Winter Garden Homes For Sale & Real Estate - 951 homes

Remarks: Under contract-accepting backup offers. 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)

Remarks: A home that doesn’t just offer a place to live—but a lifestyle to love. Experience modern living at its finest in this beautifully appointed home, privately set within one of Hamlin’s most desirable locations. A chef inspired kitchen showcases sleek 42" cabinetry, quartz surfaces, a generous island with designer lighting, and top tier appliances. The fenced backyard with elegant brick pavers leads to a rear entry 2 car garage, creating a seamless blend of style and function. The refined primary suite features a spacious walk in closet and a spa like bath with dual vanities, while upstairs laundry adds everyday convenience. Perched at one of Hamlin’s highest elevations, this residence offers unmatched access to luxury amenities, scenic trails, waterfront leisure, premier dining, boutique shopping, and the renowned Winter Garden lifestyle. A sophisticated retreat in a community experiencing exceptional growth. Sunset walks along the water, weekend movies at the luxury theater, fresh finds at the local markets, and endless dining and shopping options. Just minutes from Winter Garden Village and the charm of historic Plant Street, this is a place where convenience meets connection, and where every day feels a little more inspired.

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

Listing Agent: Claudia Panella (407-947-5026)

Remarks: Luxury fully furnished 2-bedroom, 2-bathroom condo-hotel located in a high-demand resort area of Orlando. This unit offers a spectacular water park view and is part of a professionally managed resort, designed exclusively for short-term rentals. The layout features a spacious living area with access to a private balcony, a fully equipped kitchen, and a split-bedroom floor plan ideal for guests. Resort amenities include pools, spa, fitness center, restaurants, bars, playgrounds, and 24-hour security. An excellent turnkey investment opportunity in a prime tourist location, minutes from major attractions, with strong rental demand and long-term appreciation potential.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Maria Carvajal (551-331-8154)

Remarks: Public on Zillow / Realtor

Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)

Listing Agent: Saijun Gong (407-775-8533)

Remarks: Under contract-accepting backup offers. MOTIVATED OWNER GIVING LASt CHANCE BEFORE RENTING IT OUT! RARE OPPORTUNITY TO MEET THE 1% MONTHLY INVESTOR RULE IN CENTRAL FLORIDA! This two bed, two bath villa home offers low maintenance living near downtown Winter Garden. Walk into an open concept living area with two large windows giving plenty of natural light. New floors throughout. The kitchen offers solid wood cabinets, granite, and stainless steel appliances. The primary bedroom offers two closets and an ensuite bathroom. A second bathroom is down the hall going to the second bedroom. Exterior Maintainance and landscaping offers low maintenance for this beautiful villa. The community offers a pool to relax in or take your laps. The family can enjoy the pool or the large community yard right outside your doorstep. Just a short distance to Plant Street where you can enjoy the farmer’s market, dining, shops, and access to West Orange Trail downtown has to offer. Just off major highways for commuting anywhere in the Orlando area (Hwy 50, Turnpike, 429, 408, 414). Everything else you could need is right along Colonial Drive. This property qualifies for low down payment programs for primary buyers or a great opportunity to add to your investment portfolio! Aggressively priced to sell, set up your showing for this quaint villa now!

Listing is courtesy of: MOFFATT (407-988-2991)

Listing Agent: Marcus Moffatt (304-290-4020)

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 in Horizon West, Winter Garden — estimated completion summer 2026. This Kellogg Townhome features a covered entry leading into an open and expansive living, L-shaped kitchen, and dining area. The home offers a spacious private courtyard with access to the detached two-car garage. The owner’s suite is highlighted by a large walk-in closet and a private bath with dual vanities and a separate shower.

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

Listing Agent: Devahn Powell (571-234-7236)

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: Welcome to The Grove Resort & Water Park, a premier condo-hotel nestled in the vibrant heart of Winter Garden, FL. This beautifully furnished 2-bedroom, 2-bathroom unit is designed for ultimate comfort and convenience, making it an incredible investment opportunity or a perfect vacation retreat. Step inside to find a spacious open floor plan, featuring a stylish kitchen with modern appliances, sleek countertops, and ample storage. The inviting living and dining areas flow effortlessly onto a private screened balcony, where you can unwind and soak in the tranquil surroundings. The primary suite is a true retreat, offering a spa-like en-suite bathroom complete with a soaking tub, separate glass-enclosed shower, and dual vanities. A generously sized second bedroom and full bathroom ensure plenty of space for guests to feel right at home. As a resident or guest at The Grove Resort, you’ll enjoy world-class amenities, including a thrilling water park with slides, a lazy river, surf simulator, multiple pools, a full-service spa, fitness center, and on-site dining options. Plus, with 24-hour concierge service and a hassle-free rental program, this property offers both luxury and convenience. Located just minutes from Walt Disney World and Orlando’s top attractions, this condo presents an unparalleled opportunity to own a slice of paradise. Don’t miss out—schedule your private tour today!

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Allan Kardosh (407-499-4466)

Remarks: Looking for a Vacation Home in Orlando, this unit is a rare find with the Best Views in the Resort! This stunning 7th-floor condo at The Grove Resort & Spa offers breathtaking water views and front-row unobstructed seats to Disney fireworks reflecting over the lake each night. This fully furnished, all-inclusive condo-hotel provides a truly hands-off investment opportunity with onsite property management and a full-service rental program. Located in Building 1, this luxury 3-bedroom, 2-bath unit is perfectly situated just steps from restaurants, pool and resort amenities. Features an open floor plan with modern furnishings and all necessary housewares. The spacious primary suite includes a king bed, while both guest bedrooms have queen beds for comfortable guest accommodations. The fully equipped kitchen features stainless steel appliances, including refrigerator, range, microwave, and dishwasher. A private laundry closet with washer and dryer adds convenience for guests. Owners and guests alike will enjoy relaxing on the private screened balcony overlooking the water.The Grove Resort has exceptional amenities including multiple resort pools, Surfari Surf Park, Lake Austin with fishing dock and paddleboats, Escape Spa, fitness center, on-site restaurants, sundry shop, arcade, and youth activity center. Ideally located just minutes from Walt Disney

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

Listing Agent: Alexis Mckenzie (321-438-9670)

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: Experience modern townhome living in this beautifully designed three-story residence located in Parkview at Hamlin in Winter Garden. This thoughtfully planned home features three private suites, including a convenient first-floor suite and a spacious third-floor primary suite, offering flexibility and privacy for today’s lifestyle. The second floor serves as the heart of the home, showcasing an open-concept living room and kitchen ideal for entertaining. The open kitchen is appointed with 42" cabinets, white quartz countertops, and stainless steel GE appliances, while vinyl plank flooring enhances the main living areas with durability and style. A covered lanai provides the perfect space to relax and enjoy Florida living. Designed with interiors inspired by our Milan Collection, this townhome blends chic design and modern finishes—all set within one of Winter Garden’s most desirable communities near shopping, dining, and everyday conveniences.

Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)

Listing Agent: Reed Williams (813-918-4491)

Remarks: Located in the gated community of Hickory Hammock, this beautiful corner-unit townhouse offers 3 bedrooms, 2.5 bathrooms, and a spacious upstairs loft perfect for a home office, media room, or flex space. This well-maintained home features stylish upgrades throughout, including wood-look ceramic tile downstairs and engineered hardwood flooring upstairs, along with brand-new paint and carpet for a fresh, move-in-ready feel. The open living areas lead to a screened back porch overlooking a peaceful green park area with no rear or side neighbors, creating a rare sense of privacy and open space. Additional highlights include a 2-car garage, washer and dryer included, whole-home water filtration system, and UV lights installed on the AC unit for enhanced air quality and efficiency. Residents of Hickory Hammock enjoy outstanding resort-style amenities, including a community pool, volleyball courts, and lake access with a private dock perfect for fishing and enjoying the waterfront lifestyle. With its premium corner location, thoughtful upgrades, and exceptional community amenities, this home offers the perfect blend of comfort, convenience, and low-maintenance living in sought-after Winter Garden.

Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)

Listing Agent: Tracey Mcfadden (321-217-7808)

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)

Remarks: Under contract-accepting backup offers. This is the one you’ve been waiting for! Tucked away on a peaceful cul-de-sac and situated on an expansive half-acre corner lot, this stunning Horizon West home, in the highly sought-after community of Independence, offers exceptional curb appeal, privacy and luxury living at every turn. Inside, experience soaring, double-height ceilings and an abundance of natural light that fills the spacious, open-concept living area. The thoughtfully designed floor plan features a private office, a formal dining room and an oversized main living space with incredible two-story ceilings and breathtaking views of the resort-style pool and outdoor entertaining areas. At the heart of the home is the chef’s kitchen, complete with extensive cabinetry and storage, a large center island and top-of-the-line stainless steel appliances, perfectly designed for both everyday living and entertaining. The spacious owner’s suite is a true retreat, featuring custom walk-in closets and a spa-inspired bath designed for relaxation. An additional main-level living space offers incredible flexibility and can easily serve as a private guest retreat or multigenerational living suite. Upstairs, entertainment takes center stage with a spacious bonus and playroom, an included pool table and an impressive, dedicated private home theater, featuring luxury powered seating for eight with a built-in projector and amazing quality in-wall surround sound for the ultimate movie-night experience. Outside, enjoy your private backyard oasis. The inviting and refreshing oversized pool showcases a stone wall spillover water feature and Baja sun shelf, all surrounded by lush landscaping for added privacy. The expansive lanai offers two separate seating areas, plus a natural gas fire pit and outdoor kitchen, creating the perfect setting for family fun and entertaining. Beyond the pool area, you’ll find more than 2,000 square feet of private, fenced backyard space with lush grass, shaded by mature trees, ideal for play, pets or relaxing outdoors. Additional upgrades include an oversized, three-car garage plus workspace, a dependable, powerful 20-kilowatt-hour Kohler whole-house generator, two tankless water heaters, a newly-upgraded HVAC and pool equipment and newer pool solar panels, all offering added efficiency and peace of mind. In a community known for its beautiful lake views, incredible scenery and abundant natural wildlife, this home also offers nightly views of Disney fireworks, spectacular sunsets over Lake Hancock and unforgettable rocket launches, all from inside and around this beautiful home. Experience this incredible home in the ideal location for yourself, and discover luxury living at its finest.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Lynda Miller (407-620-2924)

Remarks: Located in the heart of Oakland, Florida, 2120 Gopher Tortoise Terrace offers the perfect blend of modern comfort, thoughtful upgrades, and an exceptional location surrounded by nature and convenience. This beautifully cared for 3 bedroom, 2.5 bathroom townhome also presents a rare opportunity for qualified buyers to potentially assume the seller’s attractive 2.75% mortgage rate, subject to lender approval, creating the possibility for substantial savings compared to current market rates. Inside, the home welcomes you with an airy open-concept design filled with natural light and stylish laminate flooring that carries throughout the main living spaces. The spacious layout connects the living, dining, and kitchen areas seamlessly, creating an ideal setup for both everyday living and entertaining guests. The kitchen has been designed with both function and style in mind, featuring granite countertops, stainless steel appliances, a large center island with seating, and a modern tile backsplash that adds a clean, upscale touch. Several custom improvements throughout the home elevate the overall experience, including upgraded pantry organization, custom shelving in the laundry room with a built-in drying pole, and professionally designed closet systems for enhanced storage and convenience. Upstairs, the primary suite serves as a relaxing private retreat, complete with a custom walk-in closet and an upgraded en-suite bathroom featuring raised countertops and a frameless glass shower. The additional bedrooms offer flexibility for family, visitors, or a dedicated home office space. Outside, the private paved courtyard creates a peaceful setting for morning coffee, outdoor dining, or relaxing evenings with friends and family. The surrounding location is one of the home’s standout features. Positioned directly across from the West Orange Trail, residents enjoy immediate access to miles of scenic walking, running, and biking paths. Just nearby, the Oakland Nature Preserve provides beautiful natural surroundings, wildlife, and additional trails to explore. The home is also conveniently close to Downtown Winter Garden, a highly sought-after destination known for its award-winning farmers market, local restaurants, boutique shopping, and year-round events that create a true sense of community. Combining a prime location, quality upgrades, and a welcoming layout, this home delivers an exceptional lifestyle opportunity in one of Central Florida’s most desirable areas.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Andy Neal (407-619-3517)

Remarks: Under contract-accepting backup offers. Stunning four-bedroom, three-bathroom home in the highly sought-after Wintermere Pointe community, complete with a spacious three-car garage. Upon entry, you are welcomed by a bright, open-concept floor plan. The formal dining room at the front of the home flows seamlessly into the main living area, which features direct access to a large covered back porch—perfect for indoor-outdoor living. The chef-inspired kitchen is a true standout. The primary suite serves as a private retreat, featuring an ensuite bathroom with dual sinks, a garden tub, and a separate standing shower. This property is ideally situated just minutes from local schools, parks, and major highway access, putting daily conveniences and entertainment options right at your fingertips. Schedule your showings today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)