Winter Garden Homes with Private Yard Exterior Features

Winter Garden Homes with Private Yard Exterior Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes, vibrant downtown area, and rich history, Winter Garden offers a unique blend of small-town charm and modern amenities. With its warm, sunny climate and friendly community, this thriving city is the perfect place to call home.

One of the standout features of homes in Winter Garden is their private yards, providing residents with a personal oasis to relax and entertain. Imagine stepping out into your lush backyard, whether it be for a morning coffee or an evening barbecue with friends. These private outdoor spaces are perfect for gardening, playing with pets, or simply enjoying the Florida sunshine.

The homes in Winter Garden range from cozy bungalows to spacious family residences, catering to a variety of lifestyles and preferences. Many properties boast beautifully landscaped yards, complete with mature trees and colorful flora, creating a serene retreat just steps from your door.

In addition to its stunning homes, Winter Garden is celebrated for its vibrant community life. The historic downtown area features charming shops, delectable dining options, and a lively farmers market, all set against the backdrop of stunning architecture. With easy access to the West Orange Trail and nearby lakes, outdoor enthusiasts will find plenty of opportunities for hiking, biking, and water activities.

Come experience the allure of Winter Garden, where beautiful homes with private yards await you in a community that feels like family. Your dream home is just around the corner!

Newest Winter Garden Homes with Private Yard Exterior Features

1323 Azalea Way, Winter Garden
$189,000
3 Beds ⋅ 2 Baths ⋅ Westside Twnhms Ph 03 SubDv. ⋅ 34787 Zip Code
This 3-bed, 2-bath townhome is just minutes from Historic Downtown Winter Garden, Plant Street Market, farmers markets, boutique shops, and local dining. Enjoy easy access to major highways, top-rated schools, Walt Disney World, and Central Florida’s theme parks. Whether you’re adding to your rental portfolio or looking for a property in a highly desirable area, this one offers location, lifestyle, and investment potential all in one.

1323 Azalea Way, Winter Garden
517 Garden Heights Drive, Winter Garden
$589,900
4 Beds ⋅ 2 Baths ⋅ Garden Heights SubDv. ⋅ 34787 Zip Code
Welcome home to 517 Garden Heights Drive, right in the heart of Winter Garden's golf cart district. This fully renovated 4-bedroom, 2-bath modern farmhouse sits on a third of an acre, about a mile from the shops, restaurants, and events on Plant Street, with Lake Apopka views right from your driveway. The big-ticket items are already taken care of: a brand-new roof (July 2025), new water heater (2025), and HVAC replaced in 2021. Inside, nearly 2,000 square feet has been completely refreshed with new tile flooring, fresh paint and texture, and modern wood accent paneling. The open floor plan centers around a shiplap fireplace, with new ceiling fans and light fixtures throughout. The kitchen is the true showpiece, featuring quartz countertops, shaker cabinets, gold hardware, stainless steel appliances, and statement pendant lighting. Both bathrooms were redesigned with custom tile and dual vanities, and the primary suite adds a sliding barn door and a spa-style bath. Step out to the screened-in porch with its own wet bar, overlooking a huge backyard made for weekend gatherings or slow mornings with coffee. A 2-car garage gives you plenty of room for storage, tools, and the golf cart. And no HOA! Move-in ready, beautifully updated, and minutes from everything that makes Winter Garden such a special place to call home. Come see it for yourself.

517 Garden Heights Drive, Winter Garden
1442 Coluso Drive, Winter Garden
$585,000
3 Beds ⋅ 2 Baths ⋅ Magnolia Wood Fifth Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in a desirable golf cart community, just 2 miles from historic Downtown Winter Garden! This home offers LVP and tile flooring, double-pane windows, a cozy wood-burning fireplace, a 6-year-old AC system, and a spacious Florida room with sliders for enjoying Florida living. The saltwater pool features a 5-year-old pump and heater, while recent exterior paint adds to the home's appeal. Outdoor amenities include an RV-ready setup with RV connection and a dedicated pad for your boat or RV, plus an oversized shed for additional storage. A whole-home generator, approximately 3 years old, with a 500-gallon propane tank provides added peace of mind. The beautifully landscaped property also features an impressive variety of fruit trees, including 5 peach, 2 plum, 2 nectarine, 1 apple, starfruit, small and large banana, pineapple, and lemon trees. Located in a golf cart-friendly community and minutes from Downtown Winter Garden's shopping, dining, and entertainment, this home offers a wonderful blend of convenience, comfort, and Florida lifestyle.

1442 Coluso Drive, Winter Garden
1362 Union Club Drive, Winter Garden
$910,000
3 Beds ⋅ 3 Baths ⋅ Oakland Parka F1 & F2 SubDv. ⋅ 34787 Zip Code
Welcome to 1362 Union Club Drive in Oakland Park, where a charming park-front setting and inviting outdoor spaces create a wonderful place to call home. A large front porch overlooks the park, providing the perfect spot to enjoy your morning coffee, relax with a book or take in the neighborhood scenery. With no rear neighbor, the home also offers a wonderful sense of privacy. This 3-bedroom, 2.5-bath home features all bedrooms upstairs, including a spacious primary suite that also enjoys peaceful park views. The main living areas are downstairs, with convenient access to the backyard and pool. Outside, you'll find a beautiful pavered pool area that offers plenty of space for relaxing and entertaining. Between the park views from the front porch and the private setting in back, this home offers exceptional outdoor living. Located in the desirable Oakland Park community of Winter Garden, this home presents an opportunity to enjoy one of the area's sought-after neighborhood settings while adding your own personal touches inside.

1362 Union Club Drive, Winter Garden
8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Turnkey, Vacation Property in Lakeshore Preserve Winter Garden. Toll Brothers Model home. Professional interior designed for the model. The property occupies one of Lakeshore Preserve’s most open and airy homesites next to the park. The park's open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open park space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer upon entering. Key design and home features: Smart home technology, shiplap wall detailing, dramatic and rich wood beam trim ceilings. Plantation shutters throughout. The kitchen features a massive center island, farmhouse sink, custom backsplash, abundant cabinetry to include deep drawers and natural-gas cooking. Triple sliding glass doors connect the great room to expansive outdoor living, featuring: a fully equipped, built in summer kitchen. Outdoor dining and lounge spaces enclosed on all sides by luxury motorized retractable screens. Beyond the retractable screens, the backyard expands to feature an outdoor putting green, more lounge area and a built-in stone fireplace with modern glass-rock insert. Positioned at the rear of the first floor, the primary suite includes a custom walk-in closet and a striking primary bath with opposing vanities, a private water closet and a dramatic walk-through shower. Custom tile extends from the floor up the shower walls, with opposing shower systems, multiple shower heads and built-in bench seating. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes ensuite bath and walk-in closet, while the other two share a hall bath. When not occupied by guests, the second living room serves as a private lounge, media room, or office space. Turnkey includes: all living area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Utility features to this home: tankless water heater, low-E windows, smart-home technology, in-wall pest system and HOA-maintained grounds around the home and inside the fenced in back yard. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds, sand volleyball court. All surrounded by lake. Cable, one-gig internet and ground maintenance are included in the HOA fee. This executive collection home sits on one of the most unique homesites within Lakeshore Preserve. Privacy and sun-drenched light, Toll Brothers coveted upgrades, and this transitional design style fully finished by an interior designer for this model home.

8836 Lakeshore Pointe Drive, Winter Garden
6329 Manuscript Street, Winter Garden
$515,000
5 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Welcome to this spacious 5-bedroom, 3.5-bath home offering 2,773 sq. ft. of living space! Built in 2013, this home features a comfortable and functional layout with generously sized bedrooms, walk-in closets, and well-maintained living spaces throughout. The kitchen features stainless steel appliances, a kitchen island, and plenty of space for everyday use and entertaining. The primary bathroom includes dual sinks, a separate shower, and a tub. Additional features include an open front porch and a 2-car garage. The roof, A/C, electric water heater, and other major components are original to the home (2013, per seller).

6329 Manuscript Street, Winter Garden
150 Hammock Preserve Loop, Oakland
$879,000
4 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Some homes simply sit in a neighborhood. This one feels like it belongs there. Welcome to 150 Hammock Preserve Loop, a 2023 Rockwell Homes residence tucked into the heart of Oakland Park, where the front porch looks out toward mature oak trees and the best parts of the Winter Garden lifestyle are never far from home. Step inside and you’re immediately greeted by a dedicated office to the left of the entry, creating the perfect work-from-home space while keeping it separate from the main living areas. Throughout the home, thoughtful custom updates give each space a personality of its own. The primary suite is conveniently located on the main floor, while the additional bedrooms and spacious loft are upstairs, creating a layout that offers both separation and flexibility. A rare three-car garage provides the extra space that can be difficult to find in Oakland Park, whether you need room for vehicles, golf carts, bikes, storage, or all of the above. Out back, the generous yard offers plenty of room to create your own outdoor retreat, including space for a future pool. But what makes this home especially difficult to replicate is everything beyond the front door. Oakland Park is one of Winter Garden’s most sought-after communities for a reason. Tree-lined streets, front porches, parks, playgrounds, two resort-style community pools, a clubhouse, dog park, waterfront spaces, and miles of trails create a neighborhood designed to actually be enjoyed. Hop on your bike and connect to the West Orange Trail, or grab the golf cart and head toward Downtown Winter Garden for a morning at the Farmers Market, drinks at Crooked Can, dinner along Plant Street, boutique shopping, community events, and everything surrounding Plant Street Market. Here, weekends can start with coffee on the front porch beneath the oaks, turn into an afternoon by the pool or on the trail, and end with a golf cart ride into Downtown Winter Garden. Built in 2023, filled with custom touches, complete with a dedicated office, rare three-car garage, and a backyard ready for what comes next, 150 Hammock Preserve Loop offers more than a beautiful home. It offers the Oakland Park lifestyle that makes this neighborhood so special.

150 Hammock Preserve Loop, Oakland
2107 Bay Line Road, Oakland
$625,000
3 Beds ⋅ 2 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code
Welcome home to Hull Island, where thoughtful upgrades, a private preserve setting, and resort-style amenities come together. Extended driveway upgraded with builder. This beautifully maintained 3-bedroom, 2-bath home backs to protected conservation land with no rear neighbors. High ceilings, electronic shades, and abundant natural light give the home an open, airy feel. The chef’s kitchen features an oversized granite island, a gas stove, pot filler, 42-inch cabinets, and additional upper cabinetry for storage. Tile backsplash, built in conventional oven and microwave. From the kitchen, you can look out over the pool while preparing meals. The spacious primary bedroom has been updated to the larger size upgrade with the builder. Master bathroom features a double vanity and a very large walk in shower with dual showerheads and a built-in bench, providing both comfort and convenience. Built in 2024, this custom fully automated SALT WATER 7FT screened-in pool area and overhead waterfall is made for relaxing and entertaining. You can control everything for the pool and waterfall , the color, the raindrops you can make it heavy or light all from the fingertips of your phone. It includes a summer kitchen with a sink and a gas fire pit that you can control with your phone. The home also offers a washer and dryer, an electric tankless water heater, and a recently installed Generac natural-gas whole-house generator designed to turn on automatically during a power outage. This home also has an irrigation system heling you keep the landscaping looking its best year- round! This home also has a water softener! The HOA is $165 per month, with no CDD. Community amenities include a resort-style pool, playground, dog park, and a boardwalk leading to a dock and fishing pier on Lake Apopka. Residents also have a private entrance to the 120-acre Oakland Nature Preserve. Downtown Winter Garden, the West Orange Trail, farmers markets, shopping, dining, golf, and pickleball are all close by. Home built in 2021 builder: M/I Homes Of Orlando LLC With its preserve views, inviting outdoor space, and convenient location, and privacy this move-in-ready home is a rare find. The photos are not virtually staged—this home truly is breathtaking! Seller has an assumable mortgage at a low interest rate of 2.375%!!!

2107 Bay Line Road, Oakland
5416 Golden Apple Drive, Winter Garden
$925,000
5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 5416 Golden Apple Dr, an exceptional 5-bedroom, 3.5-bath home in WINCEY GROVES, just moments from the heart of Hamlin. The experience begins at the UPGRADED DECORATIVE-GLASS FRONT DOOR, opening to warm wide-plank flooring, statement lighting, clean architectural details, and a contemporary staircase with black metal accents. Continue into the main living space and the home’s personality really comes through. A dramatic CUSTOM WOOD-SLAT MEDIA WALL WITH BUILT-IN CABINETRY anchors the room, while the open kitchen brings everyone together around an expansive island with stone countertops, abundant cabinetry, stainless steel appliances, and modern pendant lighting. Throughout the home, DESIGNER LIGHT FIXTURES, CUSTOM MILLWORK, BUILT-INS, AND MOTORIZED WINDOW TREATMENTS elevate the spaces well beyond standard builder finishes. Behind the scenes, an ALEXA-INTEGRATED SMART HOME SYSTEM provides convenient control of multiple connected features throughout the residence. The floor plan is equally thoughtful, with the PRIMARY SUITE AND MAIN BEDROOMS LOCATED DOWNSTAIRS for comfortable everyday living. Even the primary suite has something unexpected—a CONCEALED ENTRY DOOR that blends discreetly into the wall before opening to an oversized retreat with a bay-window sitting area overlooking the pool and custom walk-in closets. Upstairs feels like its own private destination, featuring a GUEST BEDROOM, FULL BATH, AND EXPANSIVE BONUS LIVING AREA WITH A BUILT-IN BEVERAGE CENTER, WINE COOLER AND MINI REFRIGERATOR—perfect for overnight guests, extended family, movie nights, a game room, or simply having an entire second living space away from the main level. Then the experience moves outside. MOTORIZED RETRACTABLE SCREENS allow the covered lanai to transition from open-air living to a screened retreat at the touch of a button, overlooking a HEATED SALTWATER POOL, expansive paver deck, tropical landscaping, and fully fenced backyard. And when evening arrives, DISNEY FIREWORKS LIGHT UP THE HORIZON from the comfort of your own backyard. The location completes the picture, with HAMLIN TOWN CENTER APPROXIMATELY ONE MILE AWAY and convenient access to dining, shopping, entertainment, SR-429, Horizon West, Walt Disney World, and everything the Winter Garden area has to offer. At 5416 Golden Apple Dr, it isn’t one upgrade that makes the difference—it’s how thoughtfully everything has been brought together. Schedule your private showing and experience it for yourself.

5416 Golden Apple Drive, Winter Garden
14371 Shocklach Drive, Winter Garden
$700,000
3 Beds ⋅ 2 Baths ⋅ Latham Park North SubDv. ⋅ 34787 Zip Code
Every single day, you’ll experience the ultimate Central Florida lifestyle in your own private backyard paradise. Tucked into the coveted Latham Park community of Winter Garden, just two miles from Disney’s Magic Kingdom, this pristine 2018-built home pairs luxurious outdoor living with unbeatable convenience to world-class entertainment, shopping, and dining. Surrounded by updated curb appeal, mature landscaping, and a quiet neighborhood setting, it offers a rare combination of comfort, style, and resort-style amenities right at home. Inside, the light-filled floor plan feels crisp, elevated, and completely turn-key, highlighted by elegant crown molding and durable wood-look tile floors running throughout the main living areas. High tray ceilings accentuate the main open-concept living and dining spaces, leading seamlessly into a dedicated flex space. Showcasing true Florida indoor-outdoor living, the home features both a standard sliding door and a triple sliding glass door that opens directly from the flex space out to the pool area. At the center of it all is a modern chef’s kitchen designed for both quiet mornings and hosting friends. It boasts 42-inch cabinets, sleek quartz countertops, under-cabinet accent lighting, a gas range, and premium stainless steel appliances. Conveniently nearby, an oversized laundry room comes fully equipped with a washer and dryer while providing exceptional extra storage space. For total peace of mind and remarkable efficiency, the home is secured with a SimpliSafe security system, equipped with a tankless water heater, and features fully paid-off solar panels for ultra-low electricity bills. The primary suite serves as your private sanctuary, featuring a custom built-in walk-in closet system and a beautifully appointed primary bathroom complete with a luxurious, walk-in shower. Two additional spacious bedrooms with luxury vinyl flooring provide exceptional flexibility for family, guests, or a dedicated home office setup. Step out back into your personal outdoor oasis—a custom screen-enclosed pool deck featuring a stunning heated saltwater pool and spa, built-in controllable LED lighting overhead and within the enclosure, and a Char-Broil outdoor kitchen perfect for weekend barbecues. The fully fenced backyard ensures a private, safe space for relaxation or outdoor fun. Beyond your doorstep, enjoy Latham Park’s vibrant community events, pool, playground, and spectacular views of the Disney fireworks right from within the neighborhood—plus access to top-tier schools including Panther Lake Elementary, Hamlin Middle, Horizon High, and Windermere Prep. From private poolside relaxation to nightly magic nearby, this is a rare gem in one of Winter Garden’s most sought-after pockets.

14371 Shocklach Drive, Winter Garden
2696 Bobcat Chase Boulevard, Oakland
$515,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!

2696 Bobcat Chase Boulevard, Oakland
1606 Beulah Road, Winter Garden
$409,000
3 Beds ⋅ 2 Baths ⋅ Orange Cove SubDv. ⋅ 34787 Zip Code
LOCATION, LOCATION, LOCATION, Exceptional value is found with this spacious 3 bedroom, 2 bathroom home. You will appreciate the fully remodeled home with new flooring, kitchen cabinets and countertops, hall and master bathrooms, roof, water heater, pluming, and covered porch. This property is located across the street from Winter Garden High School and 5 minutes away from downtown Winter Garden and convenient access to major highways.

1606 Beulah Road, Winter Garden
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