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$270,000
2 Beds 2 Baths Tucker Oaks SubDv. 34787 Zip Code
Gorgeous, move-in ready, 2/2 townhome inside gated community of Tucker Oaks! This second floor unit has just been refreshed with new paint and carpets throughout. It offers an open space kitchen/dining/family room combo perfect for entertaining. Spacious kitchen with updated cabinets and appliances, will be suitable for anyone that loves to cook! Dual masters in a split floorplan with spacious rooms and large closets, and includes a 1-car garage! Low monthly HOA! Tucker Oaks community offers a pool, walking paths, basketball courts, BBQ area, playground, and pet park, all conveniently located near Winter Garden Village, with easy access to Hwy 50, Florida's Turnpike, and the 429! Whether you plan to move in or use it for an investment property, you don’t want to miss out on this gem!

15325 Oak Apple Court Unit 8A, Winter Garden

$1,325,000
5 Beds 7 Baths Canopy Oaks Ph 1 SubDv. 34787 Zip Code
UPGRADES GALORE in this Award Winning Delray Model, MOVE-IN-READY! This Pool Estate offers a rare opportunity to indulge in luxury living. The two-story home boasts 4,409 square feet of living area with five bedrooms, five bathrooms, two half-bathrooms, and a three-car garage. (It's 5,844 square feet, counting the garage, front entry, lanai, and rear balcony.) Exquisite finishes, Italian Architecture, a second-floor balcony, a 2-story foyer, a Juliette balcony, and a magnificent Chef's kitchen are just a few of the features that will have you upon entry. The amazing kitchen is truly the heart of the home and features 42" cabinetry with second-tier upper lighted hutch stack for even more storage space, soft close doors and drawers, over and under ambient lighting, and crown molding. The cabinet-front door to the pantry eloquently blends with the cabinetry and upgraded Jenn-Air appliances. KitchenAid Double Oven.  The oversized prep island has a sink, and there is a convenient pot filler water faucet on the gas cooktop wall. There is a fabulous 200-bottle wine cellar nestled under the stairs with wine refrigeration/storage and wrought iron-gated entry. The MAIN FLOOR master suite is both spacious and private and features a luxurious walk-in shower, free-standing soaking tub, and walk-in closet. There is an additional guest bedroom with an en-suite bath on the main floor, great for guests or in-laws. Upstairs, you will enter the large gathering room with rich wood floors, tray ceiling, and a built-in desk which opens up to a 22-foot second-floor balcony. There is a theatre room jhas  Epson projector with a HEOS sound system that connects to Indoor and outdoor and rock speakers. Upstairs three additional en-suite bedrooms, one being designed as a "second master suite". The spacious, covered lanai is enclosed with 3-panel stacking slider doors, creating an expanded and open outdoor living space. The lanai includes a summer kitchen, a large pool with spa. Canopy Oaks is a gated enclave of luxury homes in Winter Garden. !Reading nook with built in book shelves Canopy Oaks, located in Winter Garden, Florida, is a unique blend of high-end luxury homes and suburban tranquility. This gated enclave, developed by the distinguished home builder A.R. Bailey, features 49 classic estates, each meticulously crafted to cater to the specific needs and desires of homeowners, includes scenic nature trail, a children’s play park and a community post office. An exceptional estate at an exceptional value Canopy Oaks is located on Roper Road between Winter Garden’s downtown historic district and the Winter Garden Village shopping complex. With convenient access to major highways such as 429, 408, and the turnpike, as well as its proximity to world-renowned attractions like Disney World® and Universal Studios®, this home presents an exceptional opportunity for easy commuting.

659 Canopy Estates Drive, Winter Garden

$695,000
5 Beds 3 Baths Summerlake Pd Ph 3b SubDv. 34787 Zip Code
Welcome home! This bright and beautifully maintained five-bedroom, three-bathroom home with an office nook is located in the highly sought-after community of Summerlake in Winter Garden. Offering over 3,200 square feet of living space, a spacious fully fenced backyard, and a three-car tandem garage, this home features fresh exterior paint in 2024, brand new carpeting upstairs, and luxury vinyl plank flooring on the stairs and in the downstairs guest suite. The kitchen boasts wood cabinets, granite countertops, a newer gas stove, newer refrigerator, center island, breakfast bar, and an eat-in nook, all flowing seamlessly into the living and dining spaces. Sliding doors with plantation shutters open to a screened porch and extended paver patio overlooking the backyard. The upstairs primary suite offers his and hers walk-in closets, dual sinks, a soaking tub, and a walk-in shower. All upstairs bedrooms include walk-in closets, and an expansive loft is perfect for a game room or second living area. Community amenities include a resort style pool, clubhouse, fitness center, fishing dock, zipline, playgrounds, tennis and basketball courts, dog park, and nightly Disney fireworks views. Conveniently located just minutes from Hamlin Town Center, Winter Garden Village, Historic Downtown Winter Garden, and FL 429, with easy access to Orlando’s top attractions including Disney, Universal Studios, and SeaWorld.

15019 Purple Martin Street, Winter Garden

$551,000
3 Beds 2 Baths West Lake Hancock Estates SubDv. 34787 Zip Code
• Well-Priced & Gorgeous THREE-Bedroom, Two-Bath, Concrete-Block, Single-Family Home on a Large, CORNER Lot… with and A-RATED SCHOOLS in the Sought-After Horizon West Area! HOLY COW! • Home is in an Excellent Location Where You can WALK to the Amazing COMMUNITY CENTER Just Across the Street! You will be Thrilled with the Fantastic Condition with All Brand-New LAMINATE FLOORING… and So Freshly PAINTED the home even SMELLS New! • OPEN KITCHEN Overlooking the Family Room & SCREENED PORCH! Nice! Never Run out of Hot Water with a Tankless Gas Water Heater too! • The Affluent Neighborhood of West Lake Hancock Estates is part of the New HAMLIN TOWN CENTER, a 30,000 Acre Master-Planned Community with nearby walkable Shopping, Restaurants, Nature, Hospitals and Endless Entertainment! • You will feel like you are Living in a Family-Oriented Small Town, while also being an established and Master-Planned Community Hosting Virtually all the Resident-Amenities You Could Ever Hope for…all for an Affordable $209/ month! • The Community Clubhouse is RIGHT ACROSS THE STREET from your New Home where you can just WALK Over to Enjoy the Massive, Resort-Style Community POOL & Splash Pad and a 24/8 Resident-Access FITNESS CENTER! Surrounding the Clubhouse residents can enjoy the Sports Lawn, the Firepit, a Covered Pavillion, abundant PICNIC SPACES, Canoes for Rent, the Playground Overlooking the LAKE, the DOG PARK, Miles of Walking Trails…the Waterfront Pavillion to Enjoy the Sunset… and Evening Views of the Disney Fireworks! • Love the Water? Take advantage of your Private BOAT RAMP & BOAT DOCK just for Neighborhood Residents on 467-Acre LAKE HANCOCK! Need storage for your boat, RV, jet skis and trailer?...There is a new neighborhood storage rental facility just 3 minutes away! • You will be living just Minutes Away from so many nearby Dining & Shopping Options You’ll Never Need to Leave the Area at our New HAMLIN TOWN CENTER SHOPPING District, including a Publix & Walmart! You will always have something FUN to do here with the Cinepolis Luxury Movie Theatre, the Urban Air Trampoline Park… the New HORIZON WEST REGIONAL PARK, a 220-Acre Outdoor Orange-County Mega Park…and the exciting New Horizon West 45-Acre SURF PARK too! • For those Golfers, the Well-Known Orange County National Golf Center & Lounge sits next to this Community! • Within a quick 20-minute Drive, you can Use your Annual Passes to the Walt Disney World Parks for a Lifetime of Disney Magic… or be in the Historic Downtown WINTER GARDEN VILLAGE with its Boutique Shopping and Restaurants! • In less than 30 minutes, You will be at Universal Orlando or SeaWorld, or an Easy Commute to DOWNTOWN ORLANDO… and the Orlando International Airport in less than 45 minutes away! Nice! • The Rest of Central Florida is Just Around the Corner with Your Home being only 5 Minutes from the 429 Expressway, with easy Access to the Florida Turnpike & Interstate 4! • Sought-After, A-Rated Schools: Independence Elementary, Bridgewater Middle and Horizon High School…and Many Nearby Private Schools as Well! Say YES!

7500 Lake Hancock Boulevard, Winter Garden

$398,800
3 Beds 3 Baths Hickory Hammock SubDv. 34787 Zip Code
For the first time on the market, this impeccably maintained luxury townhome—offered by its original owner—delivers style, comfort, and location at one of Winter Garden’s best values. Perfectly cared for and thoughtfully updated, it’s truly move-in ready. The remodeled kitchen flows seamlessly into a sun-filled great room with soaring ceilings, creating an open and inviting space. Step out to the screened lanai and enjoy peaceful views with no rear neighbors, the perfect setting for coffee at sunrise or quiet evenings outdoors. Upstairs, the owner’s suite is a private retreat with two walk-in closets and a beautifully finished bath. A large loft has been enclosed to create a versatile third bedroom without a closet, ideal for guests, an office, or a cozy den. With a new air handler installed just two years ago and a spacious two-car garage, comfort and practicality are built in. Behind the gates of Hickory Hammock, resort-style living is at your doorstep—an elegant clubhouse, oasis beach entry pool, tennis courts, fitness center, playground, beach volleyball, dog park and a lakeside park with fishing pier on Johns Lake create a community unlike any other. Location is everything, and here you are minutes from the 429 expressway, less than 20 minutes to Disney and Downtown Orlando, and a short drive to Downtown Winter Garden’s charming brick-lined streets, bustling Saturday Farmers Market, year-round festivals, Crooked Can Brewery, boutique shops, and countless dining options. Outdoor lovers will appreciate the West Orange Trail just moments away. Served by a highly sought-after K-12 school district and near several private school campuses, this home combines lifestyle, convenience, and exceptional value. Priced to sell quickly, it’s a rare find—move fast before it’s gone.

15206 Sunrise Grove Court, Winter Garden

$989,900
4 Beds 4 Baths Waterleigh Ph 2b SubDv. 34787 Zip Code
Stunning Emerald serie house, Selden model built in 2018 well maintained, featuring 4 bedrooms, 3.5 bathrooms, and approximately 2,920 sq ft of living space. Situated on a premium corner lot of about 10,585 sq ft, this home offers a 3-car tandem garage, spacious backyard, private wooded views, and a screen-enclosed private pool—perfect for year-round Florida living. The open-concept design includes a formal dining room, elegant foyer with wrought-iron staircase, and a gourmet kitchen with a large island, 42” cabinets with crown molding, granite countertops, stainless steel appliances, and a convenient drop zone from the garage. The owner’s suite boasts a tray ceiling, a spa-like en-suite bathroom with dual sinks, a garden tub, and a spacious walk-in closet. Additional features include a durable concrete tile roof, dual A/C units, and numerous upgrades: exterior lighting, sealed paver driveway and porch, landscape lighting, decorative stonework, epoxy-finished garage floor, and professional landscaping. Lawn care is included with HOA fee. Located in the highly sought-after Waterleigh community in Winter Garden, residents enjoy resort-style amenities: two community clubhouses, 4 resort-style pools, 2 fitness center, beach volleyball, 2 tennis courts, mini-golf, community garden, dog park, fishing pier, and scenic walking/biking trails. The neighborhood is beautifully landscaped with lakes, green spaces, and planned community events. Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, and easy access to SR-429 for a quick commute to Orlando and Walt Disney World. Zoned for top-rated schools: Atwater bay Elementary, Water Spring Middle, and Horizon High School.

10007 Little Alcove Loop, Winter Garden

$737,500
4 Beds 4 Baths Summerlake Pd Ph 1b-A Rep SubDv. 34787 Zip Code
Welcome to this beautifully upgraded residence in the sought-after Summerlake community of Horizon West, Winter Garden. Perfectly situated on an estate-size corner lot, this property offers exceptional privacy with no neighbors on one side and peaceful greenspace views. Spanning nearly 3,600 sq ft, the home features 4 bedrooms, 3.5 bathrooms, a private office, formal living room, and even a hidden theater room! A charming front porch sets the stage for the inviting interior, where extended tile flooring flows throughout the main living areas for a seamless, elegant look. At the front of the home, the private office features stylish sliding doors and a large window—ideal for working from home—while the versatile formal living room can easily serve as a dining room. The gourmet kitchen is the heart of the home, showcasing upgraded cabinetry, granite countertops, a large breakfast island, modern pendant lighting, tile backsplash, stainless steel appliances, gas cooktop, and a custom walk-in pantry. The dishwasher and microwave are brand-new. The kitchen opens to the dining area and spacious family room, which leads to a covered lanai and fully fenced backyard—perfect for entertaining or adding a pool. A custom bar with cabinetry, extra seating space, and a beverage fridge makes hosting a breeze, while the guest powder bath downstairs features a newer vanity. You’ll also appreciate the oversized under-the-stair storage. Upstairs, built-in storage cabinetry leads to a hidden door revealing the private theater room with board-and-batten accents—ideal for movie nights or as a bonus space. The oversized primary suite offers a sitting area, dual walk-in closets, and a spa-like bathroom with dual vanities, updated lighting, an oversized walk-in shower, soaking tub, and linen closet. Three additional bedrooms and two full bathrooms are also located upstairs, along with an oversized laundry room featuring space for extra storage or a hobby table, plus a newer washer and dryer. Additional highlights include overhead garage storage, gutters, a fully fenced yard, and a new A/C system (2023). The oversized covered lanai provides ample seating for gatherings. Enjoy the privacy of the corner lot with plenty of space for backyard games, gardening, or a future pool. Summerlake residents enjoy resort-style amenities, including a clubhouse, fitness center, resort-style pool with splash pad, tennis courts, playgrounds, dog park, half basketball court, and scenic walking trails. The HOA even includes lawn maintenance. Zoned for A-rated schools—including Summerlake Elementary right in the neighborhood—and just minutes from Hamlin Town Center, SR 429, and Walt Disney World, this home perfectly blends convenience, comfort, and luxury. Schedule your private showing today—this one won’t last! Make sure you check out the video!

8000 Key West Dove Street, Winter Garden

$645,000
4 Beds 3 Baths Stoneybrook West D SubDv. 34787 Zip Code
Video and 3D walkthrough available! Welcome to a neighborhood unlike any other in Winter Garden! Stoneybrook West has a 24-hour guarded gate, a 7,700 square foot town center, Olympic-sized swimming pool with splash zone, fitness center, playground, tennis courts, basketball courts, pickleball courts, fishing/viewing pier, private boat ramp, and a community activity calendar! The HOA DUES INCLUDE INTERNET and CABLE! This home has an amazing POND VIEW and NO REAR NEIGHBORS. You can’t miss the charming curb appeal when you arrive. Enter the home to find a layout designed for both entertaining and everyday comfort. The FORMAL LIVING AND DINING SPACES at the front of the home offer a comfortable setting for hosting friends and family, while the OPEN-CONCEPT KITCHEN AND FAMILY ROOM at the back of the home provide a seamless flow for relaxed gatherings. The spacious kitchen is ready for home chefs, featuring generous counter space, a WALK-IN PANTRY, stainless steel appliances, stylish tile backsplash, and a convenient breakfast bar. Slide open the doors to your SCREENED PATIO and FULLY FENCED BACK YARD—ideal for pets, play, or simply soaking in the view. This home offers excellent multi-generational living or guest accommodations with a BEDROOM AND FULL BATHROOM DOWNSTAIRS. Upstairs, a VERSATILE LOFT area awaits—perfect as a second living room or media space. The loft and the primary suite open to the SCREENED BALCONY, where you can unwind and take in the view. The primary suite also features a garden tub, walk-in shower, dual vanities (plus a makeup area), and a MASSIVE WALK-IN CLOSET. Enjoy everyday convenience with an upstairs laundry room complete with cabinet storage and utility sink. Additional upgrades include a NEW ROOF (2023), NEW WATER HEATER (2023), AC (2019), surround sound wiring in the family room and loft, CEILING FANS and great storage throughout! Balforn Tower Way is conveniently located near the resident’s gate and is just minutes away from the community town center, golf clubhouse, great schools, restaurants, shopping, a hospital and entertainment. NOTE: THE SELLERS ARE OFFERING A $10,000 BUYER CREDIT FOR PAINT AND CARPET WITH A FULL-PRICE $675,000 OFFER!

2549 Balforn Tower Way, Winter Garden

$1,570,500
3 Beds 4 Baths 34787 Zip Code
A Rare Slice of Serenity in the Heart of Horizons West — 5526 Tiny Road Almost five acres in the middle of one of Central Florida's most sought-after communities isn't just rare — it's nearly impossible to find. While the rest of Horizons West builds closer together, 5526 Tiny Road sits on almost five rolling, private acres surrounded by open sky, a private pond, and natural Florida landscape — all within walking distance of community trails, top-rated schools, and the brand-new Orange County Library currently under construction just steps away. This is the property buyers spend years waiting for. The freedom of acreage. The convenience of community. No HOA. No compromise. The custom-built 2007 estate offers 2,400 square feet of thoughtfully designed living space — three bedrooms, a spacious loft, and 2.5 bathrooms inside, plus a half bath in the oversized 3.5-car garage built for the enthusiast, the workshop, the toys, or all three. The open-concept layout is filled with natural light, anchored by a gourmet kitchen and flowing living spaces designed for both everyday comfort and effortless entertaining. Step outside and the property truly comes alive. A front gazebo attached to the home frames sweeping views across the acreage. The screened rear lanai overlooks a nature preserve. Sunrises and sunsets paint the elevated ridge in a way that no subdivision lot can replicate. Wild turkeys, native birds, and open Florida sky are your neighbors. Just a short ride to Hamlin Town Center, Disney World, SR-429, and everything Horizons West continues to build around you — including planned road enhancements to Tiny Road itself, with landscaped medians and expanded sidewalks that will further elevate the entrance to this property. Properties like this don't come back to market. Once it's gone, it's gone — because there is nothing left to build like it here. 3 Bed | Loft | 2.5 Bath + Garage Half Bath | 3.5-Car Garage | Almost 5 Acres | No HOA | Custom 2007 Build | Private Pond | Horizons West / Independence-Summerport

5526 Tiny Road, Winter Garden

$2,125,000
5 Beds 5 Baths Hickory Hammock Ph 1d SubDv. 34787 Zip Code
This LAKEFRONT Home with PRIMARY AND 3 SECONDARY BEDROOMS ON the MAIN FLOOR was RENOVATED FROM TOP TO BOTTOM and is located in the very desirable GATED Community of HICKORY HAMMOCK. The moment you walk through the front door, you will have gorgeous VIEWS OF THE BEAUTIFUL 2400-ACRE JOHN’S LAKE. The interior continues with the COUNTLESS UPDATED CUSTOM FINISHES including VERY HIGH-END LUXURY VINYL PLANK FLOORING throughout the entire first floor, QUARTZ COUNTERTOPS, 53” EUROPEAN-STYLE KITCHEN CABINETS, TWO-PIECE CROWN MOLDING, and 7” BASE MOLDING. ALL 5 BEDROOMS HAVE WALK-IN CLOSESTS WITH CUSTOM BUILT-INS. You will find one additional Bedroom and Full Bathroom upstairs alongside a HUGE BONUS ROOM with plush carpet and extra thick padding. Entering the home from the garage, you will find a beautifully designed MUD SPACE and then enter the laundry room to find a BUILT-IN SMOOTHIE/COFFEE BAR with upper and lower cabinets, drawers, and a BUILT-IN SINK. There’s also an ingenious “SECRET” SPACE that’s currently being used as an art room. The home features a whole-home filtration/softener and R.O. water system. Alarm system and cameras are paid in full and included. Additionally, this home provides a SCREENED-IN SALTWATER POOL. Inside the screened patio, you’ll enjoy entertaining with a SUMMER KITCHEN, complete with a built-in grill, refrigerator, sink, and granite countertop. This home provides extraordinary entertaining space, both inside and out. This home also features an OVERSIZED 3-car garage with Lots of OVERHEAD STORAGE RACKS and a SPLIT AIR CONDITIONER. The PRIVATE DOCK IS EQUIPPED WITH WATER AND ELECTRICITY AND BOAT LIFT. There is a FULLY FENCED backyard leading to your dock where you can watch DISNEY FIREWORKS OR GO ENJOY BOATING, PADDLE BOARDING, KAYAKING, OR JET SKIING ON THE INCREDIBLE 2400 ACRE JOHN’S LAKE. *BONUS - SOLAR PANELS ARE OWNED – NO ADDITIONAL PAYMENTS – SAVE MONEY ON YOUR ELECTRIC BILL* THIS EXCEPTIONALLY DESIGNED AND UPDATED LAKEFRONT HOME TRULY OFFERS IT ALL. Schedule your private showing today.

16098 Johns Lake Overlook Drive, Winter Garden

$836,000
5 Beds 5 Baths Summerlake Pd Ph 1b-A Rep SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Ideally situated in the highly desirable community of SUMMERLAKE, this spacious two-story 5-bedroom, 4.5 bathroom property with flexible layout allows for a multi-generational family. Sitting on a PRIME LOT with WATER views and located on a quiet, tree lined street, this residence shows like new - why wait to build when you can move in here immediately! Built in 2016, the property is IMMACULATELY PRESENTED, includes cabinetry upgrades, features tray ceilings and has recently been painted both on the exterior & interior. NO CARPETS! At the heart of the home is the expansive OPEN PLAN CONCEPT kitchen and family room, flowing into a separate dining area. Water views are a bound from several rooms with plenty of natural light throughout. The GOURMET KITCHEN is a chef’s dream with stainless steel appliances (including new 2025 natural gas stovetop, refrigerator & microwave), built-in wall oven, ample cabinetry, sprawling central island with seating, granite countertops, glasstile backsplash and walk-in custom BUILT-OUT PANTRY. Exuding luxury in a modern setting, the first floor also includes a welcoming foyer area, home office with built in cabinetry, additional flex room (play area or formal living room or second study) and a separate guest powder half bath serving the living room areas. Completing the 1st floor is a well-appointed bedroom with walk in closet and full ensuite bathroom. Located on the 2nd floor is the spacious primary bedroom, which is a true retreat featuring a separate sitting area, an oversized walk in closet and impressive ensuite bathroom consisting of dual vanities, a walk-in shower and soaking tub. The LOFT AREA is sizeable and offers more living space/game room and boasts access to a PRIVATE BALCONY overlooking the lake. There is a conveniently located laundry room and 3 further well-proportioned bedrooms, each with ample walk-in closet space. With a separate split a/c unit for the DIY enthusiasts, the 3-CAR TANDEM REAR ENTRY GARAGE (also large driveway to accommodate additional cars) is provided access to the home via a utility area with useful cabinetry storage and counter space. Enjoy the outdoor Florida lifestyle either sitting under the shade of the COVERED PATIO AREA or out on the turfed BACKYARD (this space is currently a blank canvas – the possibilities are varied from adding an outdoor kitchen, patio area with fire-pit, privacy fence around the yard or even adding a pool). Summerlake offers many AMENITIES including a lakeside clubhouse and resort-style pool, playground, tennis courts, dog park and walking trails. With close proximity to top rated schools, local shopping, restaurants & entertainment at Hamlin, Horizon West and downtown Winter Garden as well as easy access to major highways/roads, the theme parks and Orlando International Airport, don’t miss out on this exquisite gem, BOOK YOUR VIEWING TODAY! Virtual walk-through tour and video available.

7930 Summerlake Pointe Boulevard, Winter Garden

$1,780,000
5 Beds 5 Baths N/A SubDv. 34787 Zip Code
Exquisite New Construction in the Heart of Winter Garden’s Golf Cart District – Over 4,000 Sq Ft of Craftsman Charm! Step into timeless style and modern luxury with this brand new Craftsman-style masterpiece, perfectly situated on a charming cobblestone one-way street in the highly sought-after Golf Cart District of historic Winter Garden. Boasting over 4,000 square feet of beautifully appointed living space, this 5-bedroom, 4.5-bathroom estate offers the perfect blend of character, comfort, and convenience—all with NO HOA dues or restrictions. Set on over a third of an acre, the home impresses at first glance with custom landscaping, a massive covered front porch, and timeless curb appeal. Inside, enjoy warm wood flooring throughout, striking custom wooden beams in the foyer, and a spacious great room with electric fireplace—all flooded with natural light. Designed for entertaining, the open-concept layout includes a chef’s kitchen with custom cabinetry, gas appliances including professional grade gas range, built-in refrigerator and freezer stacks, walk-in pantry, wet bar with wine refrigerator, and a spacious island. Step outside to your private oasis complete with a large covered and pavered back patio, summer kitchen (grill + outdoor refrigerator), fenced yard, and a sparkling pool with heated spa—perfect for entertaining year-round. The downstairs primary suite offers a peaceful retreat with a spa-inspired bath, spacious shower, and massive walk-in closet finished with built-ins. A second downstairs bedroom with its own walk-in closet and nearby bath is perfect for guests or a home office. Upstairs, you'll find three additional bedrooms (each with walk-in closets), a loft living area, and even a second laundry/utility room for added convenience. The main laundry room downstairs is oversized, filled with natural light and extensive cabinetry, and an adorable mudroom just off the garage. Additional features include: Two-car garage PLUS a golf cart garage, dual tankless gas water heaters, gas appliances, and fully fenced back yard. This rare Winter Garden gem offers the best of both worlds—new construction luxury with the charm of Downtown Winter Garden living. Just moments from shops, dining, and everything downtown Winter Garden is known for. Don’t miss this opportunity to own a truly one-of-a-kind home in one of Central Florida’s most desirable communities.

958 Tildenville School Road, Winter Garden

$550,000
3 Beds 4 Baths Winding Bay Ph 1b SubDv. 34787 Zip Code
Under contract-accepting backup offers. Disney fireworks views, single-story living, low HOA — just 3.9 miles from Disney. Welcome to Winding Bay in Winter Garden, where location, lifestyle, and long-term value come together in one beautifully maintained home. This pristine 3-bedroom, 3.5-bath residence with a flexible bonus room offers the perfect setup for everyday living, visiting guests, remote work, or a potential future sleeping space with proper modification and verification. From the moment you arrive, the home makes a statement with its brick-paved driveway, stone-accented façade, and inviting curb appeal. Inside, the bright open floor plan is designed for comfort and function, featuring a dedicated built-in desk area, an oversized mudroom, an adjacent laundry room, custom cabinetry, and generously sized guest suites. The heart of the home is the chef-inspired eat-in kitchen, complete with 42-inch soft-close cabinetry, quartz countertops, designer backsplash, vented range hood, built-in microwave, massive walk-in pantry, and an oversized island with seating for up to eight — ideal for entertaining, hosting family, or gathering after a day at the parks. The open dining and family room are filled with natural light and flow seamlessly to the custom-designed backyard, where you can relax and enjoy direct views of Disney fireworks from home — a rare and memorable feature that truly sets this property apart. Winding Bay offers a peaceful, pride-of-ownership atmosphere with no short-term rentals permitted, helping preserve the neighborhood feel while still keeping you minutes from Disney, dining, shopping, schools, and major conveniences. Residents also enjoy a community pool, dog park, and a low HOA of just $102/month. Move-in ready, meticulously maintained, and positioned in one of Winter Garden’s most desirable communities, this home is ideal for owner-occupants, Disney professionals, second-home buyers, or anyone seeking proximity to the magic without the noise, crowds, or rental turnover. Private showings available by appointment.

15456 Gilligan Court, Winter Garden

$2,000,000
5 Beds 6 Baths Isles/Lk Hancock Ph Iii SubDv. 34787 Zip Code
Welcome to 14640 Pylon Court, an extraordinary waterfront home located in the highly sought after gated community of the Isles of Lake Hancock—one of Florida’s most exclusive water ski neighborhoods. This custom-designed residence offers over 4,400 square feet of luxurious living space, five bedrooms, five full and one-half baths, a 4-car garage, and sweeping water views from both the front and back of the home. Set on a premium lot with direct views of the world-renowned championship ski courses, this home offers the ultimate blend of privacy, elegance, and recreational lifestyle. Inside, rich hardwood flooring flows through spacious, light-filled living areas, including a formal dining room with detailed ceilings, a private study, and a great room with soaring ceilings, custom built-ins, a fireplace, and expansive sliding glass doors. The gourmet kitchen features a massive island, gas appliances, double ovens, and ample cabinetry—perfect for both casual family living and entertaining on a grand scale. The luxurious primary suite includes a sitting area with lake views, dual walk-in closets, a soaking tub, walk-in shower, and dual vanities. The first-floor media room offers the perfect space for movie nights or game-day gatherings, while two additional bedrooms and a balcony complete the home’s thoughtful layout. The expansive screened lanai is ideal for outdoor living, featuring a sparkling pool, summer kitchen, manicured grounds, and tranquil water vistas. As a resident of this exclusive 54-home community, you’ll enjoy access to a residents-only boat ramp, tennis courts, playground, and recreation area. Located just minutes from all of the shopping and amenities at Hamlin, yet tucked away in a quiet, gated enclave, this home offers a rare opportunity to own one of Central Florida’s most sought-after waterfront properties—where luxury meets lifestyle.

14640 Pylon Court, Winter Garden

$546,000
5 Beds 4 Baths Alexander Ridge SubDv. 34787 Zip Code
Location! Location! Location!  That's just the beginning of the benefits to this wonderful home! This 5 bedroom ( 5th bedroom or tremendous bonus room ) with 4 full baths including an ensuite plus aforementioned bonus room gives you all the space you need to stretch out your growing family or have multiple offices while working from home and a possible home theatre. Centerpiece Kitchen with 42" upper cabinets with crown molding, solid surface counters complimented by stainless steel appliances. All tile in the living areas, 4 way split floor plan and more. Master suite has a garden tub, separate shower and double sink vanity with granite counters plus a walk-in closet. Exterior offers a  freshly painted exterior in July 2025, trimmed palm trees and a fully fenced backyard with plenty of room to run around. Community features include a pool, playground and open multipurpose field. Location benefits include walking distance to The Goddard school and The Foundation Academy, a short drive to The Winer Garden Grove filled with restaurants and shopping and also Downtown Winter Garden where you will find boutique shops and restaurants and a farmers market on the weekend along with the famous West Orange Trail. Easy access to Disney, SR 429, Florida Turnpike, SR 408, and I4.

2337 Aurelius Drive, Winter Garden

$893,000
4 Beds 4 Baths Waterside/Johns Lake Ph 1 SubDv. 34787 Zip Code
Significant PRICE IMPROVEMENT! Owners very motivated! Incredible MOVE-IN READY home in one of the most sought-after communities in one of the most desirable cities around Orlando! If you are looking for your dream home with easy access to downtown Orlando, Disney, the charm of downtown Winter Garden (and Farmers Market on Saturdays), and FL-429, come see this 4 bedroom / 3.5 bathroom, 2,934 sq ft, 3-car garage, single story Waterside community home! Built in 2019, this home has been lovingly cared for, meticulously maintained, and generously upgraded (over $45,000 in upgrades!) by the original (and only) owners. *** Be sure to check out the 3D layout of the home included in this listing! Copy and paste this link into your browser's address bar for the VIDEO Walk-through TOUR: tourbuzz.net/2342755?idx=1 (If the website on which you are viewing this property does not show the link or the 3D floor plan, contact your Realtor for those today!) *** No detail was overlooked in the design of this home, from the 300+ sq ft paver breezeway and courtyard, to the elegant practicality of the open-concept living areas (living room, dining room, kitchen, dinette with bar), to the SECOND PRIMARY SUITE, to the plentiful windows allowing abundant natural light and exception views to the BACKYARD OASIS. Upon entering the home, note the 8' doors and 9.5' ceilings, rounded archways and crown molding, accent beams in the dining room tray ceiling, custom lighting, and consistent use of beautiful and functional Silestone and luxury vinyl plank flooring. The kitchen features all stainless steel appliances, GAS STOVE, and HUGE SERVICE ISLAND with breakfast bar, and TWO WALK-IN PANTRIES. The large primary suite (over 530 sq ft) features a bathroom with separate vanities, large step-down shower with bench, garden tub, and privacy toilet, with an 80+ sq ft walk-in closet and direct access to the lanai. *** Upgrades include LUXURY VINYL PLANKING added to all common/wet areas in 2021 (bedrooms remain carpeted), an additional 16'x16' PAVER PATIO with PERGOLA (to match the existing 14'x18.5' paver patio, featuring an INCLUDED custom, hand-made dining table with seating for 12 and outdoor cabinetry with fridge/freezer), TANKLESS WATER HEATER, additional bar cabinetry, engineered wood lanai ceiling, "mudroom" bench and shelving, landscaping, courtyard drip irrigation, new paint, draperies, and more! Owners are also including the LG washer and dryer and courtyard furnishings in the sale of this property. *** This home is designed to impress with phenomenal entertainment capability yet with privacy for your family members and guests (a double-split bedroom layout)! *** The Waterside community features a modern fitness center, play and swim lane pool with lake view, clubhouse, park and playground.

16712 Rusty Anchor Road, Winter Garden

$2,165,000
5 Beds 5 Baths West Lake Hancock Estates SubDv. 34787 Zip Code
This home truly has it all. Nestled in The Overlook at Hamlin—one of the most vibrant and sought-after lakefront communities—this custom Taylor Morrison residence combines luxury, energy efficiency, and everyday convenience. Ideally located just minutes from Disney with easy access to Hwy 429, the home offers both lifestyle and location. Set on the scenic shores of Lake Hancock with nightly Disney Firework Displays, the thoughtfully designed floor plan features all main living spaces on the first floor, plus an upstairs media room or optional fifth bedroom with private bath. The primary suite is a tranquil retreat with stunning lake views and a spa-inspired bath. High ceilings with crown molding and wood beams, abundant natural light, and a stacked stone fireplace create a warm, inviting atmosphere. Gorgeous tile floors flow throughout. The chef’s kitchen impresses with a natural gas cooktop, quartz island, French door oven, and walk-in butler’s pantry. Step outside to your private lakefront oasis—a screened lanai with resort-style saltwater pool and spa, sun shelf with umbrellas, and a summer kitchen plus pizza oven station, perfect for entertaining. Just beyond, a floating dock offers direct lake access. Enjoy low utility costs thanks to a fully paid-off whole-house solar system and a tankless gas water heater—average electric bills are just $78/month. Additional features include a gated front courtyard for added privacy and security, and access to Overlook’s resort-style amenities, including a fitness center, community pool and splash pad, parks, and a private boat ramp for residents. Furnishings may be available.

7346 John Hancock Drive, Winter Garden

$1,049,000
6 Beds 5 Baths Oxford Chase SubDv. 34787 Zip Code
Architecturally Distinctive and Thoughtfully Designed – “The Yorkshire” in the popular Oxford Chase community. From the moment you arrive, this executive-style residence immediately distinguishes itself as one of a kind. Designed with impact and elegance, the entry welcomes you with a charming front patio that creates a natural and inviting transition into the home. Built by Mattamy Homes, the home offers nearly 4,700 square feet of expertly crafted living space, featuring 6 bedrooms, 4.5 baths, and an exceptional layout that blends openness with purpose. At the heart of the home is a grand rotunda foyer - a striking architectural centerpiece that seamlessly connects multiple spaces and sets the tone for the home’s refined, yet functional, design. The two-story family room impresses with magnificent ceilings and natural light, while the spacious kitchen was designed to be the true gathering place - anchored by an oversized quartz island with seating and storage, and equipped with a natural gas cooktop, double ovens, and stainless-steel appliances. A mix of white and soft gray cabinetry provides a timeless, modern aesthetic. Adjacent to the kitchen, a built-in desk nook is perfect for remote work or organization, and the spacious mudroom leads to an oversized laundry room with extensive cabinetry, deep sink, and folding counter. The first floor includes a formal dining room and a bedroom with double-doors - ideal for a home office or playroom. A private downstairs guest suite includes its own ensuite bath and walk-in closet. The primary suite, also on the main level, features dual walk-in closets, a garden tub, and a large walk-in shower for a spa-like retreat. Upstairs, a massive bonus room offers versatile space for games, media, or relaxation – plus the dedicated media room, accessed through double doors and featuring a charming rotunda alcove, is perfect for a home theater, reading lounge, or additional office space. Three more bedrooms are located on the second floor, including a private suite and two connected by a jack-and-jill bathroom. Step outside to a serene and private backyard oasis, complete with a screened saltwater pool, portable fire pit, and no rear neighbors - an ideal setting for entertaining or unwinding with the family. Additional features include a split 3-car garage with a generator bypass, offering generous space for storage, hobbies, or recreational gear, along with a freshly painted interior for a move-in-ready feel. Conveniently located in the gated community of Oxford Chase, residents enjoy natural gas, low HOA fees, walking trails, a dog park, and playground - elementary school and middle school kids can walk to top-rated schools (located just outside the gate) and just minutes from Winter Garden Village shopping, major highways and the charm of downtown Winter Garden. Move-in ready. Schedule your private tour today - this truly one-of-a-kind home won’t last long.

14778 Ellingsworth Lane, Winter Garden

$418,000
4 Beds 3 Baths Hamlin Reserve SubDv. 34787 Zip Code
Must See!! This is the one!! Seller is offering $5000.00 credit towards buyer’s closing costs with a full price offer. Beautifully maintained Hamlin Reserve townhome with 4 bedrooms, 3 full bathrooms, 2 car garage and is ready to move-in. You will feel right at home the moment you enter the front door. The pristine condition of this home features newer wood plank-look porcelain tile flooring, designer wood plank accent wall, spacious kitchen with 42" cabinets, quartz countertops, tile backsplash, energy star stainless steel appliances and walk-in pantry. Special touches throughout the home include fresh paint, 5 1/4" baseboards, recessed smart lights, ceiling fans, 1 year old refrigerator, 2 year old washer & dryer, Whole house water filtration system, UV lights in A/C system, newer 2021 air handler motor, and in-wall pest control system. The oversized primary bedroom with private balcony, en-suite bathroom and walk-in closet is on the 2nd floor. 1 bedroom with full bathroom on the first floor and 2 bedrooms and full guest bathroom on the 2nd floor. Enjoy your tranquil private courtyard just outside the living room with a Florida friendly garden. The landscaped front lawn with Florida friendly trees, plants and natural rocks is maintained by the HOA. The HOA fee includes maintenance of the building’s exterior, roof replacement, community pool, clubhouse, playground, dog park, multiple trails and green spaces throughout the community. Location, Location, Location!!! Just steps to the community pool. Conveniently Located in the heart of Horizon West, one of the nation’s fastest growing communities. Just 9 miles from Walt Disney World. A-Rated Schools. A stones throw from Orlando Health Horizon West Hospital, Cinépolis Luxury Cinemas, Orange County Nat’l Golf Center, Horizon West Regional Park, the ever growing Hamlin Town Center with all major shopping, dining, entertainment, miles of lakefront trails, boardwalks, and year-round events. Easy access Hwy 429, I-4 and the FL Turnpike and the upcoming New Independence Parkway extension to Lake County.

15458 Honeybell Drive, Winter Garden

$365,000
3 Beds 3 Baths Signature Lks-Pcl 01a SubDv. 34787 Zip Code
Welcome Home to this beautiful 3-bedroom, 2.5-bathroom townhome located in the highly sought-after Independence community! This neighborhood is known for its world-class amenities and strong community atmosphere! Open the door to a formal dining or sitting room with beautiful wood flooring filled with natural light. The open kitchen includes stainless steel appliances, bar-top seating, and large tile flooring. The living room connects you to your outside private, fenced backyard, perfect for relaxing, grilling out, pets, and easy access to the detached two-car garage. Upstairs, you’ll find wood floors throughout, along with all three spacious bedrooms, two full bathrooms, and a convenient laundry closet. As a end unit, coupled with the park directly across the street the home offers you more green space and privacy. Home has brand new AC (2025), New Water Heater (2025), New Smoke decors (2025), and New water efficient toilets in the the bathrooms (2025). Residents enjoy access to two resort-style pools, two fully equipped fitness centers, tennis and basketball courts, and over six miles of bike and walking trails. Beautiful parks, green spaces, and two private lakes with boat ramps provide serene spots for relaxation and water activities. A dedicated Lifestyle Team organizes exciting community events throughout the year, including seasonal festivals, fireworks displays, and food truck gatherings, fostering a vibrant and connected neighborhood. Situated just minutes from Disney and top Orlando attractions, with easy access to Hwy 429 and the Florida Turnpike, this home offers convenience, entertainment, and a true sense of community. The HOA fee covers high-speed internet, cable, exterior paint, roof replacement when needed, exterior and interior pest control, and landscaping maintenance. A must see!

14433 Vashons Way, Winter Garden

$700,000
5 Beds 4 Baths Avalon Reserve Village 1 SubDv. 34787 Zip Code
PRIME Winter Garden location off Hardwood Marsh and Avalon! It’s not often a home hugs you when you walk through the door, the hint of warmth through the window and the enveloping feeling of home. A true place of stillness that is so hard to find nowadays. The Hawthorne model is really the perfect floor plan! With space for everyone still managing to embody an inviting coziness with over 3,500 sq ft of living space for you, your family…an unexpected guest! A quaint entry with 2 areas for an office, formal living opens up to a 2-story ceiling in the family room with adjacent kitchen! A large island has seating and room for a full size dining table in the breakfast nook! An abundance of windows and sliding glass doors reveal a lovely view of the tropical foliage. Enjoy cooking while watching movies keeping everyone together! The thoughtful design gives ample prep space and tons of cabinet storage! This perfect entertaining area spills into the oversized screened lanai that can be enjoyed year round with an array of fruit trees and a natural privacy from the mature landscape. The primary suite is on the first floor ensuring you can enjoy this home even into your golden years! A relaxing escape with back yard views, ensuite bath with large soaking tub, shower, dual vanities and 2 walk-in closets! Again, storage is not an issue in this home! On the second floor, stairs lead to a huge loft/bonus room that peers over the family room with a half wall that aids in noise reduction. Want a more open feel? Check out Etsy’s decorative railings to personalize your loft! Built-in character ensures many creative ways to utilize the space! This upstairs is “cart wheel” worthy and the options are endless! The bedrooms are spread apart giving every occupant their own area! A centrally located study/art nook even has an opening to the downstairs so you never miss the words "dinner's ready"! This fantastic layout allows you to fulfill your every wish for not only a beautiful, but organized space! No more trying to make things work, because it all fits! They say #1 rule in buying real estate is LOCATION & this community of well manicured lawns ensures your biggest investment is a good one! You can still find that hometown feel you see in movies, with the weekly Farmer's Market in Historic Downtown, soccer and baseball fields bustling on Saturday mornings! Monthly and seasonal events are also abundant and so fun! Pop over to Epic or Disney for the afternoon or enjoy delicacies from around the world at Epcot! All just a short drive from home! The house across the street recently sold for 870k!

1073 Vinsetta Circle, Winter Garden

$575,000
6 Beds 4 Baths Oaks/Brandy Lake O SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. The epitome of luxury just minutes from downtown Winter Garden! You won’t believe your luck with this stunning, large, 6 bedroom, move-in-ready home situated on a premium lot in one of Winter Garden’s most desirable communities! Bursting with high-end upgrades and thoughtful design details, this home redefines luxury and comfort. Step through the custom front door into a meticulously maintained interior featuring new tile flooring throughout the first floor (installed July 2025), fresh interior paint (July 2025), and a brand-new roof (April 2025). The home also boasts exterior paint from 2023, so all the big-ticket items are already done! The primary suite is conveniently located on the first floor, complete with a seamless glass shower, granite surfaces, custom California closets, and tile accents that give it a spa-like feel. The entire home is adorned with designer blinds, custom lighting, fans, and fixtures, and custom interior paint that adds warmth and sophistication. Enjoy open concept living areas that flow seamlessly to an enclosed lanai, perfect for year-round entertaining or relaxing. Both porches are beautifully tiled, and the bricked garden areas enhance the home’s charming curb appeal. Upstairs features a huge bonus loft, ideal for a home theater, game room, or extra office space. Every bedroom, including the pantry and garage, has been upgraded with California closets, offering an abundance of smart storage. Additional features include: • Central vacuum system • Custom showers • New upgraded gutters • Rear garage entry with workbench • Across from the community pool Located just a mile from historic Downtown Winter Garden and the West Orange Trail, and only minutes to Winter Garden Village, this home offers a perfect balance of location, luxury, and lifestyle. Don’t miss this rare opportunity—homes like this don’t come around often at this price!

909 Brandy Oaks Loop, Winter Garden

$500,000
4 Beds 3 Baths Highland Ridge SubDv. 34787 Zip Code
Under Construction. Brand new, energy-efficient home available by Jul 2025! Open first floor boasts a spacious great room and dining area that flow seamlessly together. Upstairs primary suite features an oversized walk-in closet, dual sinks, and a standing shower. Visit the Highland Ridge community and explore new bungalow homes for sale in Winter Garden, FL. This neighborhood offers easy access to major employment centers and great schools. Visit us today and see the benefits of our energy-efficient features that all Meritage Homes are built with.* Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

12023 Bracco Street, Winter Garden

$775,000
5 Beds 5 Baths Lakeside At Hamlin SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to 15148 Lake Bessie Loop, an inviting and spacious home located in the peaceful Lakeside at Hamlin community of Winter Garden. This beautifully cared-for residence offers a perfect blend of comfort, function, and thoughtful upgrades, making it ideal for both everyday living and special moments with family and friends. Step inside to experience an open concept layout filled with natural light and a warm, welcoming feel. The living areas flow effortlessly into a large kitchen featuring a wide open island, abundant cabinetry, under-cabinet lighting (added in 2024), and a custom range hood (installed in 2025), all designed to bring people together. Throughout the home, you’ll find beautiful vinyl plank flooring that enhances the open feel and adds durability. One of the standout features of this home is the spacious upstairs loft, paired with a large bedroom and one and a half bathrooms. The loft and back porch are equipped with built-in speakers, perfect for relaxing evenings, movie nights, or entertaining guests. The main living area also includes an entertainment center with a built-in electric fireplace (installed in 2025), creating a cozy and stylish atmosphere. Outside, the private backyard is set up for enjoyment with an outdoor kitchen and vented hood (installed in 2024), ideal for weekend barbecues or casual get-togethers. Additional updates include shutters and blinds (installed in 2023), a vinyl fence (installed in 2023), gutters (installed in 2023), garage storage racks (installed in 2024), and the home is wired for two electric vehicle chargers (wiring completed in 2023 and 2024), providing added flexibility for future EV needs. Lakeside at Hamlin is a family-friendly community surrounded by walking trails and scenic spaces. It is conveniently located near SR 429 and Avalon Road, with easy access to Horizon West and downtown Winter Garden. The area continues to grow with exciting new restaurants and entertainment options nearby, along with highly rated public and private schools. Whether you are searching for a home that brings together comfort, lifestyle, and location, or you are looking to invest in one of Central Florida’s most desirable areas, 15148 Lake Bessie Loop offers a rare opportunity to enjoy it all.

15148 Lake Bessie Loop, Winter Garden