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2139 Tillman Avenue, Winter Garden
$825,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code
STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a den, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden

16773 Broadwater Avenue, Winter Garden
$2,575,000
7 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury lakefront living in this exceptional 7-bedroom Mansfield floor plan, offered for sale for the first time by its original owner. Perfectly positioned along nearly 100 feet of shoreline on the spectacular 2,600-acre Johns Lake, this remarkable residence offers approximately 6,300 heated square feet of thoughtfully designed living space, breathtaking panoramic water views, and a rare walkout basement ideal for multigenerational living. Impressive curb appeal and a welcoming courtyard entrance set the stage for soaring ceilings, expansive living areas, and unforgettable lake views from the moment you enter. The magnificent great room is flooded with natural Florida sunshine, featuring an electric fireplace and sweeping views of Johns Lake. The recently renovated gourmet kitchen is a showpiece, boasting an oversized center island, freestanding natural gas range, and separate full-size refrigerator and freezer. The main level features a luxurious owner's suite, dedicated home office, and additional ensuite bedroom. Upstairs, an expansive bonus room complements three generously sized bedrooms and two full bathrooms, providing exceptional flexibility for family and guests. What truly distinguishes this extraordinary lakefront estate is the enormous walkout basement, offering endless possibilities for a home theater, fitness center, entertainment lounge, game room, or custom bar. A SECOND OWNER'S SUITE provides an incredible opportunity for an in-law retreat, extended family accommodations, or private multigenerational living quarters. Thoughtful planning by the original owners includes future pool connections, natural gas stub-outs for additional coach lighting, preplumbing and gas connections for an outdoor summer kitchen, and numerous additional ceiling fan locations. Additional enhancements include plantation shutters, custom closets, and a whole-home natural gas backup generator. Step outside to an expansive backyard showcasing breathtaking 180-degree panoramic views of Johns Lake. Your private covered boat dock with low-maintenance composite decking and boat lift creates the ultimate waterfront lifestyle, with boating, fishing, watersports, and sunset cruises right from your backyard. Spanning Orange and Lake counties, Johns Lake is renowned for its expansive open waters, scenic shoreline, and exceptional fishing. Located within the gated community of Waterside on Johns Lake, residents enjoy resort-style amenities including a beautiful clubhouse, state-of-the-art fitness center, community swimming pool, and playground. This highly desirable Clermont and Winter Garden corridor offers access to sought-after K–12 schools & Foundation Academy, Montverde Academy, and Windermere Prep School. Ideally situated along Marsh Road, this exceptional location places you minutes from outstanding shopping, dining, and entertainment in both Clermont and Winter Garden. Enjoy convenient access to Walt Disney World, SR 429, SR 408, Florida's Turnpike, and Downtown Orlando. Historic Downtown Winter Garden is just minutes away, offering charming boutiques, acclaimed restaurants, the West Orange Trail, community festivals, and its famous Saturday Farmers Market. Combining extraordinary square footage, a rare walkout basement, dual owner's suites, private boating access, and nearly 100 feet of pristine Johns Lake frontage, this remarkable property delivers an unparalleled opportunity to embrace the Florida lakefront lifestyle.

16773 Broadwater Avenue, Winter Garden

726 Regina Circle, Oakland
$695,000
5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code
Welcome to 726 Regina Circle in Oakland, Florida! This spacious two-story home offers five bedrooms, four bathrooms, and an inviting layout designed to accommodate a variety of living needs. The interior features vaulted ceilings, a formal dining area, and comfortable living spaces, including a family room with a fireplace. The kitchen offers granite countertops, a breakfast bar, an island, and ample cabinetry, creating a functional space for everyday living and entertaining. The primary suite features an en-suite bathroom with dual vanities and a separate soaking tub and shower. Step outside to enjoy the private swimming pool and outdoor space, ideal for relaxing or entertaining guests. A two-car garage provides additional parking and storage. Conveniently located in the Oakland and Winter Garden area, the property offers access to nearby shopping, dining, parks, trails, and major roadways. Schedule your private showing and discover the possibilities this home has to offer.

726 Regina Circle, Oakland

13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden

15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden

1956 Portcastle Circle, Winter Garden
$429,000
4 Beds ⋅ 3 Baths ⋅ Stone Creek Unit 4 SubDv. ⋅ 34787 Zip Code
Beautifully updated and move-in ready! Welcome to 1956 Portcastle Circle in Winter Garden's Stone Creek community. This bright and inviting two-story home features an open-concept main living area filled with natural light, tile flooring, recessed lighting, and a seamless flow between the kitchen, dining, and living spaces. The newly remodeled kitchen showcases shining cabinetry, light countertops, stainless steel appliances, updated fixtures, and a spacious breakfast bar with sink and dishwasher overlooking the main living area. Sliding glass doors lead directly to the backyard, creating an easy indoor-outdoor connection. Upstairs, brand-new carpet adds warmth and comfort throughout the bedrooms and hallway. The remodeled bathrooms feature fresh contemporary finishes, including updated vanities, fixtures, and elegant marble-look tile. A convenient downstairs powder room, spacious bedrooms, ample closet space, large windows, and a flexible open floor plan further enhance the home's appeal. Major updates also include a NEW ROOF, providing added value and peace of mind. Conveniently located near Winter Garden shopping, dining, entertainment, and major roadways, this beautifully refreshed home combines modern updates, functionality, and an excellent location.

1956 Portcastle Circle, Winter Garden

14807 Winter Stay Drive, Winter Garden
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14807 Winter Stay Drive, a beautifully upgraded luxury residence located in the heart of Horizon West in Winter Garden. Spanning 3,856 square feet of refined living space on an oversized lot, this 5-bedroom, 4-bathroom home combines upscale comfort, privacy, and resort-style living. The outdoor sanctuary is custom-built for the Florida lifestyle, featuring a fully fenced backyard, a heated saltwater pool and spa, a spacious covered lanai with retractable awnings, and scenic sunset views overlooking the prestigious Orange County National Golf Course. Inside, the open-concept layout flows effortlessly for everyday living and grand entertaining. The gourmet kitchen boasts premium appliances, upgraded finishes, and an expansive quartz center island. The primary suite offers a private retreat with a spa-inspired bathroom, complemented by custom closets and a dedicated drop zone for extra organization. Upstairs, a large bonus room provides flexible space for a home theater, media room, or executive office, while an oversized 3-car garage offers generous vehicle and storage space. Value-adding upgrades include an owned solar panel system to significantly reduce energy costs. Situated just 0.5 miles from The Mark Plaza and minutes from Horizon West Hospital, top-rated dining, and shopping, this home offers fast access to SR 429, Florida’s Turnpike, and Walt Disney World. Schedule your private tour today.

14807 Winter Stay Drive, Winter Garden

190 Roper Drive, Winter Garden
$795,000
3 Beds ⋅ 2 Baths ⋅ Westlake Manor 1st Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated, turn-key home located just a 10-minute walk north of Downtown Winter Garden, tucked away in a beautiful established neighborhood with mature surroundings and an oversized 0.34-acre lot. With no HOA, a large fenced yard, and extensive upgrades inside and out, this property offers a rare combination of location, space, and quality. The home features block and slab construction with new stucco and approximately 1,750 square feet under air, including the original 1,500-square-foot footprint plus an additional 250-square-foot enclosed and finished porch. The well-designed floor plan offers 3 bedrooms and 2 bathrooms, along with an oversized interior storage/laundry room and an oversized two-car garage. The exterior has been completely refreshed with new stucco, fresh exterior paint, new vinyl fence, new soffits, updated exterior lighting, a new paver driveway, and a new landscaping package, creating exceptional curb appeal. The expansive lot is fully enclosed by a new vinyl privacy fence with a double gate providing convenient access to the rear yard for large vehicles, trailers, boats, or recreational equipment. A motion-sensor security light adds an additional layer of convenience and security. Roof 2019 and AC 2024. Inside, the renovation continues with new insulation, new ductwork, fresh paint and texture, new baseboards, luxury vinyl plank flooring, new ceiling fans and lighting, and updated door hardware throughout. The bathrooms have been completely redesigned with high-end custom tile work and designer finishes. The kitchen is a standout feature, offering 42-inch cabinetry, new appliances, a counter-depth Frigidaire Gallery refrigerator, slide-in range, and an oversized island finished with a stunning marble waterfall edge that coordinates beautifully with the marble backsplash. Bright, dimmable recessed lighting completes the space and creates an inviting atmosphere for both everyday living and entertaining. Additional features include an oversized storage/laundry room under air and an oversized two-car garage equipped with a new garage door opener and recessed lighting. Every detail has been thoughtfully addressed, creating a home that is truly move-in ready. Four-point, WDO, and wind mitigation reports are available in the MLS for review. With its proximity to Downtown Winter Garden, no HOA, expansive 0.40-acre lot, extensive renovation, and exceptional outdoor space, this is a property that offers the best of convenience, privacy, and modern living.

190 Roper Drive, Winter Garden

24 W Garden Avenue, Winter Garden
$698,800
4 Beds ⋅ 4 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
RARE OPPORTUNITY IN THE HEART OF WINTER GARDEN’S HIGHLY SOUGHT-AFTER GOLF CART DISTRICT! Completely remodeled and move-in ready, this impressive 4-bedroom, 4-bath, single-story home sits on an oversized lot directly across from Tanner Hall, Newton Park and the public boat ramp to Lake Apopka—and best of all, there is NO HOA! Extensive renovations have transformed this home with a beautiful new kitchen ( NATURAL GAS RANGE! ), remodeled bathrooms, new flooring, fresh interior and exterior paint, and updated windows, creating a fresh, modern feel throughout. The roof was replaced in 2017 and the water heater in 2013. The spacious open great room floor plan is ideal for both everyday living and entertaining, while the oversized owner’s suite provides a private retreat. Two additional bedrooms feature true ensuite baths, offering exceptional flexibility for family, guests, multigenerational living or a private home office. Step outside to the huge covered and screened rear patio overlooking the expansive backyard with plenty of room to relax, entertain and enjoy the Florida lifestyle. The location is truly hard to beat. Walk across the street to Newton Park, Tanner Hall, the Lake Apopka fishing pier and public boat launch, or hop in your golf cart for a short ride to historic Downtown Winter Garden and everything Plant Street has to offer. Enjoy an incredible collection of restaurants, breweries, coffee shops, boutiques and entertainment, along with year-round festivals, community events and the famous Saturday Winter Garden Farmers Market. Outdoor enthusiasts will love being just a quick bike ride from the popular West Orange Trail and minutes from Lake Apopka. Located in a sought-after K-12 school district with convenient access to SR 429, this location provides an outstanding combination of small-town charm, recreation and accessibility to the greater Orlando area. With four bedrooms, four full baths, extensive renovations, an oversized lot, NO HOA and an exceptional location in the Downtown Winter Garden golf cart district, opportunities like this are increasingly difficult to find. Exceptional value, incredible lifestyle and truly move-in ready—this one is PRICED TO SELL!

24 W Garden Avenue, Winter Garden

12349 Westfield Lakes Circle, Winter Garden
$729,000
5 Beds ⋅ 3 Baths ⋅ Westfield Lakes Ph 04 A-F SubDv. ⋅ 34787 Zip Code
Welcome to Westfield Lakes, a charming community nestled along the shores of Lake Beulah in desirable Winter Garden! This beautifully maintained custom built Morrison Home offers 5 bedrooms, 3 full baths, a 3-way split bedroom floor plan. The thoughtful floor plan includes a private bedroom and full bath separated from both the primary suite and additional bedrooms, making it ideal for guests, extended family, or an in-law suite. The home is on an oversized lot with no rear neighbors. From the moment you step inside, you'll appreciate the soaring 12-foot ceilings, abundant natural light, crown molding, and thoughtful design throughout. The spacious kitchen features 42-inch cabinetry, rich granite countertops, upgraded appliances, and plenty of room to gather with family and friends. The open family room is pre-wired for surround sound and overlooks the extended covered lanai and private backyard, creating an ideal space for entertaining or simply enjoying the peaceful Florida lifestyle. The oversized lot offers plenty of room to add a pool. The private primary suite is thoughtfully separated from the additional bedrooms and features a tray ceiling, direct access to the covered lanai, dual vanities, a large garden tub, and a separate fully tiled shower and a custom closet with built ins, which add both functionality and a custom feel. The fifth bedroom offers flexibility as a home office, den, or guest space. Additional features include 18-inch tile flooring, a spacious 3 car garage with epoxy flooring, brick paver driveway, brick privacy fencing, professional landscape edging, and a recently painted exterior. Major updates provide added peace of mind with a NEW ROOF in February 2026, NEW WATER HEATER and NEW A/C October 2026, plus the freshly painted exterior Sept 2026. Westfield Lakes offers residents a beautiful neighborhood park, tennis courts, and a fishing pier along Lake Beulah. Ideally located near West Orange High School, Roper YMCA Family Center, Winter Garden Village, historic Downtown Winter Garden, dining, shopping, entertainment, dog parks, the West Orange Trail, and major roadways including the 429, Turnpike, and 408. This is more than a home, it's an opportunity to enjoy the space, privacy, and lifestyle that make Westfield Lakes such a special place to call home. Come see it for yourself!

12349 Westfield Lakes Circle, Winter Garden

8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
TURNKEY Florida second home. Seasonal residence. Lock-and-leave lifestyle. This home is designed for true indoor-outdoor living, with comfort, entertaining and everyday ease extending from the interior to the outdoor living spaces. Three wall-mounted televisions—in the great room, screened lanai and upstairs loft—are included with the home. Expansive open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open green space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer introduces the interior. Key design features include shiplap wall detailing, wood-beam ceilings in the great room and primary suite, and plantation shutters throughout. The chef’s kitchen features a massive center island, farmhouse sink and abundant cabinetry. Triple sliding glass doors connect the great room to an expansive screened lanai with a fully equipped built-in summer kitchen, including a beverage refrigerator and grill, outdoor dining for six and a dedicated sofa and lounge area. Motorized retractable screens make the space easy to open or enclose. An outdoor putting green and built-in stone fireplace complete the backyard setting. For seasonal owners coming to Florida for the winter months, the lifestyle extends beyond the home. The resort-style community pool overlooks the lakes and includes its own fire-pit area, with the clubhouse and fitness center nearby. Lake views from the pool and fitness center create a serene setting for enjoying the Florida season. The first-floor primary suite is quietly positioned at the rear of the home. A wood-beam ceiling adds architectural character, while the primary bath is finished extensively in custom tile. Opposing vanities give each person dedicated space, complemented by a private water closet and an oversized walk-in shower with opposing shower systems, multiple shower heads and built-in bench seating. Custom tile extends from the floor through the shower walls. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes an en-suite bath and full closet, while the other two share a hall bath. When not occupied by guests, the second living room works naturally as a private lounge, media room or office. Turnkey includes living-area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds and sand volleyball court. Cable, one-gig internet and grounds maintenance are included in the HOA fee. This Toll Brothers former model home occupies an especially open homesite within Lakeshore Preserve, combining green-space exposure, natural light and added privacy with extensive builder upgrades and a fully realized transitional interior design.

8836 Lakeshore Pointe Drive, Winter Garden

23 Zachary Wade Street, Winter Garden
$512,000
4 Beds ⋅ 2 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Lakeview Reserve welcomes you HOME! Set on a spacious .23 ACRE LOT with NO REAR NEIGHBORS, this single story 4-bedroom, 2-bath home offers an inviting combination of space, updates and classic Winter Garden charm! Recent improvements include a NEW WATER HEATER (2024), NEW COUNTERTOPS (2024), FRESH PAINT (2024) and NEW FLOORING (2024) throughout much of the home, plus a NEWER ROOF (2021) and UPDATED A/C (2018). Mature landscaping and tree-lined streets create beautiful curb appeal, while HIGH CEILINGS and plenty of natural light make the interior feel open and bright. The thoughtful SPLIT-BEDROOM FLOOR PLAN features both formal and casual living spaces, giving you flexibility for everyday living and entertaining. The PRIMARY SUITE enjoys its own private wing, and both bathrooms offer convenient access to the generous SCREENED LANAI. At the heart of the home, the kitchen features updated countertops and is ready for your personal touch. Step outside to a spacious backyard with no rear neighbors and a large screened lanai that extends the living space outdoors – ideal INDOOR/OUTDOOR LIVING! Lakeview Reserve is an established GATED COMMUNITY with a LOW HOA and a COMMUNITY DOCK ON LAKE APOPKA. You will enjoy cruising around the GOLF CART DISTRICT, and easy access to HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, local shopping, dining and recreation. Zoned for TOP-RATED SCHOOLS – Tildenville Elementary, Lakeview Middle and West Orange High, with convenient access to SR 50 and the Florida Turnpike. With a versatile layout, two car garage and a fantastic location close to everything Winter Garden has to offer, this home is ready for its next chapter. Call today and make it your next chapter as well!

23 Zachary Wade Street, Winter Garden

1809 Delafield Drive, Winter Garden
$735,000
4 Beds ⋅ 3 Baths ⋅ Emerald Ridge SubDv. ⋅ 34787 Zip Code
LUXURIOUS, RENOVATED & RESORT-STYLE LIVING IN WINTER GARDEN! Welcome home to 1809 Delafield Dr., an impressive 4-bedroom, 2.5-bath home offering approximately 3,605 square feet of beautifully designed living space. Location is everything! Enjoy the convenience of Winter Garden with easy access to shopping, restaurants, entertainment, major highways, Disney, and Central Florida’s most popular attractions. Downtown Winter Garden and Winter Garden Village are just part of what makes this area such a desirable place to live. Inside, the spacious open-concept floor plan offers multiple living and dining areas, creating the perfect setting for everyday living and entertaining. Beautiful laminate flooring runs throughout the home, while the completely renovated kitchen features stunning natural stone countertops, real wood cabinetry, and a spacious layout that flows seamlessly into the living areas.

1809 Delafield Drive, Winter Garden

5074 Breezy Acres Street, Winter Garden
$1,159,900
7 Beds ⋅ 5 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional expression of modern luxury in Winter Garden’s highly sought-after Wincey Groves community. Crafted by Dream Finders Homes, this impressive 2021 Sweetwater residence offers more than 4,700 square feet of beautifully appointed living space, with 7 bedrooms, 4.5 baths, and two additional flex rooms that provide the extraordinary potential to create a 9-bedroom estate. Designed for those who value both refined living and remarkable versatility, this move-in-ready residence offers an unparalleled combination of scale, sophistication, and functionality in one of Central Florida’s most desirable destinations. A striking enhanced elevation, extended driveway, and welcoming front porch create an impressive first impression. Beyond the entry, an abundance of natural light illuminates the open-concept interior, where soaring ceilings, 9-foot doors, upgraded engineered hardwood flooring, and expansive sliding glass doors create a seamless sense of space and connection. Thoughtful design details throughout the residence create an atmosphere that is simultaneously elegant, comfortable, and effortlessly livable. The main-level primary suite is a private sanctuary, enhanced by additional windows that bathe the room in natural light. The spa-inspired en-suite bath delivers a luxurious retreat with an oversized soaking tub designed for two, an upgraded glass-enclosed shower, and beautifully selected finishes. Also on the main level, a private office provides an ideal setting for remote work, while a sophisticated half bath serves guests. A third garage bay has been thoughtfully converted into a fully equipped home gym, offering a dedicated space for fitness and wellness. At the center of the home, the gourmet kitchen is designed to be both a showpiece and a gathering place. An oversized island anchors the space, complemented by sleek quartz countertops, wrap-around cabinetry, double ovens, built-in microwave, farmhouse sink, under-cabinet lighting, and exceptional storage. Whether hosting an elegant dinner party or enjoying a quiet morning at home, this kitchen is perfectly suited to every occasion. Upstairs, generously proportioned bedrooms are paired with expansive walk-in closets and a convenient Jack-and-Jill bath. The home’s entertainment offerings are equally impressive, with a dedicated theater and game room creating an elevated destination for movie nights, gaming, and unforgettable gatherings. Two additional flex rooms offer exceptional adaptability, with endless possibilities for guest suites, creative spaces, study areas, multi-generational living, or additional work-from-home accommodations. Modern conveniences further enhance the residence, including smart-home technology, fiber-optic internet, a fully hardwired security system with cameras, and dual AC units for year-round comfort. Front and rear covered porches extend the living experience outdoors, overlooking a private, fenced backyard that provides an inviting setting for entertaining, relaxing, and enjoying Florida’s year-round lifestyle. Ideally located near top-rated schools, scenic parks, and the vibrant Hamlin Town Center, residents enjoy convenient access to premier shopping, dining, entertainment, and everyday amenities. More than a residence, this is a lifestyle defined by space, sophistication, versatility, and opportunity. Experience the exceptional firsthand with a private showing.

5074 Breezy Acres Street, Winter Garden

330 Lake Amberleigh Drive, Winter Garden
$509,900
4 Beds ⋅ 2 Baths ⋅ Amberleigh 47/7 SubDv. ⋅ 34787 Zip Code
Virtually Staged. One owner. Twenty-four years. A floor plan that still works exactly as intended. Behind the gates of Amberleigh, an enclave of just 65 residences, 330 Lake Amberleigh Drive lays out four bedrooms and two baths across 2,138 square feet, all on a single level. Block construction, a roof and HVAC both replaced in 2017, and a seller-paid 12-month warranty answer the big-ticket questions before you ask them. The two-car garage is finished, and the 7,840-square-foot lot leaves room to garden, grill, or simply spread out. Start the morning on the West Orange Trail. End the evening on Plant Street, where downtown Winter Garden's farmers market, breweries, and restaurants are minutes away. Zoned for Maxey Elementary, SunRidge Middle, and West Orange High per OCPS 2026-27; buyer to verify. The first chapter here lasted more than two decades. The next one is yours to write.

330 Lake Amberleigh Drive, Winter Garden

1118 Maidenmoor Road, Winter Garden
$460,000
4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

5506 New Independence Parkway, Winter Garden
$629,000
5 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 5506 New Independence Pkwy, offering a flexible floor plan with 5 bedrooms, 3.5 bathrooms, and a dedicated office in the highly sought-after Independence community of Winter Garden. Step inside to a bright, refreshed interior featuring a renovated kitchen with white cabinetry, quartz countertops, an oversized island with seating, stainless steel appliances, and updated finishes. New luxury vinyl plank flooring adds a fresh, modern look throughout the primary and upstairs living areas, while tile flooring provides durability in the main living spaces. The versatile layout offers plenty of room to live, work, and entertain. The dedicated office provides a separate workspace, while the 5th bedroom upstairs can easily be converted back into an open loft to fit your needs. The primary suite features a spacious bath with dual sinks, granite countertops, a soaking tub, and separate shower. Outside, enjoy a covered rear patio, fenced backyard, and plenty of space to create your own outdoor retreat, including the potential to add a pool. A rear-entry garage and welcoming front porch complete the home. Located in Winter Garden's popular Independence community, this home combines flexible living space, thoughtful updates, and a backyard ready for your vision. Schedule your private showing today and see everything 5506 New Independence Pkwy has to offer!

5506 New Independence Parkway, Winter Garden

502 Palm Drive, Winter Garden
$699,700
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Experience the PERFECT blend of comfort, charm, and functionality in this UNIQUE Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story LOFT and a versatile 4th bedroom with its own half bath—perfect for guests, a MEDIA room, or FLEXIBLE living space. The thoughtfully designed first floor features a private primary suite with an ensuite bath, two additional bedrooms sharing a full bath, a spacious & inviting FAMILY room, and a beautifully appointed kitchen that truly serves as the heart of the home. Kitchen features include built-ins and French doors that open to a gorgeous deck, creating an ideal setting for indoor/outdoor entertaining. A formal dining room and PRIVATE office with French doors provide additional space and convenience. Step outside to enjoy peaceful outdoor living in the EXCEPTIONAL oversized landscaped backyard, complete with a private patio/deck perfect for relaxing or entertaining. A 3-car GARAGE plus a dedicated GOLF CART garage adds exceptional convenience and storage. Located in highly sought-after Downtown Winter Garden, this home is close to top-rated schools, shopping, parks, West Orange Trail, and popular dining destinations. Enjoy the unique lifestyle of a golf-cart-friendly downtown district while being just minutes from everything you need. ON-SITE Generator for Hurricane season (AS/IS) w/sale. Recent updates include a New Roof (2020), New hot water tank (2026), New mini-split for 2nd floor (2026), A/C Main (2023), and fresh interior paint (2026) New Luxury vinyl in Office, 2nd & 3rd Bedrooms. (2026) Buyers....Come discover all this wonderful home has to offer and make it yours!

502 Palm Drive, Winter Garden

8001 Pond Apple Drive, Winter Garden
$688,800
5 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
You will not find a better buy in Winter Garden.. new improved price for one lucky buyer...FIRST TIME EVER OFFERED FOR SALE BY THE ORIGINAL OWNER! FORMER MODEL HOME TOO ! This exceptional five-bedroom, three-bath residence with a dedicated office, expansive bonus room and three-car tandem garage is ideally positioned on an oversized corner lot of more than one-quarter acre, directly across from the community’s spectacular resort-style clubhouse and amenities. From the covered front porch, enjoy tranquil views of the large community pond, or retreat to the private backyard and unwind beside the fire under the stars. Thoughtfully designed for both everyday living and entertaining, the first floor features a private bedroom and full bath, an elegant formal dining room, a well-appointed kitchen with generous cabinetry and workspace, and an open-concept great room that creates an inviting central gathering space. A dedicated office tucked off the main living area provides the perfect space for working from home, studying or a quiet retreat. Upstairs, an impressive oversized bonus room provides incredible flexibility for a media room, game room, home gym or additional living space. The spacious primary suite offers a peaceful retreat with a luxurious garden bath, large walk-in shower, dual vanities and two walk-in closets. Convenient direct access from the primary suite to the laundry room is an exceptional feature that adds functionality to everyday living. Three additional oversized secondary bedrooms provide plenty of space for family and guests. The home’s location within the community is truly special. Step across the street to enjoy the resort-style clubhouse, sparkling community pool, tennis and basketball courts, fitness center and even a zip line, all beautifully situated overlooking a pristine pond. The HOA fee also includes lawn care, adding both convenience and value. Beyond the community, the location is equally impressive, with easy access to the 429 expressway, Hamlin’s popular shopping, dining and entertainment district and Walt Disney World Resort. An abundance of additional shopping and dining destinations are just minutes away in every direction. Families will appreciate the highly sought-after K-12 school options, along with convenient proximity to Windermere Preparatory School and Foundation Academy campuses. Rarely does a home combine an oversized corner lot, exceptional floor plan, direct proximity to resort-style amenities, beautiful pond views and first-time-ever ownership history. This is a special opportunity to make an outstanding Central Florida home your own.

8001 Pond Apple Drive, Winter Garden

13360 Sunny Retreat Lane, Winter Garden
$595,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden

301 Valencia Court, Winter Garden
$665,000
4 Beds ⋅ 3 Baths ⋅ Valencia Shores SubDv. ⋅ 34787 Zip Code
Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large, beautifully landscaped lot with mature trees and established landscaping in desirable Winter Garden. This inviting home offers a comfortable and functional floor plan with plenty of space for everyday living, entertaining and hosting family and friends. Inside a beautiful stone fireplace creates a warm and inviting focal point, while the interior laundry room adds everyday convenience. Step outside to enjoy the spacious backyard, with plenty of room to add a pool, creating the opportunity to design your own private Florida retreat. One of the property’s standout features is its location within the Winter Garden golf cart district, allowing you to enjoy the sought after golf cart lifestyle. Take a golf cart ride toward historic downtown Winter Garden and enjoy its popular restaurants, shops, Farmers market, entertainment, community events and small town charm.Numerous updates have been made to the home to include a new roof in 2021, A/C 2020, master bathroom,guest bathroom remodel in 2023 and Kitchen 2017.

301 Valencia Court, Winter Garden

2202 Redmark Lane, Winter Garden
$810,000
5 Beds ⋅ 4 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code
Welcome to a home where thoughtful design, custom details, and relaxed Florida living come together. Located in a gated Winter Garden community, this 5-bedroom, 3.5-bath residence offers generous space for everyday living and entertaining, including a private office, formal dining room, spacious living room, great room, and versatile upstairs bonus room. The first-floor primary suite provides privacy and convenience, while an interior laundry room with a utility sink adds everyday functionality. This home has been maintained as a smoke-free, pet-free residence. At the heart of the home, the great room opens seamlessly to an expansive kitchen with generous storage and a welcoming eat-in area. Custom built-ins, a stone-surround electric fireplace, and ceiling speakers make the great room an inviting place to gather or unwind. Crown molding, upgraded lighting, Pottery Barn curtain rods, and plentiful closet space reflect the attention to detail throughout. Fresh interior paint enhances the move-in-ready appeal, while custom office cabinetry creates a beautiful and functional workspace. An upgraded wrought-iron staircase adds architectural character and leads upstairs, where the flexible bonus room offers space for a media room, playroom, fitness area, or additional living room. Sliding glass doors open to a screened outdoor retreat featuring a covered lanai and sparkling saltwater pool with a sheer-fall water feature. Enjoy leisurely Florida afternoons, sunset views, and evenings spent entertaining. The outdoor living area is pre-wired for television and equipped for speaker connectivity, making it easy to personalize your gathering space. Recent updates include a new HVAC system installed in January 2026 with a damper system and remotely controlled thermostat, a water heater installed in 2024, and fresh exterior paint completed in 2026. A spacious three-car garage with an additional storage closet beneath the stairs, an elegant paver driveway, and a transferable Massey termite bond further enhance the home’s appeal. Community amenities include a playground, tennis and pickleball courts, soccer field, and picnic area. Ideally located for enjoying Walt Disney World and other Central Florida attractions, this home also offers access to top-rated schools and Winter Garden’s dining, shopping, entertainment, and recreation. Convenient access to State Road 429, Florida’s Turnpike, and State Road 535 makes traveling throughout Central Florida easy. Orlando International Airport is approximately 33 miles away.

2202 Redmark Lane, Winter Garden

2157 Wintermere Pointe Drive, Winter Garden
$765,000
5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated residence offering an additional den, approximately 3,197 square feet of comfortable living space, and a two-car garage. Set on an oversized 0.29-acre lot in the gated Wintermere Pointe community, this home blends generous living areas with thoughtful, contemporary upgrades. Inside, you’re greeted by a bright, open layout finished with fresh neutral colors, crown molding, updated lighting, and attractive flooring throughout the main living areas. The floor plan provides multiple spaces for entertaining, dining, working from home, or simply relaxing. The completely redesigned kitchen serves as the heart of the home, featuring:Extensive shaker-style cabinetry, Dramatic stone countertops, Classic subway-tile backsplash, Under-cabinet lighting, Stainless-steel appliances, Double wall ovens, Contemporary range hood, Oversized waterfall island with abundant workspace and storage, built-in window seat with additional cabinetry, Separate beverage area with wine storage and beverage refrigerators. The kitchen opens naturally to the expansive living and dining areas, creating an inviting atmosphere for everyday living and gatherings. Large windows and sliding glass doors bring in natural light and offer easy access to the outdoor living space and spacious backyard. The first-floor den provides a versatile area that can serve as a home office, study, media room, or guest retreat. With five bedrooms and four bathrooms, the home offers comfortable accommodations and a layout designed for both privacy and flexibility. The upstairs layout includes a spacious bonus area that can easily be converted into a movie theater room. With existing built-in cabinetry and space for a refrigerator or beverage center, it’s an ideal setup for a private entertainment space, gaming room, or family media lounge. This home is located in one of Winter Garden’s highly regarded school zones, serving: Lake Whitney Elementary School, SunRidge Middle School, West Orange High School. Families appreciate the strong academic reputation and convenient proximity to these schools. This area is Prime Winter Garden Location. Just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways—including SR 429, Florida’s Turnpike, and SR 408—this move-in-ready home offers space, style, and accessibility in one of Winter Garden’s established gated communities. Schedule Your Private Showing Come experience the comfort, upgrades, and welcoming atmosphere of this beautifully updated Winter Garden home.

2157 Wintermere Pointe Drive, Winter Garden

2027 Rickover Place, Winter Garden
$729,000
5 Beds ⋅ 4 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code
Welcome to 2027 Rickover Place, located in the highly desirable gated community of Bronson’s Landing in Winter Garden! This beautiful home offers a spacious and versatile floor plan designed for both comfortable everyday living and entertaining. The home features split living spaces, providing flexibility and plenty of room to spread out. Upstairs, you'll find a spacious loft that can easily be transformed into a home office, media room, game room, playroom, or additional living area—the possibilities are endless. A three-car garage provides ample space for vehicles, storage, or hobbies. Bronson’s Landing offers an inviting, well-maintained neighborhood setting with a welcoming community atmosphere, creating a wonderful place to enjoy all that Winter Garden has to offer. Enjoy the convenience of being just minutes from Winter Garden Village, with an abundance of shopping, dining, and entertainment nearby. Easy access to SR-429 makes traveling throughout Central Florida convenient, while the home’s location near area schools adds to its appeal. With its gated community, flexible living spaces, three-car garage, and fantastic Winter Garden location, this home has so much to offer. Schedule your private showing today!

2027 Rickover Place, Winter Garden

2549 Balforn Tower Way, Winter Garden
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden

368 N Boyd Street, Winter Garden
$774,900
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Add 02 SubDv. ⋅ 34787 Zip Code
Exciting news for potential buyers! We've just reduced the listing price significantly and we're offering $10,000 in closing cost assistance or a rate buydown, your choice! This is a fantastic opportunity to make Winter Garden even more affordable! This Downtown Winter Garden stunner has continued to evolve with thoughtful, high-value upgrades that make it even more exceptional today. Located in the much sought after golf cart district and just steps from Plant Street’s restaurants, markets, and year-round events, this home blends timeless character with modern convenience in a way few properties can match. Originally reimagined with a full professional remodel in 2023 — including brand-new roof, windows, electrical, plumbing, insulation, luxury vinyl plank flooring, Bosch appliances, Carrara quartz surfaces, and a magnificent, redesigned kitchen. Additional upgrades include a newly constructed one-car garage with parking pad - 2026 and a whole-home generator providing both functionality and peace of mind rarely found in homes of this era. These additions compliment the already impressive split-floorplan featuring 4 bedrooms (and bonus room), 2.5 baths, an oversized island kitchen with fireplace feature wall, gallery-style windows, and a private primary suite with walk-in closet. Every inch of this home reflects quality, style, and intention — from the high-grade materials used throughout to the continued improvements that elevate daily living. Homes like this, with extensive permitted renovations and meaningful new upgrades, simply do not come to market often in Winter Garden. Homes this special in the heart of Winter Garden are rarely available for long — claim it before it’s gone.

368 N Boyd Street, Winter Garden

426 Duff Drive, Winter Garden
$790,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
***SELLER AGREES TO PAY UP TO $10,000 TOWARDS BUYER'S CLOSING COSTS WITH ACCEPTABLE OFFER***Some rooms virtually staged***Welcome to this award winning model, move-in-ready San Remo V floor plan by MI Homes, located in the highly desirable gated community of Glynwood in Winter Garden. Lovingly maintained by its original owners, this exceptional residence offers 4 bedrooms, 4 bathrooms, a private office with a coat closet for a 5th bedroom option and bonus room. From the moment you step inside, you'll appreciate the soaring vaulted and coffered ceilings, elegant 8-foot doors, neutral designer finishes, plantation shutters, and beautiful architectural details throughout. As you enter the grand foyer, you'll be welcomed by soaring ceilings and beautifully appointed wall sconces and accent lighting above, that create a warm and sophisticated first impression. The foyer takes you to a formal living room, while the private office features custom built-in shelving and warm luxury vinyl. The formal dining room, accented with crown molding flows seamlessly into the spacious family room. The gourmet kitchen, showcasing 42-inch cabinetry with crown molding and hardware, Cambria quartz countertops, a glass tile backsplash, center island, double ovens, a cooktop, breakfast bar, and a pantry with custom pullouts. Overlooking the breakfast nook and family room, the kitchen offers views of the backyard through a miter window and sliding glass doors that open up to the covered lanai. The first-floor owner's suite is a luxurious retreat with a tray ceiling, crown molding, two walk-in custom shelving closets, with dual vanities, a corner soaking tub, an oversized tiled walk-in shower, and a private water closet. Also on the main level are two generously sized guest bedrooms, one with it's own bathroom that serves as a pool bath for a beautiful pool in the future:-) Upstairs, you'll find an expansive bonus room, a fourth bedroom, a full bathroom and an air-conditioned storage room provides valuable additional space. This home has had many improvements since original purchase, including, ROOF (12/2019), downstairs HVAC system 8/2017; inside and outside unit, New interior and exterior paint(Exterior painted 3/2026), new luxury carpet 5/2025, two front rooms with new luxury COREtec LVP 3/2026, New GE Profile cooktop and GE Profile microwave 12/2025, newer GE Profile refrigerator and Bosch dishwasher, New garage door opener, with new springs and brackets 3/2025, New gutters 10/25. Updated fans and light fixtures throughout, updated kitchen with professionally painted cabinets, high-end Cambia quartz countertops, with a converted single level island & pull-out drawers in lower cabinets and custom system in pantry. Backyard can accommodate a huge pool and outdoor living space. The oversized garage has an additional 3.5ft on each side and the driveway has been widened for another parking space. Residents enjoy access to great community amenities, including a resort-style pool, clubhouse, playground, tennis & pickleball courts, and scenic walking trails. Ideally located just minutes from Winter Garden Village, historic Winter Garden, Hamlin/Horizon West, world-famous theme parks, shopping, dining, and entertainment, this exceptional home offers the perfect blend of luxury, comfort, and convenience. Super convenient access to the 429 and turnpike as well. Please look at the video!

426 Duff Drive, Winter Garden

9572 Waterway Passage Drive, Winter Garden
$840,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Why wait for new construction when you can have the Florida lifestyle you want—already completed, upgraded, and ready to enjoy? Recent appraisal completed in 10/2026 valued the property at current asking price. Welcome to 9572 Waterway Passage, a beautifully upgraded D.R. Horton Cresswell in highly sought-after Waterleigh in Winter Garden. If you're considering new construction, this home offers something a brand-new build simply can't: a move-in-ready home with thousands of dollars in thoughtful improvements already completed and an outdoor living experience designed to be enjoyed from day one. Inside, you'll immediately notice the difference. Laminate flooring extends throughout the main living areas for a clean, modern look, while a dramatic geometric accent wall adds designer style to the loft and staircase. The spacious primary suite has been elevated into a true retreat with a fully customized walk-in closet and beautifully renovated en-suite bathroom. The guest bathroom has also been tastefully updated with contemporary finishes. But the real wow factor is outside. Step into your own private Florida oasis, complete with a sparkling pool and spa, fully equipped outdoor kitchen, built-in Bluetooth speakers, privacy landscaping and low-maintenance artificial turf. Permanent exterior lighting creates an inviting ambiance and showcases the home beautifully day and night. This isn't an outdoor space you'll have to imagine someday—it is already finished and ready for pool days, backyard gatherings and relaxing Florida evenings. And there's even more value where it matters: owned solar panels provide the potential for improved energy efficiency and reduced utility costs. For buyers comparing this home with new construction, consider what you're getting here: no waiting for construction to finish, no starting from scratch with landscaping and outdoor improvements, and no need to spend years adding the upgrades that make a house feel truly special. The major transformation has already been done for you. And you still get the Waterleigh lifestyle you've been looking for, with resort-style amenities, recreation, shopping, dining, entertainment and convenient access to major roadways—all in one of Winter Garden's most desirable communities. New construction gives you a blank canvas. This home gives you the finished vision. Beautifully upgraded. Fully equipped for entertaining. Designed for Florida living. 9572 Waterway Passage is the opportunity to stop waiting for the home you want and start enjoying it now. Schedule your private showing today and see why this may be the smarter alternative to starting over with new construction.

9572 Waterway Passage Drive, Winter Garden

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