Location: Winter Garden
Do Not Show Listings
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$550,000341 Days on yellowkey MLS ID: A4660262
0 Days Off yellowkey (back on 7/2/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,702
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
1105 LINCOLN TER, WINTER GARDEN, FL 34787
$255,00021 Days on yellowkey MLS ID: O6416937
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 814 Built: 1961 Tax: $1,586 (2025)Community: Bay St ParkSingle Family
Taxes:$1,586
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. This beautifully updated 3 bedroom, 1 bathroom home offers modern comfort at an unbeatable value. With 814 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new fridge, and brand new remodeled bathrooms—giving you peace of mind and a move-in ready lifestyle. Located in the heart of Winter Garden, this home is close to shops, dining, and entertainment, all while being tucked into a welcoming neighborhood. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this gem checks all the boxes. Don’t miss this rare opportunity to own a beautifully renovated home in one of Central Florida’s most sought-after communities—for less than $300K! **All measurements must be verified by the buyer.**
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Christopher Sukhram (407-558-8460)
17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787
$565,00048 Days on yellowkey MLS ID: O6409499
4 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2114 Built: 1984 Tax: $2,608 (2025)Community: Arrowhead LakesSingle Family
Taxes:$2,608
Remarks: Florida Lake Front Charm. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge. Spring Fed Lake. A2 zoning. A+ schools. No HOA. Established Neighborhood. New Roof and Soffits Sept. 2025, New Exterior Paint Sept 2025, Refrigerator 2024, Dishwasher 2024. Owner is in the process of moving. Estate sale in progress and deep cleaning will be done before closing.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-299-3000)
Listing Agent: Dan Lu (407-454-3601)
8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787
$445,00082 Days on yellowkey MLS ID: O6399484
REDUCED by $15,000 (3.3%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1853 Built: 2016Monthly Fee: $315 Tax: $4,738 (2025)Community: Summerlake Pd Ph 2C 2D 2ETownhouse
Taxes:$4,738
Elementary School: Summerlake Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: Move in with added peace of mind the *Community RE-ROOF and EXTERIOR PAINT Project are underway* Welcome to 8170 Bluejack Oak Drive, a beautifully situated corner unit in the heart of the Summerlake Community. Offering a spacious yard and stunning water views, this 3 bedroom 2.5 bath townhome is just what you've been looking for! Enjoy sitting on your front porch with the peaceful water views, and at the end of every day you can catch Disney’s nightly fireworks while strolling around the pond. Inside, the home features a newer AC unit (replaced 2024) with a functional and inviting layout, with a versatile bonus room and a convenient half bath just off the entry. The kitchen is well-appointed with granite countertops, oversized island, 42” cabinetry, and a generous pantry. The kitchen flows seamlessly into the dining area and spacious family room. Step outside to the extended brick patio and grassy yard, ideal for hosting, relaxing, or enjoying time with pets. Your rear-entry two-car garage adds both convenience and extra parking with a good size driveway. Upstairs, the oversized primary suite offers a peaceful retreat with beautiful sunset views. The ensuite bath featuring dual sinks, a soaking tub, separate shower, and walk-in closet. Down the hall, you'll find two additional bedrooms, both with pond views, a full bathroom, and upstairs laundry (replaced in 2022 & 2023). You'll enjoy access to resort-style amenities, including a community pool, fitness center, clubhouse, tennis courts, and basketball half-The HOA handles all landscaping, pest control, exterior maintenance and irrigation.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Stephanie Baldner (407-419-0629)
22 WINDTREE LN #203, WINTER GARDEN, FL 34787
$169,900210 Days on yellowkey MLS ID: S5139914
REDUCED by $10,000 (5.6%) on 06/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1983Monthly Fee: $300 Tax: $875 (2025)Community: Windtree Gardens Condo Ph 01Condo
Taxes:$875
Remarks: MOTIVATED SELLER. THE BEST VALUE IN WINTER GARDEN | NEW ROOF | MOVE-IN READY. Stop your search at the LOWEST-PRICED, MOVE-IN-READY home in one of Central Florida’s most coveted zip codes. This solid BLOCK-STRUCTURE residence at 22 Windtree Ln #203 features a BRAND-NEW ROOF and unbeatable proximity to the magic of DOWNTOWN WINTER GARDEN. Just minutes from your front door, you can explore the boutiques of PLANT STREET, grab a craft brew at CROOKED CAN, or enjoy the famous weekly FARMERS MARKET. For the outdoor enthusiast, IMMEDIATE ACCESS to the WEST ORANGE TRAIL offers miles of scenic biking and jogging, while nearby LAKE APOPKA provides stunning sunsets. Whether you’re commuting via easy highway access or heading to WALT DISNEY WORLD just a short drive away, this home offers an INCREDIBLE LIFESTYLE at a price point that simply doesn't exist elsewhere in the area. Don’t miss the BEST DEAL IN TOWN—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787
$1,495,00029 Days on yellowkey MLS ID: O6414639
0 Days Off yellowkey (back on 6/29/2026)
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4882 Built: 2016Monthly Fee: $168 Tax: $11,216 (2025)Community: Waterside/Johns Lake Ph 1Spa: YesSingle Family
Taxes:$11,216
Elementary School: Hamlin Elementary
Remarks: An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Garry Walmsley (407-923-2134)
15039 GROVESIDE RD, WINTER GARDEN, FL 34787
$497,38087 Days on yellowkey MLS ID: O6398354
2 Days Off yellowkey (back on 7/2/2026)
INCREASED by $5,000 (1.0%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 2026Monthly Fee: $247 Tax: $1,375 (2025)Community: Parkview At HamlinTownhouse
Taxes:$1,375
Remarks: Under Construction. Ready in August 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex space. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787
$679,00019 Days on yellowkey MLS ID: O6417697
1 Days Off yellowkey (back on 7/2/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2281 Built: 2022Monthly Fee: $171 Tax: $7,948 (2025)Community: Hull Island/Oakland Ph 2Single Family
Taxes:$7,948
Elementary School: Tildenville Elem
Remarks: Under contract-accepting backup offers. This turnkey, better-than-new single-story home offers an elegant and modern retreat within Oakland’s highly desirable waterfront community of Hull Island. Nestled in a friendly neighborhood surrounded by nature, the property immediately welcomes you with tasteful customizations, upgraded lighting, and stylish accent walls that bring warmth and character to the entire layout. The thoughtfully crafted split floor plan features four bedrooms and three bathrooms, maximizing both privacy and efficiency for daily living and entertaining. Right off the foyer, a comfortable guest bedroom boasts its own ensuite bath, creating an ideal setup for visitors or multi-generational families. The main living area flows seamlessly into a beautifully upgraded kitchen equipped with quartz countertops, under-cabinet lighting, a tile backsplash, and premium stainless steel appliances including a cooktop with a hood and a built-in oven and microwave. Tucked quietly away at the back of the home, the primary suite serves as a private oasis with an expansive spa-like bathroom featuring separate vanities, sleek quartz counters, a large shower, and dual walk-in closets with custom storage systems. The remaining bedrooms are equally impressive, offering ample space, custom closets, and electronic shades. The sophisticated interior transitions smoothly to a private backyard retreat where a covered lanai, extensive pavers, and a full screen enclosure set the perfect stage for relaxed Florida outdoor living. Practical needs are also effortlessly met in the two-car garage, which showcases durable epoxy flooring and a modern electric vehicle charger. Beyond the property lines, the Hull Island community provides an exceptional lifestyle centered around outdoor recreation and convenience. Residents enjoy access to a resort-style pool, a playground, a dog park, and a scenic boardwalk that winds its way to a community dock and fishing pier on Lake Apopka. Nature lovers will appreciate the neighborhood's private entrance to the 120-acre Oakland Nature Preserve, as well as close proximity to the famous 22-mile West Orange Trail, local golf courses, and pickleball courts. Complete with fast access to the Turnpike, 408, and 429, this location connects you quickly to excellent shopping, dining, and the charming downtown districts of Winter Garden, Clermont, and Oakland, while keeping Orlando’s theme parks and international airport within easy reach.
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Brian Cirillo (321-231-1068)
168 WINDTREE LN #203, WINTER GARDEN, FL 34787
$202,900267 Days on yellowkey MLS ID: O6351954
4 Days Off yellowkey (back on 6/26/2026)
REDUCED by $6,500 (3.1%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1985Monthly Fee: $260 Tax: $2,004 (2024)Community: Windtree Gardens Ph 6Condo
Taxes:$2,004
Remarks: Virtually Staged. **BACK ON MARKET: Owner Paused listing to fully remodel the home!** This 2-bedroom, 2-bath second-floor condo in the sought after community of Windtree Gardens is truly a must see now! LOW HOA! Featuring New kitchen cabinets, New quartz countertops, New appliances, New luxury vinyl-plank flooring throughout, New bathroom vanities, New fans and fixtures, and fresh interior paint. Conveniently located walking distance to Starbucks, less than 2 miles to the 429, and just minutes from dining and shopping! Come see this home today, before it goes!!!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erik Mcginnis (407-948-6518)
1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,046,0006 Days on yellowkey MLS ID: G5114517
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3863 Built: 2017Monthly Fee: $187 Tax: $10,792 (2024)Community: TwinwatersSingle Family
Taxes:$10,792
Middle School: Bridgewater Middle
Remarks: Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jay Winston (407-497-1112)
120 BLUE STONE CIR, WINTER GARDEN, FL 34787
$747,90047 Days on yellowkey MLS ID: O6409811
REDUCED by $2,000 (0.3%) on 06/05/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2529 Built: 1998Monthly Fee: $68 Tax: $4,291 (2025)Community: Westfield LakesSpa: YesSingle Family
Taxes:$4,291
Remarks: Seller will contribute up to $10,000 towards buyers closing costs. Welcome to this spacious waterfront pool home located in the highly desirable Westfield Lakes community of Winter Garden! Situated on a scenic pond-front lot, this home offers beautiful water views and an open floor plan designed for comfortable living and effortless entertaining. The expansive kitchen overlooks the main living areas and features abundant cabinetry, a center island, and seamless flow throughout the home. Large windows fill the space with natural light while showcasing the peaceful backyard setting. The split-bedroom layout provides added privacy, while the screened pool and covered lanai create the perfect setting to enjoy Florida living year-round. The pool also features solar heating installed in 2022 for added efficiency and extended enjoyment throughout the seasons. Major updates include a newer roof (2019), updated HVAC system (2024), and newer water heater (2026), offering valuable peace of mind for the next owner. This home offers a fantastic opportunity for buyers looking to personalize a property with solid major-system updates and exceptional bones. Featuring a spacious layout and prime waterfront setting, the home is ideally located near shopping, dining, major highways, West Orange High School, Winter Garden Village, and downtown Winter Garden. With so much potential in a highly desirable area, this property is ready for someone to bring their vision and make it truly shine. Call today for your private showing!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Mark Hite, Jr (321-948-7680)
1642 CHANDELLE LN, WINTER GARDEN, FL 34787
$709,9006 Days on yellowkey MLS ID: G5114093
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2918 Built: 2006Monthly Fee: $167 Tax: $8,474 (2025)Community: Belle Meade-Ph I B D & GSpa: NoSingle Family
Taxes:$8,474
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-story home in the highly sought-after gated community of Belle Meade — zoned for Whispering Oak Elementary (10/10 GreatSchools rating, top 5% of all schools in Florida), SunRidge Middle, and West Orange High School. With 2,918 square feet of thoughtfully designed living space, a 3-car garage, and a fenced corner lot spanning 0.27 acres, this home offers the space, privacy, and top-tier school access today's families are searching for. Major systems have already been taken care of for you — enjoy true peace of mind with a brand new roof (February 2024), backed by a CertainTeed SureStart warranty that's fully transferable to the new owner, and a brand new Trane 5-ton AC system (2025) with a 10-year warranty through 2035. No surprise repairs, no looming replacements — just move in and relax. Inside, soaring cathedral and vaulted ceilings, tray ceilings, crown molding, and wood flooring create an elegant, open feel throughout. A separate laundry room adds everyday convenience, and the fifth bedroom functions as a versatile den/utility space — ideal for a home office, playroom, or guest suite. The primary suite is a true retreat, featuring dual walk-in closets, dual vanities, a spa-style soaking tub, a separate standing shower, and a private water closet. Step outside to your fully screened and covered patio — perfect for entertaining or simply enjoying Florida's year-round sunshine, rain or shine — overlooking the private, fenced backyard. Belle Meade is a secure, gated community known for its lush landscaping, sidewalks, welcoming neighbors, and an on-site dog park. You're just minutes from Winter Garden Village at Fowler Groves — Central Florida's premier outdoor shopping and dining destination — and a short drive from historic Downtown Winter Garden's Plant Street, home to the award-winning Saturday Farmers Market, Crooked Can Brewing Company, and some of the area's best restaurants. Lake Apopka and several highly rated golf courses, including West Orange Country Club and Orange County National Golf Center (home to PGA Tour and LIV Golf events), are also just minutes away. Commuters and theme park lovers alike will appreciate the unbeatable location: Walt Disney World is approximately 15–25 minutes away via SR 429, with Universal Studios and SeaWorld each roughly 20–30 minutes via the Florida Turnpike. Downtown Orlando is approximately 20–25 minutes away via SR 408 or SR 50, and Orlando International Airport is about 30–35 minutes via the Turnpike. This is a rare opportunity to own a move-in ready home with major systems already updated, zoned for one of Florida's top-rated elementary schools, in one of Winter Garden's most desirable gated communities. Schedule your private showing today!
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Nikhil Vashist (352-901-3786)
13759 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787
$309,00047 Days on yellowkey MLS ID: O6409757
REDUCED by $19,500 (5.9%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1647 Built: 2007Monthly Fee: $206 Tax: $855 (2025)Community: Orchard A1-A26 B1 B2 C D1-D4Townhouse
Taxes:$855
Elementary School: SunRidge Elementary
Remarks: This home provides modern comfort, thoughtful design, and an unbeatable Winter Garden location. This beautifully maintained home features an open and inviting floor plan with plenty of natural light, creating a warm and welcoming atmosphere from the moment you walk in. The spacious kitchen is designed for both everyday living and entertaining, complete with generous counter space, ample cabinetry, and seamless flow into the main living areas. The bedrooms provide flexibility for family, guests, or a home office setup, while the primary suite provides a relaxing private escape with well appointed finishes and plenty of space to unwind. The photos of the living room and bedrooms have been virtually staged to showcase the home's beautiful potential and help buyers envision the possibilities. Enjoy living just minutes from shopping, dining, entertainment, and top rated schools, with convenient access to Hamlin, downtown Winter Garden, Disney, and major roadways throughout Central Florida. Residents also enjoy community amenities including a pool area, playground, scenic surroundings, and a strong sense of community. This is an incredible opportunity to own a home in one of Winter Garden’s most sought after locations.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
WINTER GARDEN, FL 34787
$217,5006 Days on yellowkey MLS ID: O6420656
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 942 Built: 2005Monthly Fee: $378 Tax: $2,727 (2025)Community: Southern Pines CondoSpa: NoCondo
Taxes:$2,727
Remarks: Beautiful 1BR/1BA condo with a bright open floor plan, spacious solarium/flex space, granite countertops, walk-in closet, and interior laundry. Located in the gated Southern Pines community featuring a resort-style pool, fitness center, indoor basketball and racquetball courts, tennis courts, playground, and clubhouse. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and entertainment. Northeast-facing unit with abundant natural light and excellent community amenities.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787
$459,00012 Days on yellowkey MLS ID: O6420071
REDUCED by $20,000 (4.2%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1817 Built: 2025Monthly Fee: $204 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Taxes:$1,424
Remarks: Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
16509 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787
$414,99012 Days on yellowkey MLS ID: O6420095
REDUCED by $32,510 (7.3%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1567 Built: 2025Monthly Fee: $208 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Remarks: Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
16558 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787
$464,99012 Days on yellowkey MLS ID: O6420061
REDUCED by $5,510 (1.2%) on 07/02/2026
2496 BARONSMEDE CT, WINTER GARDEN, FL 34787
$875,00011 Days on yellowkey MLS ID: G5114233
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4184 Built: 2002Monthly Fee: $210 Tax: $8,903 (2025)Community: Stoneybrook West 47/78Spa: YesSingle Family
Taxes:$8,903
Remarks: Under contract-accepting backup offers. Welcome home to 2496 Baronsmeade Ct Winter Garden situated in the much sought after golfing community of Stoneybrook West !!! This 4 Bedroom, 41/2 Bath pool home backing onto the golf course offers over 4,000sqft of living space with so many upgrades and 3 car garage with paved driveway. The tile ROOF was replaced in 2022, the AC's were replaced in 2021, kitchen and bathrooms fully renovated, new flooring throughout, all windows have custom vinyl shutters to keep the Florida heat out and save on utility bills. As you enter the home we have a formal living and dining area with built in wine bar, a huge open space with double story entry. The kitchen was fully remodled with a large center Island with Quartz countertops with waterfall edge. Lots of cabinet space and a walk in pantry, bar seating and breakfast nook. The kitchen over looks the great room wih vaulted ceilings and a gas fireplace as the focal part of the room. New sliding glass doors lead out to the huge screaned lanai with a salt water pool and spa and a built in BBQ that comes with the sale of the home. Plenty of space to enjoy the Florida lifestyle with a full sized bathroom. The Primary bedroom is downstairs and offers a large bedroom with bonus living space/home office/work out area, walk in closet and a renovated bathroom with dual vanities, large walk in shower and separate tub. Upstairs we have a enourmous loft space with built in desk space, ideal for home office/pool table/media/living space. There are 3 additional oversized bedrooms and 2 additional bathrooms to complete the upstairs. The laundry room is situated downstairs just off the garage. Stoneybrook West has so much to offer with a golf course, Restaurant, Fitness Center, Olympic Sized Swimming Pool, Playground, tennis courts, pickle ball, bastket ball and so much more. The low HOA fee covers Cable/Internet/Guarded gated community and access to all the amenities. Ideally located next to major HWYs, Disney, short commute to Orlando, Restaurants and shopping. This home has so much to offer with all the major upgrades already completed. Call today for your own private tour !!!
Listing Agent: Sarah Gholami (352-346-7857)
15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787
$344,90075 Days on yellowkey MLS ID: O6401625
REDUCED by $4,100 (1.2%) on 06/25/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1699 Built: 2008Monthly Fee: $285 Tax: $4,779 (2025)Community: Tucker OaksCondo
Taxes:$4,779
Remarks: Great Winter Garden Corner unit located in the gated community of Tucker Oaks in sought-after Winter Garden, this beautifully upgraded townhome offers a bright open-concept layout along with 3 bedrooms and 2.5 bathrooms. This stunning home offers the perfect blend of modern upgrades and serene privacy. As one of the few units backing directly onto a lush conservation lot, you’ll enjoy peaceful, wooded views and extra natural light that only a corner position can provide. Relax on your back patio with no rear neighbors and a private forest backdrop. The community offers a pool, walking paths, basketball courts, BBQ area, playground, not to mention, minutes from the West Orange Trail and downtown Winter Garden’s charm. You deserve this home.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Ali Mazahaem Flores (407-485-4177)
729 MEADOW GLADE DR, WINTER GARDEN, FL 34787
$515,00054 Days on yellowkey MLS ID: O6407943
REDUCED by $14,000 (2.6%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2070 Built: 2011Monthly Fee: $72 Tax: $3,138 (2025)Community: Covington Park A B D E F G & JSingle Family
Taxes:$3,138
Remarks: Virtually Staged. Welcome to the highly sought after GOLF CART DISTRICT of downtown Winter Garden! Located in Covington Chase, this beautifully maintained home offers functionality, charm, and the unbeatable lifestyle that makes Winter Garden one of Central Florida’s most loved communities. Situated on a desirable corner lot, the curb appeal immediately stands out with mature landscaping, lush lawn space, and a welcoming exterior that makes a lasting first impression. Step inside and you will find a spacious open floor plan designed for both comfortable everyday living and entertaining guests. Natural light fills the home and creates a warm and inviting atmosphere throughout. The kitchen is truly the heart of the home featuring granite countertops, beautiful cherry cabinetry, closet pantry, breakfast bar seating, and plenty of prep space for cooking and hosting. The open concept layout allows full views into the family room so you never miss a moment while entertaining or spending time with family and friends. Sliding glass doors lead directly out to the screened lanai creating seamless indoor and outdoor living. The partially vinyl fenced backyard offers both privacy and flexibility with plenty of room to design the pool of your dreams, create an outdoor kitchen, garden space, or simply enjoy the Florida sunshine. Whether hosting weekend barbecues or relaxing after a long day, this outdoor space provides endless possibilities. The split bedroom floor plan offers privacy and convenience for everyone. The spacious secondary bedrooms are thoughtfully positioned with access to a guest bathroom that could easily function as a future pool bath. The primary suite offers a relaxing retreat with generous space and functionality. Inside laundry adds even more convenience to daily living. What truly makes this home special is the incredible Winter Garden lifestyle. Hop on your golf cart and head into historic downtown Winter Garden where you can spend your evenings enjoying local restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals, and community events year round. Cool off at the splash pad, bike or walk the scenic West Orange Trail, and experience the award-winning Winter Garden Farmers Market every Saturday morning which has become one of the most beloved attractions in Central Florida. Residents of Covington Chase also enjoy access to community amenities including a pool, playground, parks, and walking areas, all while being conveniently located near major highways, shopping, dining, and top rated schools. The location offers the perfect blend of peaceful neighborhood living with easy access to everything Winter Garden and Orlando have to offer. This is more than just a home. It is a lifestyle that so many are searching for and very few neighborhoods can truly offer. Come experience the charm, convenience, and golf cart lifestyle of downtown Winter Garden for yourself. Schedule your private showing today!
Listing Agent: Erica Diaz (407-897-5400)
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