Winter Garden Homes with Sidewalk Exterior Features

Winter Garden Homes with Sidewalk Exterior Features

Welcome to Winter Garden, Florida – a charming city that perfectly blends small-town warmth with modern conveniences. Nestled just west of Orlando, Winter Garden boasts a rich history, picturesque landscapes, and a vibrant community spirit that makes it an ideal place to call home. Known for its beautiful downtown area, you can stroll along the historic streets lined with boutique shops, delightful cafes, and a variety of dining options that cater to every palate.

One of the standout features of homes in Winter Garden is their inviting sidewalk exterior. These charming sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote a sense of community and connectivity. Imagine taking evening walks with family and friends, waving to neighbors, or enjoying a leisurely bike ride on the tree-lined paths that wind through this friendly city.

Winter Garden is also home to lush parks, scenic lakes, and a plethora of recreational activities. Whether you're an outdoor enthusiast or simply looking for a peaceful retreat, the city offers ample opportunities for hiking, fishing, and picnicking. The West Orange Trail, a popular destination for walkers and cyclists, meanders through the area, providing a perfect backdrop for active living.

As you explore the real estate options in Winter Garden, you'll find a diverse selection of homes that cater to various lifestyles and budgets. With their beautiful sidewalks and welcoming neighborhoods, these homes are not just places to live; they’re gateways to a vibrant community life. Embrace the charm of Winter Garden and discover your dream home in this delightful Florida city today!

Newest Winter Garden Homes with Sidewalk Exterior Features

14026 Frasier Street, Winter Garden

14026 Frasier Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code

SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden

2010 Boss Hewett Street, Oakland

2010 Boss Hewett Street, Oakland

5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland

9380 Bolshoi Alley, Winter Garden

9380 Bolshoi Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Tribute/Ovation SubDv. ⋅ 34787 Zip Code

SELLER PROVIDING UP TO $10,000 TOWARD BUYER CLOSING COSTS! Welcome to this nearly NEW townhome in the heart of highly desirable Horizon West! Built in 2025, this 3-bedroom, 2-and-a-half-bathroom residence offers the appeal of newer construction in one of Central Florida’s fastest-growing communities. Enjoy the convenience of having Publix and an expanding selection of shopping, dining, and everyday essentials just across the street! The unit is equipped with upgraded QUARTZ countertops, tile throughout the first floor & a cozy private courtyard. The home’s prime location also provides easy access to State Road 429, making commuting throughout Central Florida a breeze. Just minutes away, the popular Hamlin area offers an exciting mix of restaurants, retail, entertainment, and recreational opportunities. Whether you’re searching for a primary residence or a low-maintenance lifestyle, this townhome offers an excellent combination of location, convenience, and modern living. With construction completed in 2025, buyers can enjoy the benefits of a newer home without the wait of building from the ground up. Don’t miss your opportunity to own a nearly new townhome in the heart of Horizon West!

9380 Bolshoi Alley, Winter Garden

2139 Tillman Avenue, Winter Garden

2139 Tillman Avenue, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code

STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

14656 Pylon Court, Winter Garden

14656 Pylon Court, Winter Garden

7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a den, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden

5705 New Independence Parkway, Winter Garden

5705 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code

WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden

17361 Bal Harbour Drive, Winter Garden

17361 Bal Harbour Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lk-Ph 2b SubDv. ⋅ 34787 Zip Code

Welcome to this spacious 4-bedroom, 2.5-bath home offering approximately 2,931 square feet in the desirable Waterside at Johns Lake community. The open floor plan features a versatile front room ideal for a home office, formal dining room, or additional living space. The kitchen offers granite countertops, stainless-steel appliances, abundant cabinetry, and an open connection to the family room. An additional flex room provides even more space for entertaining, relaxing, or creating a game room. All four bedrooms are located upstairs, including a generous primary suite with a walk-in closet, dual-sink vanity, and walk-in shower. Additional features include an interior laundry room, attached two-car garage, and a covered paver lanai for enjoying the Florida lifestyle. Community amenities include a pool, clubhouse, fitness center, playground, sidewalks, and access to Johns Lake. Conveniently located near shopping, dining, Downtown Winter Garden, Hamlin, and FL-429. New photos coming soon!!!

17361 Bal Harbour Drive, Winter Garden

5513 New Independence Parkway, Winter Garden

5513 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Independence / Signature Lakes Ph 02 SubDv. ⋅ 34787 Zip Code

Nestled in the heart of the desirable Winter Garden, this beautifully updated 3-bedroom, 2-bathroom SALTWATER POOL HOME offers 1,920 square feet of thoughtfully designed living space, modern elegance, and an exceptional resort-style lifestyle! From the moment you arrive, you’ll fall in love with the picturesque curb appeal, lush landscaping, charming brick-paver walkway, and inviting covered front porch. Step inside to discover a bright, open-concept floor plan featuring beautiful bamboo flooring, abundant natural light, and inviting living spaces perfect for everyday comfort and entertaining. The heart of the home is the stunning kitchen, completely remodeled in 2019! Featuring gorgeous quartz countertops, rich cabinetry, stainless steel appliances, stylish pendant lighting, and an expansive island with seating, this space is designed for gathering and making memories. A charming, sun-filled dining nook completes the picture! Your own private backyard oasis awaits! Step through beautiful French doors to your sparkling SALTWATER POOL, surrounded by an expansive screened enclosure and spacious covered lanai. Whether you're enjoying a refreshing afternoon swim, hosting weekend gatherings, or relaxing in the shade, this outdoor retreat makes every day feel like a vacation! Additional highlights include a convenient rear-entry garage with a beautifully finished epoxy floor. The lifestyle doesn't stop at your front door! Enjoy RESORT-STYLE COMMUNITY AMENITIES and a vibrant calendar of year-round events, including themed movie nights, ice cream socials, fireworks, and seasonal celebrations. Even better, the HOA includes internet and cable. Ideally located in the beautiful Winter Garden, walkable to schools, shopping, dining, entertainment, and conveniently located to Central Florida attractions, this home offers the perfect blend of modern comfort, neighborhood charm, and Florida living. More than a home....it's a lifestyle! Schedule your private showing today! *Wine fridge and weather station on the lanai screen does not convey.

5513 New Independence Parkway, Winter Garden

11947 Shine View Lane, Winter Garden

11947 Shine View Lane, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Torrey. A two-story all concrete block construction single-family home features 5 bedrooms and 4.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai that looks over a pond. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a bedroom and a full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11947 Shine View Lane, Winter Garden

13006 Serene Glade Road, Winter Garden

13006 Serene Glade Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code

Winter Garden, Florida | Former Model Home | 3 Bedrooms | 2.5 Bathrooms FORMER MODEL HOME • DESIGNER UPGRADES • WINTER GARDEN THIS ONE WILL GET YOUR BUYERS’ ATTENTION! Welcome to 13006 Serenade Glade, an exceptional 3-bedroom, 2.5-bath former model home where luxury, style, and thoughtful upgrades come together beautifully. This is not your typical resale! Built to impress and showcased as a model, this home features extensive upgrades, elevated finishes, designer details, and a beautifully appointed interior that immediately stands out from the competition. The open and inviting floor plan offers an effortless flow for entertaining, while the spacious living areas create the perfect combination of comfort and sophistication. The kitchen is a true focal point, complemented by upgraded finishes and a seamless connection to the living and dining spaces. The primary suite offers a private retreat, while the additional bedrooms provide excellent flexibility for guests, family, or a home office. Every detail was selected to make this home stand out—and it shows. From the upgraded flooring and lighting to the enhanced fixtures and finishes, this former model home delivers the polished look buyers are searching for without the hassle or expense of doing the upgrades themselves. Located in desirable Winter Garden, this is a fantastic opportunity for buyers looking for a home that feels special from the moment they walk through the door. FORMER MODEL HOME • 3 BEDROOMS • 2.5 BATHROOMS EXTENSIVELY UPGRADED • DESIGNER FINISHES • MOVE-IN READY Bring your buyers—this is one they’ll remember

13006 Serene Glade Road, Winter Garden

8943 Lakeshore Pointe Drive, Winter Garden

8943 Lakeshore Pointe Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Phase I SubDv. ⋅ 34787 Zip Code

ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TOO MANY UPGRADES TO LIST!!! LOCATION, LOCATION, LOCATION!!! FROM THE TIME YOU ARRIVE, YOU WILL IMMEDIATELY FALL IN LOVE WITH THE OVERSIZED FRONT PORCH, WATERVIEW OF THE COMMUNITY FOUNTAIN, AND MORE THAN ENOUGH ROOM TO ENJOY OUTDOOR LIVING! THIS LUXURIOUS TOLL BROTHERS DANTE ITALIANATE FLOORPLAN HAS IT ALL! THIS HOME HAS AN OPEN CONCEPT WITH HIGH CEILINGS, LOTS OF WINDOWS ALLOWING FOR NATURAL LIGHT, HUGE SLIDING DOORS WHICH LEAD TO A PRIVATE BRICK PAVERED COURTYARD AND A COVERED WALKWAY TO YOUR TWO CAR GARAGE. WALK INTO YOUR SPACIOUS KITCHEN WHICH INCLUDES A MASSIVE ISLAND AND AN ADDITIONAL BREAKFAST BAR, BOTH WITH UPGRADED QUARTZ COUNTERTOPS. YOU WILL LOVE YOUR NEW KITCHEN WHICH INCLUDES AN UPGRADED CABINET PACKAGE ADDING ADDITIONAL CABINETS FOR AMPLE SPACE, 42" CABINETS, CROWN MOLDING, STAINLESS APPLIANCES AND NATURAL GAS FOR COOKING. MANY ENERGY SAVING FEATURES INCLUDING TANKLESS WATER HEATER, FOAM INSULATION, SOLID CONCRETE BLOCK WALLS FROM THE FOUNDATION THROUGH THE ATTIC AND MORE. ENJOY RESORT STYLE AMENITIES WHICH INCLUDE A POOL, FITNESS CENTER, CLUBHOUSE WITH BREATHTAKING LAKE AND GOLF COURSE VIEWS, KAYAK AND PADDLE BOARD LAUNCH, TWO PLAYGROUNDS, FIREPIT, SUMMER KITCHEN, HAMMOCKS AND DOG PARK. LAKESHORE PRESERVE IS LOCATED IN THE HAMLIN AREA, ONLY TEN MINUTES FROM MAJOR TOURIST ATTRACTIONS. YOU WILL ALSO FIND NEW SCHOOLS, NEW RESTAURANTS, NEW HOSPITAL, PLENTY OF SHOPPING AND ENJOY THE NEW CINEPOLIS RECENTLY BUILT - EASY ACCESS TO ALL THAT CENTRAL FLORIDA HAS!! SCHEDULE YOUR APPOINTMENT TODAY, YOU WILL NOT BE DISAPPOINTED!!!

8943 Lakeshore Pointe Drive, Winter Garden

17664 Japonica Bloom Drive, Winter Garden

17664 Japonica Bloom Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation Phase 2 & 3 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Built in 2025, this Ashton Woods Duval II home in Northlake at Ovation offers 5 bedrooms, 4 full bathrooms, 1 half bathroom, and 3,663 square feet of living space. A striking two-story family room with expansive windows fills the heart of the home with natural light and opens to a spacious kitchen featuring a large island with seating, built-in oven and microwave, electric cooktop, range hood, and abundant cabinetry. A separate dining room and dedicated office provide additional space for entertaining and working from home. The first-floor guest suite offers a bedroom and full bathroom, while the upstairs loft provides flexible space for a second living area, hobbies, or exercise. The spacious primary suite features a walk-in closet, dual vanities, and a large glass-enclosed shower. An upstairs laundry room with cabinetry and a sink adds everyday convenience. Enjoy the covered, screened lanai and backyard, along with an attached two-car garage and paver driveway. Community amenities include a pool, clubhouse, playground, and dog park. Located in Winter Garden with access to SR 429, shopping, dining, and Central Florida attractions.

17664 Japonica Bloom Drive, Winter Garden

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