Winter Garden Homes For Sale & Real Estate - 951 homes

Remarks: From the moment you step through the front door of this thoughtfully designed 5-bedroom, 5-bath home in Winter Garden’s sought-after Watermark community, it feels like home. Natural light pours into the open-concept living space, where everyday moments unfold with ease. Cook family meals in the stunning kitchen featuring quartz countertops, a custom backsplash, stainless steel appliances, an oversized island, and a walk-in pantry with built-in shelving. Gather around the island for morning coffee or late-night laughs, while Sonos in-ceiling surround sound sets the tone throughout the main living areas. Downstairs, the private guest suite is perfect for visitors or multigenerational living, while the dedicated office offers a quiet space to focus or create. Upstairs, the loft becomes the hub for game nights or movie marathons, with three additional bedrooms and a luxurious primary suite just down the hall. Every detail has been carefully chosen, from designer lighting and ceiling fans in all rooms and common areas to wood-look tile and plush carpeting underfoot. Function meets style in the laundry room, complete with cabinetry, a tile backsplash, and a deep utility sink. Additional enhancements include a water softener system, epoxy flooring in the oversized 2-car garage, and 7-inch seamless gutters that add both form and function to the exterior. Outside, enjoy the covered lanai and fully fenced backyard, perfect for future pool plans or peaceful evenings. With ample storage and access to top-rated schools, shopping, dining, and resort style amenities, this home offers more than just space. It offers a lifestyle. Come see how it feels to come home.

Listing is courtesy of: DIDOMENICO REALTY GROUP (407-922-3277)

Listing Agent: Michael Didomenico, Jr (407-922-3277)

Remarks: Welcome to your private oasis in the highly desirable community of Waterleigh! This rare gem stands out as one of the few homes in the neighborhood to feature its very own private, heated saltwater pool, complete with a spacious covered patio, an impressive newly screened lanai, and the ultimate privacy of no rear neighbors. Boasting one of the most sought-after single-story designs, this open and light-filled home welcomes you with sophisticated new wainscoting architectural details and brand-new, upgraded flooring throughout all four bedrooms. The heart of the home is an incredible gourmet kitchen featuring a massive quartz island illuminated by high-end glass pendant lighting, premium appliances, custom cabinetry, and a stunning backsplash that flows seamlessly into the spacious living and dining areas. Unwind in a luxurious primary suite showcasing elegant tray ceilings and a grand walk-in closet outfitted with a brand-new custom organization system. The upgraded primary bath offers a spa-like experience with granite counters, double sinks, a large shower, and an oversized soaking tub. Every detail has been meticulously enhanced, including a fully renovated laundry room, a pristine epoxy-finished garage floor, sealed and cleaned outdoor pavers, and a freshly repainted exterior. The home is also equipped with permanent outdoor Govee smart lights, allowing you to easily customize your exterior illumination for holidays or everyday ambiance. Located just 15 minutes from Walt Disney World, you can even enjoy the magic of the nightly Disney fireworks right from your own home. Waterleigh offers an unmatched, low-maintenance resort lifestyle where the HOA includes all lawn care, giving you more time to enjoy the two community clubhouses, resort pools, fitness centers, garden, mini-golf, volleyball, and scenic lake viewing docks. Schedule your tour today to experience this highly upgraded, move-in-ready masterpiece!

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Stephanie Nelson (321-536-0729)

Remarks: Virtually Staged. Under Construction. Pre Design Center Pricing Sample Image Welcome to this beautifully designed newer-construction home in the highly sought-after Hamlin Meadows community of Winter Garden, this spacious residence offers modern finishes, an open-concept layout, and a prime location just minutes from Hamlin Town Center, shopping, dining, top-rated schools, and major highways. Inside, you’ll find a bright and inviting floor plan featuring a large kitchen with upgraded cabinetry, stainless steel appliances, stone countertops, and an oversized island overlooking the main living and dining areas — perfect for entertaining. Pricing does not include design selections; you have the opportunity to customize the home to fit your taste

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

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

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

Remarks: Virtually Staged. Under Construction. Sample Images The Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and two and a half bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality.

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES The Amelia is a beautifully designed one-story offering three bedrooms and two baths, thoughtfully arranged for comfortable everyday living. The open concept layout features a spacious great room, dining room combo with no wasted space. 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: Price Improvement – Welcome to 5966 Cypress Hill Rd, located in the highly sought-after Independence community of Winter Garden. This well-maintained home offers a rare blend of privacy, space, and lifestyle amenities. Situated on a larger-than-average lot with no rear neighbors, the home backs up to an open area, creating a peaceful and private setting—perfect for relaxing or entertaining. Features include a covered side lanai, extended driveway, and detached garage, offering both functionality and additional space. Enjoy resort-style living in Independence, including: • Two private boat ramps with access to Lake Speer and Lake Hancock • Two clubhouses, pools, fitness centers, and sports courts • Internet included through Spectrum as part of the HOA • Walking trails, parks, and frequent community events • Internet included through Spectrum as part of the HOA The home is zoned for top-rated schools and conveniently located near shopping, dining, and major highways. Solar System: Property includes a solar system with an existing loan. Buyer to assume solar loan. Note: Water softener not included but may be purchased separately. Solar loan assumption required; details available upon request.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Mahmoud Mango (321-830-4678)

Remarks: Virtually Staged. ORCHARD HILLS HOME FOR SALE **HOA takes care of front and back lawn maintenance **4-Bedroom **3.5-Bathrooms **2-car Garage **Fresh Interior Painting **New Coach Lights **Two-Story Foyer ** As soon as you enter there is a OFFICE/Flex room with a half Bathroom for convenience and also connects to a Coffee/Cocktail Bar for enjoyment. *Open Floor Plan features: Gourmet Kitchen with a BUILT-IN Double Oven, Cooktop, Microwave and Dishwasher and a BIG Kitchen Island. *Ceramic Tile in Wet Areas *Neutral color Luxury Vinyl Plank throught *9ft CEILINGS *DOWNSTAIRS Master Suite with Space for a Seating Area *Master Suite Large Walk-In Closet *Master Bathroom has a FLOATING TUB and Separate Shower. UPSTAIRS: You will find a LOUNGE/GAME ROOM and the other 3 BEDROOMS with 2 FULL BATHROOMS. There is Laundry Room with enough space for storage and a COVERED Screened Lanai Porch overlooking the FENCED yard for Privacy. The yard is a good size for a Private Pool in the future. NO REAR NEIGHBORS **Walking Distance to COMMUNITY POOL, FITNESS, CLUBHOUSE. This home is located near TOP RATED Schools and Modern Hospital with easy commute to DisnweyWorld, Dr Phillips Restaurant Row and Shopping at Winter Garden Village and the New HAMLIN. Call for your Private Showing.

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

Listing Agent: Avi Maganda (321-287-5340)

Remarks: Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Nicole Prince (407-712-5688)

Remarks: Imagine a home that adapts beautifully to every stage of your life. Tucked away in Winter Garden’s coveted Summerlake, this rare four-bedroom townhome stands out with a prized first-floor bedroom and full bath. Whether you desire a luxurious downstairs suite, an inviting guest retreat, or a quiet home office, this ground-level sanctuary offers unmatched flexibility and ease without the daily stairs. The light-filled open layout flows effortlessly into a gorgeous chef’s kitchen, boasting rich granite countertops, a massive prep island, and stainless appliances perfect for gathering. Upstairs, three additional spacious bedrooms and a cozy loft offer private retreats for family, hobbies, or movie nights. Step out to your private, walled courtyard—a sunny oasis for morning lattes or peaceful evenings under the stars. Enjoy maintenance-free living, resort amenities, and nightly Disney fireworks dancing over your neighborhood. This exceptional four-bedroom home is the perfect blend of comfort and style.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: David Decristo (407-974-3362)

Remarks: A TRUE SHOWCASE LOCATED IN HORIZON WEST.. Are you looking for the finest of MODERN LUXURY in this "architecturally" designed estate? Situated in one of the Top Rated communities in Winter Garden, at Encore Ovation, on a 0.38-acre premium lot.FENCE IS ALLOWED. Boasting over $200,000 in QUALITY UPGRADES, this residence features, 5 bedrooms and 4 bathrooms. Step onto the elegant 48 X 48 ceramic tiling that flows throughout the main level, transitioning to rich engineered hardwood on the second floor. A striking custom wood and TEMPERED glass staircase serves as a focal point, leading to a spectacular second floor entertainment gallery enclosed in TEMPERED glass with private balcony. A GOURMET DREAM KITCHEN , featuring custom wood cabinetry, Exotic Quartzite countertops, and a custom-fitted pantry. Equipped for the foodie enthusiast, with a SUB -ZERO refrigerator for peak freshness, a Wolf precision oven, a Thermador hub, and a dual-zone wine chiller, for years of gatherings and conversations. Retreat to the oversized travertine-floored lanai, overlooking a sprawling backyard already prepped with plumbing for a summer kitchen-the perfect. The perfect canvas for a custom infinity pool. Other features include;motorized designer blinds, custom lighting installations, and high-efficiency ceiling fans. A spacious garage with built-in overhead storage racks. HOA INCLUDES LAWN CARE AND BASIC LANDSCAPING, for true low-maintenance living.Enjoy resort-style community amenities just steps from your home.These include a clubhouse, fitness center, community pool and steps from a dog park and walking trails. End your day on your private Master Suite balcony, embracing breathtaking sunsets over Lake Mac. Welcome to paradise!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Renee Rodriguez (407-927-2055)

Remarks: Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden.  Welcome to the Arlington w/ Extended Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, wrap-around cabinetry, ample counter space, and an open layout that connects directly to the living areas, perfect for everyday living and entertaining. The owner’s suite and additional main-floor bedrooms are thoughtfully placed to maximize privacy and comfort. Upstairs, a spacious loft provides versatile space for a media room, play area, or home office, along with an additional bedroom, ideal for family or guests. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

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

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

Remarks: Under contract-accepting backup offers. Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bonus. Discover the newest community by Dream Finders Homes in the highly sought-after Hamlin, Winter Garden. Welcome to the Arlington, an award-winning single-story open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, wrap-around cabinetry, and ample counter space, connecting directly to the living areas—perfect for everyday living and entertaining. The owner’s suite and additional main-floor bedrooms are thoughtfully placed to maximize privacy and comfort, making this home ideal for families or multi-generational living. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bonus. Discover the newest community by Dream Finders Homes in the highly sought-after Hamlin, Winter Garden. Welcome to the Arlington, an award-winning single-story open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, wrap-around cabinetry, and ample counter space, connecting directly to the living areas—perfect for everyday living and entertaining. The owner’s suite and additional main-floor bedrooms are thoughtfully placed to maximize privacy and comfort, making this home ideal for families or multi-generational living. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bonus. Discover the newest community by Dream Finders Homes in the highly sought-after Hamlin, Winter Garden. Welcome to the Arlington, an award-winning single-story open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, wrap-around cabinetry, and ample counter space, connecting directly to the living areas—perfect for everyday living and entertaining. The owner’s suite and additional main-floor bedrooms are thoughtfully placed to maximize privacy and comfort, making this home ideal for families or multi-generational living. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

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

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

Remarks: Virtually Staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria Bonus offers 5 Bedrooms, 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.“It includes high-speed fiber optic internet.”

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. Welcome to the Biscayne, a thoughtfully designed two-story home offering the perfect balance of space, comfort, and flexibility. Featuring four bedrooms and three bathrooms, this floor plan is ideal for both everyday living and entertaining. The main level showcases an open-concept layout where the dining area flows seamlessly into the expansive great room and well-appointed kitchen, creating a welcoming space for gatherings. A versatile flex room on the first floor offers endless possibilities and can be used as a home office, fitness space, or optional guest bedroom. Step outside to the covered patio, perfect for relaxing or hosting outdoor get-togethers. Upstairs, a spacious primary suite complete with a walk-in closet and private bath, providing a comfortable retreat at the end of the day. A bonus room adds additional living space, ideal for a media room, playroom, or secondary lounge. The conveniently located upstairs laundry room enhances everyday functionality. Located in the desirable Hamlin Meadows community, residents enjoy a thoughtfully planned neighborhood with a variety of homesites, including rear-load townhomes and single-family homes. Just minutes from Hamlin Town Center, you’ll have easy access to shopping, dining, and entertainment

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

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

Remarks: Welcome to an exceptional residence where luxury, lifestyle, and location converge in one of Winter Garden’s most desirable communities. Situated on a hard to find oversized premium corner lot, this stunning 4-bedroom, 4-full bath home offers 3,424 square feet of thoughtfully designed living space, perfectly positioned to capture serene park views in the front and tranquil pond vistas in the rear. From the moment you arrive, the home’s elevated presence and expansive setting set the tone. Inside, you are greeted by a light-filled, open-concept layout designed for both elegant entertaining and everyday comfort. The spacious floor plan flows seamlessly, enhanced by refined finishes and generous living areas. At the heart of the home, the kitchen and great room spaces connect effortlessly to the outdoors, where your private resort-style retreat awaits, outdoor living at its finest! Step outside to your private POOL (built in 2022)—a true showpiece designed for relaxation and entertaining. The fully fenced backyard with a sleek metallic fence offers both privacy and unobstructed views, creating the perfect balance of security and openness. Whether hosting gatherings or enjoying a quiet evening, the backdrop of the pond and open skies delivers an unparalleled sense of tranquility. And as the sun sets, prepare for a truly magical experience—nightly views of the MAGIC KINGDOM FIREWORKS right from your backyard create a one-of-a-kind ambiance that elevates everyday living into something extraordinary. INTERIOR HIGHLIGHTS: 4 Bedrooms | 4 Full Bathrooms. A spacious DEN located in the first floor is currently set as a guest room, with the convenience of a full bathroom in the first floor with access to the pool. A spacious BONUS ROOM located on the second floor– ideal for a media room, office, or playroom. Expansive GREAT ROOM and entertaining areas including a STUDY SPACE off of the kitchen and a DINETTE SPACE. A thoughtfully designed layout with functional flow! Recent Update:A/C UNIT REPLACED in late 2025, offering peace of mind and energy efficiency for years to come. Park views from the front – providing openness and privacy. Pond views from the rear – creating a serene and picturesque backdrop. Oversized corner lot enhances curb appeal and outdoor space. This is more than just a home—it’s a lifestyle property that blends natural beauty, luxury amenities, and a prime location. From quiet mornings overlooking the pond to evenings watching Disney fireworks, every day here feels elevated.

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

Listing Agent: Sulamit Sanchez (305-528-7778)

Remarks: Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden!  Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom.   The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting.  Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC system (3 weeks old) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home.  Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Lorie Gullian (407-928-8078)

Remarks: Virtually Staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria offers 4 Bedrooms, 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando, where Dream Finders Homes proudly presents Serenade at Ovation. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.“It includes high-speed fiber optic internet”

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

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