home also features a private in-law suite with its own separate entrance. The space includes a sleeping area, small seating/living space, private bathroom, kitchenette area with refrigerator and countertop workspace, and an eat-in area — ideal for multigenerational living, long-term guests, a private home office setup, or potential income-producing opportunities. The upstairs bedrooms open onto a rear balcony, creating a true retreat feel among the mature trees and landscaped surroundings. The primary bath features angular ceilings, oversized triangular windows, and a custom mosaic tile tub and double vanity that reflect the home’s original retro contemporary character. Outdoors, enjoy a sparkling swimming pool surrounded by shade trees, an expansive paver deck, and a fully fenced yard ideal for entertaining, gardening, or creating a private oasis. Members of Dommerich Beach Civic Association can enjoy lake access at the Dommerich Boat Ramp! Recent updates include new roof 2024, along with a transferrable shingle warranty, both A/C HVAC units replaced 2019 and 2023, hot water heater was replaced in 2019, 2023 electrical work done, 2022 high end Samsung dishwasher installed, transferrable premium home appliance warranty expiring Feb 3 2027, gas-powered portable generator and underground utilities. This home presents an exciting opportunity for buyers seeking architectural character and the chance to personalize a spacious residence with cosmetic updates including flooring, wall finishes, and modern design enhancements. Conveniently located near top-rated dining, shopping, parks, and major commuter routes, Maitland remains one of Central Florida’s most desirable established communities, known for its timeless charm, mature landscapes, and exceptional location.

751 Sequoia Trail, Maitland

2466 Fieldingwood Road, Maitland
$595,000
4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code
Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 bedroom, 2 bathroom home has been completely renovated from top to bottom with a fresh, modern feel that is move-in ready and designed for today’s lifestyle. From the moment you arrive, you will notice the clean exterior, updated landscaping, and quiet street that sets the tone for the rest of the home. ALL major systems have been updates: Roof 2022, Plumbing 2024, Hot Water Heater 2024, AC 2016, and newer pool equiptment. Inside, the layout flows effortlessly with light-filled living spaces, updated flooring, and a bright, open feel throughout. The kitchen and main living areas connect seamlessly, making it perfect for both everyday living and entertaining. Step outside to your private backyard retreat featuring a newly refreshed pool and spacious deck area. This is the kind of space that feels like Florida living should. Whether you are hosting friends or enjoying a quiet evening at home, this backyard delivers. The bedrooms offer comfortable, flexible space for families, guests, or a home office, while the primary suite provides a clean and calming place to unwind. Located in English Estates, you are just minutes from Winter Park with easy access to 17-92, 436, and Red Bug Lake Road. Commuting is simple with quick access to I-4 and the express lane entrance, getting you to downtown Orlando efficiently. If you are looking for a fully updated home with a pool in a central location that actually makes your day-to-day life easier, this is one you need to see in person.

2466 Fieldingwood Road, Maitland

1447 Caring Court, Maitland
$595,000
3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
Beautiful move-in ready home in the highly sought-after gated community of Montacino, located in the heart of Maitland. This single-story Mediterranean inspired home boasts three spacious bedrooms, including the grand Primary bedroom suite with its private spa-inspired bathroom with a jacuzzi tub, another inviting full bathroom, a convenient half bath, and a separate office or den great for remote work or hobbies. The split plan allows for plenty of privacy and includes a formal dining room, a chef's kitchen with a spacious eat-in area overlooking the gorgeous family room with a gas-ready fireplace, which leads to the peaceful screened-in back porch. Elegant Tray ceilings, eight-foot doors, charming archways and recessed lighting add to the allure of this home. With an oversized two-car garage and a nicely appointed interior laundry room, this low-maintenance home offers plenty of storage, and carefree living. The affordable HOA fee provides privacy and security with the gated entrance, access to the sparkling community pool, professional maintenance of all the lush landscaping, and scenic paved paths overlooking tranquil Lake Charity. Don't miss your chance to live in this elegant community, which is zoned for top-rated schools, and is perfectly located near Interstate 4, the Maitland Town Center and popular downtown Winter Park. Schedule your private showing today!

1447 Caring Court, Maitland

1781 Tonto Trail, Maitland
$590,000
4 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Welcome to 1781 Tonto Trail, a 4-bedroom home in one of Maitland's most desirable neighborhoods, offering just under 1,900 square feet of living space, a split bedroom floor plan, and access to the Winter Park Chain of Lakes. Located on a corner lot just under a quarter acre, this move-in ready residence combines functionality, comfort, and an exceptional Maitland location. Inside, you'll find a formal living room and formal dining room that provide flexible spaces for entertaining, working from home, or everyday living. The spacious family room serves as a central gathering area and connects seamlessly to the home's thoughtful layout. The private primary suite features an ensuite bathroom and double closets, creating a comfortable retreat. Bedrooms two and three offer large walk-in closets, providing abundant storage and flexibility for family, guests, or home office needs. The split bedroom design enhances privacy while maintaining a practical flow throughout the home. Residents of Dommerich Estates enjoy access to highly regarded schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. A voluntary low-cost HOA provides access to a private boat ramp on the Winter Park Chain of Lakes, creating opportunities for boating, fishing, paddleboarding, and waterfront recreation. The location places you short distance to the Maitland Community Park, Maitland Social, and Maitland City Centre, offering convenient access to local dining, recreation, events, and community amenities. Whether you're looking for more space, access to top-rated schools, or the lifestyle benefits of a lake-access community, this 4-bed home in Dommerich Estates delivers a rare opportunity to enjoy one of Maitland's most established and sought-after neighborhoods.

1781 Tonto Trail, Maitland

2634 Ultra Vista Drive, Maitland
$583,900
3 Beds ⋅ 2 Baths ⋅ Brittany Gardens SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully appointed single-story, single-family home located in one of Maitland’s most exclusive gated communities. Nestled on the tranquil shores of Howell Creek and overlooking protected conservation land in the front, this residence offers a rare combination of privacy, natural beauty, and refined living. Step inside to an open and airy layout filled with natural light and serene water views. This residence features a split floor plan with 3 Bedrooms and 2 Full Bathrooms. The Floor Plan includes a Foyer, Formal Dining room with architectural designs, spacious living room with a gas fireplace, Open concept kitchen with generous cabinetry and countertop space, and a cozy dinette. The living spaces are thoughtfully designed for both relaxation and entertaining, featuring new vinyl plank flooring throughout the home. The primary suite offers a tranquil retreat with its own en-suite bath, while the additional bedrooms are ideal for family, guests, or a home office. Enjoy the outdoors in your private backyard oasis, where mature landscaping and direct frontage to Howell Creek create a serene setting for morning coffee or evening sunsets on the tiled screened porch or extended tile patio. The gated community provides added security all within a quiet, well-maintained environment. Just minutes to Park Avenue in Winter Park, Maitland Social, City Centre and Lake Lilly where you can enjoy Local Dining, Kelly's Ice Cream, Boutique Shopping, Farmer's Markets and Parks. Interlachen Country Club, The Racquet Club, WP9 are easily accessible. I-4, 417, Maitland Exchange and all the daily living needs such as Publix, Walgreens and CVS are within reach. Brittany Gardens Residents enjoy beautiful Common Areas that include Access to Howell Creek from the shore for fishing or non motor boat adventures and Brittany Park.

2634 Ultra Vista Drive, Maitland

1149 Charming Street, Maitland
$580,000
4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
The Enclave at Maitland (Montacino), Beautifully Updated, First Floor Primary Bedroom, Oversized 20' x 26' Garage, Gated Community Living in the Enclave at Maitland which is highly sought-after, offering the perfect blend of style, comfort, and maintenance-free living. This fully updated Spanish-style townhome features 4 bedrooms, 3.5 bathrooms, a private paver courtyard, and an oversized attached two-car garage measuring approximately 20' x 26'—providing valuable extra space for storage, hobbies, a workshop area, or larger vehicles. One of the home's most desirable features is the spacious first-floor Primary Suite, offering privacy and convenience along with a beautifully updated en-suite bath featuring dual vanities, a soaking tub, separate shower, and walk-in closet. The thoughtfully designed floor plan is enhanced by soaring 9'8" ceilings on the main level, extensive crown molding, ceiling fans, and abundant natural light throughout. At the heart of the home is a stunning remodeled kitchen featuring 42-inch cabinetry with crown molding, granite countertops, stainless steel appliances, breakfast bar seating, and a cozy breakfast nook overlooking the private courtyard. The kitchen, all bathrooms, and even the laundry room have been tastefully updated, providing a move-in-ready experience for the next owner. You've got to see it! Upstairs you'll find a second private suite with its own updated bathroom, two additional bedrooms, another full bath, and a conveniently located laundry room. Closet organizer systems throughout the home provide exceptional storage and functionality. Residents enjoy access to a resort-style community pool overlooking picturesque Lake Charity, all within the security and convenience of a gated neighborhood. Ideally located near Maitland Boulevard and I-4, this exceptional location provides easy access to Downtowns of Orlando, Maitland and Winter Park, with premier shopping, dining, entertainment, and major employment centers. Offering a rare combination of updated finishes, flexible living space, oversized garage storage, and an unbeatable location, this exceptional townhome is ready to impress even the most discerning buyers.

1149 Charming Street, Maitland

1917 Hewett Lane, Maitland
$580,000
4 Beds ⋅ 2 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code
Welcome to this stunning, fully renovated single-story block home in the heart of Maitland, offering the perfect blend of modern design and everyday comfort. This 4-bedroom, 2-bath residence features a desirable split layout and open floor plan, creating an ideal space for both entertaining and family living. The brand-new kitchen is a true showpiece, complete with KitchenAid appliances, custom cabinetry, quartz waterfall countertops, and an oversized island that anchors the space. Engineered hardwood floors run throughout, complemented by abundant natural light from new windows and sliding glass doors. Major upgrades include a new electrical panel, new AC, new water heater, new insulation, and full re-piping—giving peace of mind along with style. The spacious primary suite offers a private en-suite bath and walk-in closet, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your private backyard oasis featuring a sparkling pool and fully fenced yard—perfect for entertaining, pets, or relaxing Florida evenings. Ideally located near Maitland’s shopping, dining, parks, and top commuter routes, this move-in-ready home delivers quality, comfort, and location all in one.

1917 Hewett Lane, Maitland

2318 Castlewood Road, Maitland
$580,000
4 Beds ⋅ 3 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. You know it is your house as you walk on your brick pavers to your front porch. As you enter the wide double doors they beckon you inside. This is your Rutenberg style floorplan home which is designed for both comfort and style. Heart of the Home: The Kitchen is at the center of the home and has been thoughtfully updated with solid wood cabinets, a functional working island, ample drawer space, and a spacious pantry. The cozy eat-in nook overlooks your brick paver-surrounded, screened-in pool, creating a perfect spot for morning coffee or casual meals. Living Spaces: The family room opens easily, featuring a charming brick fireplace with an electric crackle for ambiance. Three additional bedrooms are thoughtfully arranged, including a pool-planned bathroom and a secondary ensuite bath for guests or family. Formal Living & Dining An L-shaped formal living and dining room divides the home, offering elegant spaces for entertaining or relaxing. Primary Suite Retreat The updated primary suite is a true retreat, featuring a private water closet, step-in shower, double sinks, and double closets. Wide doors throughout make movement easy and accessible. Convenience & Extras Laundry facilities are conveniently located on the way to the two-car garage, where you’ll also find a carbonated water filter just outside the door for fresh, sparkling water. Outdoor Living For those who love the outdoors, the large cobblestone deck wraps around the screened-in pool, providing plenty of space for entertaining year-round. There’s a fire pit in the backyard to enjoy. We are proud to offer reality staging and reality renovations with stage, style & design by dakini.

2318 Castlewood Road, Maitland

448 Plumhollow Lane, Maitland
$575,000
4 Beds ⋅ 3 Baths ⋅ Stonewood SubDv. ⋅ 32751 Zip Code
Nestled on a gorgeous tree-lined street, this charming residence exudes warmth, elegance, and timeless appeal. From the moment you arrive, the excellent curb appeal draws you in — with an established landscaped yard, paver driveway and walkways, classic brick exterior with shutters, and newer front and garage doors that set the tone for what awaits inside. Step into an inviting home where quality craftsmanship meets modern updates. The updated kitchen is a true showpiece, featuring granite countertops, solid wood cabinetry, tiled backsplash, breakfast bar with pendant lighting, and stainless steel appliances, including a Bosch dishwasher (2024) and a new double oven (2021). Throughout the main living areas, you’ll find gleaming hardwood floors and crown molding, enhancing the home’s sophisticated style. Large windows and solar tubes in the kitchen and family room fill the space with beautiful natural light. Enjoy two cozy wood-burning fireplaces — one in the family room and one in the living room — each flanked by built-in shelving and cabinetry. The living room’s large picturesque window offers the perfect spot for seasonal décor or simply enjoying the tranquil view. A separate dining room with built-in cabinets, crown molding, and sliders to the back porch makes entertaining effortless. The primary suite is spacious and serene, featuring a walk-in closet, crown molding, and a beautifully updated en suite bath with granite counters, tiled shower with glass enclosure, updated lighting and fixtures, and a new TOTO toilet. The three oversized secondary bedrooms offer ample closet space; one is currently used as an office. The updated guest bath includes granite countertops and modern finishes. The large inside laundry room, conveniently located off the kitchen, provides abundant cabinet and counter space, a utility sink, and two pantries, plus a private half bath with a new high-rise toilet for guests. Step into the tiled Florida room, where large windows and motorized retractable screens invite you to relax and enjoy the gorgeous, manicured backyard views. Off the Florida room, a brick porch with a retractable awning and coach lights provides a peaceful spot for morning coffee or evening gatherings. The fenced backyard features a paver-lined walkway and lush landscaping for added privacy and charm. Recent updates include: HVAC (2023) • Whole House Water Softener (2021) • Washer (2023) • Dryer (2019) • Water Heater (2021) • Porch Awning (2016) • Range (2021) • Refrigerator (2016) • Bosch Dishwasher (2024) • Roof (2013) replumbed (2002) Located near Maitland Avenue, I-4, and 414, this home offers easy access to dining, shopping, parks, the Maitland Farmers Market, and top-rated schools. Come see why homes in Stonewood are so highly sought-after — this one truly has it all: charm, comfort, and convenience in one of Maitland’s most picturesque neighborhoods.

448 Plumhollow Lane, Maitland

671 Brookside Road, Maitland
$575,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
Experience refined living in this impeccably maintained 4Bd/2Ba pool home with a spacious layout, perfectly situated in a desirable, well-established neighborhood close to shopping, dining and everyday essentials. The customized kitchen is a true showpiece—featuring an expansive pull-out pantry, double pull-out corner cabinet system, built-in spice rack, and a spacious island designed for both function and elegance. Abundant natural light, updated flush mount lighting, and ample storage create a space that is as beautiful as it is practical. Throughout the home, you’ll find timeless finishes including crown molding, wood-look porcelain tile, and double-pane windows that enhance both style and comfort. Step outside to your private oasis—an extra-large refinished pool (2017) surrounded by premier artificial turf and lush landscaping offering the perfect balance of luxury and low maintenance. The oversized garage impresses with extra shelving, an insulated door with DC quiet opener and battery backup, and the refrigerator is included. Peace of mind comes with thoughtful updates: Roof (2021), HVAC (2016), and new ductwork, R30 insulation and aluminum soffits (2024). A home where craftsmanship meets comfort—modern sophistication and meticulous care make this a rare opportunity not to be missed. CALL TODAY to schedule your private viewing.

671 Brookside Road, Maitland

2491 Lauder Drive, Maitland
$575,000
5 Beds ⋅ 3 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
Nestled on a spacious corner lot in the highly sought-after Dommerich/Highland Park neighborhood, this distinctive two-story Mid-Century home offers both character and flexibility. With 5 bedrooms and 3 full baths, the layout is ideal for multigenerational living or accommodating guests with ease. Upstairs, the 5th bedroom serves as a private in-law suite, complete with a walk-in closet, full bath with shower, and ample room for a cozy sitting area or studio-style setup. On the main floor, the primary suite features its own bathroom and a generous walk-in closet, offering comfort and privacy. The heart of the home is a beautifully renovated kitchen with timeless shaker-style cabinets, granite countertops, soft-close drawers, stainless steel appliances, and a charming island perfect for casual meals or morning coffee. Adjacent to the kitchen is a built-in workspace, ideal for a home office or study station. Just off the kitchen, the family room invites relaxation with it's wood burning fireplace, beamed ceiling, and seamless access to the outdoor living area. Step through the sliding doors to your private screened-in pool oasis, complete with updated pool equipment and a spacious backyard ideal for entertaining or gardening. Located just minutes from top-rated Maitland schools, well known restaurants, boutique shopping, scenic lakefront parks, and major highways. Popular Winter Park, downtown Orlando, and area attractions are all within reach. Don't miss the opportunity to make this one-of-a-kind property your forever home.

2491 Lauder Drive, Maitland

2666 Derbyshire Road, Maitland
$571,430
3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 9 SubDv. ⋅ 32751 Zip Code
RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian Hills. The finished product “punches above it’s weight” in every possible way. KITCHEN offers two-tone, solid wood cabinetry topped with contemporary quartz counters. Stylish finishes including an undermount sink with long-neck faucet, upgraded black-matte cabinet door pulls and a modern stainless steel appliance package create a delightful cooking environment. LARGE LIVING SPACES including living / bonus / dinette and separate family rooms offer an abundance of options catering to a variety of lifestyle preferences and activities. BEDROOMS within this split-plan layout include His/Hers closets in the primary suite and a large 2nd bedroom and 3rd bedroom situated privately in the far corner of home. FLOORING throughout the home, upgraded Luxury Vinyl Plank was laid “wall-to-wall” and topped with upgraded 5 ¼“ baseboards, creating a peaceful yet contemporary feel to every room. BATHROOMS (both primary and secondary) have been fully remodeled including sinks, faucets, shower, tub, toilets, lighting and more. FINISHES including modern door hardware & hinges, ceiling fan and LED lighting throughout, wire rack shelving in all closets, updated electrical outlets and switches all combine to bring this vintage home up to today’s look & feel. OUTSIDE, a covered area on the back patio lanai provides the perfect shaded gathering place amidst a sun-filled day splashing in the inground swimming pool. Fully fenced and private, the backyard offers an oasis for sunbathing and a midnight swim. 4-POINT inspection items including roof (2023), hot-water heater (2025), HVAC (2019) will provide peace of mind. COMMUNITY events and activities abound within Indian Hills. Kewannee Park, a county park, offers walking trails and a boardwalk, fishing ponds, basketball court, and playgrounds all within walking distance. A-Rated Seminole County Public School district.

2666 Derbyshire Road, Maitland

1750 Pocahontas Path, Maitland
$565,000
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.

1750 Pocahontas Path, Maitland

2136 Mohican Trail, Maitland
$565,000
3 Beds ⋅ 2 Baths ⋅ Highland Park Estates | Dommerich SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Nestled in the desirable Highland Park Estates within the highly sought-after Dommerich area and a desirable school district, this charming home offers timeless character and incredible potential to make it your own. The retro-style kitchen opens to an inviting family room highlighted by a classic brick accent wall, while the shared brick pass-through fireplace and original terrazzo flooring seamlessly connect the family room to the formal living room. The formal dining room features elegant crown molding and chair railing, and French doors lead to a brand-new, expansive screened patio (2025) overlooking a beautifully fenced backyard filled with mature citrus trees. The exterior was freshly painted in 2025, adding crisp, updated curb appeal. Recent improvements provide peace of mind, including replumbing on the kitchen side of the home, a new dishwasher heat pump, and a new HVAC system installed in 2024. With solid updates already in place, you’ll have the perfect foundation to bring your personal vision to life.

2136 Mohican Trail, Maitland

1135 Thunder Trail, Maitland
$552,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Hills Fifth Add SubDv. ⋅ 32751 Zip Code
Distinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcome to this truly unique residence in the highly desirable Dommerich Hills neighborhood, where character, thoughtful updates, and a versatile layout come together to create the ideal setting for modern living. Perfectly situated just minutes from Winter Park and Maitland—and zoned for Dommerich Elementary, Maitland Middle, and Winter Park High—this home combines charm with convenience in one of Central Florida’s most sought-after locations. The spacious two-story design features four bedrooms plus a flexible bonus room, two full bathrooms, and two half baths. The main-level primary suite offers both privacy and comfort, complete with direct access to the backyard retreat. Upstairs, dual staircases provide easy flow to additional bedrooms and extensive hidden storage that spans the length of the home. The bonus room, outfitted with a Murphy bed and an adjacent half bath, is perfect for guests, a home office, or a fifth bedroom option. At the heart of the home, the chef’s kitchen is as functional as it is stylish, boasting gas appliances, butcher block counters with pop-up outlets, spice and oil niches, appliance hideaways, a pet nook, and a convenient pass-through window to the outdoor entertaining space. A butler’s pantry with beer and wine fridge, commercial-grade washer and dryer, and built-in bar elevate both everyday living and entertaining. Recent updates bring peace of mind: new roof (2022), HVAC (2019), windows (2021), garage door, tankless gas water heater, water softener, and new city sewer connection. Gas lines for the dryer, grill, or generator add extra efficiency. Outdoors, enjoy the Florida lifestyle in a private setting with a deck, gazebo, outdoor shower, and pergola-covered seating area. A private well feeds the irrigation system, keeping the landscaping lush year-round, while a cedar façade enhances curb appeal and architectural detail. This is not a cookie-cutter home—it’s a property designed for those who appreciate creativity, comfort, and functionality. With its top-rated schools, prime location, and a floor plan built for today’s needs, this Dommerich Hills treasure is a rare opportunity. Schedule your private showing today—homes like this don’t come along often.

1135 Thunder Trail, Maitland

1231 N Lake Sybelia Drive, Maitland
$550,000
3 Beds ⋅ 2 Baths ⋅ Lake Sybelia Shores First Add SubDv. ⋅ 32751 Zip Code
Virtually Staged. LOCATION! LOCATION! LOCATION! Set on a beautiful street lined with multi-million dollar homes and beautifully landscaped yards, this 1,785-square-foot, 3-bedroom, 2-bathroom single-story home offers comfortable, practical living with no HOA. The location puts the best of the area right at your doorstep. You are within short walking distance to Homer Hough Park on Lake Sybelia where you have access for kayaking or paddle boarding! A quick 3-minute drive (less than a mile) brings you to Lake Lily Park, the Maitland Community Center, and the Maitland Public Library. You are also just minutes from the new Maitland downtown shops, the Maitland Art Center, the local Farmers Market, top-rated schools, Winter Park dining, and I-4. Inside, walking through the double entry doors brings you into a bright foyer with a direct view straight into the backyard through a wall of windows. The open layout features fresh paint and newer energy-efficient windows, with easy-to-maintain laminate flooring throughout the main living areas and bedrooms, and tile in the kitchen and bathrooms. The central kitchen features granite countertops, a breakfast bar, and stainless steel appliances, including a new refrigerator and dishwasher. Right off the 2-car garage and kitchen, a large indoor laundry room acts as a functional mudroom with a utility sink and space for added storage. The primary bedroom includes a walk-in closet and an ensuite bath, while two guest bedrooms share a full hall bathroom. Out front, a circular driveway provides convenient extra parking. In the back, new sliding glass doors lead to a spacious, fully fenced yard with plenty of room for a pool, garden, or patio. Also, move in with total confidence knowing this home is backed by transferable Florida Pest Control warranties covering both Drywood and Subterranean termites. Key mechanical updates include a 2021 roof, updated plumbing and electrical, and a recently serviced dual AC system.

1231 N Lake Sybelia Drive, Maitland

251 W Horatio Avenue, Maitland
$550,000
3 Beds ⋅ 1 Baths ⋅ Osborne Manor SubDv. ⋅ 32751 Zip Code
This is a once in a lifetime opportunity to lovingly restore one of Maitland's oldest, historic homes, built in 1886, or choose to build your own dream home on this almost half an acre lot. It is situated in the prime location of the Maitland/Winter Park area; steps from beautiful Lake Sybelia. Most of the million-dollar homes in the neighborhood have recently been rebuilt. When you take a walk inside; you will be taken back to early Florida; with the wrap around wood porch, original windows, hardwood floors and high ceilings. There is so much character in this home! There is also a guest cottage out back that could be restored as well. This home and lot are in a very sought-after location and neighborhood, surrounded by beautifully appointed redone, large homes all around Lake Sybelia. This is a unique opportunity no matter what you as the buyer choose; restore or build in one of the prettiest neighborhoods and locations in Central Florida.

251 W Horatio Avenue, Maitland

1132 Charming Street, Maitland
$550,000
4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
Welcome home to a rare find, one of the largest floor plans in the community, sitting right on Lake Charity. This Mediterranean style townhome greets you with sweeping water views, mature landscaping, and a peaceful stillness that is hard to find this close to everything. Inside, wood floors and tile carry you through the first level. Plantation shutters run throughout the home and you'll find real wood cabinetry, a detail that speaks to the quality of this build. A large family room and dining room combo with a half bath offers plenty of space to entertain. The kitchen features newer appliances and granite countertops, opening into a bright and functional living space. The primary suite is located on the first floor and is oversized, with double vanities, a jacuzzi tub plus separate shower, and a walk in closet. Head upstairs to a spacious landing area that connects three additional bedrooms, featuring walk in closets with closet systems, along with two full bathrooms. Step outside to the true showstopper. Townhomes rarely feel private, but this courtyard is your own Mediterranean oasis. Grow plants, entertain, or simply enjoy the quiet. Another great feature of this home is the all new energy efficient windows and new AC unit, keeping utilities low without sacrificing comfort. Walk through the covered entry to your oversized two car garage, a rare find, offering plenty of room for both vehicles plus storage. As a resident, you'll enjoy a resort style community pool overlooking Lake Charity, all within a gated neighborhood. Minutes from Maitland Boulevard and I4, you're close to Downtown Orlando, Maitland, and Park Avenue. If you're looking to be in the heart of Maitland with the space, privacy and lake views to match, this is the home for you.

1132 Charming Street, Maitland

2464 Derbyshire Road, Maitland
$550,000
3 Beds ⋅ 3 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Fully renovated pool home on a desirable corner lot in the highly sought-after English Estates with NO HOA! This move-in-ready 3-bedroom, 2 and 1/2 bath residence showcases extensive recent upgrades and modern finishes throughout, offering the perfect blend of style, comfort, and functionality. Brand-new roof, new fence, new flooring throughout, fresh interior and exterior paint, updated electrical, updated windows and doors, modernized kitchen and bathrooms, upgraded lighting and fixtures, updated cabinets and countertops, and new appliances. Additional enhancements include new baseboards, plumbing updates for an added half bath, professional landscaping with new mulch and plants, and pool equipment upgrades including a new motor and pool pump. The inviting open floor plan features spacious living areas filled with natural light, a beautifully updated eat-in kitchen, and thoughtfully renovated bathrooms designed for modern living. The garage laundry area adds convenience, while the expansive corner lot provides excellent curb appeal and additional outdoor space for entertaining, relaxing, or future enhancements. Ideally located just minutes from Highway 436, shopping, dining, schools, parks, and everyday conveniences, this property offers both exceptional lifestyle appeal and strong long-term value. Whether you are searching for a primary residence, seasonal home, or investment opportunity, this extensively upgraded property is truly move-in ready. Schedule your private showing today and experience the quality, upgrades, and convenience this exceptional English Estates home has to offer!

2464 Derbyshire Road, Maitland

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