Location: Winter Garden , 34787
Do Not Show Listings
936 KYLEE ALY, WINTER GARDEN, FL 34787
$675,00023 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,058
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
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)
375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787
$334,90052 Days on yellowkey MLS ID: O6377205
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1464 Built: 2001 Tax: $4,413 (2024)Community: Regal Pointe Ph 01 43/129Single Family
Taxes:$4,413
Elementary School: Maxey Elem
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
1720 PORTCASTLE CIR, WINTER GARDEN, FL 34787
$389,90080 Days on yellowkey MLS ID: O6377195
2 Days Off yellowkey (back on 2/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2004Monthly Fee: $46 Tax: $5,520 (2024)Community: Stone Creek Unit 4Spa: NoSingle Family
Taxes:$5,520
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to this fantastic, move-in ready, 4-bedroom, 2.5-bathroom, two-story home with a two-car garage. Enter the foyer leading directly into the open-concept living room and kitchen. The kitchen is functional and stylish, featuring laminate countertops, an island, and stainless steel appliances. Conveniently located off the kitchen are the laundry room, a half bathroom, and access to the two-car garage. All four bedrooms are located on the second level, with the primary suite situated at the rear of the home for privacy. A small flex space upstairs is perfect for a reading nook or a small office area. The primary bedroom features a walk-in closet and an attached ensuite with dual sinks and a tub/shower combo. Schedule your showings today!
7036 TWILIGHT BAY DR, WINTER GARDEN, FL 34787
$524,900166 Days on yellowkey MLS ID: S5137842
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1914 Built: 2023Monthly Fee: $180 Tax: $750 (2023)Community: MezzanoTownhouse
Taxes:$750
Elementary School: Summerlake Elementary
High School: Horizon High School
Tax Year: 2023
Middle School: Horizon West Middle School
Remarks: Motivated Seller-Excellent investment opportunity in the exclusive Mezzano community of Winter Garden. This fantastic Stone House–style townhouse, built in 2023, is currently tenant-occupied through February 28, 2027, providing immediate rental income from day one. The residence features a modern 4-bedroom, 3.5-bathroom layout, including a primary suite on the first floor, a junior suite upstairs, and premium finishes throughout. Designed with an open-concept interior and abundant natural light, the property also includes a private patio and an EV charger. Strategically located just minutes from Hamlin Town Center, Flamingo Crossings, and top-rated A+ schools, it offers long-term value in one of Central Florida’s premier growth corridors. Residents enjoy access to a resort-style pool and playground. This is a turn-key asset for any portfolio seeking a high-quality property in a prime location.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Carola Garcia De Montenegro (407-616-5098)
1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787
$519,900232 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
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)
3467 BUOY CIR, WINTER GARDEN, FL 34787
$629,000104 Days on yellowkey MLS ID: G5106141
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2610 Built: 2020Monthly Fee: $152 Tax: $5,995 (2025)Community: Lakeview PreserveSingle Family
Taxes:$5,995
Elementary School: None
High School: None
Middle School: None
Remarks: This move-in ready lakeview home offers 4 bedrooms, 3 full bathrooms, and a spacious bonus room that can easily serve as a 5th bedroom or versatile flex space. The main level features four bedrooms, two full bathrooms, and an open concept kitchen, dining and living area, along with an extended two-car garage. Designed for both comfort and functionality, this home includes tile throughout the main living areas, new carpet in all bedrooms, tray ceilings in the living room and primary suite, and quartz countertops in the kitchen and bathrooms. Upstairs, a generously sized bonus room with full-bathroom and two closets offers flexibility as a future in-law suite, home office, media or game room. Additional highlights include ample storage throughout and an interior laundry room with cabinetry and utility sink. Enjoy outdoor living from your covered front porch, fully fenced backyard, and screened-in patio overlooking John’s Lake. Located in Lakeview Preserve, this gated community offers a clubhouse, resort-style pool with zero-entry, playground, splash pad, fitness center, centralized mailboxes, and a community dock and kayak launch on John’s Lake, creating the perfect combination to enjoy Florida living.
Listing is courtesy of: CAM REALTY & PROPERTY MANAGEME (407-929-1852)
Listing Agent: Chelsea Eckert (407-455-2785)
1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787
$1,450,000Listed 04/17/2026 12:24PM MLS ID: V4948569
Bed: 7 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4700 Built: 2019Monthly Fee: $97 Tax: $9,199 (2025)Community: Mcallister LndgSingle Family
Taxes:$9,199
Remarks: Experience refined Florida living in this stunning energy-efficient estate, perfectly positioned on an expansive corner lot in the highly sought-after Winter Garden area. Just minutes from Historic Downtown Winter Garden and within close proximity to Orlando’s world-renowned theme parks, this exceptional residence offers the ideal blend of elegance, comfort, and convenience. This impressive two-story home features 7 spacious bedrooms and 4 beautifully appointed bathrooms, thoughtfully designed to accommodate multi-generational living. A luxurious owner’s suite and guest bedroom on the main floor provide flexibility and privacy, while five additional bedrooms are situated upstairs on either side of a generous game room and private home theater, creating the ultimate setting for entertainment and relaxation. At the heart of the home lies a chef-inspired gourmet kitchen, complete with a breakfast bar, and café dining area, all seamlessly flowing into the expansive family room and overlooking the covered lanai. Elegant upgraded tile plank flooring enhances the main living areas, while plush carpeting adds comfort to the bedrooms and bonus spaces. Formal living and dining rooms, provide both sophistication and functionality. Step outside to your private backyard oasis, where a gorgeous in-ground swimming pool, summer kitchen, and oversized covered lanai create the perfect environment for year-round entertaining. The fully fenced yard ensures privacy and ample space for outdoor enjoyment. Car enthusiasts and active families will appreciate the three-car tandem garage with an additional single-car bay, ideal for extra parking, storage, or a golf cart. Modern smart home technology enhances convenience and security, while the home’s energy-efficient construction promotes a healthier, quieter lifestyle and significant savings on utility costs. Residents also enjoy access to exceptional community amenities, including a dock on Lake Apopka, scenic parks, and walking trails, all contributing to the vibrant and active Winter Garden lifestyle.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-862-9966)
Listing Agent: Nell Adams (386-315-3967)
16838 OLD HIGHWAY 50, WINTER GARDEN, FL 34787
$875,0003 Days on yellowkey MLS ID: O6399357
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1795 Built: 1972 Tax: $4,787 (2025)Community: Lake Highlands 23-22-26Mobile Home
Taxes:$4,787
Elementary School: Grassy Lake Elementary
High School: Lake Minneola High
Middle School: East Ridge Middle
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Rare opportunity to own 5 acres of highly versatile land near Orlando, Clermont, and Winter Garden, located at 16838 Old Highway 50 in a rapidly growing corridor of Lake County. This property offers 300 feet of frontage and is already divided into three parcels, with agricultural, commercial, and residential zoning, making it ideal for developers, builders, investors, or anyone searching for land for sale in Orlando, Clermont development land, Winter Garden acreage, or Central Florida investment property. Positioned in a high-growth area with ongoing expansion and development, this property is a prime candidate for residential development, mixed-use, or future commercial use. Currently on the property are two manufactured homes, including a fully remodeled home updated within the last two years with a new kitchen, new flooring, and extensive renovations completed down to the studs—perfect for immediate occupancy, rental income, or use as part of a private family compound. The second is a 4-bedroom, 2-bath manufactured home that has already been improved and is currently used for storage, but can easily be converted into an in-law suite, guest home, or additional living space. The property also features a city-converted self-watering system (contact listing agent for full details). With ample space for animals, horses, barns, horse stables, workshops, and agricultural use, this property offers endless possibilities for equestrian living, farming, development, or multi-generational living. Flexible zoning, prime frontage, proximity to major growth areas, and rare acreage make this a standout opportunity for anyone looking for land for sale in Orlando, Clermont land, Winter Garden development land, or Central Florida acreage with future upside. Opportunities like this are rare in such a high-growth location.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,325,00040 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
Elementary School: Lake Whitney Elem
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 Agent: Sean Flatley (609-208-8204)
161 SUNSET WALK DR, WINTER GARDEN, FL 34787
$529,025Listed 04/17/2026 6:00PM MLS ID: O6400288
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 2026Monthly Fee: $149 Tax: $400 (2025)Community: Westhaven At OvationTownhouse
Taxes:$400
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Under Construction. The Rinker Elite floorplan at Westhaven at Ovation offers a spacious, thoughtfully designed layout perfect for modern living. Featuring an open concept main living area, this home seamlessly connects the kitchen, dining, and great room, making it ideal for both everyday comfort and entertaining. Generous bedrooms, a versatile loft or flex space, and upscale finishes throughout provide both functionality and style. With attention to detail and energy efficient features, the Rinker Elite delivers a perfect blend of luxury and convenience.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Devahn Powell (571-234-7236)
628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787
$525,00038 Days on yellowkey MLS ID: O6389653
0 Days Off yellowkey (back on 4/11/2026)
REDUCED by $4,900 (0.9%) on 04/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1850 Built: 2018Monthly Fee: $336 Tax: $3,620 (2025)Community: Heritage At Plant Street Community AssocSpa: NoTownhouse
Taxes:$3,620
Elementary School: Dillard Street Elem
Remarks: Under contract-accepting backup offers. Live the downtown Winter Garden lifestyle in this beautifully upgraded CORNER UNIT townhome in the sought-after community of Heritage at Plant Street—perfectly located in the GOLF CART DISTRICT with direct access to the renowned WEST ORANGE TRAIL. Built in 2018 by M/I Homes and meticulously maintained by its original owners, this 2-story, 3 bedroom, 2.5 bath townhome with a 2-car garage offers the ideal combination of low-maintenance living, thoughtful upgrades, and a prime corner location. With HOA-covered exterior maintenance—including the roof and grounds—you’ll spend less time on upkeep and more time enjoying everything downtown living has to offer. The coveted corner placement provides extra privacy, abundant natural light, and a common area GRASSY SIDE YARD perfect for pets or play, while a large guest parking lot sits conveniently just steps from the front door. Inside, the Windham II floor plan features soaring ceilings and a bright, open layout. A light-filled den off the foyer with three large windows offers flexibility as a home office, playroom, or second living space. The heart of the home is the DESIGNER KITCHEN, showcasing slate GE Profile appliances, a NATURAL GAS COOKTOP AND CUSTOM RANGE HOOD, stacked convection wall oven and microwave, and 42" dark shaker cabinetry with hardware. SILESTONE countertops, tiled backsplash, under-cabinet LED lighting, and stylish pendant lights complete the space. The large island with breakfast bar and included barstools opens seamlessly to the dining area and great room, creating the perfect setup for entertaining. Corner-unit placement provides windows on two sides of the great room and dining area, creating a bright, naturally lit living space. The entire first floor features durable large format ceramic tile flooring, while the staircase has been upgraded with dark engineered wood for a polished, low-maintenance look. A spacious laundry room with full-size washer and gas dryer, upper cabinets, and an oversized under-stair storage nook adds everyday convenience. Upstairs, the private primary suite offers a large walk-in closet and an elegant en-suite bath with raised-height dark shaker cabinetry, Silestone double vanity, and a tiled walk-in shower with seamless glass enclosure. Two additional bedrooms share a well-appointed bathroom with matching finishes and a tiled tub/shower combination. Step outside through the French door with built-in blinds to your private, screened brick-paver courtyard, offering both covered and open seating areas—perfect for relaxing or entertaining while overlooking the grassy side yard. The adjoining two car garage with alley access includes screened sliders for a cross breeze into the patio area. Energy-efficient features include ENERGY STAR double-pane Low-E windows, HVAC, insulation, and appliances. The ROOF, HVAC, and INSTANT HOT GAS WATER HEATER were installed in 2018 and have been regularly serviced. The home also features modern high end, noise free ceiling fans with remotes in all bedrooms and living areas, faux wood blinds throughout, and a NEUTRAL INTERIOR PALETTE ready for your personal style. Residents enjoy neighborhood amenities including a POOL and DOG PARK, all just minutes from the shops, dining, and vibrant atmosphere of historic downtown Winter Garden. Spring into the season of easy living—this rare corner-unit opportunity is your key to enjoy everything downtown Winter Garden is famous for.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Kim Blaylock (407-497-9321)
11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$899,990124 Days on yellowkey MLS ID: O6367437
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $200 Tax: $1,989 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Under Construction. Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share an upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh the Seacliff includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. This home is open for self-touring 7 days a week. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
14626 BLACK QUILL DR, WINTER GARDEN, FL 34787
$799,9001 Day 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
Middle School: Bridgewater Middle
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)
213 W TILDEN ST, WINTER GARDEN, FL 34787
$765,00066 Days on yellowkey MLS ID: O6381848
0 Days Off yellowkey (back on 3/2/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 1972 Tax: $8,105 (2025)Community: Westlake Manor 1St AddSingle Family
Taxes:$8,105
Remarks: Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combines charm with modern upgrades. Completely redesigned in 2021, this home showcases numerous upgrades, including new roof, new HVAC, recently installed Whole-House Water Filtration System, stunning new kitchen, new granite countertops, large center island with storage cabinets, built in walk-in pantry. Additional upgrades include double paned windows, new exterior/interior doors, fully renovated bathrooms, porcelain tile flooring throughout the home. Step outside into your own private oasis, you'll find a wood fenced beautiful backyard with lush landscape and patio area, ideal for relaxing and soaking up the Florida sunshine. Irrigation runs off a well. Set on a beautifully, tree-lined street shaded by majestic live oaks. This home invites you into a bright, open concept layout perfect for both relaxing and entertaining. The spacious living room flows seamlessly into the dining area and kitchen with a large center island, creating a central gathering space for family and friends. Spacious 2 car garage with EV charger outlet and custom garage door. Located in the heart of the Golf Cart District, you can walk or take your golf cart to Plant Street Market, local restaurants, charming boutiques, café spots, and the Farmers Market. Enjoy the small-town atmosphere, community events, festivals, walk or bike to West Orange Trail and enjoy the scenic beauty of nearby Lake Apopka—all with NO HOA!! This home is perfectly nestled in one of Central Florida’s most desirable and vibrant neighborhoods. This is a rare opportunity to own one of the area’s finest homes in a location that combines luxury, lifestyle and small town charm. Close to major highways, minutes to Disney, 30 mins from Orlando. Schedule your private tour today!! See why this incredible property is the best of Winter Garden living!!
Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)
Listing Agent: Alice Acosta (561-356-6385)
15555 PANTHER LAKE DR, WINTER GARDEN, FL 34787
$2,000,000Listed 04/17/2026 4:24PM MLS ID: O6400010
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4342 Built: 2016Monthly Fee: $431 Tax: $28,576 (2025)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$28,576
Remarks: Welcome to luxury living in the highly sought-after Panther Lake community in Winter Garden. This award-winning Toll Brothers Maranello model home is now available for sale —offering over 4,600 square feet of impeccably designed living space, featuring 5 bedrooms and 5+ bathrooms, all set on a premium waterfront lot. From the moment you arrive, the home makes a statement with its elegant architecture and professionally designed finishes throughout. The grand foyer opens seamlessly into an expansive great room, where natural light, volume ceilings, and refined details create a space that is both inviting and impressive. At the heart of the home is a chef-inspired kitchen, complete with a large center island, premium cabinetry, and a walk-in pantry, all overlooking a bright breakfast area. From here, step directly onto the expansive covered lanai, where indoor and outdoor living come together effortlessly. This is where the home truly sets itself apart. Enjoy your own private resort-style outdoor retreat, featuring a stunning infinity-edge pool overlooking the lake, a fully equipped outdoor kitchen, and a gas fireplace—creating the perfect setting for entertaining or relaxing in total privacy. The primary suite, located on the first floor, offers a luxurious escape with a spa-like bathroom, dual vanities, a walk-in shower, and a generous walk-in closet. Also on the main level, you’ll find a private en-suite guest bedroom as well as a separate mother-in-law suite, providing flexibility for guests or multi-generational living. Upstairs, the home continues to impress with a spacious loft featuring a built-in bar, three additional bedrooms with bathrooms, and a beautiful balcony that adds both charm and additional outdoor living space. Located in one of Winter Garden’s most desirable communities, this home offers privacy, prestige, and convenience, with close proximity to top-rated schools, shopping, dining, and major roadways. Model homes of this caliber—especially with a waterfront lot and infinity pool—rarely become available. Schedule your private showing today and experience elevated living at its finest.
Listing is courtesy of: RIGHTHOUSE REALTY LLC (407-216-8788)
Listing Agent: Tim Schmidt (407-216-8788)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,000Listed 04/17/2026 4:40PM MLS ID: O6396654
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Remarks: Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
12043 HOLYSTONE ST, WINTER GARDEN, FL 34787
$385,000223 Days on yellowkey MLS ID: O6339950
1 Days Off yellowkey (back on 4/17/2026)
REDUCED by $5,000 (1.3%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1568 Built: 2023Monthly Fee: $259 Tax: $6,198 (2024)Community: Waterleigh Ph 4ATownhouse
Taxes:$6,198
Elementary School: Waterbridge Elem
Remarks: Under contract-accepting backup offers. Motivated Seller MOVE IN READY . Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It offers a welcoming open concept as you immediately enter the foyer, with plenty of cabinet, double sink, granite countertops and a long kitchen island overlooking the dining space.The community offers great amenities such as pool, gym and a club house.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Ruth Santos (407-808-4766)
5340 BOWMAN DR, WINTER GARDEN, FL 34787
$2,195,0004 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
Elementary School: Keene Crossing Elementary
High School: Windermere High School
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)
2202 ROMANUM DR, WINTER GARDEN, FL 34787
$585,0001 Day on yellowkey MLS ID: O6398743
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1889 Built: 2015Monthly Fee: $211 Tax: $3,839 (2025)Community: Alexander RidgeSingle Family
Taxes:$3,839
Remarks: Welcome to your next home in the heart of Winter Garden—where location, lifestyle, and upgrades come together seamlessly. This beautifully updated 3-bedroom, 2-bathroom home is perfectly positioned just 20 minutes from Disney, 15 minutes from Downtown Winter Garden, and only 10 minutes to Winter Garden Village, giving you easy access to everything Central Florida has to offer. Step inside to find brand-new luxury vinyl flooring, fresh exterior paint (2024), and a bright, open feel that makes the home both inviting and functional. The enclosed Florida room adds an additional 135 square feet of living space, complete with elegant French doors—perfect for a home office, flex space, or relaxing retreat. Out back, enjoy your own private putting green—ideal for unwinding or entertaining guests. And with HOA-maintained landscaping, you can say goodbye to yard work and hello to low-maintenance living. Major updates bring peace of mind, including a new roof (2024), new AC unit (2025), and new gutters (2024). Additional features include a garage with epoxy flooring, a hybrid hot water heater, and a sleek GE Slate appliance package that adds a modern touch to the kitchen. This home checks all the boxes—location, upgrades, and lifestyle. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$825,00022 Days on yellowkey MLS ID: O6393190
REDUCED by $25,000 (2.9%) on 04/05/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3902 Built: 2005Monthly Fee: $243 Tax: $7,653 (2025)Community: Stoneybrook WestSingle Family
Taxes:$7,653
Remarks: One or more photo(s) has been virtually staged. Discounted Interest Rates Available Nestled on a premier corner lot within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced over the last two years with modern updates, ensuring a move-in-ready experience for today’s discerning buyer. Inside, the open-concept layout is anchored by a gourmet kitchen featuring quartz countertops, a central island, and stainless steel appliances, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. The well-appointed laundry room includes a high-end GE Ultra washer and dryer, along with a stainless steel utility sink for added convenience. The garage is equally impressive, featuring a heavy-duty Husky organizational system that provides exceptional storage and functionality. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier “live-play” community boasting 24-hour staffed security and a spectacular waterfront clubhouse perched on the shores of Black Lake. For the outdoor enthusiast, the amenities are unmatched: enjoy private lake access via a community boat ramp and the rare convenience of an on-site boat storage lot. Whether you are hitting the links on the championship golf course, working out in the fitness center, or relaxing at the resort-style pool, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from Winter Garden Village, 18 minutes from Walt Disney World, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule your private showing!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.