Winter Garden Homes with Other Exterior Features

Winter Garden Homes with Other Exterior Features

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just west of Orlando, Winter Garden boasts a vibrant downtown area filled with quaint shops, delicious dining options, and a rich history that can be traced back to the early 1900s. The city is renowned for its stunning natural landscapes, including lush parks and scenic lakes, making it an ideal location for outdoor enthusiasts and families alike.

One of the standout features of Winter Garden is its commitment to preserving its historic character while embracing contemporary living. The picturesque West Orange Trail meanders through the city, offering miles of paved pathways for biking, jogging, and leisurely strolls. You’ll find a community that thrives on connection, with farmers' markets, seasonal festivals, and a welcoming atmosphere that invites you to explore.

When it comes to homes in Winter Garden, you’ll discover a diverse array of properties that cater to various lifestyles and preferences. Many homes feature unique exterior elements that enhance their curb appeal, from charming porches and lush landscaping to modern architectural designs. Whether you’re looking for a cozy bungalow or a spacious family home, the real estate market in Winter Garden offers something for everyone.

With its delightful blend of history, community spirit, and beautiful homes, Winter Garden is not just a place to live—it's a place to thrive. Come experience the magic of Winter Garden, where your dream home awaits!

Newest Winter Garden Homes with Other Exterior Features

$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
$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
$724,999
4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code
FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden
$770,000
4 Beds ⋅ 3 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14975 Winter Stay Drive, where the work has already been done and the upgrades go far beyond builder basics. Thoughtfully improved inside and out, this Horizon West home pairs a warm, finished feel with the kind of practical upgrades you will appreciate for years to come. At the heart of the home, the kitchen features KitchenAid appliances installed in 2024. LVP flooring was added in 2025 and flows throughout the bedrooms. Plantation shutters, installed in 2026, add a polished finishing touch. Even the laundry room has been elevated with built-in cabinetry, granite countertops and additional storage. Outside is where this home really sets itself apart. The custom gunite pool, completed in 2024, features a swim shelf, heater AND chiller, upgraded screen enclosure and child safety fence, making it just as enjoyable in the heat of summer as it is on a cool Florida evening. The covered lanai was transformed into an outdoor living space with a fireplace, TV accent wall and recessed lighting, creating a true extension of the home for entertaining or relaxing year-round. The upgrades continue behind the scenes with a fully paid 15kW solar system, generator back-feed hookup, French drains along the east-facing gutters and downspouts, and overhead garage storage racks. Located in Winter Garden's sought-after Horizon West area, this is a home that has been intentionally upgraded, carefully maintained and designed to be lived in. Skip the projects and start enjoying the pool, the outdoor living space and everything this home has to offer from day one.

14975 Winter Stay Drive, Winter Garden
$415,000
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
$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
$364,500
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome to 1511 Sweet Apple Street, 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
$777,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b-3d SubDv. ⋅ 34787 Zip Code
PRIVATE HEATED POOL & SPA with panoramic screen enclosure on premium pond front lot. Welcome home to 15526 Mango Isle Street, a stunning single-story home nestled in the highly sought-after, resort-style community of Waterleigh in Horizon West. Step inside this spacious 4-bedroom, 3-bathroom open-concept home designed for effortless living and entertaining. The Gourmet Kitchen features a grand island with breakfast bar seating, solid surface countertops, solid wood cabinetry, a walk-in pantry, and stainless steel appliances, including a built-in cooktop and oven. The bright kitchen seamlessly opens to a wide-open family room and dining area framed by large sliding glass doors that draw your eye straight to the water views. Primary Suite feels like a tranquil sanctuary featuring elegant tray ceilings, a large walk-in closet, and an en-suite bath with a double-sink vanity and walk-in shower. Layout offers a generous split-bedroom floorplan offering optimal privacy for family and guests, plus an inside utility room. Enjoy this backyard oasis and step out through the sliding glass doors into your private sanctuary. The custom HEATED pool and integrated spa sit under a picture-frame panoramic screen enclosure, giving you unobstructed, serene views of the peaceful pond. Brick pavers cover the expansive covered lanai and pool deck, offering plenty of space for outdoor dining, lounging, and soaking in Florida's famous sunsets. The Waterleigh Community is renowned for its unmatched resort-style amenities and vibrant neighborhood atmosphere. Amenities: Access to two massive lakefront clubhouses, multiple resort-style pools, splash pads, two fully equipped fitness centers, tennis and pickleball courts, beach volleyball, walking trails, dog parks, playgrounds, and a mini-golf putting course. Location is phenomenal just minutes from Walt Disney World, top-rated Horizon West schools, Hamlin Town Center dining, shopping, golf courses, and quick access to State Road 429 for easy commutes across Central Florida. This home perfectly blends luxury, comfort, and the ultimate Florida indoor-outdoor lifestyle. Schedule your private showing today!

15526 Mango Isle Street, Winter Garden
$2,250,000
5 Beds ⋅ 5 Baths ⋅ Sanctuary/Twin Waters SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional lakefront residence, set on an expansive approximately 0.67-acre lot with breathtaking water views and a private infinity pool. Built in 2022, this impressive two-story home offers 4.132 square feet of living space with 5 spacious bedrooms and an elegant layout designed for both everyday living and entertaining. The main level features a desirable primary suite, soaring ceilings, abundant natural light and beautifully designed living spaces. High-end custom built-ins add character and functionality throughout the home, while the open design creates a seamless connection between the interior and the spectacular outdoor setting. Step outside to enjoy the private pool and generous outdoor living areas overlooking the lake. The oversized lot provides a rare sense of privacy and space while showcasing one of the property's most compelling features: its beautiful waterfront setting. Ideally located with convenient access to major roads, shopping, dining, recreation and the area's highly sought-after amenities. A remarkable opportunity to enjoy luxury living, expansive grounds and stunning lakefront views in one of Central Florida's desirable communities.

16870 Sanctuary Drive, Winter Garden
$410,000
3 Beds ⋅ 3 Baths ⋅ Stone Crk A-1 & A-2 SubDv. ⋅ 34787 Zip Code
Location, location, location! Great opportunity to purchase a two-story 3/2.5 with a loft on the second floor and a fully fenced-in yard. The bright and functional floor plan offers plenty of room for comfortable everyday living and entertaining. The kitchen features granite countertops and stainless-steel appliances, while the spacious living areas provide a welcoming atmosphere throughout the home. Enjoy your new home!

2017 Portcastle Circle, Winter Garden
$600,000
3 Beds ⋅ 3 Baths ⋅ Amberleigh SubDv. ⋅ 34787 Zip Code
Welcome to a home that feels as inviting as it is impressive, tucked into the quaint gated community of Amberleigh, just minutes from the charm of historic Downtown Winter Garden and the West Orange Trail. With more than 2,600 square feet of thoughtfully designed living space, this home blends warmth, character, and room to gather. Step inside and the story begins with soaring ceilings that draw your eye toward the upstairs landing, while graceful architectural details, rounded corners, decorative niches, and beautifully appointed engineered hardwood floors bring warmth and character throughout the home. The generous family room creates a natural heart of the home, while a dedicated downstairs office offers a comfortable space for working from home, reading, or tackling the day's to-do list. At the center of it all is a kitchen designed for both everyday moments and memorable gatherings. Granite countertops pair beautifully with abundant cherry cabinetry and a custom cherry wood bar top, while generous prep space, upgraded appliances, double ovens with convection, a built-in desk, and an oversized pantry make the space as functional as it is welcoming. The first-floor owner's suite offers a peaceful retreat with a tray ceiling, dual closets, dual marble vanities, a dual-head shower, and a relaxing Roman tub. The formal dining space is currently used as a living room; the living room is used as an office. Upstairs, the home continues to unfold with spacious secondary bedrooms and a generous bonus room, creating a wonderfully flexible second living space for movie nights, games, hobbies, or simply relaxing at the end of the day. Thoughtful details continue throughout with marble vanities in the secondary baths, ceramic tile in the foyer, laundry room, and secondary bath, convenient under-stair storage, and a four-zone irrigation system. Behind the scenes, meaningful updates bring added comfort and efficiency to everyday living. Several efficient features: New roof in 2024. Newer HVAC systems provide refreshed climate control, with the system serving the upstairs featuring advanced air filtration. Foam-filled block walls on the downstairs. A new energy-efficient hot water heater and whole-home water softener add to the home's thoughtful improvements, while energy-efficient insulated windows along the rear of the home help enhance year-round comfort. Move-in ready and wonderfully located, this is a home made for comfortable mornings, lively gatherings, movie nights upstairs, and evenings spent enjoying everything Winter Garden has to offer. Downtown dining, local shops, community events, and miles of recreation along the West Orange Trail are all just minutes away. A charming gated setting, generous living spaces, thoughtful updates, and the Winter Garden lifestyle come together in a home ready for its next chapter.

393 Lake Amberleigh Drive, Winter Garden
$614,999
4 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
**** STUNNING 4 BEDROOM + LOFT | 3.5 BATH HOME IN HARVEST AT OVATION | MODERN LIVING IN WINTER GARDEN **** Welcome to this beautifully maintained 4-bedroom + loft, 3.5-bath single-family home located in the highly sought-after Harvest at Ovation community in Winter Garden. Thoughtfully designed with an open-concept floor plan, stylish finishes, and generous living spaces, this exceptional residence offers the perfect combination of elegance, comfort, and everyday functionality. Step inside to an inviting foyer that leads into a bright and expansive living and dining area, seamlessly connected to the gourmet kitchen—creating the ideal setting for entertaining, family gatherings, or simply enjoying day-to-day living. The versatile flex space on the main level can easily be used as a home office, playroom, fitness room, or additional sitting area to suit your needs. Upstairs, you'll find a spacious loft that serves as the perfect second living room, media room, or workspace. The luxurious primary suite provides a private retreat featuring a spa-inspired ensuite bathroom with dual vanities, an oversized walk-in shower, and generous closet space. Three additional bedrooms and well-appointed bathrooms offer flexibility for family, guests, or multigenerational living. Located in one of Winter Garden's most desirable communities, Harvest at Ovation offers outstanding amenities and an unbeatable location just minutes from SR-429, Walt Disney World, Hamlin Town Center, top-rated schools, shopping, dining, and countless entertainment options. Meticulously cared for and move-in ready, this home provides the opportunity to enjoy the benefits of newer construction without the wait. Whether you're searching for your primary residence or your next Central Florida home, this property offers the perfect balance of location, space, and modern design. Schedule your private showing today and experience everything this exceptional Winter Garden home has to offer!

16319 Honey Harvest Street, Winter Garden
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