Winter Garden Single Family Homes For Sale - 723 homes

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. 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)

Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions

Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)

Listing Agent: Sylvester Harding (407-557-3119)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE Welcome to the Arlington with Bonus and 6 Bedrooms! This stunning 4,236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE Welcome to the Arlington with Bonus and 6 Bedrooms! This stunning 4,236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026 The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large walk-in closet and a private bath with a free-standing tub, a separate shower with a seat, and a private toilet area. The second floor features a spacious loft, and large secondary bedrooms. The Griffin is well planned for a comfortable, luxurious lifestyle. Model home available for walkthrough.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: Under Construction. Waterleigh presents the Clearden. This amazing 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’ll find the first bedroom complete with ensuite bathroom and a powder room across the hall. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and additional three bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity sinks and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor for convenience. This home features a two car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Clearden includes a Smart home technology package which allows you to control your home with your smart device while near or away. *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)

Remarks: Welcome to 8018 Bowery Drive, a spacious 5-bedroom, 3-bathroom home perfectly positioned in Winter Garden right on the edge of Windermere. This layout offers flexibility and comfort for everyday living while also providing the space to entertain. Upstairs, you’ll find the private primary suite, a generous loft, a full bathroom, and three additional bedrooms, two of which offer nightly views of Disney fireworks right from the window. Downstairs features two separate living spaces, plus a conveniently located bedroom and full bathroom ideal for guests or in-laws. Step outside through the telescoping sliding glass door to enjoy a large covered porch and private backyard with no rear or side neighbors. Curb appeal shines with a paver driveway and charming wrap-around front porch. Just minutes from the 429, Disney, and all that Windermere has to offer, this home blends location, privacy, and everyday convenience. Don’t miss the chance to make this beautiful home yours!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 15' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: **We've just introduced a significant price reduction, creating an exceptional opportunity for new owners. ** **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway. Built in 2018, this one-story multigenerational estate offers 3,170 sq ft of refined living on a nearly 1/3-acre lot, just a quick golf cart ride from **Plant Street’s award-winning restaurants, live music, boutique shops, the famous Saturday Farmer’s Market, the Crooked Can Brewery, and the scenic West Orange Trail**. Take a look at Virtual Tour Link 2 to see all the exciting and fun things available to you in the downtown and historic area of Winter Garden. Inside, soaring 12-ft ceilings and natural light flow through an open, flexible layout with four bedrooms, four full baths, and a private office. The gourmet kitchen anchors the home with solid wood cabinetry, quartz countertops, an oversized island, walk-in pantry, and a full suite of KitchenAid Professional appliances with natural gas. The primary suite features a recessed ceiling, expansive custom walk-in closet, and a spa-inspired bath. Fully retractable sliders open to a covered lanai surrounded by mature, professionally designed landscaping and privacy fencing — your own private Florida retreat after a day of exploring downtown. Premium upgrades include smart-home technology, motorized shades, whole-home water filtration, 8-ft solid core doors, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Just minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408, this address blends luxury living with the unbeatable charm and excitement of Downtown Winter Garden. Opportunities like this in Stanton Estates are rare. **Welcome to the lifestyle everyone wants**

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Joe Thomas, Jr (813-724-1922)

Remarks: Under Construction. Waterleigh presents the Torrey. 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 and butler’s pantry and a half bath. 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 walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Off of the family room customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a game room and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Wterleigh, the Torrey includes a Smart home technology package which allows you to control your home with your smart device while near or away. *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)

Remarks: Stunning 5-bedroom, 4.5-bath home located in the highly sought-after Highlands at Summerlake Groves in Horizon West. Built in 2018, this spacious two-story residence offers over 3,600 square feet of living space with an open-concept layout, a gourmet kitchen with oversized island, and a large upstairs loft perfect for entertainment or a home office. The primary suite features a walk-in closet and spa-style bathroom. Conveniently located near Hamlin Town Center, top-rated schools, and major highways including 429, this home combines modern comfort with prime location.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Alexandre Zapparoli Llc (321-444-8701)

Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large walk-in closet and a private bath with a free-standing tub, a separate shower with a seat, and a private toilet area. The second floor features a spacious loft, and large secondary bedrooms. The Griffin is well planned for a comfortable, luxurious lifestyle. Model home available for walkthrough.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: This stunning 4-bedroom, 3.5-bath residence sits proudly in the highly sought-after Hawksmoor community of Winter Garden. Designed with a modern open-concept layout and upgraded with premium finishes, this home blends elegance, functionality, and comfort. Perfectly positioned near the Orange County National Golf Center and Lodge—home to the nation’s largest driving range—this property also offers quick access to Orlando Health Hospital, brand-new top-rated schools, shopping, fine dining, and entertainment. With Highway 429 just minutes away, world-famous Orlando theme parks are practically at your doorstep. House is leased until Nov/2026 and buyer must honor the contract. Step inside and be welcomed by soaring ceilings and a bright, spacious floor plan. The luxurious primary suite with a spa-inspired ensuite is conveniently located on the main level, while the second floor offers three beautifully designed bedrooms, a bonus living/play area, and ample space for family or guests. A flex room on the first floor can serve as a home office, library, or formal dining area. At the heart of the home, you’ll find a chef’s kitchen featuring stainless steel appliances, custom 42" cabinetry, oversized granite island seating up to six, walk-in pantry, and butler’s bar connecting to the dining/flex space. Perfect for both everyday living and entertaining. Outside your door, Hawksmoor provides resort-style amenities, including a zero-entry pool with splash area, clubhouse with private rental options, fitness center, yoga lawn, Zen garden, and community walking trails around picturesque lakes and ponds. This is more than just a house—it’s a lifestyle. Don’t miss the chance to make this exceptional property your new home in one of Winter Garden’s most desirable communities.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Alexandre Zapparoli Llc (321-444-8701)

Remarks: Under Construction. Welcome to 17124 Beachgrass Alley, in Winter Garden, Florida: a new construction home built by M/I Homes, offering 1,983 square feet of thoughtfully designed living space. This home features a well-crafted floorplan combining quality design with everyday functionality. This home features 3 bedrooms, 2.5 bathrooms, an open-concept living space perfect for daily living and entertaining, a lanai, and a 2-car rear-load garage This home showcases an open-concept living space that creates a seamless flow between the family room, kitchen, and dining area, making it ideal for both relaxed evenings and hosting guests. The floorplan is designed with intention, ensuring each room serves a clear purpose while maintaining a cohesive feel throughout. Upstairs, the owner's bedroom offers a private retreat, complete with an en-suite bathroom and walk-in closet for added convenience. The overall layout reflects a commitment to quality design, with clean lines and functional spaces that make everyday living comfortable. Situated in a desirable Winter Garden neighborhood, this home benefits from proximity to parks and outdoor recreation areas, providing easy access to green spaces for families and individuals alike. The surrounding neighborhood offers a welcoming atmosphere with well-maintained streets and a sense of connection to the outdoors.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Stacie Brown Kelly (407-221-4954)

Remarks: Step into better-than-new living with this beautifully upgraded home that rival's today's new construction--without the wait. This exceptional five-bedroom, four-bathroom home situated on Lake Star located in the highly desirable Horizon West area. The inviting entryway leads to a spacious, bright, and open-concept layout filled with abundant natural light and wood look plank tile flooring on the lower level. This Ashton Woods "Superior" floor plan has been upgraded to include a downstairs 5th Bedroom/In-law suite. The gourmet kitchen features a neutral color palette, sleek quartz countertops, lots of cabinet storage, under cabinet lighting, a white farmhouse apron front single bowl sink, modern appliances, including a stainless-steel wall-mounted vent hood, smooth surface cooktop, built-in oven and microwave complemented by a tile backsplash. An open-concept design seamlessly connects the kitchen to the expansive family room, providing an ideal space for entertaining. The first-floor primary bedroom suite offers a tray ceiling and a luxurious bath featuring double vanities, garden tub and a walk in glass framed shower with multiple headed jets. Three additional well-appointed bedrooms upstairs provide ample space for family and guests. The home also features a formal dining room, a den, and a spacious game room, offering versatile living options. A beautiful, stained oak staircase with open stair rails. Elegant finishes, including plantation shutters on all the windows and neutral tones create a timeless aesthetic throughout the residence. Outdoors, the property boasts a well-maintained exterior, and a paver driveway leading to the two-car garage. The spacious lot includes a covered lanai with plumbing already in place to create a summer kitchen of your dreams, and a scenic lakefront view, providing a peaceful and tranquil setting. The community amenities include a clubhouse, a pool, a dog walk park, and a playground, offering convenient recreational opportunities. Conveniently located near shopping, dining, top-rated schools and world-famous Orlando attractions, including Disney parks, Downtown Winter Garden and 40 minutes to the Orlando International Airport. This home is also within minutes of Florida's Western Beltway 429, providing easy access to the area's major thoroughfares. Why wait months for new construction when you can have it all--right now?

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Dee Lund (407-925-7781)

Remarks: Welcome to this beautifully upgraded home in Winter Garden, where style, comfort, and thoughtful design come together seamlessly. From the moment you step inside, you’re greeted by an open, bright, and airy layout, enhanced by elegant farmhouse-inspired finishes and abundant natural light throughout. The main home features no carpet, creating a clean and modern aesthetic, while stunning custom built-in cabinetry in the kitchen, living room, and bedrooms adds both sophistication and functionality. At the center of the home, the spacious kitchen is designed to impress, featuring a large island perfect for entertaining, elegant finishes, and seamless flow into the living and dining spaces. Every detail has been thoughtfully selected, and with tons of upgrades throughout, this home feels elevated at every turn. One of the standout features is the private studio above the garage, ideal for guests, extended family, a home office. Located in the desirable Osprey Ranch community, this home is just minutes from Walt Disney World and everyday conveniences. Even better, you are just steps from the resort style amenities, including the community pool, splash pad, cabana, and playground, offering the perfect blend of lifestyle, convenience, and community living.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Carolina Fortes Ribeiro (407-956-7674)

Remarks: The Suncrest II is a spacious rear-load garage home featuring a convenient first-floor Extra Suite. With 10-foot ceilings and an expansive open-concept living area, this thoughtfully designed home offers approximately 2,500 square feet of comfortable living space with stylish finishes throughout. Currently being used as a builder’s model home, this property is being sold fully furnished with professional designer décor and is leased back to the builder through January 27, 2027, presenting an excellent investment opportunity with secured lease income during the lease term. At the rear of the home, the main living area is anchored by a beautifully designed gourmet kitchen, featuring stainless steel appliances, 42” light cabinetry, quartz countertops, and generous workspace, perfect for both everyday living and entertaining. The home also offers a spacious lanai and private courtyard-style lawn, ideal for outdoor enjoyment. Upstairs, you will find a versatile loft area along with three additional bedrooms, providing ample space for family, guests, or a home office. Located in Osprey Ranch, a beautiful community of new single-family homes in Winter Garden, FL, residents enjoy excellent amenities, a prime location, and thoughtfully designed homes, making this community a wonderful place to call home.

Listing is courtesy of: KICANTO REALTY (305-744-2297)

Listing Agent: Cristiane Leon (305-744-2297)