Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida—a vibrant city that beautifully blends small-town charm with modern amenities. Nestled just west of Orlando, Winter Garden is known for its picturesque landscapes, historic downtown, and a strong sense of community. With its lush parks, scenic lakes, and a rich cultural heritage, this city offers an idyllic setting for families, retirees, and everyone in between.

One of the standout features of Winter Garden is its commitment to creating a walkable environment. Homes with sidewalks are a hallmark of many neighborhoods in this charming city, encouraging residents to enjoy leisurely strolls, morning jogs, or evening bike rides. The tree-lined streets and well-maintained sidewalks invite you to explore the area, making it easy to connect with neighbors and enjoy the outdoors.

The community atmosphere in Winter Garden is enhanced by its array of local shops, restaurants, and farmers' markets, all easily accessible from your front door. The historic downtown area, with its quaint boutiques and delightful eateries, is perfect for weekend outings or casual weekday dinners. Additionally, the city hosts year-round events, including festivals and farmer's markets, fostering a strong sense of belonging among residents.

Whether you’re looking for a cozy single-family home or a spacious property for your growing family, Winter Garden’s homes with sidewalks offer an inviting lifestyle that encourages outdoor living and community engagement. Discover the charm of Winter Garden, where your dream home awaits in a neighborhood designed for connection and comfort.

Newest Winter Garden Homes with Sidewalks Community Features

14501 Grove Resort Unit 2304, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Short Sale. Experience the Ultimate Orlando Resort Lifestyle & Investment Opportunity! Welcome to The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations, ideally located just minutes from Walt Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. Enjoy a fully furnished, turnkey 2-bedroom, 2-bath condominium that offers the perfect blend of comfort, style, and investment flexibility. The spacious open-concept floor plan features a beautifully appointed kitchen, bright great room, oversized windows, and a private balcony overlooking the peaceful courtyard. The split-bedroom layout provides privacy, while two spa-inspired bathrooms feature garden tubs, tiled showers, and dual vanities. With a sleeper sofa in the living room, the residence comfortably accommodates up to six guests. Step outside your front door and discover an extraordinary resort experience. The spectacular Surfari Water Park features a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Additional amenities include multiple pools and hot tubs, a 20-acre activity lake with private dock, fishing, fitness center, full-service spa, arcade, game room, and an array of on-site dining options including Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, and Byte. Convenient shuttle transportation to Disney World, Universal Studios, and SeaWorld adds even more appeal for vacation guests. As a short-term rental property, owners may enjoy personal use, while professional on-site management can handle bookings, housekeeping, maintenance, and guest services. Whether you're looking for a personal Orlando getaway, a vacation home, or a hands-off investment opportunity, this property offers an exceptional combination of resort amenities, flexibility, convenience, and income potential. Experience the magic of Orlando while owning your own piece of the vacation lifestyle at The Grove Resort & Water Park!

14501 Grove Resort Unit 2304, Winter Garden
13557 Parkfield Way, Winter Garden
$650,000
4 Beds ⋅ 3 Baths ⋅ Encore At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location!  Minutes from Walt Disney World and all that Winter Garden has to offer with the new hospitals, stores, restaurants, downtown Winter Garden, Horizon West and the list goes on! Single stories are hard to come by and this MI Home is waiting for you!  It sits on a gorgeous conservation lot with no neighbors on one side. Sit on the front porch or the back patio and enjoy the good life!  Walk to the pool, fitness center and dog park. The perfect community to walk or bike.  This 4 bedroom 3 bath rare find single story is move in ready-well maintained, built in 2021, quartz countertops, NEW AC, huge walk-in closet in the primary bedroom, a popular 3 way split floor plan, and ample room for entertaining with the dining room and large family room.  The home is stunning with its gorgeous wooded and pond view. Lawn Care is included in the HOA leaving you time to enjoy all Central Florida has to offer!  Schedule your showing today!

13557 Parkfield Way, Winter Garden
13211 Lakeshore Grove Drive, Winter Garden
$715,000
4 Beds ⋅ 4 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code
Amazing Floorplan!! Three way split floorpan with 4 bedrooms and an office located on the first floor. Formal dining and living rooms. Corian kitchen counters with wood cabinets. Large spacious bonus room on the second level with half bath. Screen enclosed pool with large lanai. Large vinyl fenced in backyard. ROOF 2023. Gated Community with basketball court, playground and dock to Lake Luntz. Located just a few minutes from Winter Garden Villages and access to the 408 near Stoneybrook Parkway. All furniture is available for purchase.

13211 Lakeshore Grove Drive, Winter Garden
9766 Amber Chestnut Way, Winter Garden
$429,900
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 3 SubDv. ⋅ 34787 Zip Code
Space, location, and the Horizon West lifestyle—all in one. Live minutes from Disney without feeling like you live in the middle of the tourist district. This 3-bedroom, 2.5-bath Watermark townhome gives you nearly 2,000 sq. ft., a dedicated first-floor office and an attached 2-car garage. High and tray ceilings, abundant natural light and an open floor plan make the space feel even larger. The kitchen brings granite countertops, espresso cabinetry, stainless steel appliances and a large island together with the dining and living areas. Upstairs, the primary suite includes a walk-in closet and private bath, with two additional bedrooms nearby. Watermark adds even more value outside the home, with community pools, clubhouse, fitness center, playgrounds and more. Hamlin, Flamingo Crossings, shopping, dining, SR-429 and Walt Disney World are all nearby—giving you the convenience of Horizon West without sacrificing the neighborhood feel.

9766 Amber Chestnut Way, Winter Garden
17602 Japonica Bloom Drive, Winter Garden
$785,000
5 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Luxury new construction home near Walt Disney World theme parks! The spacious 5 bedroom, 4 bathroom design offers the perfect combination of style, functionality, and comfort. The home features a 3-car tandem garage, a covered front porch and a covered backyard lanai, ideal for outdoor relaxation or entertaining. The heart of the home is the chef-inspired gourmet kitchen, which includes solid surface countertops, an island, and high-end stainless steel appliances, such as a cooktop, range hood, built-in oven and microwave, and dishwasher. The spacious living area is designed with upgraded flooring and enhanced with natural light flowing in through dual-pane energy-efficient windows. Sliding glass doors allow access to the covered backyard patio, seamlessly blending indoor and outdoor living spaces. The private primary suite is a true retreat, featuring an extended sitting room off of the bedroom. The primary bathroom features a dual sink vanity with Delta faucets, ceramic tile flooring, a luxurious shower with a glass enclosure and a freestanding bathtub. Additional features include an upgraded lighting package, towel bars, and a huge walk-in closet, offering plenty of storage and comfort. The secondary bedrooms are generously sized, with each second floor bedroom surrounding a spacious loft. Additional features of this exceptional new home include a full sprinkler system, a complete landscaping package, energy-efficient construction, garage door openers, and a utility area with ceramic tile flooring. The home also boasts all 8' doors on the first floor, pre-plumb for a laundry sink, fully upgraded design finishes, including Revwood flooring, and a new home warranty for peace of mind. Call today to schedule a tour!

17602 Japonica Bloom Drive, Winter Garden
15223 Evergreen Oak Loop, Winter Garden
$500,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 3b-4 3b-5 & 3 SubDv. ⋅ 34787 Zip Code
Welcome to the highly sought-after Independence community in Winter Garden! This spacious 4-bedroom, 3.5-bath home offers 2,502 square feet with a versatile layout that includes two primary suites—one conveniently located downstairs and a second upstairs. The open main living area features tile flooring and brings together the living room, dining area, and kitchen, creating plenty of space for everyday living and entertaining. The kitchen is equipped with granite countertops, stainless steel appliances, a center island, and pantry for additional storage. The downstairs primary suite offers the convenience of first-floor living, with an en suite bath featuring a double vanity, walk-in shower, and soaking tub. A separate half bath is also located downstairs for guests. Upstairs, you'll find the second primary suite plus two additional bedrooms connected by a Jack-and-Jill bathroom. A 2-car rear-entry garage completes the home. Independence offers an impressive lineup of community amenities, including two clubhouses, two community pools, fitness centers, parks, and miles of walking and biking trails. Enjoy a prime Winter Garden location near A-rated schools, shopping, dining, entertainment, medical facilities, and major roadways. Don’t miss your chance to make this spacious Winter Garden home your own! *Aerial photo property lines are an estimate and to be verified by buyer.

15223 Evergreen Oak Loop, Winter Garden
4540 Gliding Wave Street, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 4540 Gliding Wave St, located in the highly sought-after gated, waterfront community of Lakeview Preserve in Winter Garden! Built in 2022 by Pulte Homes, this beautifully maintained Spruce model offers an exceptional blend of modern design, thoughtful upgrades, & comfortable living. Featuring 3-beds/2-baths, a stunning office w/custom built-in cabinetry, a 2-car garage w/epoxy flooring, & 2,144 sq. ft. of thoughtfully designed living space. This home is sure to impress! As you enter, you are greeted by a spacious foyer & premium luxury vinyl plank flooring that flows seamlessly throughout the home. To your right, elegant double doors open into an impressive private office—an ideal space for working from home or creating a relaxing personal retreat. Continue into the heart of the home, where the kitchen, dining, & living areas come together in a breathtaking open-concept design. This expansive layout is perfect for entertaining guests, family, or simply enjoying everyday living. The gourmet kitchen is truly a showstopper! Featuring Pulte Homes’ coveted Chef’s Kitchen pkg, it boasts: Quartz countertops, Upgraded range countertop, Stylish range hood, oven w/microwave combo, beautiful kitchen island, Stainless steel appl, Elegant pendant lighting, & Under-cabinet lighting. This kitchen delivers both style & functionality. The entertaining continues as you open the sliding glass doors to the fully enclosed lanai, creating an inviting extension of your living space. Here, guests can relax & enjoy the peaceful surroundings while taking in the beautiful view of your premium homesite—w/no rear neighbors! And when the mood strikes, your built-in 5-speaker surround sound system sets the perfect atmosphere with your favorite easy-listening music. Retreat to the spacious owner's suite, this private sanctuary features a large walk-in closet with an amazing custom closet system, an oversized walk-in shower, abundant linen storage, & a double vanity. Add’l upgrades: Crown molding, Built-in drop zone w/cabinetry conveniently located at the garage entry, Security system, Reverse Osmosis System–under counter kitchen water filtration system, the home has also been pre-plumbed for a whole-house water softener, Gutters, LED lighting, Built-in pest control system. The HOA fee includes access to an impressive collection of resort-style amenities. Families will appreciate the community's proximity to highly rated schools, while outdoor enthusiasts will love the direct access to Johns Lake, complete with a kayak launch & dock. Lakeview Preserve offers convenient access to shopping, dining, entertainment, & outdoor recreation. Historic Downtown Winter Garden is approx. 8 miles away, while Winter Garden Village is less than 7 miles from the community. With easy access to State Road 50, 27 & the 429 Expy, residents enjoy convenient travel throughout Central Florida, including our world-famous attractions such as Walt Disney & Universal. Golf enthusiasts will appreciate the proximity to at least 4 major golf properties. For those who love walking, jogging, or cycling, the scenic 22-mile West Orange Trail is just 15 mins away. Combining modern upgrades, an open-concept design, resort-style amenities, & a prime Winter Garden location, this home offers the low-maintenance lifestyle you've been looking for! Don't miss this incredible opportunity, schedule your private showing today & discover why so many residents are proud to call Lakeview Preserve home!

4540 Gliding Wave Street, Winter Garden
8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Turnkey, Vacation Property in Lakeshore Preserve Winter Garden. Toll Brothers Model home. Professional interior designed for the model. The property occupies one of Lakeshore Preserve’s most open and airy homesites next to the park. The park's open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open park space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer upon entering. Key design and home features: Smart home technology, shiplap wall detailing, dramatic and rich wood beam trim ceilings. Plantation shutters throughout. The kitchen features a massive center island, farmhouse sink, custom backsplash, abundant cabinetry to include deep drawers and natural-gas cooking. Triple sliding glass doors connect the great room to expansive outdoor living, featuring: a fully equipped, built in summer kitchen. Outdoor dining and lounge spaces enclosed on all sides by luxury motorized retractable screens. Beyond the retractable screens, the backyard expands to feature an outdoor putting green, more lounge area and a built-in stone fireplace with modern glass-rock insert. Positioned at the rear of the first floor, the primary suite includes a custom walk-in closet and a striking primary bath with opposing vanities, a private water closet and a dramatic walk-through shower. Custom tile extends from the floor up the shower walls, with opposing shower systems, multiple shower heads and built-in bench seating. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes ensuite bath and walk-in closet, while the other two share a hall bath. When not occupied by guests, the second living room serves as a private lounge, media room, or office space. Turnkey includes: all living area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Utility features to this home: tankless water heater, low-E windows, smart-home technology, in-wall pest system and HOA-maintained grounds around the home and inside the fenced in back yard. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds, sand volleyball court. All surrounded by lake. Cable, one-gig internet and ground maintenance are included in the HOA fee. This executive collection home sits on one of the most unique homesites within Lakeshore Preserve. Privacy and sun-drenched light, Toll Brothers coveted upgrades, and this transitional design style fully finished by an interior designer for this model home.

8836 Lakeshore Pointe Drive, Winter Garden
3413 Turningwind Lane, Winter Garden
$849,000
4 Beds ⋅ 3 Baths ⋅ Windward Cay SubDv. ⋅ 34787 Zip Code
CHARMING WINTER GARDEN POOL HOME| Located in the highly desirable Windward Cay gated community, 3413 Turningwind Lane provides everyday living feeling like a getaway. This professionally designed 4-bedroom, 3-bath home offers 2,917 square feet of beautifully updated living space, a spacious three-car garage with storage, and a private resort style backyard made for entertaining. Inside, the open, split floor plan creates ample spaces to gather while giving everyone a retreat of their own. Bamboo and hardwood flooring, plantation shutters, and crown molding are just a few of the features bringing warmth and character throughout. The Tuscany-inspired chef’s kitchen is truly the heart of the home, featuring an oversized island with seating, breakfast nook, updated glass-front and solid wood cabinetry, a newer Forno six-burner gas stove with a pot filler, and a newer GE Profile refrigerator, not to mention the abundance of space making cooking that much more enjoyable. The coffee and wine bar with refrigeration makes hosting easy and uncluttered, while the large formal dining room sets the stage for memorable meals. A dedicated office offers space to work or create, and the spacious primary bedroom and bath provide a peaceful place to unwind and features his/her closets, a jacuzzi tub and large walk in shower. The large laundry room is equally well considered, with cabinetry, a folding station, sink and a newer washer and dryer. Outside to your own personal oasis, a waterfall featured pool with a new pool heater anchors a resort-style backyard framed by lush landscaping for exceptional privacy. Relax on the large covered patio with privacy screens, enjoy the turf courtyard, and make use of the exhaust hood for your BBQ setup. The entire outdoor area sits beneath a screened enclosure with custom smart lighting integrated into its frame, creating a beautiful setting long after sunset. Thoughtful smart technology continues throughout the property with JellyFish lighting along the front perimeter, Ecobee thermostats, a Reolink security system, Rachio irrigation controls, a Ring doorbell, OmniLogic pool controls, and hardwiring for a home sound system. The roof was replaced in 2021, and the AC was replaced in 2022. Situated near the Windermere and Horizon West borders, this Winter Garden home offers convenient access to West Orange Country Club, Stoneybrook West Golf Club, highly rated schools, SR 429 and SR 535 for easy access, the Butler Chain of Lakes, Lake Apopka, and the entire fleet of the Walt Disney World resorts and theme parks. This is truly a remarkable home with impeccable taste and well maintained. Please don't hesitate to call me for private showings before its gone.

3413 Turningwind Lane, Winter Garden
7747 Green Mountain Way, Winter Garden
$2,400,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional waterfront residence on beautiful Lake Hancock in Winter Garden. Offering over 5,100 square feet of living space, this impressive 6-bedroom, 6.5-bath home features a 3-car garage and direct lake frontage. Designed for both everyday comfort and effortless entertaining, the home welcomes you with a dramatic two-story family room, expansive living areas, and two primary suites—one conveniently located on each level. At the heart of the home, the gourmet kitchen features granite countertops, an oversized curved island, double ovens, a cooktop, and an open dining area ideal for gathering with family and friends. Upstairs, additional bedrooms and a generous game room provide exceptional flexibility for family, guests, a media space, or recreation. Step outside to the screened lanai, complete with a summer kitchen, and take in the serene views of Lake Hancock. In the evenings, enjoy views of Disney’s fireworks from the comfort of your own home—an unforgettable touch to this exceptional Florida lifestyle. With generous indoor and outdoor living spaces and a remarkable waterfront setting, this Winter Garden home offers an ideal combination of space, comfort, and lakefront living. Schedule your private showing today and experience it for yourself.

7747 Green Mountain Way, Winter Garden
15515 Campden Street, Winter Garden
$359,900
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this Gorgeous Home, where CONVENIENCE, and LOW-MAINTENANCE LIVING come together in a fantastic Winter Garden location making it easy to enjoy the vibrant Winter Garden lifestyle!! Step inside this to FRESHLY PAINTED 3 bedroom, 2.5 bath home. Featuring highly desirable WOOD-LOOK CERAMIC TILE throughout the main living areas, including the spacious living room, dining area, and kitchen.The kitchen features a NEW REFRIGERATOR, while a convenient downstairs half bath and large storage closet add to the home’s functionality. Upstairs, the VERSATILE LOFT adds valuable additional living space and is perfect for a home office, media room, playroom, fitness area, or cozy second family room. Plus the convenience of an UPSTAIRS LAUNDRY ROOM. The SPACIOUS Primary suite has 2 WALK-INCLOSETS and an ensuite bathroom with DUAL SINKS. The secondary bedrooms are also spacious and the 2nd bedroom also has a WALK-IN CLOSET as well. Enjoy added peace of mind with a NEW A/C installed in 2022, ROOF approximately 3 years NEW, gutters, and fresh exterior paint completed in 2025. Enjoy Florida living with access to the COMMUNITY POOL, perfect for cooling off, relaxing, and enjoying sunny Central Florida days without the maintenance of a private pool. The HOA provides exceptional value and low-maintenance living, including pest control, lawn, exterior maintenance, roof replacement approximately every 10 years, exterior painting, community pool, and tot lot. And then there's the LOCATION! Enjoy convenient access to the charm and energy of HISTORIC DOWNTOWN Winter Garden, where brick-lined streets are filled with locally loved restaurants, cafés, boutique shops, entertainment, and the popular Farmers Market. Grab a coffee, meet friends for dinner, spend an afternoon browsing the shops, or simply enjoy the welcoming small-town atmosphere. Outdoor enthusiasts will love the 22-mile West Orange Trail, which travels directly through the heart of Downtown Winter Garden. Whether you enjoy biking, running, walking, or simply getting outside, the trail offers miles of recreation and is one of the area's signature lifestyle amenities. This is more than just a home, it’s a lifestyle!

15515 Campden Street, Winter Garden
23 Zachary Wade Street, Winter Garden
$512,000
4 Beds ⋅ 2 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Lakeview Reserve welcomes you HOME! Set on a spacious .23 ACRE LOT with NO REAR NEIGHBORS, this single story 4-bedroom, 2-bath home offers an inviting combination of space, updates and classic Winter Garden charm! Recent improvements include a NEW WATER HEATER (2024), NEW COUNTERTOPS (2024), FRESH PAINT (2024) and NEW FLOORING (2024) throughout much of the home, plus a NEWER ROOF (2021) and UPDATED A/C (2018). Mature landscaping and tree-lined streets create beautiful curb appeal, while HIGH CEILINGS and plenty of natural light make the interior feel open and bright. The thoughtful SPLIT-BEDROOM FLOOR PLAN features both formal and casual living spaces, giving you flexibility for everyday living and entertaining. The PRIMARY SUITE enjoys its own private wing, and both bathrooms offer convenient access to the generous SCREENED LANAI. At the heart of the home, the kitchen features updated countertops and is ready for your personal touch. Step outside to a spacious backyard with no rear neighbors and a large screened lanai that extends the living space outdoors – ideal INDOOR/OUTDOOR LIVING! Lakeview Reserve is an established GATED COMMUNITY with a LOW HOA and a COMMUNITY DOCK ON LAKE APOPKA. You will enjoy cruising around the GOLF CART DISTRICT, and easy access to HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, local shopping, dining and recreation. Zoned for TOP-RATED SCHOOLS – Tildenville Elementary, Lakeview Middle and West Orange High, with convenient access to SR 50 and the Florida Turnpike. With a versatile layout, two car garage and a fantastic location close to everything Winter Garden has to offer, this home is ready for its next chapter. Call today and make it your next chapter as well!

23 Zachary Wade Street, Winter Garden
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