Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida, a picturesque gem nestled in the heart of Orange County. This vibrant city perfectly blends small-town charm with modern conveniences, making it an ideal place to call home. Known for its rich history, Winter Garden boasts a thriving downtown area filled with quaint shops, delightful eateries, and a bustling farmers' market that brings the community together every Saturday.

One of the standout features of Winter Garden is its commitment to creating a family-friendly environment, and this is beautifully reflected in its Homes with Sidewalks community. As you stroll through these neighborhoods, you’ll find tree-lined streets perfect for leisurely walks or bike rides, encouraging a healthy, active lifestyle for residents of all ages. Sidewalks not only enhance the aesthetic appeal of the community but also foster a sense of connection among neighbors, making it easy to meet new friends and enjoy the great outdoors.

In addition to its charming residential areas, Winter Garden offers easy access to top-rated schools, parks, and recreational facilities, ensuring that families have everything they need right at their fingertips. The city is also conveniently located near major highways, providing quick access to nearby attractions such as Walt Disney World and Universal Studios, making it a fantastic choice for both residents and visitors alike.

With its enchanting blend of history, community spirit, and beautiful homes, Winter Garden is more than just a place to live; it's a place to thrive. Discover your dream home in this delightful city and experience all that Winter Garden has to offer!

Newest Winter Garden Homes with Sidewalks Community Features

5567 Cypress Hill Road, Winter Garden
$519,995
3 Beds ⋅ 2 Baths ⋅ Orchard Hills Ph 2 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention lawn service is included in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home has for you.

5567 Cypress Hill Road, Winter Garden
16549 Parable Way, Winter Garden
$545,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Virtually Staged. 2023 build new house! Highly desirable Storey Grove community! NO CDD.Low HOA fee! Beautifully maintained 4-bedroom, 3.5-bath home in the highly desirable Storey Grove community! Featuring a thoughtfully designed floor plan with TWO Primary suites—one conveniently located on the FIRST floor and the other upstairs—this home offers exceptional flexibility for multi-generational living, extended family, or hosting guests. The functional and versatile layout provides comfortable living spaces ideal for both everyday living and entertaining. Enjoy the convenience of living in a family-friendly community with a community swimming pool and the added benefit of having elementary and middle schools right within the neighborhood—making daily school commutes easier for busy families. one of Storey Grove's most attractive features is its convenient location near Walt Disney World, offering easy access to world-famous theme parks, shopping, dining, and entertainment. With convenient access to major highways and everyday essentials, this home combines a desirable location with comfortable Florida living. Easy Access to Major Highways, Shopping, Dining, and Entertainment Don't miss this wonderful opportunity to enjoy comfort, flexibility, and convenience in the sought-after Storey Grove community, just minutes from the magic of Disney!

16549 Parable Way, Winter Garden
14501 Grove Resort Avenue Unit 3239, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
14026 Frasier Street, Winter Garden
$464,900
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
6707 Marmalade Alley, Winter Garden
$480,000
4 Beds ⋅ 4 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. Virtually Staged. Welcome to modern living in the heart of Winter Garden! This beautifully upgraded 4-bedroom, 3.5-bath corner-unit townhome offers a spacious, thoughtfully designed floor plan with the primary suite conveniently located on the main level, featuring a beautiful shiplap accent wall, updated shower, custom closet organization, and French doors opening to the inviting front porch. Upstairs, you'll find three carpeted bedrooms, including a private ensuite, along with a versatile loft featuring laminate flooring. The kitchen boasts stainless steel appliances, granite countertops, and a stylish backsplash, opening to inviting living and dining spaces accented by beautiful wood beams and upgraded lighting. Additional enhancements throughout the home include upgraded interior doors, a water softener, and thoughtful storage solutions. Step outside to your own private retreat featuring an extended, fully paved and fenced courtyard with sealed pavers, ideal for entertaining, relaxing, or enjoying Florida evenings. The detached garage has a covered walkway to the home. Located in the desirable Hamlin Reserve community in Horizon West, this home offers convenient access to Hamlin Town Center, shopping, dining, entertainment, and everyday essentials. Enjoy nearby parks, walking trails, and outdoor recreation, with easy access to SR-429 and a short drive to Walt Disney World and Central Florida's world-class attractions. A wonderful opportunity to enjoy modern living, exceptional outdoor space, and a convenient Winter Garden location!

6707 Marmalade Alley, Winter Garden
2139 Tillman Avenue, Winter Garden
$825,000
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
5705 New Independence Parkway, Winter Garden
$399,900
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
11947 Shine View Lane, Winter Garden
$942,771
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
$498,900
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
$639,900
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
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