Location: Winter Garden
Do Not Show Listings
16217 LAKE JOHNS CIR, WINTER GARDEN, FL 34787
$1,200,00030 Days on yellowkey MLS ID: O6409098
1 Days Off yellowkey (back on 5/29/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4659 Built: 1973 Tax: $3,817 (2025)Community: Lake Johns ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,817
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 16217 Lake Johns Circle is a rare modern farmhouse retreat where luxury, craftsmanship, and family-centered design come together in extraordinary fashion. Positioned on a quiet cul-de-sac of only 15 homes with no HOA, this fully reimagined Winter Garden residence offers front-porch views toward Johns Lake and backs to protected green space, creating a setting that feels private, peaceful, and deeply connected to nature. Completed in 2025, the home underwent an extensive renovation and expansion with remarkable attention to detail and quality. Unlike typical luxury renovations, much of the craftsmanship was personally completed by the homeowners themselves-resulting in a residence that feels intentionally built rather than simply remodeled. Inside, the home unfolds with warm modern farmhouse design, engineered hardwood flooring throughout, soaring ceilings, custom millwork, curated lighting, and expansive gathering spaces designed for both everyday living and elevated entertaining. The chef's kitchen serves as the architectural centerpiece of the home, featuring professional-grade appliances, custom cabinetry, quartz surfaces, a hidden butler's pantry, beverage station, and an oversized gathering island wrapped in authentic character and texture. The floorplan was thoughtfully designed to accommodate multigenerational living and large gatherings with uncommon flexibility. Unique design moments include custom built-in bunk spaces, a secondary bedroom designed with three built-in beds, and a truly exceptional owner's retreat featuring vaulted ceilings, a private sitting area, spa-inspired bath, oversized custom closet room, and peaceful views toward Johns Lake. The upstairs loft creates an additional lifestyle space ideal for media, gaming, reading, or relaxation, while the nearly 1,500-square-foot insulated garage/workshop offers incredible versatility for vehicles, boats, hobbies, fitness, or storage. Major infrastructure improvements completed in 2025 include a new roof, new HVAC systems, new windows, new plumbing, tankless water heater, septic system, and extensive mechanical upgrades. Located minutes from Downtown Winter Garden, Oakland, the West Orange Trail, and major roadways, this is a rare opportunity to own a highly customized modern farmhouse retreat in one of Central Florida's most desirable lifestyle corridors.
Listing is courtesy of: HOMEFIRST REAL ESTATE (689-340-3007)
Listing Agent: Ed Vasquez (689-340-3007)
18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787
$724,900102 Days on yellowkey MLS ID: O6388830
0 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2924 Built: 2024Monthly Fee: $280 Tax: $10,366 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$10,366
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2024
Remarks: **POND VIEW 4-BEDROOM IN WATERLEIGH!** Don’t miss this opportunity to own a spacious 4-bedroom, 3-bath home with nearly 3,000 sq ft in one of Winter Garden’s most sought-after communities, now aggressively priced to sell quickly. Situated on a premium **pond-view lot with no rear neighbors**, this home offers peaceful water views and added privacy. The open-concept layout provides generous living space, a large kitchen ideal for entertaining, and flexibility for everyday living. Why wait months and pay more for new construction? This home is **move-in ready now** no delays, no added upgrade costs, and priced below comparable homes in the area, making it one of the **best values in Waterleigh**. Nearly 3,000 sq ft; 4 bedrooms / 3 full bathrooms; Pond view with no rear neighbors; Open-concept layout with spacious living areas; Located in amenity-rich Waterleigh **Seller is motivated. Bring all offers.** LEASE WILL BE CONSIDERED. Opportunities like this don’t last. Schedule your showing today.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Linda Morgan (404-625-5256)
9508 QUIET LN, WINTER GARDEN, FL 34787
$1,400,00029 Days on yellowkey MLS ID: O6408432
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3728 Built: 2001Monthly Fee: $17 Tax: $9,906 (2026)Community: Valley ViewSpa: YesSingle Family
Taxes:$9,906
Elementary School: Lost Lake Elem
High School: East Ridge High
Tax Year: 2026
Middle School: Windy Hill Middle
Remarks: Virtually Staged. Rare opportunity in Winter Garden's coveted Lake Avalon: a fully fenced and gated 5-acre mini-ranch in the Valley View enclave, where genuine Lake Avalon water and conservation views meet true rural freedom — bring your horses, livestock, or recreational vehicles — just minutes from Hamlin Town Center, Walt Disney World, and SR-429. Spanning nearly 3,800 SF, this thoughtfully expanded 5BR/4BA estate includes a substantial permitted addition that created an ideal wing for multi-generational living or large-scale entertaining. At its center is a redesigned custom kitchen with imported Italian cabinetry, waterfall-edge countertops, premium Thermador appliances, and a built-in Dacor smart refrigerator. A separate enclosed prep kitchen with additional appliances and laundry hookups adds rare day-to-day functionality. The layout offers dual primary suites, formal and casual living spaces, oversized tile flooring, modern LED lighting, and remodeled baths — openness and privacy as you need them. Major systems deliver long-term peace of mind: a NEW ROOF (2022) NEW HVAC (2022), an 80-gallon commercial water heater (2022), a whole-home water softener, and a 24KW whole-house standby generator with transfer switch for full backup power. Zoning flexibility, sunset and lake views, and no cookie-cutter HOA rules — one of the last true large-lot enclaves this close to Winter Garden's growth corridor. Schedule your private tour today.
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Jared Jones, Pa (407-906-5000)
611 SIGLER DR, WINTER GARDEN, FL 34787
$899,7609 Days on yellowkey MLS ID: O6415005
Bed: 4 Bath: 3.5 Gar: 22 Liv Area Sq Ft: 2432 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
Taxes:$993
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Maple floor plan, offering 4 bedrooms, 3.5 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Tatiana Souza (407-467-9914)
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$550,000322 Days on yellowkey MLS ID: A4660262
REDUCED by $25,000 (4.3%) on 06/12/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2571 Built: 2020Monthly Fee: $102 Tax: $8,702 (2024)Community: Winding Bay Ph 1BSingle Family
Taxes:$8,702
Remarks: 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.
Listing is courtesy of: NEXTHOME CASA BELLA ELITE (813-726-5646)
Listing Agent: Loren Rosenthal (813-726-5646)
15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787
$874,9007 Days on yellowkey MLS ID: O6416065
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4042 Built: 2016Monthly Fee: $180 Tax: $552 (2024)Community: Signature Lakes Ph 3B-4Single Family
Taxes:$552
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to 15121 Evergreen Oak Loop, a stunning 6-bedroom, 4-bathroom home offering over 4,200 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities. Situated on an oversized homesite with no rear neighbors, this exceptional property combines space, comfort, and privacy with beautiful conservation views and breathtaking Florida sunsets. The heart of the home is the expansive gourmet kitchen featuring stainless steel appliances, a large center island, abundant cabinetry, and an open-concept design that flows seamlessly into the main living areas—perfect for entertaining family and friends. Flexible living spaces include a first-floor bedroom and full bath, ideal for guests, a home office, or multigenerational living. Upstairs, you'll find a spacious theater room complete with reclining theater seating, projector, screen, and surround sound system—all included with the home—creating the ultimate space for movie nights, sporting events, and gaming. The luxurious primary suite serves as a private retreat with a spa-inspired bath, dual vanities, soaking tub, separate shower, and oversized walk-in closet. Step outside to enjoy peaceful conservation views from multiple outdoor living spaces, offering a level of privacy rarely found in Horizon West. Whether you're enjoying your morning coffee or winding down in the evening, this home provides the perfect backdrop for Florida living. Location is everything, and this home delivers. Just minutes away is the newly opened Horizon West Regional Park, a 215-acre recreational destination featuring an inclusive playground, walking and biking trails, picnic pavilions, athletic fields, open green space, and recreational facilities. Future phases are planned to bring additional trails, expanded recreational amenities, and nature-focused areas, adding even more value to this already exceptional location. Residents enjoy convenient access to top-rated schools, shopping, dining, major highways, Disney attractions, and everything that makes Horizon West one of Central Florida's most sought-after places to live. Offering an ideal combination of size, functionality, entertainment, and location, this is a rare opportunity to own a truly special home in the heart of Winter Garden.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Adam Jackson (407-572-6252)
16893 BROADWATER AVE, WINTER GARDEN, FL 34787
$2,795,9007 Days on yellowkey MLS ID: O6415972
Bed: 7 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6289 Built: 2019Monthly Fee: $383 Tax: $25,448 (2025)Community: Waterside 90'SSingle Family
Taxes:$25,448
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Experience elevated lakefront living in this former builder model home, perfectly positioned along the shores of Johns Lake in the sought-after Waterside community of Winter Garden. Designed to impress from the moment you enter, the residence showcases soaring ceilings, designer lighting, and expansive windows that fill the home with natural light while framing tranquil water views. The open-concept floorplan seamlessly connects the living, dining, and kitchen spaces, creating an ideal setting for both everyday living and entertaining. At the heart of the home, the chef's kitchen features an oversized island, abundant cabinetry, and generous prep space overlooking the main living areas. The first-floor primary suite serves as a private retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, walk-in shower, and two large walk-in closets. Offering six bedrooms, four-and-a-half baths, a dedicated office, formal dining room, bonus room, and an expansive upstairs game and media space, the home provides exceptional flexibility for multigenerational living, guests, remote work, and recreation. Designed to embrace its waterfront setting, the outdoor living spaces are a true extension of the home. A covered lanai with a summer kitchen overlooks a private backyard highlighted by a striking fountain, creating a resort-inspired atmosphere for entertaining or relaxing. Just beyond, a private dock provides direct access to Johns Lake for boating, fishing, paddleboarding, and unforgettable sunset views. Located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, major highways, dining, shopping, and top-rated schools, this exceptional residence offers the rare combination of luxury, space, and waterfront living in one of Central Florida's most desirable locations.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matt Tomaszewski (407-719-5956)
WINTER GARDEN, FL 34787
$558,9907 Days on yellowkey MLS ID: G5113611
0 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 15' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
6171 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$792,8057 Days on yellowkey MLS ID: G5113609
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2688 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: Virtually Staged. Under Construction. Sample Image The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering FOUR bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provide ample space for family members or guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.
1343 CASTLEPORT RD, WINTER GARDEN, FL 34787
$535,0007 Days on yellowkey MLS ID: O6414756
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2170 Built: 2001Monthly Fee: $243 Tax: $4,191 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$4,191
Remarks: Welcome to this beautifully landscaped 3-bedroom, 2-bathroom home in the 24-hour guard-gated Stoneybrook West community. Featuring a split-bedroom floor plan, the layout includes a versatile flex room ideal for a home office or den. The kitchen is equipped with white appliances and granite countertops and flows easily into the main living spaces, with ceiling fans installed throughout the home for comfort. A standout feature of this property is the seamless outdoor integration: the living room, family room, and primary suite all open directly onto a spacious, screened-in porch. The primary suite serves as a quiet retreat, complete with an attached bath featuring a garden tub and a separate walk-in shower. Residents of Stoneybrook West enjoy robust community amenities, including a clubhouse, swimming pool, golf course, tennis courts, and a private community boat dock with direct access to Black Lake.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Kristi Matthew (407-325-6107)
9481 EMERALD BERRY DR, WINTER GARDEN, FL 34787
$789,9907 Days on yellowkey MLS ID: O6414779
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2569 Built: 2023Monthly Fee: $99 Tax: $9,756 (2025)Community: Summerlake ReserveSpa: NoSingle Family
Taxes:$9,756
Elementary School: Panther Lake Elementary
Remarks: LIKE-NEW WINTER GARDEN HOME WITH DISNEY FIREWORK VIEWS! Welcome to this pristine, turnkey home in Summerlake Reserve—an exclusive Winter Garden community of just 41 homesites. Built in 2023 and kept in immaculate "like-new" condition, this exceptional Sawgrass plan features 4 bedrooms, 3 baths, and 2,569 sq. ft. under air, perfectly situated next to a peaceful neighborhood green space. HIGHLIGHTS: DISNEY VIEWS: Enjoy front-row seats to the nightly Disney fireworks display right from your front porch! SMART LAYOUT: First-floor private Owner's Suite with 9'4" ceilings and 8' doors. The second floor features a huge bonus room with an adjacent bedroom and full bath—ideal for guests or a teenager's retreat. CHEF'S KITCHEN: Upgraded with a built-in wall oven, 42" 'Basalt' cabinets, Quartz countertops, a tiled backsplash, and under-cabinet lighting. Flows seamlessly into the great room and expansive covered lanai. TOP LOCATION: Located in the heart of Horizon West, minutes from premier dining, shopping, and major highways. Zoned for top-rated schools: Panther Lake Elementary, Hamlin Middle, and Horizon High. Avoid the wait for new construction—this fully upgraded masterpiece is ready now. Schedule your showing today!
Listing is courtesy of: CORESTONE REAL ESTATE LLC (407-618-6806)
Listing Agent: Xuxi Zhao (407-618-6806)
4863 LACEWING DR, WINTER GARDEN, FL 34787
$540,00070 Days on yellowkey MLS ID: O6397857
0 Days Off yellowkey (back on 5/23/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1788 Built: 2023Monthly Fee: $171 Tax: $6,905 (2025)Community: Silverleaf Reserve BungalowsSpa: NoSingle Family
Taxes:$6,905
Middle School: Horizon West Middle School
Remarks: Located in the highly desirable Silverleaf at Hamlin in Winter Garden, this exceptional bungalow offers the perfect blend of location, lifestyle, and design. Surrounded by top-rated schools within short distance, premier dining, and a rapidly growing area with strong appreciation, this is one of the most sought-after communities in the region. This beautifully designed home features 3 bedrooms, 2/1 bathrooms, and an additional loft room, with a layout that is both functional and inviting. What truly sets this property apart is its interior. Unlike anything else currently available in the area, this home has been fully customized with high-end finishes and a cohesive, thoughtfully curated design throughout. Every element was carefully selected to create a seamless flow of elegance, comfort, and functionality. The home showcases custom-built cabinetry in every space, including closets, storage solutions, and integrated desk areas, all designed specifically for the home. The custom-made curtains were designed to fit each space perfectly, enhancing both aesthetics and comfort. Throughout the home, you’ll find LED lighting and carefully selected fixtures that complement one another, creating a warm, modern, and visually harmonious atmosphere. Custom mirrors, wood panel details, and built-in elements elevate each room, making every space feel intentional and refined. The kitchen is a true highlight a gourmet, built-in design that is highly practical, ideal for everyday living and entertaining. This is a rare opportunity to own a home that is completely move-in ready at a level rarely found, and everything has already been done with impeccable taste. Simply bring your belongings and start living. Homes like this are truly one of a kind in the area, and once you step inside, it’s impossible not to fall in love.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)
13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787
$799,900134 Days on yellowkey MLS ID: O6379591
REDUCED by $49,100 (5.8%) on 06/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2214 Built: 2023Monthly Fee: $544 Tax: $10,256 (2024)Community: Del Webb OasisSpa: NoSingle Family
Taxes:$10,256
Remarks: The neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the backyard absolutely stunninig, featuring Italian Tile Pavers, Metal Pergola and a beautiful summer kitchen with gas grill with custom outdoor lighting. As soon as you walk into the home you'll be greeted with high ceilings, beautiful crown molding throughout and luxury vinyl floors.The homes open floor plan is perfect for entertaining, featuring a large kitchen island, plenty of cabinet and countertop space. The home has an electric stove currently however this is a gas community and the seller is happy to convert it back to a gas stovetop upon your request! The living room features tray ceilings and surround sound as well as custom smart blinds! The master bedroom and bathroom has everything you want and more! Featuring a gorgeous long walk in shower, dual Sinks and a spacious walk in master closet! With over 150,000 in options added to this property, this home is truly move in ready. This home comes with leased solar panels, whole house gas generator, finished garage floors. Outdoor furniture is negotiable. No Rear Neighbors, a quick walk to the brand new community clubhouse and just a short drive from everything you need! Only 2 miles from the Disney theme park entrance! Don't Wait! Schedule your showing today.
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)
Listing Agent: John Hart, Pllc (407-432-8612)
16104 SANDHILL RD, WINTER GARDEN, FL 34787
$1,020,00021 Days on yellowkey MLS ID: O6411589
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1364 Built: 1988Monthly Fee: $3 Tax: $2,191 (2025)Community: Lake Avalon GrovesSingle Family
Taxes:$2,191
Remarks: Rare opportunity to own nearly 5 acres in the coveted Lake Avalon Rural Settlement—where horses, heritage oaks, and peaceful country living meet the convenience of Winter Garden. Escape the hustle and discover one of Winter Garden's last remaining rural neighborhoods. Set on 4.85 fully fenced acres, this picturesque property offers expansive green pastures, majestic oak and heritage trees, and the quiet, open spaces that have become increasingly difficult to find. Bring your horses, livestock, and four-legged companions. The property features a barn with tack room, two stalls with run-outs, multiple pasture areas, and plenty of room to enjoy the outdoor lifestyle Lake Avalon Rural is known for. A long driveway leads to a comfortable 3-bedroom, 2-bath home, perfectly positioned to take advantage of the property's natural beauty and peaceful surroundings. Located within the highly desirable Lake Avalon Rural Settlement, residents enjoy a unique blend of country charm and modern convenience. This close-knit community is known for its' equestrian lifestyle, small farms, wide-open spaces, and commitment to preserving the area agricultural heritage and country character. Despite its tranquil setting, you're only minutes from Historic Downtown Winter Garden, Fowler Grove, Hamlin Town Center, major highways, area attractions, shopping, dining, and top-rated schools. Whether you're dreaming of a horse property, hobby farm, or simply a private retreat beneath the shade of towering oaks, this exceptional property offers the space, freedom, and lifestyle you've been searching for. Experience the peace of country living without sacrificing the convenience of city amenities.
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Cheryl Gritzer (407-222-6530)
14280 BRAEMAR ST, WINTER GARDEN, FL 34787
$499,00057 Days on yellowkey MLS ID: TB8500322
REDUCED by $40,000 (7.4%) on 06/12/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1964 Built: 2023Monthly Fee: $100 Tax: $7,928 (2025)Community: Highland RdgSingle Family
Taxes:$7,928
Remarks: PRICE IMPROVEMENT – NOW OFFERED AT $499,000! Exceptional opportunity to own a nearly new home in the highly sought-after Highland Ridge community of Winter Garden. Built in 2023, this beautifully maintained 3-bedroom, 2.5-bath residence offers a modern open-concept floor plan with stylish finishes throughout. The spacious kitchen features granite countertops, stainless steel appliances, ample cabinet space, and opens seamlessly to the living and dining areas, making it ideal for everyday living and entertaining. Upstairs, you’ll find a generous primary suite, two additional bedrooms, and a versatile loft space. At just $499,000, this home presents one of the best values in Winter Garden for a newer construction property. Conveniently located near Downtown Winter Garden, Hamlin Town Center, shopping, dining, entertainment, major highways, and top-rated schools. Community amenities include a playground, pool, and beautifully maintained common areas. Move-in ready and priced to sell—schedule your private showing today before this opportunity is gone!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Freddy Escobar (352-217-7815)
$599,00063 Days on yellowkey MLS ID: O6399369
REDUCED by $20,000 (3.2%) on 05/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 2001Monthly Fee: $320 Tax: $4,811 (2025)Community: Woodbridge On GreenSingle Family
Taxes:$4,811
Elementary School: Keene Crossing Elementary
Remarks: Welcome to Woodbridge on the Green—one of Winter Garden’s best-kept secrets, ideally situated next to West Orange Country Club. Enjoy your own private waterfront retreat, where tranquil surroundings and breathtaking sunsets over the water create the perfect setting to share unforgettable moments with family and friends! This beautifully maintained waterfront home offers exceptional curb appeal and a spacious, single-story layout designed for comfortable living. Step inside to an inviting open floor plan filled with natural light and waterfront views. High ceilings and stylish luxury flooring enhance the home’s modern feel, creating a bright and airy atmosphere throughout. The well-appointed kitchen features custom countertops, rich wood cabinetry, and a full appliance package, with culinary nook overlooking the peaceful & gorgeous waterfront—perfect for both everyday living and entertainment. The generously sized primary suite provides a peaceful retreat, complete with closet, dual vanities, and a walk-in shower. Unwind on the screened-in lanai, where you can enjoy tranquil water views, mature oak trees, and beautiful Florida sunsets—your own private outdoor oasis. Living in Woodbridge on the Green means embracing a low-maintenance, resort-style lifestyle. The HOA takes care of all landscaping and exterior painting, and residents enjoy access to a private boat and RV storage area within the community. Recent upgrades add even more value and peace of mind, including a new AC system (2025), garage door opener (2026). Located within an “A”-rated school district, including Windermere High School—one of Florida’s top-ranked schools—this home is also just minutes from Winter Garden Village, major roadways, dining, shopping, Disney and the Magic Kingdom and all Central Florida area attractions. It is the responsibility of all prospective buyers and their agents to independently confirm the accuracy of all listing information, including measurements, specifications, and all other material details. No representations or warranties are made as to the completeness or accuracy of such information.
Listing is courtesy of: RAVENSCROFT REALTY GROUP (407-855-0005)
Listing Agent: Tom Ravenscroft, Jr. (407-222-7660)
9827 BEACH PORT DR, WINTER GARDEN, FL 34787
$1,399,99042 Days on yellowkey MLS ID: O6405480
INCREASED by $25,000 (1.8%) on 06/11/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2020Monthly Fee: $259 Tax: $11,122 (2025)Community: Waterleigh Ph 2C-2 & 2C-3Spa: YesSingle Family
Taxes:$11,122
Middle School: Water Spring Middle
Remarks: Perfectly positioned on a PREMIER WATERFRONT LOT just under half an acre, this stunning 3,910-square-foot residence delivers luxury living at every turn. Tucked away at the end of a tranquil cul-de-sac and situated on one of the few homesites in the neighborhood with no neighbors in front or behind, the property offers an exceptional sense of privacy with beautiful views of Lake Noah. A grand foyer with a dramatic wrought iron staircase sets the tone for the sophisticated interiors, where CROWN MOLDING and WAINSCOTING elevate the home throughout. The GOURMET KITCHEN is both stylish and functional, featuring a center island, glass-front cabinetry, under-cabinet lighting, designer backsplash, stainless steel appliances, and a sleek flat cooktop. A butler’s pantry and formal dining room create the perfect setup for effortless entertaining. The luxurious primary suite features a CUSTOM CALIFORNIA CLOSET SYSTEM and a spa-inspired bath with dual vanities and an oversized walk-in shower complete with double shower heads, including a RAIN SHOWER. Spacious secondary bedrooms all offer walk-in closets, with two connected by a JACK-AND-JILL BATHROOM, while the oversized upstairs loft provides flexible living space ideal for a media room, game room, or lounge. Designed for both comfort and convenience, the home also includes a 3-car tandem garage with EPOXY FLOORINGS and HANGING STORAGE RACKS, a WHOLE-HOUSE GENERAC GENERATOR, a WHOLE-HOUSE HALO WATER FILTRATION SSTEM, NEW 80-GALLON WATER HEATER, security system with cameras throughout. The backyard is a true private retreat featuring a gas-heated saltwater pool and spa with water features, SUMMER KITCHEN, FIRE PIT, screened enclosure, OUTDOOR SONOS SURROUND SOUND SPEAKER SYSTEM, upgraded LIGHTING PACKAGE, and lush professional landscaping. Beyond the screen enclosure, the fully fenced yard offers additional green space rarely found in waterfront homes. One of the property’s most unique features is the ABILITY TO BUUILD A PRIVATE DOCK on Lake Noah, offering an incredible opportunity to embrace true waterfront living in one of Winter Garden’s premier communities. Conveniently located near top-rated schools, shopping, dining, Disney, and major roadways, this home effortlessly combines luxury, lifestyle, and location into one exceptional offering. Opportunities like this do not come along often.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Silvia Kinkela, Pa (407-284-9254)
398 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787
$1,498,44044 Days on yellowkey MLS ID: O6405194
1 Days Off yellowkey (back on 6/11/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4442 Built: 2024Monthly Fee: $240 Tax: $14,707 (2025)Community: Winter GroveSpa: YesSingle Family
Taxes:$14,707
Elementary School: SunRidge Elementary
Remarks: Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Introducing the exquisite Roseland former model home! This stunning 5-bedroom, 5-bathroom, 2-car garage masterpiece boasts a homesite neighboring a pond and a luxury pool, spa, and outdoor kitchen. As a former model home, there is also an option to purchase the furniture separately. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, an enclosed flex room offers versatility, while the formal dining room invites effortless entertaining. As you travel further into the Roseland you are greeted by a grand staircase, featuring engineered hard wood plank treads and wrought iron balusters with an oak handrail. Tucked just under the staircase is a wine lover’s dream, a wine cave with built-in cabinets, quartz countertops, and stylish tile backsplash. From there, you enter the heart of the home—the open concept kitchen and living area. Equipped with built-in Whirlpool stainless steel appliances, including a beverage cooler, double oven, and built-in cooktop, the kitchen is a dream for culinary enthusiasts. Two-tone soft-close cabinetry is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. Step outside to the covered lanai and enjoy your backyard oasis complete with an inground pool and spa, as well as an outdoor kitchen. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a frameless glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A free-standing bathtub, frameless glass-enclosed shower, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink trimmed in quartz and cabinets, makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
936 KYLEE ALY, WINTER GARDEN, FL 34787
$675,00084 Days on yellowkey MLS ID: O6393910
4 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1772 Built: 2022Monthly Fee: $356 Tax: $6,058 (2025)Community: Oakland ParkSingle Family
Taxes:$6,058
Elementary School: Tildenville Elem
Middle School: Legacy Middle
Remarks: Move-in ready 3-bedroom, 2.5-bathroom single-family home in the Oakland Park community of Winter Garden, Florida. Built in 2022, turnkey condition, full appliance package included, and a low-maintenance 0.05-acre homesite designed for connected daily living without the upkeep. Oakland Park is one of those Winter Garden communities people move to on purpose. Tree-lined streets, walkable sidewalks, and a thoughtfully planned layout keep daily essentials, dining, and recreation close, while the neighborhood itself still feels calm and connected. Morning coffee runs, evening walks, and simple daily rhythms all find an easy place here. Opening the door to 936 Kylee Alley, there's an immediate sense of ease. Natural light carries across the main level as the entry gives way to connected living, dining, and kitchen spaces, creating a layout that works the way life actually happens. With approximately 1,614 square feet of heated living space, this two-story single-family home is scaled for real life. Room to gather, room to retreat, and a layout that stays connected without feeling crowded. The kitchen features white shaker cabinets, quartz countertops, a kitchen island with bar seating, black pendant lighting, and stainless steel appliances including a refrigerator, range, built-in oven, microwave, and dishwasher. The open dining area sits adjacent with a sputnik-style chandelier and large windows filling the space with natural light. Hardwood-style flooring runs through the main level. Upstairs, all three bedrooms including the primary suite are grouped together, creating a quieter, more private living area away from the main floor. The primary suite includes a walk-in closet, double vanity, and a tiled shower. A shared full bathroom serves the two additional bedrooms. The upstairs laundry room with washer and dryer included keeps the daily routine on one level. Carpeted bedrooms and ceiling fans throughout add comfort. The private courtyard-style patio offers outdoor entertaining space. Scaled for morning coffee, evening drinks, or a few favorite plants without the yard work. The attached two-car garage and compact lot reinforce the low-maintenance lifestyle this Oakland Park home is designed to support. Located in Oakland Park in Winter Garden, this home provides convenient access to downtown Winter Garden, the West Orange Trail, Hamlin Town Center, SR-429, and SR-50. The Florida Turnpike, Orlando's theme parks, and the broader Central Florida corridor are all within reach. Shopping, dining, and commuter routes sit close by in a well-maintained, association-managed community. If you are looking for a move-in ready single-family home with 2022 construction, a practical two-story layout, and a connected Winter Garden lifestyle, 936 Kylee Alley in Oakland Park is best experienced in person. Winter Garden, FL 34787. Schedule your private showing today or request additional details to take the next step.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Nelson Cruz Pa (407-901-9939)
13062 SUNSET GARDEN LN, WINTER GARDEN, FL 34787
$693,27061 Days on yellowkey MLS ID: O6400441
INCREASED by $3,000 (0.4%) on 04/30/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2686 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Stunning new construction by Toll Brothers in desirable Horizon West, Winter Garden, estimated completion early 2027. This bungalow-style home features a covered entry, elegant foyer, and private first-floor guest suite. The open-concept layout offers a spacious dining area, designer kitchen with breakfast bar, and great room with access to a private courtyard, perfect for indoor-outdoor living. Upstairs includes two secondary bedrooms and a luxurious primary suite with walk-in closet and spa-inspired bath featuring dual vanities, separate shower, and private water closet. A standout feature is the detached garage with a private suite above, complete with full bath and loft, ideal for guests, office, or flexible living space.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Devahn Powell (571-234-7236)
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