Winter Garden Homes with Private Yard Exterior Features

Winter Garden Homes with Private Yard Exterior Features

Welcome to Winter Garden, Florida – a vibrant city that beautifully blends small-town charm with modern conveniences. Nestled in the heart of Orange County, Winter Garden is renowned for its picturesque landscapes, historic downtown, and a strong sense of community. With its rich agricultural roots, the city offers a delightful mix of outdoor activities, cultural events, and a thriving local economy. Residents enjoy easy access to the scenic West Orange Trail, a network of walking and biking paths that meander through lush greenery, making it perfect for family outings or leisurely strolls.

One of the standout features of homes in Winter Garden is their private yard exteriors. Imagine coming home to your own serene sanctuary, where you can unwind amidst lush gardens or host weekend barbecues with friends and family. Many properties in Winter Garden boast spacious lots, allowing for ample outdoor living space, perfect for gardening enthusiasts or those who simply enjoy the Florida sunshine. Whether you’re looking for a cozy bungalow or a modern family home, you’ll find that many residences come equipped with beautifully landscaped yards, providing a perfect backdrop for relaxation and recreation.

With a strong sense of community, excellent schools, and a plethora of recreational activities, Winter Garden is not just a place to live – it’s a place to thrive. Discover your dream home in this enchanting city, where every day feels like a vacation in your own personal paradise. Come experience the magic of Winter Garden, where your ideal lifestyle awaits!

Newest Winter Garden Homes with Private Yard Exterior Features

580 First Cape Coral Drive, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Black Lake Park, one of Winter Garden's sought-after gated communities, where spacious family living, fantastic amenities and an enviable location come together to create the perfect Florida lifestyle! Offering 4 SPACIOUS BEDROOMS, 2 1/2 BATHROOMS, AND HUGE LOFT AREA, this beautiful home provides the ideal combination of comfort, space and functionality. The welcoming open-plan layout creates an easy flow between living spaces, making everyday family life effortless, and entertaining a pleasure. With NO CARPETS THROUGHOUT, NEWLY PAINTED INTERIOR and a NEW ROOF – INSTALLED DECEMBER 2024, this home offers even more appeal and peace of mind, with a clean, practical and easy-to-maintain living environment. Whether hosting friends, enjoying family time or simply relaxing at home, with 2834 sq ft there's room for everyone. It does not stop there. Step outside and discover what Florida living is all about! Your private fully fenced backyard retreat, features a NEW FABULOUS SALTWATER SWIMMING POOL AND SPA – INSTALLED DECEMBER 2025! Imagine soaking up the sunshine, cooling off on warm afternoons or unwinding in the spa after a busy day. With plenty of room for lounging, outdoor dining and entertaining this is an outdoor space you'll love coming home to! Life in Black Lake Park is something special! This FABULOUS, GATED, FAMILY-FRIENDLY COMMUNITY offers an outstanding range of recreational facilities, making it a wonderful place for families and those who enjoy an active outdoor lifestyle. Amenities include TENNIS COURTS, BASKETBALL COURTS, BASEBALL FIELDS, A COMMUNITY SWIMMING POOL AND PLAYGROUND, along with lovely walking paths, and COMMUNITY DOCK AND BOAT RAMP. Whether enjoying a family game, taking a leisurely stroll, spending time at the park or heading out onto the water, there's something for everyone to enjoy. It's a community where outdoor living, family fun and a wonderful neighborhood atmosphere come together. This LOCATION is hard to beat. Simply wonderful! Just minutes from the charm of Historic Downtown Winter Garden, where you'll find an abundance of restaurants, cafés, boutique shopping and the much-loved Winter Garden Farmers Market. Winter Garden Village is also close by, offering an excellent choice of shopping, grocery stores and everyday conveniences. For commuters and those who love to explore, easy access to the 429, Florida Turnpike and Highway 50 makes traveling around Central Florida very convenient. Walt Disney World and the area's world-famous attractions are also within easy reach, making this a fantastic location for enjoying everything that is available in Central Florida. Whether you're searching for your next family home, the perfect place to entertain or simply somewhere to enjoy everything the Florida sunshine has, this is an opportunity not to be missed. THIS HOME IS MOVE IN READY! COME AND DISCOVER THE LIFESTYLE WAITING FOR YOU IN BLACK LAKE PARK.

580 First Cape Coral Drive, Winter Garden
386 Railroad Avenue, Winter Garden
$130,000
2 Beds ⋅ 1 Baths ⋅ Loveless & Sewell SubDv. ⋅ 34787 Zip Code
2 bedroom / 1 bath fixer upper home on almost .25 acre lot! Exterior and interior needs renovation and updating. The home contains 660 square feet of heated space. Located just east of downtown Winter Garden, west of toll road 429. This home is just minutes from down town restaurants and shopping, convenient to everything and priced to sell. No HOA with low taxes! All room measurements are approximate. Buyer to verify independently. Cash or private money acceptable. Bring your best offer!!!

386 Railroad Avenue, Winter Garden
925 Butter Oaks Court, Winter Garden
$619,000
3 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Timeless Craftsman Charm Meets the Best of Winter Garden Living! Welcome to this inviting Craftsman-style home in the highly desirable Winter Oaks community, where small-town charm meets the convenience of modern Florida living. Located in a golf-cart-friendly neighborhood and within minutes of Historic Downtown Winter Garden, this home provides an opportunity to enjoy everything this sought-after area has to offer and more! From the welcoming double front porches to the spacious, thoughtfully designed interior, this home combines character, comfort, and functionality. The kitchen features beautiful quartz countertops, wood cabinetry, stainless steel appliances, a gas range, and a versatile island with additional storage and seating. Absolutely perfect for everyday living and entertaining! The first-floor's open concept, high ceilings and abundant natural light is an ideal way to be welcomed inside. The primary suite, also located on the first floor, is a private retreat, complete with a walk-in closet and an en-suite bathroom featuring dual vanities, a jetted soaking tub, and a separate shower. The second story, also full of character and charm, is an amazing space for loved ones and/or valued guest. Step outside to enjoy the screened lanai, fenced backyard, and separate patio ideal for friends and family gatherings, weekend barbecues or simply relaxing in the Florida sun. Residents of Winter Oaks enjoy community activities & amenities including a swimming pool, cabana, and playground. The location is equally impressive, offering convenient access to the West Orange Trail, shopping, dining, and the unique shops, restaurants, and year-round activities of Historic Downtown Winter Garden. Hurry, as this opportunity has too many amenities to list! Call today before it's gone tomorrow!

925 Butter Oaks Court, Winter Garden
14253 Country Estate Drive, Winter Garden
$1,675,000
5 Beds ⋅ 5 Baths ⋅ Country Lakes SubDv. ⋅ 34787 Zip Code
Lakefront living with room to spread out. Welcome to 14253 Country Estate Drive. Set on nearly three acres along Black Lake, this two-story brick pool home pairs timeless character with expansive water views in an established community of custom homes. Mature oaks frame the circular driveway, creating a welcoming arrival to a residence offering approximately 5,504 square feet, five bedrooms, four full baths, and one half bath. Lake views greet you from the foyer and draw you into the soaring great room, where a wood-burning stone fireplace, tall windows, and French doors create an inviting setting for everyday living and entertaining. The spacious kitchen features a generous center island, extensive cabinetry, and adjoining casual dining, while a separate formal dining room provides space for larger gatherings. The main-floor primary suite offers its own screened lanai, a quiet place to start the day overlooking the grounds. An office with a closet provides flexibility for a potential fifth bedroom, and two upstairs bonus rooms offer additional space for recreation, hobbies, or working from home. Outside, the pool, lanai, and expansive backyard make the waterfront setting the centerpiece of the home. Enjoy afternoons by the water, outdoor dining, or time on Black Lake boating, fishing, paddleboarding, and jet skiing. A side-entry three-car garage completes the property. Conveniently located near the shopping and dining at Winter Garden Village at Fowler Groves, with access to SR 429, SR 408, and Florida’s Turnpike, this home brings together spacious interiors, generous grounds, and the Florida lakefront lifestyle.

14253 Country Estate Drive, Winter Garden
271 Daniels Pointe Drive, Winter Garden
$355,000
3 Beds ⋅ 2 Baths ⋅ Daniels Crossing SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the desirable Daniels Crossing community of Winter Garden! Featuring a bright, open floor plan, fresh modern finishes, and a comfortable living and dining area, this home offers the perfect blend of style and functionality. Enjoy peaceful pond views from your backyard, creating a relaxing setting to unwind and enjoy Florida living. The split-bedroom layout provides added privacy, while the attached 2-car garage offers convenience and extra storage. Residents can also enjoy the community pool. Conveniently located near shopping, restaurants, major roadways, and the popular Winter Garden Village, this home offers both comfort and an excellent location. Don't miss the opportunity to make this home yours!

271 Daniels Pointe Drive, Winter Garden
15032 Lebeau Loop, Winter Garden
$499,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code
Like-new and just five years young, this beautifully cared-for home showcases thoughtful upgrades and attention to detail throughout. Featuring 3 bedrooms, 2.5 baths, and a dedicated office space, the inviting layout offers room to live, work, and unwind. The open kitchen features a gas range, spacious walk-in pantry, and adjacent dining area, making everyday meals and entertaining effortless. Upstairs, the generously sized primary bedroom includes a walk-in closet with custom built-ins for exceptional organization. Enjoy your own private retreat in the fenced backyard, thoughtfully enhanced with maintenance-free landscaping. A two-car garage with an EV charger, tankless gas water heater, and water softener system add everyday convenience. Community amenities include a pool, three playgrounds, two dog parks, and community mailboxes. Conveniently located near Flamingo Crossings Town Center for shopping, dining, and primary care/ER services, as well as Disney, this meticulously maintained home offers comfort, convenience, and thoughtful details inside and out.

15032 Lebeau Loop, Winter Garden
17224 Old Country Lane, Winter Garden
$1,699,000
6 Beds ⋅ 4 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
Some homes are impressive. Others have a way of making you imagine an entirely different life. Behind private electric gates, 2.38 acres of mature trees and open grounds set the stage for a home that has been completely transformed. The owners originally envisioned it as their forever home, and the work reflects that ambition. This wasn’t a matter of replacing finishes or updating a few rooms. The kitchen was relocated, living spaces were expanded, oversized windows were introduced, and the entire home was reconsidered from the ground up. What emerged is a beautifully reimagined residence that feels almost entirely new, with a warmth and character that make it equally inviting. Inside, 3,629 square feet of living space includes six bedrooms and three and a half bathrooms, all on one level. Wood beams, custom cabinetry, ZLINE appliances, a spacious pantry, and carefully selected finishes bring sophistication without sacrificing comfort. A newly created ensuite bedroom adds flexibility, while extensive improvements, including a 2025 roof, updated electrical, new flooring, and windows, speak to the depth of the transformation. The same attention carries outdoors, where a striking covered A-frame porch overlooks a newly built screened pool and spa. Beyond the enclosure, mature trees and expansive grounds offer exceptional privacy, while a separate 1,200-square-foot boat garage with two bay entries provides generous space for watercraft, recreational vehicles, and storage. Together, these outdoor spaces offer a level of versatility rarely found so close to everyday conveniences. And that’s perhaps the most remarkable part. All of this sits just minutes from Hamlin and Horizon West, with easy access to Historic Downtown Winter Garden, the West Orange Trail, and SR 429. No HOA, no need to trade convenience for acreage, and no major transformation left for the next owner to undertake. The owners’ plans ultimately changed. The home they set out to create is complete. And the opportunity to make it your own is now here.

17224 Old Country Lane, Winter Garden
13900 Lanyard Way, Winter Garden
$769,650
5 Beds ⋅ 5 Baths ⋅ Encore/Ovation-Ph 3 SubDv. ⋅ 34787 Zip Code
Short Sale. Welcome to this spacious 5-bedroom, 5-bathroom home in the desirable Encore at Ovation community in Winter Garden! Featuring a rare dual primary suite layout, this home offers an open-concept design with an upgraded kitchen showcasing a natural gas stove, oversized island, farmhouse sink, and stainless-steel appliances. The kitchen flows seamlessly into the dining and family rooms, perfect for entertaining. The first floor includes a primary suite, private den/office, and additional full bathroom. Upstairs, enjoy a versatile loft, convenient laundry room, and luxurious second primary suite overlooking the conservation area, complete with dual sinks, soaking tub, separate shower, and oversized walk-in closet. Relax on the covered back porch overlooking a private backyard with no rear neighbors. Additional features include fiber-optic internet, surround sound speakers and prewiring for security cameras. All this plus the added benefit of solar panels to help with those electricity bills. Residents enjoy resort-style amenities including a pool, fitness center, playground, dog park, and yard maintenance. Conveniently located minutes from Walt Disney World and Flamingo Crossings, offering shopping, dining, and entertainment. A rare find combining space, privacy, and an unbeatable location!

13900 Lanyard Way, Winter Garden
8877 Lakeshore Pointe Drive, Winter Garden
$650,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, completely remodeled home in beautiful Winter Garden! Offering 4 spacious bedrooms, 3.5 luxurious bathrooms, and a separate guest house. This exceptional property combines elegance, comfort, and versatility. The home features a gorgeous interior courtyard, creating a beautiful private setting perfect for relaxing or entertaining. Inside, you’ll find soaring ceilings throughout, an elegant and inviting living space, and a chef-inspired kitchen equipped with state-of-the-art appliances and exquisite finishes. The spacious bedrooms include comfort and privacy, while the luxurious primary suite features a spa-inspired bathroom with a beautiful soaking tub, an elegant walk-in shower, and generous closet space. Every detail has been thoughtfully designed to create an elegant yet welcoming atmosphere. With its complete renovation, stunning architectural features, private courtyard, and separate guest residence, this extraordinary Winter Garden home offers a truly special living experience.

8877 Lakeshore Pointe Drive, Winter Garden
8900 Sonoma Coast Drive, Winter Garden
$745,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Enjoy resort-style living in Waterleigh, a master-planned community in Horizon West, Winter Garden. This single-story home offers 3 bedrooms, 2 full bathrooms, a half bathroom, and a separate office, complemented by distinctive interior finishes and expansive outdoor living spaces. An inviting foyer features decorative wood slat accents, integrated lighting, and a floating bench. The open-concept living area showcases a tray ceiling, wood-look tile flooring, and a custom TV feature wall with a floating media console. The kitchen features cabinetry, stone countertops, a tile backsplash, pendant lighting, and a stainless steel appliance package, including a refrigerator, built-in oven, microwave, cooktop, and dishwasher. A separate dining area provides additional gathering space. The office features glass French doors, built-in cabinetry, shelving, and work surfaces. The primary suite includes custom closet organizers and an en-suite bathroom with dual sinks, illuminated mirrors, a separate shower, a soaking tub, and a private water closet. The laundry room includes a washer and dryer, while the garage offers extensive storage cabinetry and a coated floor. Step outside to a covered, screened lanai overlooking an expansive paver patio with a fire pit, fenced backyard, and wooded backdrop—an inviting setting for relaxing or entertaining. Waterleigh offers community pools, clubhouses, fitness facilities, playgrounds, and recreational amenities in a scenic setting of lakes and ponds. Enjoy convenient access to shopping and dining at nearby Hamlin, Publix within the community, historic Downtown Winter Garden, and SR-429. Nearby schools include Atwater Bay Elementary, Water Spring Middle, and Horizon High School; buyers should verify current school assignments with Orange County Public Schools. Kitchen appliances, washer, and dryer are included in the sale. Furnishings shown in the photographs are actual furnishings. Select photographs have been digitally enhanced for lighting, and flames have been digitally added to the outdoor fire pit.

8900 Sonoma Coast Drive, Winter Garden
730 Magnolia Street, Winter Garden
$825,000
5 Beds ⋅ 3 Baths ⋅ Winter Gdn Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME***730 MAGNOLIA STREET (not AVENUE). 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 6- panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

730 Magnolia Street, Winter Garden
740 Magnolia Street, Winter Garden
$825,000
5 Beds ⋅ 3 Baths ⋅ Winter Garden Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME***740 MAGNOLIA STREET (not Avenue). 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 8-panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

740 Magnolia Street, Winter Garden
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