Homes For Sale in Winter Garden 34787 - 947 homes

Remarks: Under contract-accepting backup offers. Located in Winter Garden’s sought after Golf Cart District, this spacious two story home offers a flexible floor plan and a convenient location close to downtown shopping, dining, entertainment, parks, and local events. A welcoming front elevation and beautifully maintained landscaping create great curb appeal, while the oversized homesite provides added outdoor space and privacy. Inside, the open concept layout is designed for both everyday living and entertaining. The kitchen features abundant cabinetry, generous counter space, and a large breakfast bar overlooking the living and dining areas. Sliding glass doors lead to a screened lanai and fully fenced backyard, creating an ideal space to enjoy Florida’s outdoor lifestyle. A first floor bedroom with an adjacent full bath offers flexibility for guests, a home office, or multi purpose use. Upstairs, the remaining bedrooms are thoughtfully arranged to provide comfortable separation of space. Recent updates include a newer AC system and a roof that is approximately one year old, offering added peace of mind. Conveniently located with easy access to major roadways, shopping, dining, recreation, and everything that makes Winter Garden one of Central Florida’s most desirable destinations, this home combines space, functionality, and location in one exceptional opportunity.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Jonathan Fadoul (347-366-7105)

Remarks: Virtually Staged. Under Construction. The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. The open-concept design flows seamlessly from the dining room into the expansive great room, making it perfect for entertaining. A covered patio extends your living space outdoors, ideal for relaxing or hosting gatherings. A bonus room on this level provides additional versatility, perfect for a playroom or media space. SAMPLE IMAGE

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, where Dream Finders Homes proudly present 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)

Remarks: Amazing Single Family, 4 bedrooms and 3 full bathrooms with fenced backyard for privacy and extra security. Designed for comfort and modern living, this property offers creating a clean and elegant look with modern title flooring. All pictures are real, no virtual staging or AI. The community offers excellent amenities, including a resort-style pool, fitness center, basketball court, playground, and clubhouse for residents to enjoy. Ideally located next to top-rated schools, this home allows children to walk to school, making daily routines easier and safer. The property also sits on a premium lot adjacent to a walking path, providing additional privacy and open space. This is a fantastic opportunity to own a beautiful home in a highly desirable community.

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

Listing Agent: Rodrigo Khoury Francisco (407-308-6489)

Remarks: Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard with new landscape - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. The home gym can be easily converted into a fourth bedroom, with drawings/plans available. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Top rated schools: Panther Lake Elementary, Water Springs Middle School, Horizon High School. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.

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

Listing Agent: Timothy Shepard (727-204-9618)

Remarks: Under contract-accepting backup offers. Freshly painted 1-bedroom, 1 bath. Ready to move-in. Laminate floors in the dining area, living room, and bedroom. Kitchen and Bath have ceramic tiles. Southern Pines has many amenities, like in door basketball court, a Racketball court, tennis, Volleyball, a car wash, a dog park, playground. Fully equipped Gym and theatre, Pool table in the clubhouse, BBQ Grills and a kitchen area with only a small refrigerator and sink, Great counter space with tables and chairs for small partiescual. Owner financing available, call for details. NEW PRICE!!!!

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Maria Lloret (407-929-1994)

Remarks: Located in a quiet, gated community within a highly rated school zone, this well-maintained home offers comfort, privacy, and thoughtful upgrades. The home features two AC systems, including a main unit with an electronic air cleaner, a high-efficiency water heater, and a whole-house reverse osmosis and water softening system, along with updated double-pane windows on the back of the home. A NEW ROOF (2024) adds long-term peace of mind. Inside, you'll find 18.5-foot ceilings in the family room, plantation shutters, custom drapes, and ceiling fans, with wood flooring and travertine tile that complement each other throughout. The kitchen is finished with granite countertops, tile backsplash, a cherry wood bar top, and quality appliances. With a private backyard that is great for cookouts you can enjoy the gated living in a home ideally located near major highways, Central Florida attractions, and Downtown Winter Garden. - Schedule your tour today!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Dominick Florio (321-377-4045)

Remarks: Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.

Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)

Listing Agent: Lisa Reed (407-509-7995)

Remarks: BRAND NEW CONSTRUCTION – NEVER LIVED IN – MOVE-IN READY! This is a rare opportunity to own a truly brand-new home that has never been occupied since the day it closed. No previous residents, no wear and tear, no surprises. Just a fresh start in a home that feels exactly as the builder intended. Be the very first person to live here, create memories here, and even peel the protective plastic off the brand-new appliances! Located in the highly sought-after Highland Ridge community, this stunning energy-efficient home offers a spacious open-concept design perfect for today's lifestyle. The beautifully appointed kitchen features a large center island that flows seamlessly into the dining and living areas, creating the ideal space for entertaining and everyday living. Upstairs, a versatile loft provides endless possibilities: home office, media room, game room, fitness area, or additional family space. Built by Meritage Homes in 2024, this home showcases advanced energy-efficient construction designed to provide year-round comfort, healthier indoor air quality, and lower utility costs. Ideally located in the heart of Winter Garden, you'll enjoy convenient access to top-rated schools, shopping, dining, major employment centers, and world-famous Disney attractions just minutes away. Why wait months for new construction when you can move into a never-lived-in home today? Schedule your private tour and experience what "brand new" truly means!

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Gil Semedo (617-860-9165)

Remarks: This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with washer and dryer. Osprey Ranch, in the highly sought-after Horizon West area, offers a lifestyle of comfort and recreation. Community amenities include a resort-inspired pool and cabana currently under construction, plus a splash pad, playground, and dog park. Showings must be scheduled in advance with the listing agent.

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

Listing Agent: Adriana Pl Franzoi (407-924-0872)

Remarks: Exceptional Deal Priced Below Builder’s Current Offerings! Like-New & Move-In Ready! Seller is Motivated! This stunning 5-bedroom, 3-bath Caden model by Pulte Homes has been lightly lived in and shows like new! Occupied for only a few months by its original owners, the home offers a bright, open layout with a spacious gathering room and a modern kitchen featuring quartz countertops and premium finishes. Upstairs, you’ll find the primary suite with a walk-in closet, along with three additional bedrooms and a versatile loft, perfect for a home office or entertainment space. Additional upgrades include: luxury vinyl flooring throughout, epoxy-coated garage floor, quartz countertops in the kitchen and all bathrooms. Located in the sought-after Silverleaf Reserve community, residents enjoy resort-style amenities such as a pool, pickleball court, and playground, plus easy access to A+ rated schools, shopping, dining, and major highways. Energy-efficient, fully furnished, and ready to move in, this home truly has it all!

Listing is courtesy of: ONLI REALTY GROUP LLC (352-278-8544)

Listing Agent: Vinny Machado Da Silva (352-278-8544)

Remarks: Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless craftsmanship, thoughtful design, and elevated luxury living. Spanning 4,210 square feet of livable space (5,914 total sq ft) across a thoughtfully designed floor plan, The Wildflower offers 5 bedrooms, 5 full baths, and 2 half baths, providing ample room for families who prioritize space and style. From the moment you arrive, every detail speaks to the quality and care poured into this home. Inside, a versatile loft and flex room provides endless possibilities — a home office, media room, playroom, or private retreat. The open, flowing layout is designed for both everyday living and effortless entertaining. Step outside to your own private resort. A custom pool and spa take center stage in the backyard oasis, a covered rear lanai with roll down screens, a fireplace complemented by a summer kitchen and cabana — perfect for hosting under the Florida sun. Enjoy evenings at home with a built in fire pit and beautiful landscape lighting. A 3-car garage rounds out the thoughtful features that make this home as functional as it is beautiful. Located just minutes from downtown Winter Garden's vibrant dining and shopping scene, top-rated schools, and easy access to the Florida Turnpike, The Grove offers the rare combination of peaceful small-town living with big-city convenience. Estimated completion Spring 2027. Secure your lot today and experience the Justice & Wood difference — where every home is built with excellence, without cutting corners.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Virtually Staged. Pre-Construction. To be built. The Ellington is a spacious two-story home offers 3,550 square feet of elegant living, featuring 5 bedrooms and 3.5 bathrooms, along with a generous 3-car garage. The primary suite is conveniently located on the first floor, alongside the laundry for easy access. Upstairs, you’ll find four additional bedrooms and a massive game room—perfect for family fun! Relax and unwind outside under the covered lanai. Enjoy ample space with an additional flex room, café, and walk-in closets throughout the home.

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. Welcome to this move in ready home newly built in 2021 in the gated Lakeview Preserve community. This single story home is offering 4 bedrooms, 3.5 bathrooms, with split bedroom layout and a spacious open floor plan. Step inside to find a bright and airy living space that seamlessly connects the kitchen, dining, and living areas. The gourmet kitchen is the centerpiece of the home, featuring sleek quartz countertops, a large center island ideal for gatherings, and ample cabinetry for storage. Whether you're hosting guests or enjoying a quiet night in, this layout delivers both comfort and functionality. The split bedroom design provides added privacy, with a generously sized primary suite offering a peaceful retreat. Additional bedrooms are well appointed and versatile, perfect for guests, a home office, or growing families. This gated community features resort style amenities including a clubhouse, zero entry pool, splash pad, playground, fitness center, and a private dock with kayak launch on John’s Lake, offering the ideal setting to experience the best of Florida living. Located just minutes from the charm of Downtown Winter Garden, you’ll enjoy access to boutique shopping, local dining, farmers markets, and the popular West Orange Trail for biking and outdoor recreation. Food lovers will appreciate nearby favorites like The Hangry Bison, Chef's Table at the Edgewater, and Crooked Can Brewing offering everything from casual bites to upscale dining. Convenient access to Florida State Road 429 and Florida State Road 408 makes commuting to Orlando and nearby attractions a breeze. Don't miss out on this opportunity and schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Devon Sobers (407-341-4720)

Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, quartz countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Virtually Staged. Under Construction. Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The gourmet kitchen is a standout feature, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized , ensuring that everyone in the family has their own comfortable space. This home is guaranteed to exceed your expectations with its blend of spaciousness and functionality. Sample Image

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

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

Remarks: Virtually Staged. Experience elevated living in the gated WATERFRONT community of Lakeview Reserve, ideally situated in the heart of historic downtown Winter Garden in the GOLF CART DISTRICT with LOW HOA. This impressive FIVE-bedroom, THREE-bath residence with dining space and LOFT offers an exceptional combination of space, comfort, and versatility, thoughtfully designed to accommodate both everyday living and grand-scale entertaining. Boasting a generous floor plan with expansive living areas and well-proportioned bedrooms, the home provides ample room for growing families, multigenerational living, or those seeking dedicated spaces for a home office, fitness room, or media retreat. Situated on a premium homesite spanning nearly one-quarter of an acre (.19), the property presents endless possibilities for outdoor enjoyment. Whether you envision creating a private backyard oasis, adding a custom pool, designing an outdoor kitchen, or simply enjoying the abundance of open green space, this oversized lot offers the flexibility to bring your vision to life while still providing plenty of room for recreation and relaxation. Upon entering, you are welcomed by a thoughtfully designed open-concept floor plan enhanced by new flooring and a freshly painted interior (2023-2024), creating a bright and inviting atmosphere throughout. The beautifully appointed and newly UPDATED gourmet kitchen serves as the heart of the home, featuring stainless-steel appliances, quartz countertops, shaker style cabinets, and two pantries. The living area is adjacent to the kitchen and presents a great opportunity to expand into the outdoor space creating an indoor-outdoor vibe. Designed with flexibility and comfort in mind, the main level offers a generously sized guest bedroom and a full bathroom, ideal for visitors, a home office, or multigenerational living. The laundry room and dining space are also located on the main level. Upstairs, the spacious primary suite provides a private retreat, while three additional bedrooms, full bath, and loft offer abundant space for family and guests. The primary suite includes a garden tub with separate shower, vanity, linen closet, and walk-in closet. Enjoy picturesque views of Lake Apopka from multiple vantage points throughout the home, creating a serene backdrop for everyday living. ADDITIONAL UPDATES: roof (2018), water heater (2025), downstairs AC (2024-2025), Just moments away, residents enjoy exclusive access to a private community dock overlooking the lake—an idyllic setting for morning coffee, fishing, or taking in spectacular sunset views. Located within the golf-cart district, this remarkable home places you just minutes from the charming boutiques, acclaimed dining, farmers market, and year-round events that make downtown Winter Garden one of Central Florida’s most sought-after destinations. Convenient access to major highways (Turnpike, 429, East-West Expressway) further enhances the lifestyle, placing world-renowned attractions such as Walt Disney World, Universal, and downtown Orlando within easy reach. You can access the 22 mile long WEST ORANGE Trail just footsteps outside of the community to take in cycling and exercising. Move-in ready, this exceptional residence offers a rare opportunity to enjoy luxury, convenience, and a true sense of community in one of Winter Garden’s sought after gated neighborhoods. Measurements are approximate. Buyer is responsible for verifying information.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: 16217 Lake Johns Circle is a rare modern farmhouse retreat where luxury, craftsmanship, and family-centered design come together in extraordinary fashion. Positioned on a quiet cul-de-sac of only 15 homes with no HOA, this fully reimagined Winter Garden residence offers front-porch views toward Johns Lake and backs to protected green space, creating a setting that feels private, peaceful, and deeply connected to nature. Completed in 2025, the home underwent an extensive renovation and expansion with remarkable attention to detail and quality. Unlike typical luxury renovations, much of the craftsmanship was personally completed by the homeowners themselves-resulting in a residence that feels intentionally built rather than simply remodeled. Inside, the home unfolds with warm modern farmhouse design, engineered hardwood flooring throughout, soaring ceilings, custom millwork, curated lighting, and expansive gathering spaces designed for both everyday living and elevated entertaining. The chef's kitchen serves as the architectural centerpiece of the home, featuring professional-grade appliances, custom cabinetry, quartz surfaces, a hidden butler's pantry, beverage station, and an oversized gathering island wrapped in authentic character and texture. The floorplan was thoughtfully designed to accommodate multigenerational living and large gatherings with uncommon flexibility. Unique design moments include custom built-in bunk spaces, a secondary bedroom designed with three built-in beds, and a truly exceptional owner's retreat featuring vaulted ceilings, a private sitting area, spa-inspired bath, oversized custom closet room, and peaceful views toward Johns Lake. The upstairs loft creates an additional lifestyle space ideal for media, gaming, reading, or relaxation, while the nearly 1,500-square-foot insulated garage/workshop offers incredible versatility for vehicles, boats, hobbies, fitness, or storage. Major infrastructure improvements completed in 2025 include a new roof, new HVAC systems, new windows, new plumbing, tankless water heater, septic system, and extensive mechanical upgrades. Located minutes from Downtown Winter Garden, Oakland, the West Orange Trail, and major roadways, this is a rare opportunity to own a highly customized modern farmhouse retreat in one of Central Florida's most desirable lifestyle corridors.

Listing is courtesy of: HOMEFIRST REAL ESTATE (689-340-3007)

Listing Agent: Ed Vasquez (689-340-3007)

Remarks: Virtually Staged. Rare opportunity in Winter Garden's coveted Lake Avalon: a fully fenced and gated 5-acre mini-ranch in the Valley View enclave, where genuine Lake Avalon water and conservation views meet true rural freedom — bring your horses, livestock, or recreational vehicles — just minutes from Hamlin Town Center, Walt Disney World, and SR-429. Spanning nearly 3,800 SF, this thoughtfully expanded 5BR/4BA estate includes a substantial permitted addition that created an ideal wing for multi-generational living or large-scale entertaining. At its center is a redesigned custom kitchen with imported Italian cabinetry, waterfall-edge countertops, premium Thermador appliances, and a built-in Dacor smart refrigerator. A separate enclosed prep kitchen with additional appliances and laundry hookups adds rare day-to-day functionality. The layout offers dual primary suites, formal and casual living spaces, oversized tile flooring, modern LED lighting, and remodeled baths — openness and privacy as you need them. Major systems deliver long-term peace of mind: a NEW ROOF (2022) NEW HVAC (2022), an 80-gallon commercial water heater (2022), a whole-home water softener, and a 24KW whole-house standby generator with transfer switch for full backup power. Zoning flexibility, sunset and lake views, and no cookie-cutter HOA rules — one of the last true large-lot enclaves this close to Winter Garden's growth corridor. Schedule your private tour today.

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Jared Jones, Pa (407-906-5000)