Location: Winter Garden
Do Not Show Listings
17608 DEER ISLE CIR, WINTER GARDEN, FL 34787
$1,025,000199 Days on yellowkey MLS ID: O6350825
REDUCED by $25,000 (2.4%) on 04/20/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3144 Built: 1997Monthly Fee: $207 Tax: $6,334 (2024)Community: Deer Island Ph 02Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,334
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: Bring your ideas to a truly exceptional custom home, perfectly situated in a private, gated community on the shores of breathtaking John’s Lake. Set on over an acre of a beautifully updated landscaped property with panoramic water views throughout the island, this 4-bedroom estate offers the ultimate Florida lifestyle — complete with resort-style amenities and convenient access to Historic Downtown Winter Garden, as well as Downtown Orlando and major attractions just 30 minutes or less away. Your ideas await as charm and craftsmanship are evident in every detail. Step through the front door into an inviting floor plan that seamlessly blends elegance with functionality. The spacious living room is anchored by a cozy wood-burning fireplace, enhanced by warm canned lighting and plantation shutters that frame every window. Wood flooring flows throughout the main living areas, setting a tone of timeless sophistication. The kitchen features granite countertops, KraftMaid cabinetry, Sub-Zero refrigerator, cooktop, double ovens, and a large pantry. The open design keeps the heart of the home connected to the main living space — ideal for entertaining and family gatherings but separate enough to hide the meal prep! The primary suite is a peaceful retreat, with serene views of the pool, dual walk-in closets, garden tub, separate shower, and a cleverly designed storage area. The home's split-bedroom layout ensures privacy for guests and family alike and are all thoughtfully located on the first floor. Upstairs, two large bonus rooms offer endless possibilities — from a playroom to a home theater — and includes a hidden safe room / office with skylights and easy attic access for extra security and utility. The 3 car garage features extra width for additional storage and Gladiator garage organizational wall units. Step outside into your private backyard paradise, where a sparkling saltwater pool and attached hot tub await, surrounded by pavers and an outdoor grilling station. Whether hosting a summer barbecue or enjoying a quiet evening under the stars, this backyard fenced-in space delivers year-round relaxation. Eight outdoor security cameras offer peace of mind, while a three-car garage and spacious driveway provide ample storage and parking. An in-wall pest control system, central vacuum, built-in wine bar, hidden storage and closet organization are examples of many upgrades throughout the home. This home also boasts a well water system with a full purification setup, and a laundry room inside with washer, dryer and utility sink included. Beyond the home itself and its many additional upgrades, the Deer Island community offers unparalleled amenities, including a community boat ramp for direct access to John’s Lake — perfect for boating, fishing, and water sports — as well as two catch and release fishponds, basketball courts, tennis courts, pickleball facilities and easy access to the West Orange bike trails. With stunning lake views, lush surroundings, and a true sense of privacy, this is a place where families grow, memories are made, and every day feels like a getaway. Don’t miss the opportunity to own this fabulous home, where elegance meets comfort and lifestyle meets location.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Karen Jacobs (407-579-0062)
17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787
$757,9907 Days on yellowkey MLS ID: G5111222
0 Days Off yellowkey (back on 4/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,726 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The Arlington is perfect for families of all sizes!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787
$559,00062 Days on yellowkey MLS ID: O6384745
REDUCED by $6,000 (1.1%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2472 Built: 2021Monthly Fee: $257 Tax: $7,417 (2025)Community: Waterleigh Ph 3B 3C & 3DSpa: NoSingle Family
Taxes:$7,417
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Welcome to the highly desirable Horizon West community of Waterleigh, where lifestyle, connection, and convenience come together in one of the area’s most vibrant and family-focused neighborhoods. The Clearden model is one of the most sought-after floor plans in the community, offering 4 bedrooms, 3.5 bathrooms, and a highly desirable full guest ensuite on the primary floor with its own private bath, perfect for multigenerational living, visiting in-laws, or out-of-town guests. Designed with families and entertaining in mind, the open-concept layout flows effortlessly throughout the main living areas. The kitchen features sleek stainless steel appliances, generous counter space, and abundant natural light, creating the perfect setting for both everyday living and special gatherings. Upstairs, the spacious loft provides a versatile retreat ideal for a media room, playroom, home office, or additional lounge space. As an added bonus, you can enjoy Disney fireworks right from your home, bringing a touch of magic to your evenings. Location truly sets this home apart. You are walking distance to the Phase 3 amenity center, with the resort-style pool just steps away. Waterleigh residents enjoy exclusive access to multiple pools, tennis courts, pickleball courts, fitness centers, volleyball, mini golf, scenic walking trails, and expansive green spaces. This golf cart-friendly community is filled with events and activities year-round, fostering a strong sense of community and connection for families of all ages. Zoned for A-rated schools, with both Atwater Bay Elementary and Water Spring Middle school conveniently located within the community, daily life is effortless. You’ll also enjoy nearby conveniences including Publix, Jersey Mike’s, a boutique nail salon, and Kiddie Academy, along with fine dining, shopping, and quick access to major highways just minutes from Disney. This is more than a home, it’s a lifestyle opportunity in one of Central Florida’s most dynamic and desirable communities. Don’t miss your chance to own this beautiful move in ready home in Waterleigh. Schedule your private tour today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
12934 CANOPY WOODS WAY WAY, WINTER GARDEN, FL 34787
$1,350,00042 Days on yellowkey MLS ID: O6390704
REDUCED by $20,000 (1.5%) on 04/19/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3665 Built: 2018Monthly Fee: $299 Tax: $12,379 (2025)Community: Canopy Oaks Ph 1Spa: YesSingle Family
Taxes:$12,379
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: On a quiet street, under Canopy of oak trees, residents enter the community’s gated entrance into a secluded community of 49 luxury homes. Situated on a corner lot the SANIBEL model home aka “The Castle” that won the Excel Award for THE BEST MODEL IN FLORIDA. It is a 4BR/ 4.5 Ba/ 3-car garage. This beauty comes with large entertainment areas inside and out. On the 1st floor you’ll find : Wine Cellar, Jr. Owner’s Suite, Flex/Office & a Guest Bath. Magnificent Chef’s kitchen, at the heart of the house, and features 42” cabinetry with second-tier upper lighted hutch stack for oven space. The cabinet-front door to the pantry eloquently blends with the cabinetry of the entire kitchen. 2nd Floor, the Owner’s Suite master bedroom w/balcony access. Also on this level is a large gathering room, 2 more bedrooms w/en-suite baths & large laundry room. Stunning Oasis backyard with a resort style salt-water pool & spa with a summer kitchen under a covered pergola. Built in surround sound In and outside. Just a few minutes from Plant St. Winter Garden Downtown, Winter Garden Village Shopping, Disney World, and toll road access to Downtown Orlando. This is a true Owner’s retreat.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Christian Ngoie (407-705-7525)
3633 TURNINGWIND LN, WINTER GARDEN, FL 34787
$750,00011 Days on yellowkey MLS ID: S5147897
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3412 Built: 2003Monthly Fee: $115 Tax: $5,047 (2025)Community: Windward Cay 48 125Single Family
Taxes:$5,047
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: One or more photos have virtual staging. Located in the sought-after WINDWARD CAY community, where homes rarely come onto the market – this Spacious Pool Home is now Winter Garden’s best buy! Homesite location is at the end of Turningwind Ln., on a Cul-de-Sac, POND-FRONT w/Wooded Area adjacent – a premium location within the community ** This home has been meticulously prepared for the market and is in complete “turn-key condition” throughout. EXTERIOR & INTERIOR FRESHLY PAINTED this April, along with BRAND NEW LAMINATE WOOD installed in Formal Living, Dining & Family Rooms, BRAND-NEW CARPETING installed throughout the rest of the interior, with original Ceramic Tile (mint condition) in high-traffic spaces and wet areas ** New Light Fixtures installed in Dining Room & Kitchen Casual Dining space. NEW POOL SCREENING installed on 4/13/26 ** Primary floor features Formal Living & Dining Rooms at Entry, with Crown Molding accenting the spaces. The Formal Living Room can function as a Home Office as an alternative use for the space. The OPEN FLOOR PLAN flows from the formal spaces to the Spacious Family Room & HUGE Kitchen w/Large Casual Dining Area. There is an abundance of Cabinetry (medium-tone wood), Corion Countertops, and all Appliances Convey – including Washer/Dryer in the adjacent laundry room, which includes a wash tub ** Bedroom #5 is an ideal “guest bedroom” with “pool bath” adjacent, featuring a beautifully REMODELED SHOWER ** Second floor features a HUGE PRIMARY SUITE w/Tray Ceiling & Crown Molding, (2) WI Closets, Linen Closet, En-Suite Bathroom w/Dual Sinks, Jetted Garden Tub, Shower & Water Closet. Bedrooms #2, #3 are both Large with WI Closets, Bedroom #4 has built-in closet ** The HUGE BONUS ROOM is at end of the corridor, with adjacent FULL BATHROOM w/Shower. The Bonus Room offers a multitude of uses including game room, teen hide-away, craft room, etc. A hallway bathroom serves the spare bedrooms upstairs, along with the bonus room full bathroom ** Finally, the Family Room has (2) sets of sliders – opening up onto the Large Covered Lanai and Screened Pool with Pond Frontage, and adjacent Wooded Area. The child-safety-gate is located in the garage, with spare paint and extra paint/flooring materials. The Cul-de-Sac location means slow traffic and better safety for pets & play ** Important improvements include: Roof replaced Jan 2018; Pool Resurfaced/Retiled in 2018, and HVACs are dated 2017 (lower), 2012 (upper); both serviced this April ** Room sizes are approximate and may be verified by buyers ** This home has been meticulously prepared for the market and is priced to sell quickly! Check the comps in Windward Cay and you will find that fully renovated homes here sell for MUCH HIGHER PRICES ** Windward Cay is located a short drive from the Winter Garden Village Shopping Center, featuring Target, Lowes, Best Buy and many other shops and restaurants. The wildly popular “Downtown Plant Street area” is roughly a 10-min drive away, featuring quaint shops, restaurants, Crooked Can Brewery and various activities and events year-round. SR 429 is by Winter Garden Village, with access to I-4, the Florida Turnpike, and all destinations throughout Central Florida including Disney, Universal Orlando Theme Parks, Florida Beaches and so much more ** Be sure to view all photos and 3-D walk-through tour! Virtually staged photos are not guaranteed to match actual photos, including room size, color, dimension, etc.
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Frank Plesko (407-421-6412)
1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787
$519,900240 Days on yellowkey MLS ID: S5133690
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2035 Built: 2001Monthly Fee: $33 Tax: $6,403 (2024)Community: Tuscany Ph 02Single Family
Taxes:$6,403
Elementary School: Maxey Elem
High School: Ocoee High
Remarks: Golf cart district * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden.It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Mingke Li (352-973-2303)
5340 BOWMAN DR, WINTER GARDEN, FL 34787
$2,195,00012 Days on yellowkey MLS ID: O6398618
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5749 Built: 2017Monthly Fee: $230 Tax: $16,854 (2026)Community: The Cove At HamlinSingle Family
Taxes:$16,854
Tax Year: 2026
Remarks: Lakefront living, done at scale. Set along approximately 160 feet of shoreline on Lake Hancock, this five-bedroom, six-and-a-half-bath residence delivers expansive water views, refined finishes, and a layout designed for both everyday living and effortless entertaining. From the moment you enter, soaring ceilings, arched architectural details, and wide-plank hardwood floors create a sense of openness and flow. A wall of arched windows floods the home with natural light and draws your eye straight through to the lake beyond. At the center, a chef’s kitchen anchors the space—featuring a generous island, porcelain farm sink, custom cabinetry, glass tile backsplash, and a full suite of Wolf and Sub-Zero appliances. The kitchen opens seamlessly to the family room and breakfast area, all positioned to capture the view. The primary suite is tucked privately on the main level, offering a true retreat with tranquil lake views, a spa-style bath with soaking tub and walk-in shower, dual vanities, and an oversized closet. Upstairs, four additional bedrooms with en-suite baths are complemented by a spacious game room and dedicated media room—creating separation and flexibility for guests or family. Outdoor living is just as compelling. A covered lanai and upper-level balcony overlook the water, with ample space to design a custom pool and private dock. Located near Hamlin Town Center, Winter Garden Village, and major roadways, the home offers both convenience and a true waterfront lifestyle, with community amenities including a pool, fitness center, playgrounds, and dock access
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
16137 WIND VIEW LN, WINTER GARDEN, FL 34787
$575,000246 Days on yellowkey MLS ID: O6335769
REDUCED by $14,000 (2.4%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2016Monthly Fee: $283 Tax: $6,800 (2024)Community: WaterleighSingle Family
Taxes:$6,800
Elementary School: None
Remarks: Price Improvement! This beautiful home offers the best value in the neighborhood. More than 10K in upgrades. See attached Features sheet. A perfect balance of comfort, style and convenience in one of Winter Garden's most sought-after communities-Waterleigh....offering the best in resort-like amenities! A preferred lender credit of up to $2,000 toward buyer's closing costs is being offered. This 4 Bedroom, 3.5 Bathroom Cleardon model home is truly turn-key. Fantastic location in calm & peaceful phase 1 with no neighbors behind and a park in front. Showcasing a bright, spacious interior with open floor plan, loft space and plenty of storage and quality finishes delivering on style and value. A few highlights include Luxury Vinyl Plank with a refined hardwood aesthetic throughout the entire home, No carpet anywhere, a beautiful stacked-stone wall anchoring the family room, upscale window hardware, on-trend greenery feature-wall in the lanai which is completely screened in, fenced rear yard, pavered patio, large front porch, 2nd floor balcony, 2 car garage with added overhead storage racks, pavered driveway with rear alley access. Waterleigh living means enjoying resort-style amenities everyday! 3 beautiful pools, lakes, clubhouses, 3 fitness centers, playgrounds, walking trails, beach volleyball, dog park, mini golf and more. The low HOA also provides residents with lawn and landscape maintenance. Zoned for top rated schools. Located near downtown Winter Garden and quick access to all major commuter roadways, restaurants, shopping, the magic of Disney and Orange County National Golf Course are all nearby. Something for everyone and the Best of Winter Garden! Make an appointment for a private tour today! Click on the link for a walk thru 3D tour!
Listing is courtesy of: IRON VALLEY REAL ESTATE CENTRAL FLORIDA (407-203-9595)
Listing Agent: Leslie Weeks (215-873-7674)
671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,325,00048 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)
14626 BLACK QUILL DR, WINTER GARDEN, FL 34787
$799,90010 Days on yellowkey MLS ID: O6399975
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2907 Built: 2016Monthly Fee: $215 Tax: $6,816 (2025)Community: Overlook At HamlinSpa: YesSingle Family
Taxes:$6,816
Elementary School: Independence Elementary
Remarks: MINT CONDITION 4 bedroom pool home in Overlook at Hamlin! Original Owners have taken great care of this Taylor Morrison Jamestown model with EXTENDED PRIMARY SUITE AND EXTENDED LANAI! Natural Gas Community! GAS cooktop and GAS Tankless Hot Water Heater. Lots of crown moldings and picture frame moldings throughout. PLANTATION SHUTTERS as well. NEW AC SYSTEM 2025! The Outdoor space features a GAS HEATED SPOOL (Yes, combination Pool and Spa!) Travertine Decking and screened enclosure. The back yard is also fenced for privacy and pets. There is also a space for pets with synthetic turf, so no cutting grass in the backyard. Beyond the pool area is a dry retention area, so NO REAR NEIGHBORS! This property is expected to go quickly so don't delay in making your appointment!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Thomas Moffett (407-375-6498)
936 KYLEE ALY, WINTER GARDEN, FL 34787
$675,00031 Days on yellowkey MLS ID: O6393910
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
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)
9354 MCLAREN ALY, WINTER GARDEN, FL 34787
$529,50045 Days on yellowkey MLS ID: O6390060
REDUCED by $15,500 (2.8%) on 04/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2014 Built: 2020Monthly Fee: $257 Tax: $614 (2025)Community: Waterleigh Ph 3ASingle Family
Taxes:$614
Remarks: Welcome to resort-style living in the HIGHLY sought-after Waterleigh community in Winter Garden! This beautifully maintained home offers the perfect blend of comfort, upgrades, and an unbeatable location just minutes from world-class attractions and everyday conveniences! Situated on a special lot with an open green area right in front of the home, you’ll enjoy a sense of space that’s perfect for families to play, neighbors to gather, or simply relaxing outdoors while enjoying the peaceful surroundings. Step inside and you’ll immediately notice the beautiful luxury vinyl plank and ceramic tile flooring throughout the home, NO carpet, giving the space a clean, modern feel while also being durable and easy to maintain. The layout is designed with convenience in mind, featuring the primary suite on the first floor, creating a peaceful retreat with privacy and easy access at the end of the day. The laundry room is also located downstairs, making daily routines simple and efficient. Upstairs, you’ll find two additional bedrooms along with a versatile loft space that can easily become a playroom, movie lounge, study area, or even a home office, perfect for growing families or anyone who wants flexible living space! One of the highlights of this home is the extended lanai with a screened birdcage enclosure, creating a comfortable outdoor living area where you can enjoy morning coffee, host weekend barbecues, or unwind in the evenings while enjoying the Florida breeze. Additional thoughtful touches include an upgraded blind for the screened door, and a Murphy bed upstairs that will remain with the home, offering extra convenience for guests or multi-use spaces. Living in Waterleigh means enjoying a lifestyle that truly feels like a year-round vacation. Residents have access to four incredible amenity centers with multiple resort-style pools, fitness centers, tennis courts, pickleball courts, sand volleyball, walking trails, and even mini putt-putt. Even better, LANDSCAPING IS INCLUDED in the HOA, allowing you to spend less time on yard work and more time enjoying the community. The home is also just a short distance from the Phase 3 amenity center, making it easy to take advantage of everything Waterleigh offers. Families love the location, especially being zoned for highly rated schools including Atwater Bay Elementary School, Water Spring Middle School and Horizon High School. Everyday conveniences are right within the community, including Publix, a nail salon, and dining options like McDonald's and Jersey Mike's! Waterleigh is also a golf-cart-friendly neighborhood. You’ll also appreciate being just minutes from entertainment and shopping like PopStroke, Cinépolis Luxury Cinemas, and TJ Maxx! Residents can even catch glimpses of the fireworks from Walt Disney World Resort lighting up the sky! If you’ve been looking for a home where comfort, community, and lifestyle come together, this is the kind of place where lasting memories are made. Schedule your private showing today!
393 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787
$615,000101 Days on yellowkey MLS ID: O6374079
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2684 Built: 2002Monthly Fee: $117 Tax: $2,690 (2025)Community: AmberleighSingle Family
Taxes:$2,690
High School: None
Middle School: None
Remarks: Located in a quiet, gated community within a highly rated school zone, this well-maintained home offers comfort, privacy, and thoughtful upgrades. The home features two AC systems, including a main unit with an electronic air cleaner, a high-efficiency water heater, and a whole-house reverse osmosis and water softening system, along with updated double-pane windows on the back of the home. A NEW ROOF (2024) adds long-term peace of mind. Inside, you'll find 18.5-foot ceilings in the family room, plantation shutters, custom drapes, and ceiling fans, with wood flooring and travertine tile that complement each other throughout. The kitchen is finished with granite countertops, tile backsplash, a cherry wood bar top, and quality appliances. With a private backyard that is great for cookouts you can enjoy the gated living in a home ideally located near major highways, Central Florida attractions, and Downtown Winter Garden. - Schedule your tour today!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
15183 SERENADE DR, WINTER GARDEN, FL 34787
$789,00014 Days on yellowkey MLS ID: O6398436
1 Days Off yellowkey (back on 4/19/2026)
Bed: 7 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4438 Built: 2010Monthly Fee: $167 Tax: $3,859 (2024)Community: Belle Meade Ph 02 HSingle Family
Taxes:$3,859
Elementary School: Whispering Oak Elem
Remarks: Under contract-accepting backup offers. Priced below market value and packed with exceptional upgrades, this stunning home in the highly sought-after Belle Meade community is an incredible opportunity. Offering over 4,400 square feet of living space, this spacious 7-bedroom, 4-bathroom residence features oversized bedrooms and soaring ceilings on both levels, creating an open and airy feel throughout. Designed for both comfort and entertaining, the upstairs bonus room includes its own bar, while the air-conditioned sunroom provides the perfect space to relax and enjoy year-round. Step outside to a fully fenced backyard set on more than a quarter acre, complete with two mature mango trees for a true Florida touch. This home also offers outstanding peace of mind with major recent improvements, including a new roof in 2023, new windows, a whole-house water filtration system, and fully paid-off solar panels—an incredible value and long-term savings for the next owner. Families will love the top-rated school zoning for Whispering Oak Elementary, Sunridge Middle, and West Orange High, along with the added convenience of being directly across from Foundation Academy, one of Winter Garden’s premier private schools. For recreation and leisure, West Orange Country Club is just one mile away, offering golf, tennis, and more. Ideally located near Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and New Independence, this home also provides easy access to Disney, Universal, Orlando International Airport, and major highways including the 429, Turnpike, and 408. This is the perfect blend of size, upgrades, location, and value—schedule your private showing today.
Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)
Listing Agent: Brandt Myers (407-758-7166)
15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787
$579,90011 Days on yellowkey MLS ID: O6396640
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2626 Built: 2013Monthly Fee: $128 Tax: $6,746 (2025)Community: Johns Lake Pointe A & SSingle Family
Taxes:$6,746
Remarks: Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjacent to the John Lake Conservation Area, you'll also enjoy easy walking and biking access to Tucker Ranch, the future site of a holistic wellness center, teaching farm, playground and family activity hub. Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.25-acre corner lot. Enjoy the comfort of a newer A/C unit and handler installed in January 2025 and freshly painted interiors (2022) that create a crisp, modern ambiance. The spacious eat-in kitchen features a large island with seating for four, ample cabinetry, a custom pantry, and extensive counter space—perfect for gatherings or morning routines. The first floor features a flexible private bonus room that can easily serve as a home office, study, or a welcoming fifth bedroom for overnight guests. The primary suite includes a beautifully crafted walk-in closet, while the custom laundry room offers built-in cabinetry and a convenient hanging bar for added functionality. Just beyond the living space, the screened-in lanai invites you to relax and unwind. Situated on a prime corner lot, the property also boasts a generously sized yard with endless potential for outdoor enjoyment. The epoxy-coated two-car garage is both functional and stylish, freshly painted and equipped with motion-sensor lighting for your convenience. This Meritage home is solid construction with 6 panel doors throughout and spray foam insulation in the attic. Community amenities include a pool, clubhouse, fitness center, yoga studio, pickleball and tennis courts—everything you need for a vibrant, active lifestyle. With its thoughtful design, abundant amenities, and unbeatable location, this home offers the perfect blend of comfort, convenience, and community.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lauren Marason (610-223-7086)
711 BURCH AVE, WINTER GARDEN, FL 34787
$400,000279 Days on yellowkey MLS ID: O6328082
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1154 Built: 2003 Tax: $1,837 (2024)Community: BurchshireSingle Family
Taxes:$1,837
Remarks: Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all the charm and convenience of Winter Garden living. One great bonus is the additional room with its own private entrance—perfect for a home office or a guest space. Step outside to your own private backyard retreat. Shops, restaurants, parks, and the West Orange Trail just a short drive away, this home offers the perfect blend of comfort, character, and location in one of Central Florida’s most desirable communities.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Carina Davis (407-242-2925)
10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787
$1,170,000157 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
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)
869 BENDING OAK TRL, WINTER GARDEN, FL 34787
$535,000167 Days on yellowkey MLS ID: O6358341
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1975 Built: 2012Monthly Fee: $109 Tax: $5,262 (2024)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$5,262
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in The Oaks at Brandy Lake; Situated in the highly desirable golf cart district of Winter Garden. The home offers an open-concept layout featuring a spacious dining and living area with sliding glass doors that leads to a covered patio and FENCED back and side yard. The kitchen includes stainless steel appliances (New Refrigerator 2024), (New Garbage Disposal 2025) and generous counter space. The home features FULLY PAID SOLAR PANELS and rear 2-car garage (New Garage Door Opener 2025) and ample parking in the front of the home. Residents have access to community amenities including a pool and playground. Conveniently located a little over 1 mile away from Downtown Winter Garden, you can enjoy the weekly Farmer's Market and plethora of shops and restaurants. You also have access to major highways (about a 5 minute drive to 429 and Turnpike).
Listing Agent: Xiomara Pratts (407-993-2865)
13259 SERENE GLADE RD, WINTER GARDEN, FL 34787
$778,5318 Days on yellowkey MLS ID: G5111211
0 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2689 Built: 2026Monthly Fee: $160Community: Serenade At OvationSingle Family
Remarks: One or more photo(s) has been virtually staged. Under Construction. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando, where Dream Finders Homes proudly presents Serenade at Ovation. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or exploring local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.“includes high speed fiber optic internet”
12050 BRACCO ST, WINTER GARDEN, FL 34787
$489,9008 Days on yellowkey MLS ID: O6398494
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2023Monthly Fee: $110 Tax: $7,195 (2025)Community: Highland RidgeSingle Family
Taxes:$7,195
Remarks: Modern Living Meets Prime Location in Horizon West! Welcome to this stunning 2023-built Meritage Home in the sought-after Highland Ridge community. This energy-efficient "Bungalow" style residence features 3 bedrooms, 2.5 bathrooms, and a versatile second-floor loft—perfect for a home office or media room. The open-concept main floor boasts a gourmet kitchen with a large quartz island, sleek cabinetry, and stainless steel appliances, all flowing into a bright living area bathed in natural light thanks to its desirable Southern exposure. Energy Efficiency: Built with Meritage’s signature spray-foam insulation and Energy Star appliances, ensuring year-round comfort and significantly lower utility bills. Community & Location: Enjoy resort-style amenities including a pool, cabana, pickleball courts, and playground. Ideally located just minutes from Walt Disney World via Western Way and walking distance to the vibrant Flamingo Crossings Town Center for dining, shopping, and entertainment. Quick access to SR-429 makes commuting a breeze. Don’t miss your chance to own a like-new home in Winter Garden’s fastest-growing corridor!
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Clarisse Sousa (407-873-0458)
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