Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community, Winter Garden offers a delightful blend of small-town charm and modern amenities. With its rich history and abundant recreational opportunities, it’s no wonder that families and individuals are flocking to this beautiful area.

As you explore Winter Garden, you'll discover a variety of homes that cater to diverse lifestyles, particularly those located within the inviting Homes with Sidewalks community. These neighborhoods are designed to foster a sense of connection among residents, featuring well-maintained sidewalks that encourage leisurely strolls and friendly neighborly interactions. Imagine enjoying a morning jog or an evening walk with your loved ones, all while soaking in the warm Florida sunshine.

Winter Garden is also home to a thriving downtown area, where you can find an array of shops, restaurants, and cultural attractions. The historic district, with its charming brick streets and vibrant local businesses, invites you to experience the rich tapestry of community life. Additionally, the city boasts numerous parks and outdoor spaces, perfect for family picnics, weekend sports, or simply unwinding in nature.

With its excellent schools, convenient access to major highways, and a strong sense of community, Winter Garden is an ideal place to call home. Whether you’re looking for a cozy bungalow or a spacious family residence, the Homes with Sidewalks community offers an inviting atmosphere that makes it easy to settle in and make lasting memories. Come discover your dream home in Winter Garden, where community and comfort meet!

Newest Winter Garden Homes with Sidewalks Community Features

5960 Flowering Cherry Bend, Winter Garden
$604,990
3 Beds ⋅ 2 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
**Location, location, location!** This brand-new Dream Finders home is perfectly positioned in the highly desirable Hamlin area, just minutes from Hamlin schools, the Hamlin Town Center, shopping, dining, and quick access to State Road 429. From here, convenience is truly at your doorstep. While the location shines, this home packs an impressive amount of functionality into 1,772 square feet. The open-concept design features a spacious kitchen with quartz countertops, wood cabinetry, stainless-steel appliances, and a large island overlooking the living and dining areas. The split-bedroom layout offers a private primary suite on one side of the home, complete with dual sinks, a soaking tub, separate shower, and walk-in closet. Two additional bedrooms are tucked away in their own separate wing, creating a comfortable and flexible space for family, guests, or a home office. With modern finishes, a covered patio, backyard, and two-car garage, this move-in-ready home delivers big on comfort, convenience, and personality—all in one of Hamlin’s most sought-after locations.

5960 Flowering Cherry Bend, Winter Garden
1229 Winter Green Way, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Village Grove Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. This charming 2-bed, 1.5-bath townhouse delivers peak Central Florida convenience. Step inside to discover a bright, open interior highlighted by high ceilings and a stylish kitchen finished with sleek granite countertops. Meticulously maintained and move-in ready, it serves as the perfect low-maintenance starter home or turnkey addition to an investment portfolio. Five minutes to historic downtown Winter Garden, and under 30 minutes to Disney. Easy highway access rounds out a truly prime location. Tour Today!

1229 Winter Green Way, Winter Garden
922 Marsh Reed Drive, Winter Garden
$679,000
5 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe A & S SubDv. ⋅ 34787 Zip Code
Picture a Saturday here. Coffee at the kitchen island while the pool glistens under the Florida sun. Cannonballs by noon, burgers on the grill by five, and a movie night in the loft once everyone dries off. Welcome to 922 Marsh Reed Drive, a 5 bedroom, 3 full bath saltwater pool home in Johns Lake Pointe that has been cared for like a prized possession and is ready for its next chapter. The first impression sets the tone: tropical landscaping, a brick paver driveway, a three car garage, and a covered front porch with a cheery red door. Step inside and the tiled foyer opens to a formal dining room framed by tall windows and warm natural light, the kind of room that turns holiday dinners and Sunday suppers into traditions. Keep walking and the home opens up. The kitchen is the true gathering spot, with 42" espresso cabinets, granite counters, a tiled backsplash, stainless appliances, built-in double wall ovens, pendant lighting, and a large island where homework, snacks, and conversation all happen at once. A walk-in pantry with custom shelving keeps the grocery runs organized. The eat-in dining area sits right off the kitchen with sliding glass doors to the pool, so you can keep an eye on the swimmers while dinner comes together. The family room flows right alongside, finished with crown molding, plantation shutters, and wiring for surround sound. Game day, movie night, or a lazy Sunday nap, this room handles it all. Hosting overnight company? A first-floor bedroom next to a full bath makes a private guest retreat or a quiet home office away from the upstairs bustle. Head up the staircase with wrought iron spindles and you’ll find a huge loft that gives everyone room to spread out: game room, playroom, homework zone, or second living room. Three secondary bedrooms share a full bath, and the laundry room is right here on the second floor with custom cabinetry, which means no more hauling baskets up and down the stairs. The primary suite is split to its own side of the second floor, with windows on two sides and room for a reading chair. The en suite bath feels like a getaway, with dual sinks and granite counters, a frameless glass shower, a separate garden tub for long soaks, and two walk-in closets so nobody has to negotiate for hanger space. Then there’s the backyard, where this home really shines. The saltwater pool is heated by solar panels, extending swim season well beyond summer. An extended paver deck has room for a full grill lineup, a dining table, and lounge chairs, with an electric retractable awning for shade when you want it. Vinyl privacy fencing wraps the entire yard, giving you a private oasis with plenty of grass for playing catch or running through the sprinkler. Smart upgrades work quietly in the background: rain gutters around the entire home, French drains in the yard, whole-home water softening system, and a central vacuum in the garage. Life in Johns Lake Pointe adds even more to love, with a resort-style community pool, clubhouse, fitness center, tennis courts, playground, and walking trails. Bike the West Orange Trail, catch the Saturday farmers market in Historic Downtown Winter Garden, explore Tucker Ranch, or shop and dine at Winter Garden Village, all just minutes away. SR 429, SR 408, and the Florida Turnpike make commutes and theme park days easy. Homes like this don’t come along often. Schedule your private showing and see why this one is ready to feel like yours.

922 Marsh Reed Drive, Winter Garden
651 Autumn Oaks Loop, Winter Garden
$535,000
3 Beds ⋅ 2 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Live the Winter Garden lifestyle you've been dreaming of in the Winter Oaks community, with oak-lined streets and golf cart access to downtown. Situated in the Golf Cart District, this park-side residence overlooks majestic oaks and open green space. The 3-bedroom, 2-bath, 1,768 sq ft home features a 2021 ROOF, 2021 HVAC, UPDATED LIGHT FIXTURES, a GAS STOVE, a REAR-ENTRY 2-CAR GARAGE, and a RECENTLY PAINTED INTERIOR, with freshly painted bedrooms, baths and laundry room. As you walk in, you're greeted by natural light and an open, welcoming feel. A formal dining room and an open kitchen flow into the spacious family room, which leads out to a NEWLY RE-SCREENED back patio overlooking a beautifully manicured lawn and garden. The primary suite includes a spacious walk-in closet and a private bath with dual sinks, a soaking tub, and a separate shower. Winter Oaks offers a community pool, cabana, playground, and scenic pond. Hop in your golf cart to Plant Street for dinner, a show at the Garden Theatre, or the Saturday farmers market. Minutes from the West Orange Trail, Tucker Ranch, and Newton Park, Winter Garden Village with an easy drive to SR 429 and the Florida Turnpike. Convenient access to Disney, Universal, Epic Universe, and downtown Orlando. Schedule your private showing today!

651 Autumn Oaks Loop, Winter Garden
13728 Fox Glove Street, Winter Garden
$649,900
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West Ut 04 48 48 SubDv. ⋅ 34787 Zip Code
Spacious 5-bedroom, 3.5-bath home with 3,391 square feet overlooking the 14th hole of the golf course in Stoneybrook West. The main floor features a primary suite, a second bedroom with its own en-suite bathroom, and a separate powder room. Upstairs are three additional bedrooms and a full bathroom. The home features high ceilings, an open floor plan, plenty of natural light, and a 2-car garage. Sliding glass doors open to a large covered patio and screened-in private pool with golf course views. Recent improvements include a new roof (2025), upstairs AC (2025), and downstairs AC (2022). Stoneybrook West is a 24-hour guard-gated community with a clubhouse, fitness center, community pool, tennis courts, playground, and access to Black Lake with a private boat ramp. Conveniently located near Winter Garden Village, downtown Winter Garden, and SR-429.

13728 Fox Glove Street, Winter Garden
949 Celadon Street, Winter Garden
$2,195,000
5 Beds ⋅ 5 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Discover exceptional custom craftsmanship in this J&J Builders home, located in a golf cart-friendly community just minutes from downtown Winter Garden and the West Orange Trail. Featuring 5 bedrooms and 4.5 bathrooms, this home offers a thoughtfully designed open floor plan with beautiful views of Lake Apopka. The spacious chef's kitchen is the heart of the home, featuring high-end Sub-Zero and Miele appliances and creating an ideal setting for everyday living and entertaining. A dedicated office offers the flexibility to serve as a potential sixth bedroom. The stunning upstairs primary suite is a true retreat, showcasing dramatic cathedral beamed ceilings and breathtaking lake views. An additional private suite downstairs offers flexibility for guests or multigenerational living, while two additional upstairs bedrooms share a bath. The home also features a separate in-law suite with its own kitchenette, providing even more versatility for extended family or visitors. Designed for comfortable living and effortless entertaining, the home seamlessly blends indoor and outdoor living. Step outside to your own private retreat, featuring a heated inground pool and spa, an inviting covered lanai, and a fully equipped outdoor kitchen with automatic retractable screens. Gather around the natural gas fire pit with included outdoor furnishings and enjoy beautiful Florida evenings. Additional highlights include a large garage attic storage room with convenient accordion-style metal access stairs, offering valuable extra storage space. Enjoy the best of Winter Garden living with custom craftsmanship, high-end finishes, versatile living spaces, resort-style outdoor amenities, and convenient access to the area's beloved shops, dining, and outdoor recreation!

949 Celadon Street, Winter Garden
15625 Murcott Harvest Loop, Winter Garden
$650,000
3 Beds ⋅ 3 Baths ⋅ Highlands At Summerlake Groves Phase 1 SubDv. ⋅ 34787 Zip Code
Beautifully appointed SINGLE-STORY home in the highly desirable Summerlake community of Horizon West! The GOURMET KITCHEN is sure to impress with a massive center island, stainless steel appliances, GAS COOKTOP, built-in wall oven and microwave, stunning backsplash, and walk in pantry. 8 FOOT DOORS, CROWN MOLDING, and Phillips Hue SMART LIGHTING are some of the additional design upgrades. You will love the open, inviting floor plan. The open office offers flexibility and can easily be converted into a 4TH BEDROOM. Enjoy energy efficiency and significant savings with SOLAR PANELS, which will be PAID IN FULL AT CLOSING, and an average electric bill of approximately $30 per month! Additional energy upgrades include a TANKLESS WATER HEATER and a NEW HIGH-EFFICIENCY AC SYSTEM with TWO UV FILTERS. Summerlake is a natural gas community offering an impressive array of amenities, including a clubhouse, RESORT-STYLE POOL, fitness center, tennis and basketball courts, playgrounds, parks, and miles of walking and biking paths, with scenic boardwalks connecting lakes and natural areas. The HOA also includes CABLE AND INTERNET! Conveniently located near Hamlin Town Center for shopping, dining, coffee shops, and entertainment, with additional shopping and restaurants at Winter Garden Village. Enjoy the charm of Historic Downtown Winter Garden, Plant Street Market, the weekly farmers market, and the West Orange Trail. Golf enthusiasts will appreciate nearby Orange County National Golf Center. Easy access to SR-429 puts Walt Disney World and the greater Orlando area within easy reach. This home offers the perfect combination of style, comfort, energy efficiency, and an outstanding Horizon West lifestyle!

15625 Murcott Harvest Loop, Winter Garden
2004 Lake Roberts Landing Drive, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Lake Roberts Landing SubDv. ⋅ 34787 Zip Code
Welcome to 2004 Lake Roberts Landing Drive, an exclusive gated community in the heart of Winter Garden. This spacious single-story home has 4 bedrooms, 2.5 bathrooms, and a beautiful pond view. The split-bedroom floor plan gives everyone their own space. The primary suite sits apart from the secondary bedrooms for added privacy. Generous living and dining areas make it easy to entertain or relax with family. At the heart of the home, the kitchen has a breakfast bar, plenty of counter space, and a pantry. It opens to the family room, so you can cook and still be part of the conversation. The primary suite is a peaceful retreat, with a spacious bedroom, dual vanities, a garden tub, and a separate shower. Step out to the covered lanai and enjoy the views. It's an ideal spot for morning coffee, dinner outdoors, or unwinding at the end of the day. Lake Roberts Landing offers the privacy of a gated neighborhood. It's close to shopping, dining, and entertainment in Winter Garden, with easy access to SR 429. Don't miss this chance to own a lakefront home in one of Winter Garden's most desirable gated communities. Schedule your private showing today.

2004 Lake Roberts Landing Drive, Winter Garden
1218 Painted Bunting Avenue, Oakland
$517,500
3 Beds ⋅ 2 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. **WELCOME HOME** Pond views, beautiful upgrades, and an unbeatable location just minutes from Downtown Winter Garden! BUILT IN 2020 with FRESH EXTERIOR PAINT (2026), this SINGLE-STORY home in the charming Longleaf at Oakland community offers a sought-after floor plan, stylish finishes, and a fantastic location with no direct front or rear neighbors. A welcoming COVERED FRONT PORCH overlooks a peaceful community pond, creating a tranquil setting to relax and enjoy the view. Inside, LUXURY VINYL PLANK FLOORING flows throughout the home, complementing the light, bright, and OPEN LIVING SPACES. The home chef will appreciate the well-appointed kitchen featuring QUARTZ COUNTERTOPS, timeless cabinetry topped with crown molding, a gray ARABESQUE MOSAIC TILE BACKSPLASH, stainless steel appliances, a BUILT-IN OVEN and microwave, cooktop with vent hood, and a spacious ISLAND with PENDANT LIGHTING. A convenient BUILT-IN WORK SPACE just off the kitchen is ideal for a home office or homework station. The thoughtfully designed floor plan offers comfortable bedrooms and beautifully finished bathrooms with granite countertops and gray cabinetry, plus CUSTOM CLOSET built-ins in one of the secondary bedrooms. POCKET SLIDING GLASS DOORS open to the SCREENED LANAI, complete with roller shades for added comfort and privacy. Beyond the porch, a FENCED BACKYARD provides a rare bonus for this style of home, offering outdoor space while still enjoying the convenience of a 2-CAR REAR FACING GARAGE with epoxy flooring. Additional street parking is available out front. Even better, the HOA takes care of the lawn maintenance! Longleaf at Oakland is a quaint, welcoming community with a pool and playground just steps from your front door. Outdoor enthusiasts will love being just a 5-minute stroll from the West Orange Trail, while the shops, restaurants, farmers market, and charm of Historic Downtown Winter Garden are all less than 10 minutes away! Commuters will appreciate quick access to the Florida Turnpike, SR 50, and SR 429, with Lake Apopka, parks, shopping, and everyday conveniences all nearby. ZONED FOR TOP RATED SCHOOLS - Tildenville Elementary, Lakeview Middle, and West Orange High School. Enjoy the benefits of NEWER CONSTRUCTION, thoughtful UPGRADES, LOW MAINTENANCE LIVING, and a prime Oakland location without sacrificing proximity to everything Winter Garden has to offer. Schedule your tour today!

1218 Painted Bunting Avenue, Oakland
6099 Flowering Cherry Bend, Winter Garden
$829,496
4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Find room to spread out in this thoughtfully configured Biscayne, Elevation B, at Avalon Woods. Four bedrooms and three full baths include a first-floor bedroom and full bath, giving you flexibility for guests or a home office. The open great room, dining area and gourmet kitchen make it easy to stay connected, with laminate flooring adding warmth to the main living spaces. The kitchen brings together an island, quartz countertops, white cabinetry, a built-in oven, electric cooktop, microwave and range hood. Upstairs, the extended primary suite offers generous walk-in storage and a spa-style shower, while a spacious bonus room gives you another place to relax, play or gather. Two additional upstairs bedrooms and an upstairs laundry room with cabinets and a sink add everyday convenience. Open the hidden sliding glass door to the covered rear lanai for a quiet morning or an easy evening outdoors. A covered front porch, stone accents and an attached two-car garage complete the picture. Discover the possibilities of this home under construction in Winter Garden.

6099 Flowering Cherry Bend, Winter Garden
9218 Holliston Creek Place, Winter Garden
$860,000
4 Beds ⋅ 4 Baths ⋅ Watermark Ph 2b SubDv. ⋅ 34787 Zip Code
Delight your clients with this unique opportunity in Watermark, one of the most desirable communities in Winter Garden. This elegant two-story residence combines sophistication, comfort, and impeccable finishes in every detail, featuring over $150,000 in upgrades that elevate the home's overall quality and value. It offers 4 bedrooms, 3 full bathrooms, and 1 powder room, along with a simply enchanting outdoor area designed to provide unforgettable moments. Upon entering, a spacious and welcoming foyer leads to open-concept living areas, where the living room and dining room connect harmoniously, creating a bright and airy space ideal for entertaining family and friends. The beautiful porcelain tile floors enhance the elegance of the property. The kitchen is a true highlight, equipped with appliances, high-quality wood cabinetry, and ample countertop space, combining functionality and style for everyday living. On the second floor, all bedrooms provide greater privacy and comfort. The bedrooms feature closets and carpeting, creating a cozy atmosphere. The primary suite is a special retreat, featuring two walk-in closets and a spacious bathroom with dual sinks, offering both practicality and sophistication. The laundry room is also located on the upper floor and includes a sink, washer, and dryer, providing added convenience to the family's routine. Outside, the property impresses with a fully equipped summer kitchen featuring a built-in grill, granite countertops, cabinetry, and a sink — perfect for gatherings and family moments — integrated with a private heated pool, allowing year-round enjoyment with comfort and exclusivity. Living in Watermark means enjoying resort-style amenities, including a community pool, modern fitness center, tennis court, playground, green areas, and tree-lined sidewalks for outdoor walks. The location is another major advantage: just minutes from Hamlin Town Center, with excellent restaurants, cafés, movie theater, and supermarkets; easy access to Walt Disney World Resort; and close to Florida State Road 429, providing convenient access to Orlando and the entire region. Additionally, it is surrounded by highly rated schools and all the conveniences that Winter Garden offers. A complete home, offering leisure, comfort, and a prime location. Don't miss the opportunity to live or invest in one of the best addresses in the region.

9218 Holliston Creek Place, Winter Garden
14838 Driftwater Drive, Winter Garden
$389,900
3 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 3b-6 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Step onto the relaxing front porch and into a 3-bedroom, 2.5-bath townhome that flows beautifully. Enter through the formal living room and dining room, then pass the stairs and the downstairs guest bath into the open family room and kitchen. The kitchen has stone countertops, wood cabinetry and a large walk-in pantry. The whole space looks out onto your private cobblestone courtyard, a great place to entertain or to slip away and unwind after a long day. Privacy is all yours. 18-inch ceramic tile flooring runs through the first floor, and all appliances stay, including the washer and dryer. Upstairs, natural light fills the spacious primary suite, complete with a large walk-in closet. The 2-car rear-load garage is entered from the alley, just beyond the courtyard, which keeps the front of the home clean and quiet. Signature Lakes offers a resort-style pool, a fitness center, a clubhouse and community events all year. Hamlin, Winter Garden Village, 429 and 535 are all close by. Zoned for A-rated schools (buyer to verify). Move-in ready and low maintenance in one of Winter Garden's most desirable communities.

14838 Driftwater Drive, Winter Garden
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