Winter Garden Homes with Other Exterior Features

Winter Garden Homes with Other Exterior Features

Welcome to Winter Garden, Florida – a hidden gem nestled in the heart of Orange County. Known for its charming historic downtown, this vibrant city seamlessly blends small-town warmth with modern conveniences. With its picturesque landscapes, lush parks, and a rich cultural scene, Winter Garden is not just a place to live; it’s a lifestyle.

The city boasts a variety of homes, each with unique exterior features that enhance their curb appeal. From Mediterranean-style villas with terracotta roofs to contemporary designs featuring sleek lines and expansive windows, there’s something to suit every taste. Many properties offer additional features such as spacious patios, inviting porches, and beautifully landscaped gardens, perfect for entertaining or simply enjoying the Florida sunshine.

Winter Garden is also renowned for its outdoor recreational activities. The West Orange Trail, a scenic 22-mile path, invites residents to explore on foot or by bike, while the nearby Lake Apopka offers opportunities for fishing, kayaking, and wildlife viewing. With a strong sense of community, local farmers' markets, and seasonal festivals, there’s always something happening in this lively city.

Families will appreciate the top-rated schools and a variety of family-friendly amenities, including parks, playgrounds, and community centers. Whether you’re searching for a cozy bungalow or a spacious family home, Winter Garden’s real estate market has something for everyone. Discover the charm and beauty of Winter Garden, where your dream home awaits amidst a backdrop of stunning landscapes and a welcoming community spirit.

Newest Winter Garden Homes with Other Exterior Features

7186 Wild Strawberry Run, Winter Garden
$750,000
4 Beds ⋅ 4 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed 4-bedroom, 3.5-bathroom home in the highly desirable Independence community of Winter Garden! Offering a thoughtful blend of space, comfort, and lifestyle, this home features an additional private office, a spacious bonus room, and a unique layout designed for both everyday living and entertaining. Step inside to discover generous living spaces, a modern kitchen perfect for gathering with family and friends, and a spacious primary suite designed for comfort and relaxation. The additional office provides an ideal space for working from home, while the large bonus room offers endless possibilities—a media room, game room, or second family lounge. The home features a convenient half-bath on the first floor, a Jack-and-Jill bathroom, and a detached garage located at the rear of the property, adding character and functionality to the home's layout. Outside, enjoy a nicely sized backyard with room to create your own private outdoor retreat, including the potential to add a pool (subject to applicable approvals). Whether you envision weekend barbecues, outdoor entertaining, or simply relaxing in your own space, the possibilities are yours to explore. What truly makes this location special is the lifestyle waiting right outside your door!Horizon West, offering amenities and outdoor spaces designed to bring recreation, relaxation, and community connection together. Residents can enjoy: Community swimming pools for cooling off and enjoying the Florida sunshine Clubhouses and fitness centers for recreation and wellness Scenic walking and biking trails for outdoor exercise Community parks and playgrounds for outdoor fun Sports courts and beautifully maintained green spaces for an active lifestyle The location is equally appealing, with convenient access to shopping, restaurants, cafés, schools, and everyday essentials. Explore nearby Hamlin and Winter Garden Village for additional dining, shopping, and entertainment options. And when it's time for adventure, Walt Disney World and Central Florida's world-famous attractions are within driving distance, making weekend outings and family fun easy to enjoy. Whether you're looking for room to grow, space to work from home, or a community that offers amenities beyond your front door, this home presents an opportunity to enjoy the best of the Winter Garden lifestyle. Enjoy the space. Embrace the community. Make Winter Garden home.

7186 Wild Strawberry Run, Winter Garden
1539 Hawkesbury Court, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code
Welcome to 1539 Hawkesbury Court, located in the desirable Winter Garden area of Central Florida! This single-family home offers an excellent opportunity to enjoy the convenience, amenities, and lifestyle that make Winter Garden a sought-after place to call home. Conveniently located near shopping centers, restaurants, grocery stores, parks, and everyday essentials, residents can enjoy easy access to a variety of local conveniences. Explore the charm of historic Downtown Winter Garden, known for its unique shops, local restaurants, cafés, and welcoming atmosphere. The popular West Orange Trail is nearby, offering miles of scenic paths for walking, jogging, and cycling. Winter Garden Village provides an array of retail stores, dining options, and entertainment for added convenience. The property's location also offers access to major roadways, including Florida's Turnpike and State Road 429, making travel throughout the greater Orlando area convenient. Enjoy proximity to recreational opportunities, golf courses, and outdoor activities, while remaining within reach of Orlando's employment centers, attractions, and entertainment destinations. Whether you're looking for a place to call home or exploring real estate opportunities in the growing Central Florida market, this property presents an opportunity to enjoy the many benefits of the Winter Garden lifestyle.

1539 Hawkesbury Court, Winter Garden
923 Colie Alley, Winter Garden
$610,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Short Sale. ~ IT IS WORTH THE WAIT! Discover the opportunity to own a nearly new David Weekley home in the highly desirable Oakland Park community of Winter Garden. Built in 2022, this SUMMERTON MODEL in McKinnon Square offers the style, space and location buyers are looking for — all within a community known for its beautiful streetscapes and exceptional amenities. The charming FRONT PORCH gives the home a welcoming personality, while inside, soaring ceilings, generous windows and an open layout create an easy sense of space. The kitchen serves as the natural gathering point, with a well-appointed design that connects seamlessly to the dining and living areas — a comfortable setup for both everyday life and entertaining. Upstairs, all of the bedrooms are conveniently grouped together, along with a FLEXIBLE LOFT AREA that can evolve with your needs. Use it as a home office, media room, play space, reading area or simply enjoy the extra room to spread out. Life here extends well beyond the home itself. OAKLAND PARK IS A GOLF-CART-FRIENDLY COMMUNITY with pools, clubhouse facilities, parks, playgrounds, a dog park and plenty of opportunities to enjoy the outdoors. The WEST ORANGE TRAIL AND LAKE APOPKA are nearby, while Historic Downtown Winter Garden is just a golf-cart ride away, putting restaurants, local shops, breweries, coffee spots, entertainment and the popular Farmers Market within easy reach. Location is another standout. Schools are conveniently nearby, including the elementary school approximately .5 miles away, middle school 1.1 miles and high school 3 miles. Orlando Health Hospital is approximately 1.8 miles away, while Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike provide easy access throughout Central Florida — including Disney and the area’s major attractions. NEARLY NEW, MOVE-IN READY AND SET IN ONE OF WINTER GARDEN’S MOST SOUGHT-AFTER COMMUNITIES, this short-sale opportunity is one you’ll want to see before it’s gone! Buyer and buyer agent to verify all data and measurements.

923 Colie Alley, Winter Garden
13557 Parkfield Way, Winter Garden
$650,000
4 Beds ⋅ 3 Baths ⋅ Encore At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location!  Minutes from Walt Disney World and all that Winter Garden has to offer with the new hospitals, stores, restaurants, downtown Winter Garden, Horizon West and the list goes on! Single stories are hard to come by and this MI Home is waiting for you!  It sits on a gorgeous conservation lot with no neighbors on one side. Sit on the front porch or the back patio and enjoy the good life!  Walk to the pool, fitness center and dog park. The perfect community to walk or bike.  This 4 bedroom 3 bath rare find single story is move in ready-well maintained, built in 2021, quartz countertops, NEW AC, huge walk-in closet in the primary bedroom, a popular 3 way split floor plan, and ample room for entertaining with the dining room and large family room.  The home is stunning with its gorgeous wooded and pond view. Lawn Care is included in the HOA leaving you time to enjoy all Central Florida has to offer!  Schedule your showing today!

13557 Parkfield Way, Winter Garden
15007 Night Heron Drive, Winter Garden
$790,000
5 Beds ⋅ 4 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this absolutely immaculate 5-bedroom residence, thoughtfully designed for both luxury and everyday comfort. From the moment you enter, the spacious open-concept floor plan creates an inviting atmosphere with exceptional flow between the living, dining, and kitchen areas. The gourmet-inspired kitchen is truly the heart of the home, featuring elegant granite countertops, a natural gas range, custom coffee bar, walk-in pantry, and oversized center island with bar seating—perfect for casual gatherings or entertaining guests. The expansive living area provides plenty of space to relax and entertain, while the formal dining room adds an elegant touch for special occasions. The first-floor primary suite offers a private retreat, complete with a generous walk-in closet and a beautifully appointed primary bath designed for comfort and relaxation. Upstairs, discover an impressive bonus/game room, along with four additional spacious bedrooms, providing flexibility for family, guests, a home office, or additional living space. Step outside to the spacious covered porch, an ideal setting for morning coffee, evening relaxation, or entertaining while enjoying the beautiful Florida surroundings. Located in the sought-after Summerlake community, residents enjoy an outstanding collection of resort-style amenities, including a clubhouse, fitness center, resort-style swimming pool with splash pad, dog park, bike paths, and scenic walking trails. This exceptional home combines sophisticated living, thoughtful design, abundant space, and resort-style community amenities—offering the perfect blend of comfort and Florida lifestyle living.

15007 Night Heron Drive, Winter Garden
144 Tildenville School Road, Winter Garden
$899,900
3 Beds ⋅ 1 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
The real story of 144 Tildenville School Road is the land. Opportunities to own over an acre this close to Historic Downtown Winter Garden are becoming increasingly hard to find. Beneath a canopy of beautiful mature trees, this property offers something that cannot easily be recreated: space, privacy, character, and a location within Winter Garden’s golf cart district. The existing 3 bedroom home offers nearly 1,500 square feet of living space, but step into the backyard and you quickly understand what makes this property special. This is land meant to be enjoyed. Picture evenings beneath the trees with string lights glowing overhead, friends gathered around the custom built pizza oven, dinner being prepared in the summer kitchen, music playing, and plenty of room for everyone to spread out. For the next owner, the possibilities are just as compelling as the lifestyle already here. Enjoy the property as it is, create your own private retreat, expand upon the existing outdoor spaces, or simply appreciate the increasingly rare luxury of having over an acre of land near the heart of Winter Garden. And despite the privacy, you are still connected to the lifestyle that makes this area so desirable. Being within Winter Garden’s golf cart district means trips toward Historic Downtown Winter Garden can become part of the routine. Spend Saturday mornings at the Farmers Market, enjoy dinner along Plant Street, explore local shops and restaurants, or spend an afternoon on the West Orange Trail before heading home to your own piece of Winter Garden. Homes can be renovated. Kitchens can be changed. Finishes can be replaced. But you cannot manufacture another acre of mature, established land in a location like this. That is what makes 144 Tildenville School Road different. It is not simply a home for sale. It is an opportunity to own a substantial piece of Winter Garden, with the space to enjoy today and the possibilities to make it something entirely your own tomorrow.

144 Tildenville School Road, Winter Garden
13953 Easdale Alley, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
BACK ON THE MARKET WITH A PRICE IMPROVEMENT! Don’t miss this highly upgraded Toll Brothers townhome in Westhaven at Ovation. Built in 2024, this popular floor plan that is NO LONGER AVAILABLE FROM THE BUILDER. The open-concept main level features a beautifully upgraded kitchen with quartz countertops, designer cabinetry and backsplash, stainless steel appliances, and an oversized island. Step outside to your private courtyard featuring a hot tub that can come along—perfect for relaxing and enjoying the Florida lifestyle. Additional upgrades include upgraded finishes throughout. Upstairs, the spacious primary suite offers a walk-in closet and upgraded en-suite bath, plus two additional bedrooms. Located approximately 2 MINUTES FROM THE NEARBY ELEMENTARY SCHOOL and close to Horizon West, Hamlin, shopping, dining, entertainment, and major roadways. Multiple upgrades, included spa, prime Winter Garden location, and a floor plan you can no longer purchase from the builder!

13953 Easdale Alley, Winter Garden
11367 Great Rock Street, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity** Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income. This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car garage. The open-concept layout features a kitchen with island overlooking the family and dining areas. Upstairs, the primary suite includes an oversized bathroom and walk-in closet. Residents enjoy a clubhouse, fitness center, resort-style pool, hedge maze, and dog park. Conveniently located near SR-429, US-192, and SR-545, just minutes from Walt Disney World, Orange County National Golf Center, shopping, dining, and Walmart. A great opportunity in one of Winter Garden’s most sought-after communities.

11367 Great Rock Street, Winter Garden
10119 Salt Point Drive, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code
This stylish townhome in one of Winter Garden’s most desirable resort-style communities, offers a blend of comfort, convenience, and everyday luxury. The home sits in a beautifully planned neighborhood known for its amenities,GainesvillecinfgainesLoo surroundings, and welcoming atmosphere—an ideal setting for anyone seeking a relaxed yet connected lifestyle. Its location is a major highlight. Winter Garden is home to some of Central Florida’s top-rated schools, making this property especially appealing for families who value strong educational options. You’re also just minutes from premier shopping and dining at places like Hamlin Town Center and Winter Garden Village, giving you easy access to everything from groceries to entertainment. And of course, the magic of Disney theme parks is right around the corner, making weekend outings effortless and adding a touch of excitement to everyday life. This townhome places you in a thriving, fast-growing area where convenience meets resort-style living. With beautiful community amenities, excellent schools, nearby shopping, and world-famous attractions close enough to enjoy anytime, it’s a standout opportunity in one of Winter Garden’s most sought-after.

10119 Salt Point Drive, Winter Garden
988 Stucki Terrace, Winter Garden
$230,000
3 Beds ⋅ 3 Baths ⋅ Westside Townhomes Phase 2 19/100 Lot 5 Blk 11 SubDv. ⋅ 34787 Zip Code
Beautiful Family-Oriented Townhouse in a Great Location! Well-maintained and move-in ready, this home offers low-maintenance living with a low HOA fee. Conveniently located approximately 10–17 miles from Walt Disney World, Disney Springs, and many of Orlando’s top entertainment destinations. Easy access to major highways makes commuting and exploring the area convenient. A wonderful opportunity for a family, second home, or investment property. More photos coming soon!

988 Stucki Terrace, Winter Garden
1415 Sherbourne Street, Winter Garden
$404,000
3 Beds ⋅ 3 Baths ⋅ Stone Creek 48 140 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully updated 3 bedroom, 2.5 bath home in the heart of Winter Garden, perfectly positioned for convenience, comfort, and everyday living. Enjoy being just 5 minutes from Winter Garden Village, 10 minutes from Downtown Winter Garden and Plant Street Market, and walking distance to top-rated Whispering Oak Elementary. Thoughtfully updated and move-in ready, this home offers a turnkey experience with major upgrades including a Brand New Water Heater (2026), New HVAC (2022 serviced bi-annually, most recent service in August 2026), New Roof (2019), New Vinyl Fence (2022), New Kitchen Appliances (2022), Upgraded Bathrooms (2022), and an Updated Kitchen (2022). Inside, the open concept floor plan is enhanced by high ceilings and a spacious living area that overlooks the remodeled kitchen. The kitchen features a large island, quartz countertops, subway tile backsplash, ample storage, and stainless steel appliances. The adjacent dining area seamlessly opens to a screened-in patio creating an inviting space for relaxing and enjoying indoor/outdoor living. The fully fenced backyard provides shade and plenty of room for outdoor activities. Upstairs, the spacious owner’s suite features a walk-in closet and a fully remodeled ensuite bath with double vanities, tiled floors, and a glass-enclosed shower. Two additional bedrooms share an updated bathroom featuring new tile, a new vanity, and a tub. Residents also enjoy neighborhood amenities including a newer playground with sunshades and turf, along with a nearby path leading to open green space with basketball courts, baseball and soccer fields—all en route to Whispering Oak Elementary. With thoughtful updates, desirable community amenities, and an exceptional Winter Garden location, this home is ready to welcome its next owner. Schedule your tour today!

1415 Sherbourne Street, Winter Garden
1511 Sweet Apple Street, Oakland
$339,900
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!

1511 Sweet Apple Street, Oakland
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