Winter Garden Homes with Sidewalk Exterior Features

Winter Garden Homes with Sidewalk Exterior Features

Welcome to Winter Garden, Florida – a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just a few miles west of Orlando, Winter Garden is renowned for its picturesque landscapes, vibrant community, and rich history. With its quaint downtown area, lined with historic buildings, boutique shops, and delightful eateries, residents enjoy a lively atmosphere that fosters connection and community spirit.

One of the standout features of Winter Garden is its commitment to creating a walkable environment. Many homes in this delightful city showcase beautiful sidewalk exterior features, encouraging outdoor strolls and fostering neighborly interactions. Imagine stepping outside your front door and enjoying a leisurely walk along tree-lined streets, where friendly faces greet you and the scent of blooming flowers fills the air. The sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote an active lifestyle, making it easy to explore local parks, farmers' markets, and seasonal festivals.

Winter Garden is also home to a range of housing options, from charming bungalows to modern family homes, catering to diverse tastes and lifestyles. Whether you’re a first-time homebuyer or looking to settle down, the homes here offer a perfect blend of comfort and style, with many featuring inviting porches and landscaped yards.

With its blend of natural beauty, community engagement, and convenient access to the attractions of Central Florida, Winter Garden is truly a place to call home. Come discover the charm of this enchanting city and find your perfect home with sidewalk features that invite you to enjoy the outdoors!

Newest Winter Garden Homes with Sidewalk Exterior Features

373 Eron Way Unit 47, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Charming single-story townhome in Townhomes of Winter Garden featuring 2 bedrooms and 2 full baths. Interior features low-maintenance laminate flooring throughout the main living areas and bedrooms, paired with an efficient open floor plan. Conveniently located just minutes from historic downtown Winter Garden, Plant Street dining, shopping, and major commuter routes including SR-429 and the Florida Turnpike. Easy to show—schedule through Showing Time today!

373 Eron Way Unit 47, Winter Garden
10503 Spring Arbor Lane, Winter Garden
$459,000
4 Beds ⋅ 3 Baths ⋅ Winding Bay Preserve SubDv. ⋅ 34787 Zip Code
INVESTOR ALERT! Currently tenant-occupied, this beautiful 4-bedroom, 3-bath townhome offers over 2,200 sq. ft. of thoughtfully designed living space in Horizon West’s Winding Bay Preserve. The open kitchen features 42-inch white cabinets, a walk-in pantry, and a large island overlooking the spacious dining and great room. French doors lead to a screened, fenced courtyard with access to the 2-car garage. A first-floor bedroom with peaceful conservation views and an adjacent full bathroom provides added flexibility. Upstairs, the spacious primary suite features a dual-sink vanity, walk-in shower, private water closet, and a generous walk-in closet with built-ins. Two additional bedrooms overlook the conservation area and share a full bathroom, while a versatile loft and conveniently located laundry room complete the second floor. Winding Bay Preserve offers a resort-style community pool, playground, and parks amid beautiful conservation surroundings. Conveniently located near shopping, dining, schools, and Central Florida’s world-renowned attractions. An excellent opportunity to add a tenant-occupied property to your investment portfolio! Contact us for lease details and showing availability.

10503 Spring Arbor Lane, Winter Garden
15823 Shorebird Lane, Winter Garden
$929,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to enjoy the Florida lifestyle in this beautiful Toll Brothers home in the sought-after Lakeshore Preserve community of Winter Garden. Offering 4 bedrooms, 4 full bathrooms, and 2,768 square feet, this thoughtfully designed residence combines elegant interior spaces with an outdoor living experience designed for entertaining. The heart of the home is its impressive kitchen, featuring an oversized 12-foot island, gas cooktop, convection oven, and stylish finishes. Multiple living spaces and abundant natural light create an inviting atmosphere throughout. The flexible floor plan includes a first-floor bedroom and full bathroom, additional upstairs bedrooms, a private junior suite, and a spacious primary retreat featuring tray ceilings, dual walk-in closets, two vanities, a soaking tub, and a separate walk-in shower. But the real highlight is outside. Enjoy your own private saltwater pool, beautifully appointed paver deck, and summer kitchen with natural gas. Whether hosting friends, enjoying a quiet afternoon by the pool, or making the most of Florida's beautiful weather, this outdoor space makes every day feel like a getaway. Lakeshore Preserve adds even more to the experience with its lakefront clubhouse, resort-style community pool, fitness center, barbecue area, and recreational amenities. Located in Winter Garden, this home offers an appealing combination of space, thoughtful design, outdoor entertaining, and community amenities. Come experience the home and the lifestyle for yourself.

15823 Shorebird Lane, Winter Garden
6266 Sunny Time Avenue, Winter Garden
$433,890
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Dahlia interior unit townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant tile flooring. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a brand new Whirlpool washer and dryer! With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6266 Sunny Time Avenue, Winter Garden
6367 Argent Wood Drive, Winter Garden
$449,490
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail interior unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, white cabinetry, a decorative tile backsplash, quartz countertops, and Whirlpool stainless-steel kitchen appliances- including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet, and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include wood-look luxury vinyl plank flooring throughout the first floor living areas, tile flooring in the laundry room and bathroom, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more. This new construction townhome perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind. Schedule your tour today!

6367 Argent Wood Drive, 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
7723 Green Mountain Way, Winter Garden
$2,695,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Set along the shores of Lake Hancock with approximately 80 feet of lake frontage, this exceptional Winter Garden residence offers private boating amenities and expansive indoor-outdoor living. A two-story dock with a boat lift and two Jet Ski lifts, a screened pool and spa, and sweeping lake views define this waterfront setting. Offering 6 bedrooms, 6.5 bathrooms, over 5,100 square feet, a 3-car garage, and two primary suites on separate floors, the flexible layout is ideal for multigenerational living. A paver driveway, tile roof, stone accents, and mature landscaping welcome you home. Inside, engineered hardwood floors lead past a formal dining room on the right, connected to the kitchen through a butler's pantry, and a dedicated office on the left. The impressive two-story living room features decorative wood beams, a cascading chandelier, and a floor-to-ceiling stacked-stone accent wall. Expansive sliding glass doors open to the covered lanai, seamlessly connecting indoor and outdoor living while framing views of the pool and Lake Hancock. An open staircase with wood treads and wrought-iron balusters overlooks the living area. Just off the living room, the first-floor primary suite offers direct lanai access, a walk-in closet, separate vanities, and an oversized tiled shower. The spacious kitchen features a center island, an expansive wraparound peninsula with a farmhouse-style sink, granite countertops, cream-colored cabinetry, stainless steel appliances, a natural gas cooktop with pot filler and vent hood, a built-in microwave and wall oven, decorative tile backsplash, and built-in wine storage. A separate casual dining area overlooks Lake Hancock. Beyond it are a second downstairs bedroom and adjacent full bathroom with pool access. Near the 3-car garage, the laundry room provides a utility sink, cabinetry, and counter space. A half bath completes the first floor. Upstairs, the second primary suite features a tray ceiling, French doors to a private lakeview balcony, two walk-in closets, and an ensuite bath with dual vanities, soaking tub, and glass-enclosed shower. Three additional bedrooms and three full bathrooms, including two ensuite bedrooms, offer flexible accommodations. An expansive bonus room with hardwood flooring, lake-facing windows, and French doors to a separate balcony makes an ideal second living area, game room, or media room. Outdoor living takes center stage on the spacious covered lanai, with separate dining and lounge areas, ceiling fans, and a summer kitchen featuring a stainless steel grill, vent hood, refrigerator, and countertop space. The screened pool and spa, surrounded by an expansive paver deck, overlook Lake Hancock. Beyond the shoreline, the private two-story dock features a shaded lower seating area, boat lift, two Jet Ski lifts, and an open-air upper observation deck with panoramic lake views. From the living room and upstairs balconies to the pool and dock, the water is part of everyday life here. Summerlake community amenities include a pool, fitness center, tennis courts, playgrounds, and walking paths. Convenient to Hamlin Town Center, major highways, and Central Florida's world-famous attractions, this home offers an exceptional Lake Hancock waterfront lifestyle.

7723 Green Mountain Way, Winter Garden
14501 Grove Resort Avenue Unit 3618, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
WELCOME TO THE GROVE RESORT & WATERPARK, WINTER GARDENS, ORLANDO FLORIDA. THIS BEAUTIFUL FULLY FURNISHED SABLE DESIGN CONDO IS IN AN EXCELLENT LOCATION WITH GREAT VIEWS OF WATER PARK AND MUCH MORE. THIS BEAUTIFUL SABLE DESIGN CONDO IS ON THE 6TH FLOOR WITH 3 LUXURY BEDROOMS AND 3 GREAT BATHROOMS. AND GREAT VIEWS FROM SCREENED BALCONY. YOU CAN OWN THIS BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO ALL OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING BUT NOT LIMITED TO A GREAT WATER PARK, LAZY RIVER, SWIMMING POOLS , WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTION FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE

14501 Grove Resort Avenue Unit 3618, Winter Garden
6129 Flowering Cherry Bend, Winter Garden
$748,018
4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to a home designed for easy everyday living in Avalon Woods. This single-story Anna Maria, Elevation B, offers four bedrooms and three full bathrooms across 2,235 heated square feet. A welcoming covered front porch leads into an open layout where the family room, dining area and Gourmet Kitchen bring everyone together. Prepare a favorite meal at the spacious kitchen island, with a built-in oven, cooktop and range hood close at hand, then settle in for a relaxed evening with room to spread out. The primary suite offers a quiet retreat with a spa-style shower, while three additional bedrooms provide flexibility for guests, work or hobbies. Laminate flooring adds warmth to the main living areas, with carpeted bedrooms and tile in the bathrooms. Open the sliding glass doors to the covered rear lanai and enjoy a morning coffee or an unhurried weekend. A dedicated indoor laundry room and attached two-car garage add everyday convenience. Discover the comfort and possibilities of Avalon Woods in Winter Garden. Schedule a visit to the community model home. Sample Image.

6129 Flowering Cherry Bend, Winter Garden
12542 Encore At Ovation Way, Winter Garden
$669,000
4 Beds ⋅ 4 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code
Fall in love with this 4-bedroom, 3.5-bath, 2,781 square foot home with 2-car ally-load garage. This versatile plan will wow you the minute you enter, with its impressive 2-story foyer. A bedroom with its own full bath is located up front, creating the perfect spot for guest, in-laws, or perhaps a home office. The chef of the home won’t feel ostracized in this kitchen; the family room, kitchen, and dining room are all open to each other, creating a perfect spot for family hangouts or weekend entertaining, keeping everyone in the mix. Enjoy a covered lanai located on the side of the home through the oversized sliding glass door. Head upstairs to find three more bedrooms and a loft. The loft is the perfect space for movie night, game day, or just a second hangout. It separates the owner’s suite in the back of the home from the secondary bedrooms, giving everyone the privacy, they deserve. The owner’s suite features two very impressive sized walk-in closets and a bathroom to match. You’ll be happy this Horizon West new home is built with features that meet the Energy Star® 3.1 home building requirements, saving you on the cost of ownership. It’s also backed by M/I Homes' industry leading 10-Year Transferable Warranty. Contact us today before it’s gone!

12542 Encore At Ovation Way, Winter Garden
665 Canopy Estates Drive, Winter Garden
$1,499,900
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. EXCEPTIONAL LUXURY IN THE HEART OF WINTER GARDEN! Welcome to this stunning 5-bedroom, 4.5-bathroom pool home nestled within Canopy Oaks, an exclusive, Parade of Homes award-winning gated community featuring just 49 residences. This beautifully upgraded Lockhart II model delivers an exceptional blend of elegance, comfort, and sophistication, featuring TWO luxurious primary suites, one on each floor, a 3-car garage, and private front and rear balconies. Step through the magnificent arched double doors into a breathtaking two-story foyer, where timeless architectural details and modern finishes set the tone. The thoughtfully designed interior showcases a versatile office or flex space, an exquisite wine cellar with authentic Chicago brick flooring, and a gourmet kitchen featuring a 5-burner natural gas cooktop and oversized island. A beautiful wooden staircase with custom forged-iron railings leads upstairs to generously sized bedrooms, a spacious primary suite with an impressive walk-in closet, and a dedicated home theater complete with a movie projector. RECENT UPGRADES includes 2025 A/C system, contemporary light fixtures, updated countertops, fresh interior paint, new downstairs flooring, custom closets, and a beautifully remodeled backyard. Step outside into your private retreat, featuring a sparkling pool and an inviting setting for entertaining or unwinding. LOCATION IS EVERYTHING! Just minutes from Winter Garden Village and Historic Downtown Winter Garden, enjoy convenient access to premier shopping, exceptional dining, and entertainment. With easy connections to Florida’s Turnpike, SR 429, SR 408, and Highway 50, the best of Central Florida is within easy reach. Luxury, exclusivity, and an unbeatable location come together in one extraordinary home. Schedule your private showing today!

665 Canopy Estates 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
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