Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Price: $1,000,000+
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Winter Garden - 87 properties found
15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787
$1,100,00046 Days on yellowkey MLS ID: O6390971
1 Days Off yellowkey (back on 4/24/2026)
REDUCED by $50,000 (4.3%) on 03/31/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3556 Built: 2023Monthly Fee: $128 Tax: $10,299 (2025)Community: Johns Lake PointeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,299
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to this Beautifully Designed David Weekley home, built in 2023 and meticulously maintained in the Overlook portion of Johns Lake Pointe offering over 3,500 square feet of thoughtfully designed living space on an oversized lot. From the moment you step inside, you’re greeted by luxury vinyl plank flooring, expansive 10-foot ceilings, and abundant natural light that create a warm yet refined first impression. Just off the entry, a private office provides the ideal work-from-home space, while a guest bedroom with a nearby full bath is perfectly tucked away for privacy and convenience. As you continue into the heart of the home, you’ll fall in love with the open-concept living area, where the family room, dining space, and gourmet kitchen come together seamlessly—perfect for both everyday living and entertaining. The kitchen serves as a true centerpiece, featuring an oversized island, designer finishes, and ample cabinetry, all overlooking the main living space. Upstairs, you will be greeted by a spacious bonus room that offers endless flexibility—ideal for a media room, game room, or secondary living area. The Master suite is a true retreat, complete with a private walk-out balcony, Tray ceiling and a luxurious en-suite bathroom featuring a standalone garden tub, oversized walk-in shower, and a massive walk-in closet. On the other side of the home, two bedrooms share a convenient Jack-and-Jill bathroom, while a third bedroom is nestled with a full bath just outside its door, providing privacy and ease. The upstairs laundry room adds everyday convenience. This home has been meticulously maintained throughout. The community features a resort-style pool, tennis courts, playground and clubhouse that includes a gym, yoga room, gathering area and kitchen. Neighborhood is minutes from Downtown Winter Garden and Winter Garden Village as well as within walking/biking distance from the elementary and middle school. Also conveniently located to most major highways making commuting to work easier than ever. Don't hesitate, make your appointment today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: T.J. O'Donnell (317-246-8190)
14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787
$1,099,00049 Days on yellowkey MLS ID: O6390518
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4661 Built: 2018Monthly Fee: $210 Tax: $14,115 (2025)Community: Oxford ChaseSpa: YesSingle Family
Taxes:$14,115
Remarks: Welcome to this beautifully upgraded 5 bedroom, 4 and a half bath pool and spa home located in the highly desirable, fully gated community of Oxford Chase! Zoned for top-rated schools, this home offers the perfect combination of luxury, privacy, and energy efficiency. This spacious residence features a 3-car garage, paver driveway, and impressive curb appeal. Inside, you’ll find thoughtfully designed living spaces including a formal dining room with a custom built-in bar, perfect for entertaining guests or hosting special occasions, multiple office spaces, upgraded flooring throughout, a large laundry room, private gated doggie retreat, and so much more. The primary suite is located on the first level, secluded for optimal privacy with oversized his and hers closets. Upstairs you'll find guest bedrooms, a large open air loft space, and plush movie theatre room. Step outside to your own gorgeous backyard oasis featuring a fully enclosed heated pool and spa, ideal for year-round Florida living. The backyard overlooks a peaceful green space with no rear neighbors, providing extra privacy and relaxing views. Enjoy outdoor entertaining with the fully equipped summer kitchen featuring a custom vented hood, perfect for grilling and gatherings. The home is also equipped with PAID IN FULL SOLAR PANELS offering incredible energy efficiency and the benefit of little to no electric bill. Located in a secure gated neighborhood close to top schools, shopping, dining, and major highways, this home truly has it all — privacy, premium upgrades, and resort-style outdoor living. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000151 Days on yellowkey MLS ID: O6365188
1 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Elementary School: Dillard Street Elem
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787
$2,445,00013 Days on yellowkey MLS ID: O6400891
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4817 Built: 2020Monthly Fee: $210 Tax: $17,060 (2025)Community: Overlook At HamlinSingle Family
Taxes:$17,060
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Experience lakefront luxury at its finest. Situated on the pristine shores of Lake Hancock in the gated Overlook at Hamlin, this 2020-built Mediterranean masterpiece offers the perfect blend of elegance and recreation. Boasting 6 spacious bedrooms and 5.5 baths, this home features an open-concept layout with soaring cathedral ceilings and high-end finishes throughout. The gourmet kitchen, complete with a massive island and walk-in pantry, flows seamlessly into the living areas—all offering stunning water views. Step outside to your private oasis featuring a salt-water pool and a custom composite dock (2022) ready for skiing or sunset cruises. With the primary suite on the main floor and a massive upstairs game room, there is space for everyone. Enjoy the best of Winter Garden living with top-rated schools and world-class community amenities.
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Mauro Costa (321-231-6800)
7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787
$1,246,000285 Days on yellowkey MLS ID: O6329696
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3347 Built: 2014Monthly Fee: $195 Tax: $552 (2024)Community: Signature Lakes Parcel 1DSpa: YesSingle Family
Taxes:$552
High School: Horizon High School
Remarks: SELLER MOTIVATED! Seller is offering a concession of up to $10,000 toward Buyer Pre-paids and Closing costs. Welcome to your dream oasis! This stunning 5-bedroom, 3.5-bath single-family home on Lake Hancock is a true masterpiece, offering the ultimate in luxury and comfort. With a contemporary design and exceptional features, this residence is a rare gem in the world of real estate. Upon entering this exquisite residence, you'll find a spacious living room and an elegant dining room, both thoughtfully designed for special occasions and entertaining. Continuing through the home, you'll be greeted by an exquisite open floor plan that seamlessly connects the kitchen, complete with top-of-the-line appliances, to the inviting family room. This perfect layout ensures that you're never far from the action, whether you're preparing a gourmet meal or enjoying quality time with family and friends. Natural light pours in through retractable sliding doors, creating an indoor-outdoor experience like no other. These doors lead to a captivating saltwater infinity pool and spa, perfect for relaxing on warm days or entertaining under the stars. With five generously sized bedrooms, there's plenty of space for your family and guests. The master suite is a sanctuary, featuring a spacious walk-in closet and an ensuite bath with all the luxurious amenities you deserve. Situated on a large corner lot, the property offers privacy and ample outdoor space for gardening, play, or simply basking in the sun. Your options are endless when it comes to creating your own outdoor paradise. This residence is not just a home; it's a lifestyle. Experience the epitome of elegance and modern living in every corner of this property. This home is just minutes from top-rated schools, shopping, dining, and moments away from the enchantment of Disney and Orlando's premier attractions.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Michele Acosta Gladding (407-963-6431)
9940 BLACK BEAR LN, WINTER GARDEN, FL 34787
$2,050,000353 Days on yellowkey MLS ID: O6309917
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3110 Built: 2025 Tax: $4,423 (2024)Community: Acreage & UnrecSingle Family
Taxes:$4,423
Elementary School: None
High School: None
Middle School: None
Remarks: Pre-Construction. To be built. This Custom Single-Story Modern Farmhouse by Lionshead Homes is a showstopper! Set on a serene 5-acre private oasis. Plenty of space for farm animals or just enjoy the open space and tranquil surroundings. Lionshead Homes has recently built custom homes near this property. So Buyers may view a recently completed home to get an idea of fit and finish and our quality craftmanship. Located in the Avalon Rural Settlement, you'll enjoy the country lifestyle without sacrificing proximity to shopping, entertainment and the suburban lifestyle of Hamlin and Winter Garden. Call for more information or to schedule a viewing appointment.
Listing is courtesy of: HAMLIN REALTY (321-299-4279)
Listing Agent: Edward Guerrette Llc (321-299-4279)
617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,190,00053 Days on yellowkey MLS ID: O6389100
REDUCED by $10,000 (0.8%) on 04/20/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3624 Built: 2019Monthly Fee: $255 Tax: $16,181 (2025)Community: Canopy Oaks Ph 1Spa: NoSingle Family
Taxes:$16,181
Elementary School: Lake Whitney Elem
Remarks: One or more photo(s) has been virtually staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle,” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether hosting guests or enjoying a quiet night at home, this kitchen is the heart of it all. The first floor offers exceptional flexibility with a private office and a Junior Owner’s Suite—ideal for guests or multi-generational living. Upstairs, the primary suite becomes your personal retreat with a unique round spa-inspired bathroom, oversized walk-in closet, wet bar, and access to a private balcony. Two additional en-suite bedrooms, a loft, and an upstairs laundry room complete the second level. Step outside and enjoy multiple spaces designed for relaxing and entertaining, including Trex-decked balconies, a summer kitchen, and a peaceful fountain feature. Additional highlights include surround sound wiring, a whole-home generator, and thoughtful upgrades throughout the home. Beyond the property itself, the location truly sets this home apart. You’re just minutes from Downtown Winter Garden’s award-winning farmers market, vibrant restaurants, charming boutiques, scenic parks, and top-rated schools—with easy access to major highways for commuting throughout Central Florida. Recognized as Florida’s Best Model Home by the SEBC Excel Awards, The Sanibel offers a rare opportunity to own a home that combines architectural distinction, luxury features, and an unbeatable Winter Garden lifestyle. Note: One image includes a virtually added pool to illustrate potential backyard possibilities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787
$1,200,00060 Days on yellowkey MLS ID: O6384801
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3170 Built: 2018Monthly Fee: $188 Tax: $7,979 (2024)Community: Stanton EstatesSingle Family
Taxes:$7,979
Remarks: Welcome to Golf Cart Life in Historic Downtown Winter Garden! Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this stunning contemporary masterpiece is perfectly positioned in Winter Garden's coveted Golf Cart District. Built in 2018, this one-story multigenerational estate delivers 3,170 square feet of refined living on a nearly 1/3-acre lot, just a short golf cart ride from Plant Street, the Crooked Can Brewery, the weekly farmer's market, and the West Orange Trail. Inside, soaring 12-foot ceilings and abundant natural light flow through an open, flexible floor plan with four bedrooms, four full bathrooms, and a large private office. The gourmet kitchen is the heart of the home — featuring solid wood cabinetry, quartz countertops, an oversized center island, walk-in pantry, and a full suite of KitchenAid Professional appliances with a natural gas cooktop. The primary suite impresses with a recessed ceiling, expansive custom walk-in closet, and a spa-inspired oversized bath. Step outside through fully retractable sliding glass doors to a covered lanai wrapped in mature, professionally designed landscaping and privacy fencing — your own Florida retreat. Premium finishes throughout include smart home technology, motorized shades, whole-home water filtration, 8-foot solid core interior doors, colonial-style trim, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408 — this is one of Central Florida's most desirable addresses. Opportunities like this in Stanton Estates are rare. Welcome home.
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Joe Thomas, Jr (813-724-1922)
671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,325,00056 Days on yellowkey MLS ID: O6383438
0 Days Off yellowkey (back on 4/17/2026)
REDUCED by $25,000 (1.9%) on 04/08/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4490 Built: 2019Monthly Fee: $300 Tax: $12,519 (2024)Community: Canopy Oaks Ph 1Spa: YesSingle Family
Taxes:$12,519
Remarks: Under contract-accepting backup offers. Canopy Oaks, located in Winter Garden, Florida, is a unique blend of high-end luxury homes and suburban tranquillity. This gated enclave, developed by the distinguished home builder A.R. Bailey, features 49 classic estates. The meticulously crafted community is designed to cater to the specific needs and desires of homeowners, and includes a scenic nature trail, a children’s play park, and a community post office. From the moment you arrive at this Mediterranean POOL estate home, it makes a BOLD statement with its 8-foot Solid Wood Arched double entry doors. You are greeted with cathedral ceilings, solid wood oversized French doors to the private office, elegant hand forged custom iron railings, and a unique wine cellar with a custom hand forged iron gate. Luxury details and fine craftsmanship are inside this 5 BR/4.5 Ba/2-car garage POOL home. Open Floor plan leads pleasantly into the chef-style kitchen with the perfect layout for entertaining. The kitchen includes Bespoke Samsung stainless steel appliances, including a Family Hub Refrigerator. Gas stove top, built-in oven, and built-in convection oven. Granite counters. Completing the 1st floor, in addition to the 1st MBR, is a den/office, laundry room, generous dining area, powder bath, epoxy-coated garage floor 2-car garage, Autel Level 2 EV Charger and large lanai complete with Remote controntrolled, motorized retractable patio screens (upstairs and downstairs). The lanai and pool area are designed as additional living space, with pre-plumbing and Gas for your Summer Kitchen. Tons of architectural features throughout, upgraded light fixtures. Both Primary Suites have built in Kitchenettes. The media room includes a mini kitchenette with sink and microwave, and the theatre is wired for a 5.1 in-wall sound system. Three en-suite bedrooms and a Second Master Suite can also be found on this upper floor – perfect for multi-generational options and living privacy. The upstairs primary bathroom and closet are a dream come true. The Spa style bath has granite countertops, custom wood cabinetry, spacious dual sinks, an elegant free-standing soaking tub, seperate frameless glass wall shower with a bench. The custom-made, upgraded, solid wood oversized closet is Couture-Ready. Rainsoft whole-home water filtration/treatment/softener system. Luxury saltwater pool and spa. Privacy hedges along the side yard. Pool lighting; spa with custom tile; finished pool surface; low-maintenance turf and landscaping in the backyard. Exterior lighting, LED trim lighting. The list goes on and on. This home is a must see. An exceptional estate at an exceptional value, Canopy Oaks is located on Roper Road between Winter Garden’s downtown historic district and the Winter Garden Village shopping complex. With convenient access to major highways such as 429, 408, and the Turnpike, and its proximity to world-renowned attractions like Disney World® and Universal Studios®, this home offers an exceptional opportunity for easy commuting.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Sean Flatley (609-208-8204)
10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787
$1,170,000165 Days on yellowkey MLS ID: O6361968
5 Days Off yellowkey (back on 4/2/2026)
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2020Monthly Fee: $159 Tax: $13,997 (2024)Community: Watermark Ph 4Single Family
Taxes:$13,997
Elementary School: Panther Lake Elementary
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Shi Knoblock (407-719-8651)
10472 PETRILLO WAY, WINTER GARDEN, FL 34787
$1,065,00080 Days on yellowkey MLS ID: O6382263
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4025 Built: 2022Monthly Fee: $102 Tax: $12,049 (2025)Community: Winding Bay Ph 2Spa: YesSingle Family
Taxes:$12,049
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Welcome to 10472 Petrillo Way in Winding Bay Preserve, one of Winter Garden’s most desirable communities in Horizon West. Built in 2022, this stunning K. Hovnanian Grayson Model sits on a premium corner, EAST-FACING lot with DISNEY FIREWORK VIEWS and the rare opportunity to watch Space Coast ROCKET LAUNCHES right from your front porch. This home offers 5 bedrooms, 6 bathrooms, a private office, loft, and media room, delivering a spacious and thoughtfully designed layout ideal for luxury living in Central Florida. From the moment you enter, you’re greeted by soaring ceilings, crown molding, tray ceilings, luxury vinyl plank flooring downstairs, engineered hardwood in the upstairs common areas, and a stately wrought iron staircase. A built-in speaker system enhances the home’s elevated design, while ceiling fans sourced from iconic Disney properties add a distinctive touch. The gourmet kitchen anchors the home with GE Profile stainless steel appliances, granite countertops, custom soft-close cabinetry, under-cabinet lighting, a modern hood vent, and an oversized walk-in pantry. The open-concept floor plan seamlessly connects the kitchen to the living and dining spaces, creating the perfect flow for entertaining or everyday family living. The expansive first-floor primary suite offers a serene retreat overlooking the pool, complete with motorized blackout shades, a freestanding soaking tub, dual vanities, a frameless glass walk-in shower, and a spacious walk-in closet. A separate pool bath and a downstairs secondary bedroom with ensuite make this home ideal for guests or multi-generational living, while the private office with French doors provides a quiet and functional work-from-home space. Upstairs, the home continues to impress with a large loft, a dedicated media or theater room wired for surround sound, and three additional bedrooms, each featuring walk-in closets and access to private bathrooms. The layout provides both privacy and flexibility, perfect for growing families or hosting guests. Step outside to your private backyard oasis featuring a custom heated saltwater pool and spa, screened lanai, smart pool controls, fully fenced yard, and peaceful pond views. From the upstairs front bedroom, enjoy magical Disney fireworks lighting up the night sky, a rare and enchanting feature that enhances everyday living. Located just minutes from Walt Disney World, Hamlin Town Center, Flamingo Crossings, and major highways for easy commuting throughout Orlando, this home combines luxury, location, and lifestyle. Residents of Winding Bay Preserve enjoy access to a community pool, playground, and top-rated schools within one of the fastest-growing and most sought-after areas of Winter Garden. If you are searching for a luxury pool home near Disney, a move-in-ready 2022-built home in Horizon West, or a spacious five-bedroom home in Winter Garden with high-end finishes, 10472 Petrillo Way offers exceptional value and an elevated Florida lifestyle. Schedule your private showing and experience one of Winter Garden’s premier homes today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexis Bress (407-900-0771)
441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787
$1,199,90060 Days on yellowkey MLS ID: O6385964
INCREASED by $80,900 (7.2%) on 04/02/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4001 Built: 2000Monthly Fee: $83 Tax: $5,551 (2024)Community: Courtlea OaksSpa: YesSingle Family
Taxes:$5,551
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Jennifer Coon (321-948-8056)
16788 MUSKGRASS DR, WINTER GARDEN, FL 34787
$1,600,00059 Days on yellowkey MLS ID: O6388174
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4733 Built: 2025Monthly Fee: $86Community: Lake Star At Ovation Phase 1BSingle Family
Taxes:$0
Remarks: Stunning single-story luxury residence located in the highly desirable Lake Star at Ovation community in Winter Garden. Built in 2025 by M/I Homes, this expansive home offers over 4,700 sqft of heated living space with 5 bedrooms and 4.5 bathrooms, designed with a modern open-concept layout and high-end finishes throughout. The home features a spacious 3-car garage plus additional storage space, providing both functionality and convenience. The gourmet kitchen includes built-in appliances such as a cooktop, wall oven, microwave, dishwasher, range hood, and wine refrigerator, complemented by elegant stone countertops and a large island ideal for entertaining. Situated on a premium corner homesite, the property offers exceptional privacy with scenic pond views from both the backyard and side of the home. The backyard overlooks tranquil water followed by a conservation area and an additional lake beyond the tree line, creating a layered natural backdrop that ensures long-term privacy with no future construction directly behind the property. From the backyard and main living areas, residents can also enjoy seasonal views of the Disney fireworks in the distance. Located in one of Horizon West’s fastest-growing communities, close to top-rated Water Spring schools, Hamlin Town Center, major highways, and Walt Disney World, this home presents a rare opportunity to own a newer luxury residence with privacy, views, and an exceptional location. Private showings by appointment only. Please contact the listing agent directly to schedule a tour.
Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)
Listing Agent: Pedro Vieira Neto (407-865-1672)
16669 VARONE COVE CT, WINTER GARDEN, FL 34787
$1,399,90091 Days on yellowkey MLS ID: O6375749
Bed: 7 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5613 Built: 2016Monthly Fee: $185 Tax: $15,548 (2024)Community: TwinwatersSpa: NoSingle Family
Taxes:$15,548
Elementary School: Hamlin Elementary
Remarks: Discover Unmatched Elegance in the Coveted Twinwaters Subdivision! Welcome to your dream home, a breathtaking Winter Garden pool residence built in 2016, offering the perfect fusion of sophistication, luxury, and prime convenience. This property isn’t just a house – it’s your personal sanctuary. Grand Entrance That Stuns: Be greeted by an impressive 14-foot foyer adorned with a dazzling crystal chandelier. A beautifully crafted wooden staircase with iron balusters sets the tone for the home’s elevated style. From the moment you step inside, the open-concept layout invites you to explore spaces designed for both comfort and entertainment. Exquisite Interiors: Every detail exudes elegance. Stunning wood plank accent walls, gleaming 30-inch marble tiles, intricate tray ceilings, and granite countertops throughout create a refined yet warm atmosphere. Whether hosting friends or enjoying quiet family moments, this home is the ultimate setting. First Floor Features: Luxurious Master Suite: Tray ceiling, serene ambiance, and ample space for relaxation. Versatile Guest Suite: Ideal for guests or teens, offering privacy and comfort. Functional Spaces: A large and cozy family room, private office, formal living and dining areas, plus a service pantry with wine storage and a separate laundry room. Gourmet Kitchen: A chef’s paradise with a granite island and seating, deep basin sink, custom 50” solid wood cabinets with glass accents, glass tile backsplash, built-in oven and microwave, and a walk-in pantry. Second Floor Highlights: Expansive Upper Lounge: Large windows fill the space with natural light, making it perfect for relaxation. Bonus Room: Create your dream space—whether a music studio, movie theater, gym, or private office. Second Master Suite: Spacious and serene, with luxurious finishes. Four additional bedrooms, each offering comfort and versatility. Outdoor Oasis: Your backyard is a private paradise! A covered lanai overlooks lush landscaping, a pristine vinyl fence, and a sparkling pool. It’s the perfect retreat for relaxation or entertainment. Modern Conveniences: Solar-powered electricity for energy efficiency Whole-home water purification system Tankless water heater Crown molding throughout Tray ceilings and architectural enhancements that elevate the aesthetic Over 25k in Curtain Work Prime Location & Community Perks: Located in the sought-after Twinwaters community, enjoy access to a community pool and recreation area. Nearby, explore Winter Garden Village, Historic Downtown Winter Garden, Walt Disney World, and top-rated schools. Central Florida’s major highways, shopping, dining, and entertainment are all just minutes away. This home is truly one-of-a-kind.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Tony Bardy Assis (407-796-7777)
13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$1,200,00018 Days on yellowkey MLS ID: O6399227
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3389 Built: 1998Monthly Fee: $69 Tax: $10,940 (2025)Community: Sunset LakesSpa: YesSingle Family
Taxes:$10,940
Remarks: Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Diane Sterling (407-761-0512)
1675 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,149,90046 Days on yellowkey MLS ID: O6392108
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4299 Built: 2017Monthly Fee: $184 Tax: $12,008 (2024)Community: TwinwatersSingle Family
Taxes:$12,008
Elementary School: Whispering Oak Elem
Remarks: One or more photo(s) has been virtually staged. Seller is offering up to $10,000 in concessions, creating an exceptional opportunity for today’s buyer. Where natural light, space, and lifestyle align. Presenting a rare opportunity to own a beautifully designed, move-in ready luxury residence that seamlessly blends elegance, functionality, and the life you desire. From the moment you arrive, the home’s tile roof, balcony, and charming front porch set the tone for a refined yet inviting experience. Situated on one of the community's few homesites offering a balcony, conservation views, no rear neighbors, this home stands apart in both design and presence. Step inside to an extended foyer with 10-foot ceilings, creating a grand and welcoming entrance. Thoughtfully designed with both entertaining and everyday living in mind, this home features a formal living room, along with a formal dining space that carries the same elevated feel. A conveniently placed powder bath, and an under-stair closet, add to the home’s functionality. As you move into the main living area, you’re greeted by a stunning two-story family room filled with abundant natural light. The open-concept layout flows seamlessly into a chef-inspired kitchen featuring ceiling-height cabinetry, quartz countertops, stainless steel appliances, wine fridge, and a butler’s pantry alongside a spacious walk-in pantry. A dedicated café area overlooks a serene conservation backdrop, offering uninterrupted sunrise views and a peaceful setting that truly captures the beauty of Florida living. The first-floor primary suite is privately positioned and thoughtfully designed, featuring tray ceilings, and tranquil backyard views. The spa-like primary bath includes a soaking tub, walk-in shower, dual vanities, private water closet, and a spacious custom walk-in closet with built-in shelving and drawers. For added convenience, the closet connects directly to the laundry room, pre-plumbed for a sink. Additional features on the main level include a drop zone, three-car garage access, and ceiling speakers. Upstairs, engineered hardwood flooring leads you to an expansive loft that opens to the private balcony, creating a seamless indoor-outdoor retreat. The second level also features a large game room, a dedicated media room pre-wired for a projector and sconces, and three additional bedrooms, all with walk-in closets. Two bedrooms share a Jack-and-Jill bath, while an additional en-suite and half bath provide comfort and flexibility for family and guests. Throughout the home, you’ll find elevated upgrades including 8-foot interior doors, extended sliding glass doors, and a motorized screened-in lanai, plus a backyard ready to be customized to your vision. Located in a highly desirable community with A-rated schools, residents enjoy access to a community pool, playgrounds, and scenic walking trails. The home is ideally positioned just minutes from everyday conveniences: shopping, dining, fitness, and entertainment options. Enjoy quick access to Florida’s Turnpike, connecting you to all Orlando offers, major sporting and entertainment venues, and Orlando International Airport within apprx. 30 minutes. Disney World is just 25 minutes away, while Hamlin, and Historic Downtown Winter Garden's charming farmers markets, local events, and vibrant community atmosphere are just minutes from your doorstep. Tucked away for privacy, yet close to everything that matters, this home delivers the perfect balance of peace, convenience, and lifestyle.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kenard Walker, Jr (407-779-2911)
17144 PHIL C PETERS RD, WINTER GARDEN, FL 34787
$2,550,000507 Days on yellowkey MLS ID: O6260561
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4633 Built: 1982 Tax: $1,591 (2023)Community: Lake Avalon Groves RepSpa: YesSingle Family
Taxes:$1,591
Tax Year: 2023
Remarks: Pre-Construction. To be built. 4633 sq ft of living space, set on a sprawling 2.5 acre lot. Choose from this 4 Bedroom, 4.5 Bathroom, 4 Car Garage Custom Home or Lionshead Homes will design an alternative floor plan just for you! The property exudes tranquility with its lush mature landscape, offering ample room for a pool, outdoor activities, gardening, or farm animals. Inside, the home features a modern layout with luxurious finishes, a spacious kitchen, formal and informal dining, office, game room and a lavish Master Suite which features double tray ceilings, his and her closests, large shower and a freestanding tub. Outside, the large lot provides privacy and a peaceful escape, while still being conveniently close to Winter Garden’s vibrant amenities, including shopping, dining and top-rated schools. Ideal for Homeowners seeking a rural escape without compromising accessibility. Alternative floor plans for this homesite are available upon request.
15195 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787
$1,295,00052 Days on yellowkey MLS ID: O6389732
5 Days Off yellowkey (back on 4/16/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3844 Built: 2016Monthly Fee: $235 Tax: $8,393 (2025)Community: Hickory Hammock Ph 2BSpa: YesSingle Family
Taxes:$8,393
Remarks: Under contract-accepting backup offers. Exceptional Lakefront Pool Home in the Gated Community of Hickory Hammock in Winter Garden. Positioned on a quiet cul-de-sac overlooking Lake Claire and Johns Lake Conservation, this impeccably maintained 4-bedroom, 3-bath residence showcases 3,844 square feet of thoughtfully designed living space and a 3-car tandem garage, seamlessly blending luxury, comfort, and the Florida lakefront lifestyle. The private outdoor retreat is designed for unforgettable entertaining, featuring a resort-style saltwater pool and spa with sun shelf, pool heater (2017), fire bowls, and wireless controls for the pool, spa, lighting, and water bowl. A dramatic two-story screened enclosure frames the outdoor living space while preserving peaceful lake and conservation views, creating the perfect setting for relaxing or entertaining while enjoying the tranquil waterfront setting. Inside, the home blends elegance and functionality with tile flooring throughout the first floor and engineered hardwood on the stairs and bonus room. The expansive family room features a stacked stone fireplace with wood mantle, creating a warm focal point for gatherings. Crown molding, upgraded lighting, and thoughtful details are carried throughout. The chef’s kitchen is ideal for everyday living and entertaining, showcasing espresso cabinetry, a large quartz island, glass tile backsplash, and an updated butler’s pantry and bar area with quartz counters, custom shelving, and designer tile accents. The first floor includes a bedroom and full bath, ideal for guests or multi-generational living, and all secondary bathrooms throughout the home have been beautifully updated, creating a cohesive, move-in-ready feel. An oversized custom laundry room features a sink, folding station, walk-in storage, quartz counters, and negotiable washer and dryer. Upstairs, the primary suite offers a private balcony with sweeping views of Lake Claire, conservation, and the sparkling pool below. Step onto the private balcony and take in the serene views of the pool and Lake Claire, creating a peaceful retreat to start or end your day. The fully renovated spa-style primary bathroom includes dual vanities, a glass-enclosed tile shower with rain head, and a freestanding soaking tub. A custom primary closet and flex room perfect for an office or nursery, separated by a barn door, add versatility. Additional upgrades include smart heated toilets throughout, Sonos sound system with three zones, Trex garage flooring, a 50-amp EV charger, whole-house water softener and filtration system, new dishwasher (2025), and interior and exterior paint within the last four years. The solar panels will be paid off at closing, providing energy savings, and a termite bond is in place. Residents of Hickory Hammock enjoy resort-style amenities including a clubhouse, fitness center, community pool, fishing pier, tennis courts, volleyball courts, dog park, playground, walking trails, and golf-cart friendly streets. Conveniently located near downtown Winter Garden, Winter Garden Village, major highways, and approximately 20 miles to Orlando International Airport. A rare opportunity to enjoy private lakefront living in one of Winter Garden’s most desirable gated communities.
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Denise Gregorie (407-463-0080)
15161 CANOE PL, WINTER GARDEN, FL 34787
$1,200,00020 Days on yellowkey MLS ID: O6398949
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3816 Built: 2019Monthly Fee: $385 Tax: $13,235 (2025)Community: Lakeshore Preserve Ph 2Single Family
Taxes:$13,235
Remarks: Welcome to this beautifully appointed home in the highly desirable Lakeshore community in Winter Garden, offering an exceptional combination of space, comfort, and location. Situated in a prime area close to top-rated schools, shopping, dining, and major roads, this residence is ideal for buyers seeking both convenience and an outstanding lifestyle. This spacious home features 5 bedrooms, 4 full bathrooms, and 1 half bath, with a highly functional and attractive floor plan. Upon entry, you are welcomed by a private first-floor suite, perfect for guests, in-laws, or a home office with added privacy. Upstairs, you will find the remaining bedrooms, including the generous primary suite, along with a huge loft that offers endless possibilities for a media room, playroom, second living area, or home workspace. The home also features a formal dining room, while the kitchen, breakfast area, and family room flow seamlessly together in an open-concept layout that is ideal for both everyday living and entertaining. Step outside to enjoy the brand-new outdoor gourmet area, creating the perfect setting for gatherings, weekend barbecues, and relaxed Florida living. Residents of Lakeshore enjoy access to excellent community amenities, including a well-appointed clubhouse, fitness center, and playground, all contributing to a vibrant and welcoming neighborhood atmosphere. This is a rare opportunity to own a spacious, well-located home in one of Winter Garden’s most attractive communities.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Maqueli Gewehr (863-258-5656)
5401 BOWMAN DR, WINTER GARDEN, FL 34787
$1,250,00023 Days on yellowkey MLS ID: O6390128
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4044 Built: 2015Monthly Fee: $214 Tax: $9,108 (2025)Community: Overlook At HamlinSpa: YesSingle Family
Taxes:$9,108
Remarks: Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin community, home of top-rated schools. This exceptional pool home is perfectly positioned on a premium oversized lot offering over 4k SF with lake views in the front and fireworks views in the back. The thoughtfully designed living space has a northwest-facing orientation, allowing you to enjoy breathtaking sunrise views from your backyard oasis and stunning sunset views from the front. This luxurious and meticulously maintained upgraded home features 4 to 6 bedrooms, 3.5 bathrooms, and a highly desirable first-floor primary suite designed for comfort and privacy. The open-concept floor plan is enhanced by a spacious loft and multiple flex spaces, including dedicated offices or additional bedrooms on both levels, each with elegant French doors. The expansive living area is anchored by a custom 20-foot entertainment wall complete with built-ins, a fireplace, and integrated sound, creating the perfect setting for both relaxation and entertaining. The chef’s kitchen is a true showpiece, upgraded with brand-new commercial-style Café luxury appliances (2026), gas cooktop, custom cabinetry with soft-close features, designer backsplash, upgraded lighting, and an oversized custom pantry with a butler’s area. Multiple dining spaces, including a formal dining room and eat-in kitchen, offer versatility for gatherings both large and intimate. Additional major upgrades provide peace of mind and modern efficiency; two brand-new Carrier AC systems (2026) with a 10-year warranty, whole-house water purification and softener system, and new LED lighting in the pool. The home also includes 2 tankless gas water heaters and features high-end finishes throughout, including commercial-grade luxury vinyl flooring, premium carpeting, fresh interior paint, designer lighting, and smart home enhancements such as remote-controlled window treatments and extensive wall-mounted TV connections. Step outside to your private resort-style retreat, featuring a custom 600-square-foot saltwater pool with marble decking, sun shelf, waterfall features, and panoramic screened enclosure designed to maximize views of Disney fireworks. A separate spa, added in 2024, creates the ultimate relaxation experience. The outdoor living space is complete with a fully equipped summer kitchen, built-in bar, tongue-and-groove ceilings, and professionally designed landscaping with privacy hedges and palm trees. With no direct rear neighbors and a dry retention pond behind, this home offers exceptional privacy and serene surroundings. Additional exterior highlights include an extended driveway, oversized two-car garage with space for a golf cart, full fencing with multiple access points, exterior lighting, gutters, and security features, including cameras and motion lighting. Located just a half-mile from Hamlin Town Center, this home is accessible via walking trails, golf cart, or a 1-minute drive to shopping, dining, and entertainment. Residents of the Overlook community enjoy resort-style amenities, including a clubhouse, fitness center, community pool with splash area, walking trails, dog park, playgrounds, fishing pier, and private boat ramp access to Lake Hancock. This is a rare opportunity to own a move-in-ready luxury home in one of Winter Garden’s most desirable locations, where you can experience elevated Florida living at its best. Set up a showing today before it's gone.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
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