Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Do Not Show Listings
Winter Garden - 581 properties found
9433 EMERALD BERRY DR, WINTER GARDEN, FL 34787
$729,80011 Days on yellowkey MLS ID: O6401775
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2063 Built: 2024Monthly Fee: $99 Tax: $8,457 (2025)Community: Summerlake ReserveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,457
Elementary School: Panther Lake Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Beautiful home located in highly desirable Summerlake Reserve, just minutes from Disney World, Hamlin Town Center, Publix, top-rated schools, restaurants, shopping, parks, and major highways. This spacious residence offers 4 bedrooms, 2 full bathrooms, and 1 half bath, featuring a charming covered front porch and beautifully landscaped entrance. Inside, a welcoming foyer opens to a bright and airy floor plan filled with natural light. The open-concept kitchen overlooks the main living area and features stainless steel appliances, modern wood cabinetry, breakfast bar, and generous counter space, perfect for everyday living and entertaining. Sliding glass doors lead to an impressive outdoor retreat featuring a covered lanai, upgraded modern pergola, spacious paved patio, outdoor summer kitchen with grilling area, dining and lounge spaces, and a fully fenced backyard with premium low-maintenance artificial turf—ideal for gatherings, relaxing evenings, and enjoying Florida outdoor living year-round. The private primary suite includes a spacious walk-in closet and an elegant bathroom with dual vanities. Additional highlights include a spotless 2-car garage with premium epoxy flooring, automatic garage door opener, air conditioning system, bright lighting, and ample space for storage, fitness, or workshop use. The home also features added insulation in the garage, garage door, and attic, enhancing comfort and energy efficiency. Located in an exclusive and very private HOA community with only 41 homes, this property offers added tranquility and privacy, including no rear neighbors. Perfectly positioned in one of Winter Garden’s most sought-after communities, this home offers comfort, style, and convenience in an exceptional location. Don’t miss this incredible opportunity. ""Home includes a whole-house water filtration system currently installed; however, this system is not included in the sale.""
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Victor Kubrusly (754-304-4750)
2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$750,00020 Days on yellowkey MLS ID: O6398720
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3747 Built: 2000Monthly Fee: $90 Tax: $10,152 (2025)Community: Wintermere PointeSpa: NoSingle Family
Taxes:$10,152
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Located in the GATED community of Wintermere Pointe in Winter Garden, FL, this spacious .25 acre, 5-bedroom, 3-bath pool home for sale in Winter Garden offers nearly 3,750 square feet of well-designed living space just minutes from Winter Garden Village, Windermere, Walt Disney World, AdventHealth Winter Garden, SR 429, and the Florida Turnpike. Designed for both everyday living and entertaining, the home features an open-concept layout with formal living and dining rooms, a large family room, and a centrally located kitchen that flows seamlessly into the main living areas. A DOWNSTAIRS BEDROOM and full bath provide flexibility for guests, multi-generational living, or a private home office, while upstairs, the expansive primary suite offers a true retreat with a soaking tub , separate shower, dual vanities, and two walk-in closets. Additional bedrooms are generously sized, and both a LOFT and a large BONUS ROOM create endless possibilities for a media room, game room, home gym, or additional living space. High ceilings and natural light enhance the open feel throughout the home, while the layout offers both functionality and comfort. Step outside to a screened-in PRIVATE POOL, covered lanai and extended paver patio, perfect for enjoying Florida living in Winter Garden year-round, all set on a .25 ACRE LOT with mature landscaping and a FULLY FENCED backyard for added privacy. Wintermere Pointe is a well-established gated community in Winter Garden, Florida offering tennis courts, a playground, and a LOW HOA, and is zoned for Lake Whitney Elementary, SunRidge Middle, and West Orange High. If you’re searching for homes for sale in Winter Garden FL with a pool, gated community, and flexible layout, this home offers space, location, and lifestyle in one of Central Florida’s most desirable areas.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexis Bress (407-900-0771)
15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$699,00033 Days on yellowkey MLS ID: S5146881
REDUCED by $30,900 (4.2%) on 04/28/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2931 Built: 2025Monthly Fee: $233 Tax: $9,545 (2024)Community: Harvest At OvationSingle Family
Taxes:$9,545
Elementary School: Water Spring Elementary
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: PRICED TO SELL! 5BR Corner Lot + Private In-Law Suite + Soaring Ceilings Near Amenities Rare opportunity to own a spacious 5-bedroom home with a private in-law suite above the garage. Located on a premium corner lot just steps from the amenity center, this home offers flexibility, privacy, and modern upgrades. Priced aggressively for a quick sale—this one will not last. Welcome to this beautifully designed 5-bedroom, 4.5-bathroom home offering space, flexibility, and modern comfort in a highly desirable location. Situated on a corner lot near the community amenity center, this home stands out with its thoughtful layout, soaring ceilings, and multiple private living areas—perfect for today’s lifestyle. A rare and valuable feature, the separate suite above the garage includes a private bedroom, kitchenette, and full bathroom, ideal for extended family, guests, or a dedicated home office. The open-concept first floor features a bright, inviting living space paired with a cabinet-rich gourmet kitchen designed for both everyday living and entertaining. Kitchen highlights include an oversized island with ample counter space, gas range, upgraded refrigerator, exterior-vented microwave, garbage disposal, and a hidden trash cabinet. The kitchen overlooks a paved private courtyard, creating a low-maintenance outdoor space perfect for relaxing or entertaining. A first-floor bedroom with a full bathroom and a dedicated flex space—perfect for a home office—add even more versatility. Upstairs, you’ll find a spacious primary suite with high ceilings, two additional bedrooms, and a convenient laundry room with washer and dryer. Additional features include a corner lot offering added privacy, a fence planned or installed for outdoor enjoyment, gas tankless water heater, EV charging station in the attached garage, and landscaping included. The home is walking distance to community amenities including a pool, clubhouse, and parks (currently in progress). Schedule your private showing today!—homes with this layout, location, and value don’t come available often.
Listing is courtesy of: 365 REALTY, INC. (407-944-1365)
Listing Agent: Robert Benenati (407-944-1365)
12731 GROVEHURST AVE, WINTER GARDEN, FL 34787
$620,00089 Days on yellowkey MLS ID: O6379203
REDUCED by $24,900 (3.9%) on 04/20/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3474 Built: 2006Monthly Fee: $111 Tax: $8,378 (2025)Community: Grovehurst A-DSingle Family
Taxes:$8,378
Elementary School: SunRidge Elementary
Remarks: One or more photo(s) has been virtually staged. Ideally located in the heart of Winter Garden, this home offers 3,474 sq. ft. of living space and exceptional walkability just steps from Winter Garden Village’s shopping, dining, and everyday conveniences. Recent updates include new carpet and fresh interior and exterior paint. The flexible floor plan features five bedrooms, three full bathrooms, and a kitchen with 42-inch upper cabinets, granite countertops, and an open layout to the family room with a large eat-in area. Stone Crest community amenities include a clubhouse, pool, tennis/pickleball courts, playground, and a scenic walking trail around a tranquil pond. With close proximity to AdventHealth, major highways, historic downtown Winter Garden, the West Orange Trail, and top-rated schools, this property provides excellent convenience and connectivity.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787
$529,99998 Days on yellowkey MLS ID: NS1087076
REDUCED by $38,001 (6.7%) on 05/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2474 Built: 2024Monthly Fee: $291 Tax: $2,273 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$2,273
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 16230 Carraway Bay Alley, a beautifully maintained home located in one of Winter Garden’s most desirable communities. This move-in ready residence features a functional open-concept layout with spacious living areas, abundant natural light, and modern finishes throughout. The kitchen overlooks the main living and dining areas, creating an ideal space for both everyday living and entertaining. The primary suite offers a private retreat with ample closet space and an en-suite bathroom. Enjoy outdoor living without the maintenance—HOA dues include full lawn care, providing a true low-maintenance lifestyle. Community amenities include resort-style pools, fitness centers, and scenic walking trails, enhancing the overall living experience. Conveniently located just minutes from Downtown Winter Garden, with easy access to State Road 429 and Florida Turnpike, as well as nearby shopping, dining, and top-rated schools.
Listing is courtesy of: WATSON REALTY CORP (386-428-7355)
Listing Agent: Matthew Eads (804-651-6911)
8978 SONOMA COAST DR, WINTER GARDEN, FL 34787
$1,299,50039 Days on yellowkey MLS ID: O6393744
1 Days Off yellowkey (back on 5/2/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3911 Built: 2022Monthly Fee: $277 Tax: $13,033 (2025)Community: WaterleighSpa: YesSingle Family
Taxes:$13,033
Remarks: Under contract-accepting backup offers. LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Unique Opportunity to Enjoy an Outdoor PARADISE with STUNNING LAKE, CONSERVATION & SUNSET Views! The HOA is Allowing Docks on these Special Lots – Relax, Fish or Kayak! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage. The OUTDOOR LIVING Space is SPECTACULAR - $200,000 to Duplicate! Generous COVERED Patio PLUS additional Covered CABANA SPACE is 34 FEET LONG! DELUXE Heated POOL and SPA with Upgraded Pavers, PANORAMIC SCREEN, Large SUN SHELF with Bubblers, PEBBLETEC Surface, Mosaic Accent Tile, SALT SYSTEM, LED Lights and FULLY AUTOMATED SYSTEM for Chemicals! PLUS Ledge Loungers and Basketball Hoop are Included! This MODEL PERFECT Home has a GOURMET KITCHEN with 42” Cabinets, Large Island with QUARTZ COUNTERS, Upgraded Subway Tile Backsplash, NEW PENDANT LIGHTS, Large SINGLE SINK, SS APPLIANCES including BUILT-IN OVEN and COOK TOP with VENT HOOD and FRENCH DOOR Refrigerator. ! Large Pantry and Butler Pantry add Storage! OPEN FLOOR PLAN with Views of the Patio, Pool and LAKE from Family Room and Casual Dining! First Floor Primary Suite with CUSTOM CLOSET has a Bath that Features DOUBLE Vanities, OVERSIZED SHOWER and Garden Tub. FLEX Space can be Dining Room, Office or Living Room. Convenient Powder Bath and FULLY Remodeled Laundry Room with Cabinetry, Utility Sink and RO Water System Complete the First Floor. Entire First Floor has WOOD PLANK Porcelain Tile, 8’ Doors and 5 ¼ Molding. Stairs are Engineered Wood with Wrought Iron Spindles. The HUGE LOFT separates the Upstairs. ALL 4 Bedrooms have WALK IN Closets – but Bedroom 3 has a CUSTOM CLOSET. Bedrooms 2 and 3 share Full Bath 2 and Bedrooms 4 and 5 Share a Jack-and-Jill Bathroom. These Owners Thought of Everything! Paver Path to Store Trash Bins, Gutters with LEAF GUARD, Salt Free Water Filtration System, Custom Valances, Interior Painted with QUALITY paint, AC with Ultraviolet Sanitizing, Upgraded PRIVACY Landscaping, Garage with EPOXY FLOOR, Overhead Storage Racks and CUSTOM Storage System! Waterleigh is the PREMIER LIFESTYLE COMMUNITY with 4 Resort Style Pools, 3 Clubhouses with Fitness Centers, Walking Trails, Sand Volleyball, Dog Park, Fishing and Observation Pier, Tennis, Pickleball, Playgrounds and more! HOA Does all Yard Maintenance. All this zoned for NEW Atwater Bay Elementary, Water Spring Middle School and Horizon High School! Close to Disney, Shopping, Dining, 429, I-4, 417 and a NEW PUBLIX!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Joann Best (407-963-2981)
9827 BEACH PORT DR, WINTER GARDEN, FL 34787
$1,374,9003 Days on yellowkey MLS ID: O6403588
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2020Monthly Fee: $277 Tax: $11,122 (2025)Community: Waterleigh Ph 2C-2 & 2C-3Spa: YesSingle Family
Taxes:$11,122
Remarks: Experience this LUXURY POOL HOME on nearly HALF an ACRE with the RIGHT TO BUILD a DOCK on Lake NOAH! This NORTH HAVEN plan with 5 Bedrooms, 3.5 Baths, Tile Roof, 3 Car Garage and Fenced Yard is a true DREAM HOME! DELUXE Heated Pool and Spa with HIGH END FEATURES: Pebble Surface, Deck Jets, Waterfall, Sun Shelf with Bubbler, Salt System, Gem Lights, Automation System, PANORAMIC Screen Enclosure, FIRE PIT, Audio System, and DELUXE Stacked Stone SUMMER KITCHEN with Grill, Vent Hood, Sink & Refrigerator! All this overlooks a LARGE PRIVATE YARD with Conservation and Water Views! Step inside to Enjoy a thoughtfully Upgraded Home. Leaded Glass Entry Door and Upgraded Rectangular Tile. Gourmet Kitchen with Upgraded Cabinetry, Glass Front Accent Cabinets, Large Island, SS Appliances Including French Door Refrigerator, Convection Oven and Cooktop with Vent Hood! Opens to Family Room and Casual Dining. Extensive Wainscoting and Crown Molding! Upgraded Lights and Fans! FIRST FLOOR PRIMARY SUITE overlooks Pool and Patio! Enjoy the Large Walk-In CALIFORNIA CLOSET! Primary Bath with DOUBLE VANITIES and DOUBLE Walk-In SHOWER with 4 Shower heads! Dining Room, Powder Bath, and Laundry Room with Cabinetry and Utility Sink completes the First Floor. ENGINEERED WOOD STAIRS leads to Spacious LOFT! One Hallway has Beds 2 and 3 with WALK-IN Closets and Bath 2 with DOUBLE SINKS. Second Hallway features Bedrooms 4 and 5 with WALK-IN Closets and Jack and Jill Bath 3. These METICULOUS Owners added a GENERATOR, NEW Water Filtration System, Exterior LIGHTING SYSTEM, Paver Pathway, SECURITY SYSTEM with Cameras, GUTTERS, Exterior Painted in 2024, EPOXY Garage Floor & Hanging Storage Racks. Plus, 10 Year Protection Plan on AC Units! Waterleigh is a LIFESTYLE COMMUNITY with 4 Resort Style Pools, 3 Clubhouses with Fitness Centers, Walking Trails, Sand Volleyball, Dog Park, Fishing and Observation Pier, Tennis, Pickleball, Playgrounds and more! HOA Does all Yard Maintenance. All this zoned for NEW Atwater Bay Elementary, NEW Water Spring Middle School and NEW Horizon High School! Close to Disney, Shopping, Dining, 429, I-4, 417 and a NEW PUBLIX!
Listing Agent: Sabrina Freeman (407-446-5541)
14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787
$689,99933 Days on yellowkey MLS ID: O6395287
REDUCED by $10,000 (1.4%) on 04/16/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3410 Built: 2005Monthly Fee: $100 Tax: $3,503 (2025)Community: Emerald RidgeSingle Family
Taxes:$3,503
Remarks: Expansive and Inviting! Welcome home to 14790 Tullamore Loop. Location says it all! Convenient to restaurants, shopping, highways, theme parks, and more, this gated community remains one of the most popular communities in the area. This family-oriented neighborhood with a community pool is sure to please. With an oversized lot and plenty of room to roam, the open floor plan of this 4-bedroom / 2.5-bath home awaits to impress. Large formal living and formal dining rooms are the perfect venue for family gatherings. An elegant, open kitchen, overlooking the dinette into the family room, offers granite counters, 42” cabinets, double built-in ovens, a large breakfast bar, and a huge walk-in pantry allowing space for everyone to help the cook. When the day is done, retire to the oversized second-floor primary suite, which offers a spacious bath with a double-sink vanity, shower, garden tub, and a walk-in closet, completing this special and intimate space. Anchoring 3 large secondary bedrooms, this home beckons to an active family, offering the space you need. Enjoy your morning coffee or an evening barbecue, while enjoying the peace of your private pool, a HUGE private backyard! Complete with fruit trees (recovering from the freeze), including mango, sugar apple, sapodilla, guava, loquat, pear, jackfruit, fig, lemon, orange, neem, and banana, gives an instant farm-to-table experience. While certainly offering plenty of space for everyone to claim their own piece of paradise, you’ll find peace of mind that your investment is in a location that can’t be beat! Highlights include: Roof replaced in 2020. AC replaced in 2018. Appliances replaced in 2022. All blinds replaced 2022. Whole Home water filtration and softener system. Be sure to click the link for an interactive 3D Virtual Tour and floor plan!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Rita Phillips (407-928-0573)
744 LAKE BRIM DR, WINTER GARDEN, FL 34787
$969,00055 Days on yellowkey MLS ID: O6388775
REDUCED by $26,000 (2.6%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2667 Built: 2016Monthly Fee: $203 Tax: $9,275 (2025)Community: Oakland ParkSingle Family
Taxes:$9,275
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
10043 SEQUEL ALY, WINTER GARDEN, FL 34787
$569,00070 Days on yellowkey MLS ID: O6384246
REDUCED by $1,000 (0.2%) on 04/23/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2018Monthly Fee: $100 Tax: $8,237 (2024)Community: Storey Grove Ph 1B-2Single Family
Taxes:$8,237
Remarks: About 10 minutes to Disney. Corner lot facing open green space. Main floor primary suite with a second upstairs. Opportunity to secure a BELOW MARKET rate through an ASSUMABLE MORTGAGE for qualified buyers. Located in Storey Grove in the heart of Horizon West, this home is positioned for both convenience and day to day livability. You are about 5 minutes to Publix and 15 minutes to Hamlin Town Center for dining, shopping, and everything you need close to home. The lot and orientation are what set this home apart. Instead of looking into another backyard, you face open park space and green views, bringing in more natural light and a more open feel throughout the home. All carpet on the stairs and second floor has been replaced with wood look luxury vinyl flooring, crown molding has been added throughout, and the interior has been freshly repainted so there are no immediate projects waiting after closing. The layout is flexible and practical. Two primary suites, including one on the main level, create options for guests, multigenerational living, or a private office without sacrificing bedroom space. The main living and dining areas are open and functional, while the upstairs loft works well as a playroom, media space, or work from home area. The backyard is fully fenced with an in ground sprinkler system, giving you usable outdoor space that is easy to maintain. The rear facing garage with alley access keeps the curb appeal clean and includes an EV charger, while the corner lot allows for additional nearby parking for guests. Storey Grove offers a community pool, clubhouse with gym, parks, playgrounds, and miles of sidewalks, with green space directly across the street extending your everyday living area. Zoned for Water Spring Elementary, Water Spring Middle, and Horizon High School.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999196 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Elementary School: Dillard Street Elem
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
306 DANIELS POINTE DR, WINTER GARDEN, FL 34787
$310,000115 Days on yellowkey MLS ID: O6371413
0 Days Off yellowkey (back on 3/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1326 Built: 1999Monthly Fee: $78 Tax: $4,120 (2024)Community: Daniels CrossingSingle Family
Taxes:$4,120
Remarks: Under contract-accepting backup offers. This charming 3 bedroom, 2 bath home offers a fantastic opportunity to make it your own. Featuring a fully fenced backyard, the property provides privacy and plenty of space for outdoor living, pets, or entertaining. Located just a short distance from Winter Garden Village and historic Plant Street, you’ll enjoy easy access to shopping, dining, and local events. With so much potential, this home is perfect for buyers looking to add their personal touch in a highly desirable location.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Claire Jesso (407-436-5039)
13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787
$585,00097 Days on yellowkey MLS ID: S5142297
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 2022Monthly Fee: $534 Tax: $7,519 (2024)Community: Del Webb OasisSpa: NoSingle Family
Taxes:$7,519
Remarks: One or more photo(s) has been virtually staged. Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family and villa homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories.The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane, this home is part of a desirable cluster of 2021–2023 builds with strong appreciation. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!
Listing is courtesy of: FRONTLINE FLORIDA REALTY, INC. (407-832-4888)
Listing Agent: Alan Martin (407-832-4888)
12362 BRACCO ST, WINTER GARDEN, FL 34787
$515,0003 Days on yellowkey MLS ID: O6404125
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2094 Built: 2023Monthly Fee: $105 Tax: $8,231 (2025)Community: Highland Rdg Ph 2Single Family
Taxes:$8,231
Remarks: Welcome to this exceptional home located in the highly sought-after Highland Ridge community. This beautifully maintained 4-bedroom, 2 full bathroom and 1 half bathroom residence offers generous living space and a unique blend of classic curb appeal with modern interior upgrades. The home features an open-concept layout designed for both everyday living and entertaining. The kitchen is designed for both function and style, showcasing a large island, stainless steel appliances, ample counter space, and a convenient corner pantry. It seamlessly connects to the dining and family areas, creating a welcoming and cohesive living space. Wood-look luxury vinyl plank flooring throughout main living areas on the first floor. Upstairs, you’ll find a spacious loft that can be used as a media room or flexible living area, along with a conveniently located laundry room and four bedrooms. The primary suite offers a well-designed en-suite bathroom and a walk-in closet, while the remaining bedrooms share a full bath. Ideally situated in the vibrant Winter Garden area, Highland Ridge residents enjoy access to a pool, playground, and half basketball court. The community is just minutes from the Hamlin shopping and dining district, with convenient access to major highways. Located less than 15 minutes from Walt Disney World, under 30 minutes from Universal Orlando and Downtown Orlando, and approximately 35 minutes from Orlando International Airport. Several renowned golf courses are also nearby. The property is located at the end of a quiet street with minimal traffic, this home offers exceptional privacy and tranquility, backing onto a natural preserve with no rear neighbors. Currently tenant occupied; tenants agree to vacate the property with a 30-day notice if requested by the buyer.
Listing is courtesy of: ELITE INTERNATIONAL REALTY INC (305-940-6611)
Listing Agent: Comandante De Abreu Junior (786-818-0909)
4896 PALMETTO PARK DR, WINTER GARDEN, FL 34787
$759,0003 Days on yellowkey MLS ID: OM723891
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2888 Built: 2016Monthly Fee: $188 Tax: $8,086 (2025)Community: Orchard Hills Ph 2Single Family
Taxes:$8,086
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Located in the highly sought-after Orchard Hills community, this upgraded “Hayes II” residence offers 5 bedrooms, 4 full baths, and a thoughtfully designed open-concept layout. Originally showcased by the builder, the home features curated upgrades and a layout that balances everyday functionality with refined design.A dramatic two-story foyer sets the tone upon entry, leading into a formal dining space ideal for hosting. The kitchen is designed for both form and function, featuring 42-inch cabinetry, granite countertops, stainless steel appliances, double ovens, and a spacious island that flows seamlessly into the breakfast area and main living space. A first-floor bedroom and full bath provide flexibility for guests or a private office. Upstairs, the primary suite offers generous proportions, a custom walk-in closet, and a well-appointed bath with dual vanities, soaking tub, and separate shower. Additional bedrooms are well-sized, with ample closet space, and the laundry room is conveniently located on the second level. Outdoor living is just as inviting, with an oversized screened lanai with plenty of room to add a pool and/or outdoor kitchen. The east-west orientation allows for natural light throughout the day and beautiful sunset views, and the fully fenced yard enhances privacy. Crowned with a timeless Spanish tile roof, the home is further enhanced by a new dual-zoned HVAC system (2024), providing efficient, balanced comfort throughout. Additional highlights include upgraded flooring throughout the upper level, tinted double-pane windows, a finished garage with overhead storage, and a larger homesite within the community. Residents of Orchard Hills enjoy an amenity-rich lifestyle, including a pool, clubhouse, fitness center, playgrounds, dog park, grilling area, and frequent events. The HOA covers exterior maintenance, lawn care, landscaping, and outdoor pest prevention - making life truly low-maintenance. Just minutes from Disney World, major highways, shopping and dining, this home is a rare opportunity you won't want to miss!
Listing is courtesy of: REMAX REALTY ONE (352-795-2441)
Listing Agent: Laura Bush (904-687-5170)
16294 HONEY HARVEST ST, WINTER GARDEN, FL 34787
$710,0003 Days on yellowkey MLS ID: O6403794
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2812 Built: 2024Monthly Fee: $229 Tax: $9,329 (2025)Community: Harvest/OvationSingle Family
Taxes:$9,329
Remarks: Welcome Home! Step inside this gorgeous 2024-built bungalow-style home featuring a fully detached STUDIO apartment with its own entrance, perfect for guests, in-laws, or potential rental income. This 4-bedroom, 4.5-bathroom home offers the perfect blend of space, style, and flexibility. Inside the main home, you’re welcomed by tall ceilings, an open layout, and a convenient downstairs bedroom and full bathroom. The modern kitchen is beautifully designed with a gas range, quartz countertops, shaker cabinets, and an open-concept flow overlooking the main living spaces. Upstairs, you’ll find two additional guest bedrooms, a shared full bathroom, and a conveniently located laundry room. The grand primary suite is a true retreat, featuring a spacious layout with soaring ceilings and a stunning en-suite bathroom complete with a walk-in shower, generous counter space, and an oversized walk-in closet. The studio apartment is privately accessed just outside of the garage and is fully equipped with its own full bathroom, kitchenette, and closet—making it ideal for guests or income-producing potential. Located in one of Horizon West’s most desirable communities, this home offers unbeatable convenience just minutes from Flamingo Crossings, Walt Disney World, and Hamlin Town Center.
Listing Agent: Elliott Hunt (770-355-9149)
13332 SUBURBAN TER, WINTER GARDEN, FL 34787
$714,9003 Days on yellowkey MLS ID: O6402778
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2706 Built: 1994 Tax: $2,841 (2024)Community: Citrus Cove Unit 01Single Family
Taxes:$2,841
Remarks: Welcome to a rare opportunity in sought-after Winter Garden! This spacious multi-level residence offers 4 bedrooms, 3 bathrooms, a private in-law suite with separate entrance and kitchenette, and an entertainer’s dream backyard with pool, cabana, outdoor kitchen, and oversized driveway. Situated on a generous .35-acre lot with no HOA, this home offers flexibility for multigenerational living, rental potential, boat parking, or work-from-home lifestyle. Impact windows and doors add long-term value and peace of mind. Conveniently located near shopping, dining, major highways, and lake access. A unique Florida lifestyle property you won’t find often.
Listing Agent: Veronica Figueroa (407-519-3980)
15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787
$769,9002 Days on yellowkey MLS ID: O6400896
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2931 Built: 2016Monthly Fee: $235 Tax: $5,441 (2025)Community: Hickory Hammock Ph 2ASingle Family
Taxes:$5,441
Elementary School: Whispering Oak Elem
Remarks: WELCOME to this stunning 4-bedroom, 2.5-bathroom home offering 2,931 square feet of thoughtfully designed living space, perfectly situated on a premium conservation lot across the street from a park, with a green space on the right and overlooking a peaceful and picturesque inlet off Lake Burnett. Framed by majestic oak trees draped in Spanish moss, the setting provides both privacy and breathtaking natural beauty. As you enter, you are greeted by an elegant dining room featuring a custom accent wall, setting the tone for the home’s stylish design. Double doors to the left open into a versatile office or flex space, ideal for working from home or creating a quiet retreat. The entire first floor showcases tile flooring, combining durability with a clean, polished look. Toward the back of the home, the kitchen and great room are perfectly positioned to capture serene views of the screened lanai, the beautifully landscaped yard, tranquil inlet and majestic oak trees. The spacious kitchen features 42-inch cabinets, a large kitchen island, and stainless steel appliances, creating a functional and inviting space ideal for both everyday living and entertaining. The seamless flow into the great room enhances the open-concept design, making it the true heart of the home. Natural light pours in through numerous windows, each enhanced with custom window casings, while crown molding throughout the home adds a refined architectural touch. As you make your way upstairs, you’ll notice decorative wall niches accented with molding that beautifully matches the window casings, adding character and architectural interest to the space. Upstairs, luxury vinyl plank flooring extends seamlessly through the game room as well as all of the bedrooms and closets, offering both style and functionality. The spacious primary suite is a true retreat, complete with a charming bench window seat. The en suite bathroom features a walk-in shower, double vanities, soaking tub, and a generously sized walk-in closet. The additional bedrooms are impressively sized, with two offering walk-in closets, providing ample storage for family and guests. Step outside to enjoy Florida living at its finest on the screened lanai, overlooking the serene inlet and lush landscape. The fully fenced yard features an aluminum fence with gates on both sides, blending security with unobstructed views of the natural surroundings. The exterior has been freshly painted, and the home includes a new water heater, gutters with premium LeafGuard protection, and is pre-wired for a security system for added peace of mind. Located in the highly desirable gated community of Hickory Hammock, residents enjoy resort-style amenities including a swimming pool, sand volleyball court, playground, tennis courts, a 3,600-square-foot clubhouse with catering kitchen and meeting spaces, as well as a community park. This home beautifully combines elegant style, comfort, and a one-of-a-kind setting. Don’t miss the opportunity to make 15665 Citrus Harvest your HOME!
Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)
Listing Agent: Janelle Conway (407-595-0009)
5138 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787
$745,00010 Days on yellowkey MLS ID: O6401856
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2468 Built: 2023Monthly Fee: $165 Tax: $9,407 (2025)Community: Silverleaf Reserve/Hamlin Ph 2Spa: NoSingle Family
Taxes:$9,407
Elementary School: Hamlin Elementary
Remarks: SELLER MOTIVATED!! Welcome to this masterfully designed and nearly-new 4-bedroom, 3-bathroom residence, built in 2023, that effortlessly blends modern luxury with the vibrant Winter Garden lifestyle. Nestled in the exclusive Silverleaf Reserve community, this home offers stunning curb appeal and high-end architectural details architectural details. Step inside to be greeted by a spectacular double-height ceiling in the main living area, creating an expansive, airy atmosphere flooded with natural light through oversized windows. The open-concept layout features elegant finishes throughout, seamlessly connecting the grand living space to the chef's kitchen. The kitchen is a true showstopper, complete with a large island, premium stainless steel appliances, and ample storage—perfect for both daily living and grand entertaining. Thoughtfully designed for modern convenience, this home features a dedicated upstairs laundry room, making chores a breeze. Outside, your private oasis awaits with a professional summer kitchen, ideal for Florida’s year-round outdoor dining. Plus, enjoy the magic of Disney’s nightly fireworks right from your street! Residents of Silverleaf Reserve enjoy fantastic community amenities, including a resort-style pool, basketball court, and the highly sought-after pickleball courts. Conveniently located just minutes from the Hamlin area, world-class shopping, dining, and major highways, providing easy access to Walt Disney World and Downtown Orlando. This home offers the perfect combination of luxury, space, and community. Owner is a licensed Florida Real Estate Agent. Schedule your private showing today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Vinicius Figueiredo Sobrinho (754-300-7995)
7692 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787
$875,00010 Days on yellowkey MLS ID: O6401130
0 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3855 Built: 2016Monthly Fee: $252 Tax: $7,767 (2025)Community: Summerlake Pd Ph 3ASingle Family
Taxes:$7,767
Elementary School: Summerlake Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Positioned in one of Horizon West’s most desirable communities, this Summerlake executive home blends luxury, location, and lifestyle on a scale rarely found. Set on an oversized 0.28-acre lot, this 5-bedroom, 4-bath residence offers 3,855 sqft of thoughtfully designed living just minutes from Disney and Hamlin Town Center. The true standout? A backyard canvas large enough to create a private resort pool, cabana, outdoor kitchen without compromise. Inside, elevated finishes include plantation shutters, custom wood feature walls, wrought iron staircase, granite countertops, and a gas range at the heart of the home. Smart and structural upgrades include reverse osmosis water, water softener, in-wall pest system, termite bond, hurricane window film, full alarm system, gutters, and WiFi thermostat. A screened lanai and 3-car tandem garage complete the package. Enjoy resort-style amenities, community events, trails, and included landscaping all in a location that continues to outperform. Opportunities like this don’t last especially on lots like this.
Listing is courtesy of: FIRST REGION REALTY (407-559-7333)
Listing Agent: Michelle Culbreth (321-689-6262)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.