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 rich history, vibrant community, and picturesque landscapes. Just a stone’s throw away from the bustling city of Orlando, Winter Garden offers a perfect blend of small-town charm and modern conveniences, making it an ideal place to call home.

One of the standout features of Winter Garden is its commitment to community living, exemplified by the Homes with Sidewalks. These thoughtfully designed neighborhoods invite residents to embrace an active lifestyle, with tree-lined sidewalks perfect for leisurely strolls, morning jogs, or family bike rides. Imagine your children playing safely in the front yard while you enjoy a peaceful evening walk, greeting friendly neighbors along the way. The sidewalks foster a sense of connection and camaraderie among residents, creating a warm and welcoming atmosphere.

In addition to the inviting community features, Winter Garden boasts an array of amenities that cater to all ages. The historic downtown area is brimming with delightful shops, delectable dining options, and vibrant farmers' markets, providing a lively backdrop for weekend outings. Outdoor enthusiasts will appreciate the abundance of parks and recreational facilities, including the scenic West Orange Trail, which offers miles of paved paths for biking and walking.

With its excellent schools, diverse housing options, and a strong sense of community, Winter Garden is not just a place to live; it’s a place to thrive. Discover the charm of Winter Garden and find your dream home today in this enchanting Florida city!

Newest Winter Garden Homes with Sidewalks Community Features

3 Beds ⋅ 3 Baths ⋅ Winding Bay Preserve SubDv. ⋅ 34787 Zip Code

BEAUTIFUL two-story townhome in the desirable Winding Bay Preserve community. This spacious 3 bed/2.5 bath offers low-maintenance living in a prime Winter Garden location. The main level is an open-concept with a half bathroom for guests. The kitchen features GRANITE countertops, stainless steel appliances, a large kitchen island and a breakfast bar...PERFECT for entertaining! All bedrooms are located on the second floor along with the laundry closet. The primary suite includes a WALK-IN closet and an en-suite bathroom with double vanity sinks. Enjoy outdoor living on the private back patio, which leads to the 2-car garage. The community features a POOL, playground and dog park. It is conveniently located in Winter Garden near grocery stores, restaurants and top rated schools.

11156 Hanlon Terrace Alley, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Bradford Creek SubDv. ⋅ 34787 Zip Code

Welcome to your ideal Florida sanctuary at 14145 Creekbed Cir! Nestled in the highly sought-after, gated community of Bradford Creek in Winter Garden, this stunning, fully furnished 4-bedroom, 4-bathroom residence offers the ultimate blend of luxury, comfort, and flexibility. Designed with an expansive open-concept floor plan, gourmet kitchen, and private ensuite bedrooms, the home flows effortlessly out to your private backyard oasis. Step outside into a resort-style, fully screened enclosure featuring a sparkling heated pool and relaxing spa—perfect for year-round outdoor dining, entertaining guests, or unwinding in complete privacy. As a resident of Bradford Creek, you'll enjoy a secure gated entrance and close access to the famous West Orange Trail. Located just minutes from historic Downtown Winter Garden, Winter Garden Village, and major highways, you are seamlessly connected to Central Florida’s world-class theme parks, premier dining, and upscale shopping. Whether you are searching for a move-in-ready primary residence to settle into right away or a high-value investment opportunity in a booming market, this beautiful pool home delivers exceptional versatility, long-term equity potential, and true Florida lifestyle living.

14145 Creekbed Circle, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

Beyond the gates of Waterside at Johns Lake, where tranquil lakefront living meets the energy of Winter Garden, 16795 Turtle Hatch Drive invites you into a home designed for life at its most memorable. A stately courtyard entrance creates a striking sense of arrival, opening to a grand foyer, soaring ceilings, and sun-filled interiors that feel both impressive and welcoming. This exceptional two-story residence offers 5 bedrooms, 4.5 bathrooms, an expansive bonus room, and an oversized 3-car garage, delivering the space, flexibility, and refined comfort today’s luxury buyer desires. Upgraded tile and hardwood flooring flow through the main living areas, bringing warmth and sophistication to the open-concept great room and dining spaces. Here, quiet mornings transition effortlessly into lively evenings, with generous gathering areas designed for intimate dinners, holiday celebrations, and everything in between. At the heart of the home, the gourmet kitchen is as beautiful as it is functional. Upgraded 42-inch cabinetry, granite countertops, a custom tile backsplash, stainless steel appliances, a gas cooktop, double ovens, and an oversized island with abundant seating create a natural destination for cooking, conversation, and connection. A dedicated workspace with built-in cabinetry and extensive counter space makes working from home, studying, or managing daily life seamless. The main-floor primary suite is a private sanctuary, featuring hardwood flooring, large windows, a custom walk-in closet, and a spa-inspired bath with dual vanities, a soaking tub, and an expansive tiled walk-in shower. Additional bedrooms and baths offer privacy and versatility for guests, extended household members, hobbies, or home offices. Upstairs, the oversized bonus room is a blank canvas for your lifestyle, imagine a cinematic home theater, game lounge, fitness studio, creative space, or secluded guest retreat. Thoughtful details continue in the laundry room with built-in storage, shelving, and a utility sink. Energy-efficient windows, natural gas, and a tankless water heater further enhance everyday comfort and efficiency. And when you step outside you will enjoy your resort-style pool and spa, a private backyard retreat designed to make everyday living feel like a vacation. Beyond the home, Waterside at Johns Lake elevates the experience with gated entry, a lakefront community pool, clubhouse, fitness center, private fishing dock, playground, parks, sidewalks, and scenic walking paths. It is a setting where weekends can begin with a peaceful lakeside walk, continue with an afternoon by the pool, and end beneath a brilliant Florida sunset. The address also places you near the best of Winter Garden and Horizon West, with shopping, acclaimed dining, entertainment, and leading healthcare all within easy reach. Historic Downtown Winter Garden adds timeless charm with boutiques, cafés, restaurants, breweries, the Saturday Farmers Market, Plant Street Market, and Crooked Can Brewing Company. Access to State Road 429, Florida’s Turnpike, and State Road 50 connects you to all things Walt Disney World and Universal Orlando. More than a beautiful residence, 16795 Turtle Hatch Drive is an invitation to live with greater ease, entertain with confidence, and come home to a community that feels worlds away, yet close to everything. Schedule your private tour today! ***Seller is providing up to $5,000 towards mortgage rate incentives when using their Preferred Lender.

16795 Turtle Hatch Drive, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a fully equipped kitchen and grilling area. The community also offers a park and playground, providing something for everyone to enjoy. This 1bed/1 bathroom with a flex room boast commercial grade luxury vinyl plank flooring, crown molding throughout, granite counter tops throughout the kitchen and bathroom, dedicated dining room, indoor laundry room with washer and dryer included, neutral interior wall paint, excellent natural light, ensuite bathroom, ample size primary suite walk-in closet, and more. Conveniences to be noted in the association fees are: Water, Cable, Trash, Pest Control, Roof, Exterior Building Maintenance, and Pool. Live just minutes from Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail. Getting around Central Florida is easy with quick access to SR-429, the Florida Turnpike, SR-408, and SR-50. Everyday shopping is also close by, with Publix and Costco Just minutes away. Low maintenance living at it's finest. Come see this condo today.

1315 Eastern Pecan Place Unit 202, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-2 & 2c-3 SubDv. ⋅ 34787 Zip Code

WATER & CONSERVATION VIEW | NO REAR NEIGHBORS | THREE-CAR TANDEM GARAGE | POOL READY, FENCED YARD | NEW CARPET & FRESH PAINT | MOVE IN READY -- Located in Winter Garden's sought-after Waterleigh community, minutes from Walt Disney World. The home sits on a premium oversized homesite backing to conservation, with pond views and no rear neighbors. It is part of D.R. Horton's luxury Emerald Collection, built with upgrades like a concrete tile roof and an extended tandem garage. New carpet and fresh interior paint throughout. The flexible floor plan offers four bedrooms, a first-floor bonus room, and a spacious upstairs loft. A first-floor bedroom and full bath make an ideal setup for guests, multigenerational living, or a private home office. The gourmet kitchen offers quartz counters, a built-in oven, an induction cooktop, a range hood vented outside, a butler's pantry, and a walk-in pantry. It opens to the living room and a dining room with water views. Upstairs, the primary suite features a tray ceiling, a pond-view sitting area, a garden tub, and a walk-in shower. Outside, the screened lanai with brick pavers overlooks a fully fenced backyard with room to design your own custom pool. The 38-foot tandem garage adds an epoxy floor and a Tesla EV charger that conveys. Best of all, this is maintenance-free living: the HOA handles the lawn and landscaping for you, along with resort-style amenities including community pools, clubhouse, fitness center, parks, playgrounds, and a dog park. Close to Horizon West and Hamlin shopping and dining, with easy access to SR-429. Zoned for Atwater Bay Elementary, Water Spring Middle, and Horizon High School. Seller is a licensed Florida real estate sales associate.

9982 Beach Port Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

Exquisite Sanctuary with Private Pool in Gated Waterside! Welcome home to this meticulously maintained, one-story masterpiece situated in the heart of Waterside, Winter Garden's established, sought-after gated community. Offering an unparalleled blend of luxury and privacy, this spectacular residence invites you to enjoy calming lakefront views the moment you enter the neighborhood. From the moment you step through the charming front courtyard, the home showcases exceptional quality and elegant upgrades. The gourmet kitchen serves as the heart of this open-concept layout, featuring custom cabinetry and a sun-drenched breakfast room that overlooks your private pool and a serene conservation lot. Retreat to the thoughtfully designed primary suite—a true oasis featuring a spacious walk-in closet with custom built-ins, French door opening to the covered patio, and a spa-like ensuite bath complete with dual vanities, a private commode room, garden tub, and a separate walk-in shower. Custom craftsmanship highlights every detail of this home, from the elegant coffered ceilings in the dining room to custom cabinetry and built-in closets. Off the sunlit breakfast room, a dedicated office area with custom built-in counters provides a functional workspace. Outside, enjoy a freshly painted exterior (2024) and an inviting covered screened lanai featuring a built-in outdoor grill with a sleek bar—perfect for year-round entertaining. Designed for comfortable living and entertaining, the home features a 3-way split bedroom layout, a custom-built entertainment center in the family room, and a Sonos sound system with five separate zones throughout. Embrace the ultimate Florida lifestyle in your private backyard paradise. Designed for inviting entertaining, the space includes a custom pool, spa, and a built-in outdoor grill, all set against a tranquil green space with the privacy of no rear neighbors. Watch the sunset over the lake and unwind in your own personal oasis. Residents of Waterside enjoy an exclusive atmosphere with premier amenities, including a community pool, fitness center, clubhouse, and a playground. Ideally positioned just minutes from top-rated schools, shopping, Disney, downtown Winter Garden, and major roadways, including the 429, 408, and the Florida Turnpike.

16753 Turtle Hatch Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lake Ph 2c SubDv. ⋅ 34787 Zip Code

Welcome home to Waterside on Johns Lake, a highly sought-after community in Winter Garden! This 4-bedroom, 3-full-bath, 2,030 sq. ft. single-family home sits on a desirable CORNER LOT and offers an open-concept floor plan with a great blend of functionality and living space. The first floor features a spacious great room with a custom shiplap accent wall and private in-wall electric fireplace, creating a comfortable space to relax or entertain. The great room flows seamlessly into the dining area and kitchen, which features 42-inch grey shaker cabinetry, quartz countertops, and a pantry. Also on the first floor is a full bathroom and a bedroom currently being used as an office, making it ideal for guests, a home office, or flexible living needs. A convenient mudroom with generous storage provides additional functionality. Step outside to a private patio with a dedicated seating and entertaining area, along with a large fenced-in side yard. The rear of the property features a detached 2-car garage and a private driveway with additional parking for two vehicles. Upstairs, the split-bedroom layout provides privacy and flexibility. The spacious primary suite features an oversized bedroom, walk-in closet, and private en-suite bathroom. Two additional bedrooms, a third full bathroom, and a dedicated laundry room complete the second floor. The location is hard to beat, with convenient access to Winter Garden Village, Hamlin, Horizon West, Downtown Winter Garden, and SR-429. Enjoy an easy drive to Central Florida's major attractions, including Disney, SeaWorld, and Universal Studios, as well as an abundance of shopping, dining, and entertainment options. Waterside on Johns Lake features resort-style amenities including a community pool and clubhouse, playground, park, fitness center, and community dock on Johns Lake. The home is also zoned for highly regarded A-rated schools, including Hamlin Elementary, Hamlin Middle, and West Orange High.

1372 Roxy Lane, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Orange Cove SubDv. ⋅ 34787 Zip Code

Single family residence

735 Hurley Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to Winter Oaks, where move-in-ready comfort meets the highly sought-after Downtown Winter Garden golf cart lifestyle! This beautifully updated 4-bedroom, 3-bath home offers 2,308 square feet of thoughtfully designed living space with an open-concept floor plan, high ceilings, crown molding, and a versatile split-bedroom layout designed for both privacy and functionality. The current owners have continued to enhance the home with valuable upgrades, including LVP FLOORING THROUGHOUT, NEW APPLIANCES, a WHOLE-HOUSE GENERATOR, a newly added DECK, and UPDATED LANDSCAPING. Combined with a ROOF replaced in September 2022, these improvements offer the style, functionality, and peace of mind today's buyers are looking for. At the heart of the home, the spacious gourmet kitchen features 42-inch cabinetry, new stainless steel appliances, generous prep and storage space, and a large center island that opens to the main living area—perfect for entertaining and everyday gatherings. The primary suite is conveniently located on the first floor and offers a spacious walk-in closet and en-suite bathroom with dual vanities, a soaking tub, and separate walk-in shower. Two additional secondary bedrooms are also located on the main level, providing flexibility for family, guests, or a home office. Upstairs, you'll discover an exceptionally spacious 4th bedroom with its own private full bathroom, creating an ideal guest suite, multigenerational space, or private work-from-home setup. Outdoor living is another standout feature. Outside find the fully fenced backyard featuring a covered and screened lanai, paver patio, and newly added deck, creating multiple spaces for grilling, entertaining, pets, or simply relaxing in the Florida sunshine. Updated landscaping enhances the curb appeal and completes the home's welcoming outdoor setting. And then there's the location! Winter Oaks puts you just minutes from the heart of Historic Downtown Winter Garden, where you can bike, or take your golf cart to Plant Street and enjoy award-winning restaurants, breweries, boutique shopping, live entertainment, and the popular Winter Garden Farmers Market. Outdoor enthusiasts will appreciate convenient access to the West Orange Trail, while residents can also enjoy the neighborhood community pool and cabana. With convenient access to major roadways, Orlando attractions, shopping, dining, and everyday conveniences are all within easy reach.

880 Summer Oaks Road, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code

FIRST TIME EVER OFFERED FOR SALE BY THE ORIGINAL OWNER! This exceptional five-bedroom, three-bath residence with a dedicated office, expansive bonus room and three-car tandem garage is ideally positioned on an oversized corner lot of more than one-quarter acre, directly across from the community’s spectacular resort-style clubhouse and amenities. From the covered front porch, enjoy tranquil views of the large community pond, or retreat to the private backyard and unwind beside the fire under the stars. Thoughtfully designed for both everyday living and entertaining, the first floor features a private bedroom and full bath, an elegant formal dining room, a well-appointed kitchen with generous cabinetry and workspace, and an open-concept great room that creates an inviting central gathering space. A dedicated office tucked off the main living area provides the perfect space for working from home, studying or a quiet retreat. Upstairs, an impressive oversized bonus room provides incredible flexibility for a media room, game room, home gym or additional living space. The spacious primary suite offers a peaceful retreat with a luxurious garden bath, large walk-in shower, dual vanities and two walk-in closets. Convenient direct access from the primary suite to the laundry room is an exceptional feature that adds functionality to everyday living. Three additional oversized secondary bedrooms provide plenty of space for family and guests. The home’s location within the community is truly special. Step across the street to enjoy the resort-style clubhouse, sparkling community pool, tennis and basketball courts, fitness center and even a zip line, all beautifully situated overlooking a pristine pond. The HOA fee also includes lawn care, adding both convenience and value. Beyond the community, the location is equally impressive, with easy access to the 429 expressway, Hamlin’s popular shopping, dining and entertainment district and Walt Disney World Resort. An abundance of additional shopping and dining destinations are just minutes away in every direction. Families will appreciate the highly sought-after K-12 school options, along with convenient proximity to Windermere Preparatory School and Foundation Academy campuses. Rarely does a home combine an oversized corner lot, exceptional floor plan, direct proximity to resort-style amenities, beautiful pond views and first-time-ever ownership history. This is a special opportunity to make an outstanding Central Florida home your own.

8001 Pond Apple Drive, Winter Garden

5 Beds ⋅ 6 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai is a beautiful pool, spa and cabana area, perfect for a mid day swim or watching Disney fireworks at night. The kitchens, indoor and outdoor, and sure to impress even the most fastidious of chefs with the natural gas cooktop, multiple mounted range hoods, quartz countertops and more. This property is not only a "smart home" but also environmentally conscientious with newly installed solar panels and an electric car charger. All furniture is included with the sale of this home, the only thing you need is the keys to begin living your best central Florida life. Virtual Tour Available.

15680 Panther Lake Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 1 SubDv. ⋅ 34787 Zip Code

HAVE YOU BEEN SEARCHING FOR A 5-BEDROOM HOME with a DEDICATED OFFICE, PRIVATE THEATER/MEDIA ROOM, TWO BONUS SPACES, and nearly 5,000 SQUARE FEET—but it just hasn’t been there? NOW IT IS! This stunning 5-bedroom, 4-bath home offers an exceptional combination of SPACE, LUXURY, PRIVACY, and FUNCTIONALITY, beautifully situated on a FENCED CONSERVATION LOT with NO REAR NEIGHBORS and FRESH SOD in the backyard. STORAGE GALORE! This home truly does not lack space, offering GENEROUS CLOSETS, WALK-IN STORAGE, an OVERSIZED WALK-IN PANTRY, BUTLER’S PANTRY, and thoughtful storage throughout. METICULOUSLY MAINTAINED and USED AS A VACATION HOME, this property has been kept in PRISTINE CONDITION. The OPEN-CONCEPT FLOOR PLAN features WOOD-LOOK TILE THROUGHOUT THE MAIN LEVEL, TRAY AND COFFERED CEILINGS, CUSTOM BUILT-INS, NEW FIXTURES, and abundant natural light. The GOURMET KITCHEN is designed for both everyday living and entertaining, featuring 42-INCH CABINETRY, GRANITE COUNTERTOPS, DOUBLE WALL OVENS, COOKTOP, STAINLESS-STEEL APPLIANCES, LARGE ISLAND, and an OVERSIZED WALK-IN PANTRY with abundant cabinet and counter space, all overlooking the spacious family room. The FIRST-FLOOR PRIMARY SUITE is a true retreat, complete with a sitting area, DUAL WALK-IN CLOSETS, and a SPA-INSPIRED PRIMARY BATH featuring a double-sink granite vanity, garden tub, and separate shower. The primary closet has been CUSTOM DESIGNED BY CALIFORNIA CLOSETS, providing exceptional organization and functionality. Upstairs, you’ll find FOUR ADDITIONAL SPACIOUS BEDROOMS, each with its own WALK-IN CLOSET, along with a versatile LOFT, GAME ROOM, and DEDICATED MEDIA/THEATER ROOM. With MULTIPLE BONUS SPACES, there is room for a HOME OFFICE, MOVIE NIGHTS, GAME DAYS, GUESTS, and everything in between. A JACK-AND-JILL BATHROOM with SEPARATE VANITIES adds convenience and functionality. Step outside into your PRIVATE BACKYARD OASIS, where a BEAUTIFUL SALTWATER POOL AND SPA, COMPLETED IN 2025, create the perfect setting for relaxing and entertaining. The POOL PUMP WAS UPGRADED IN 2025 to a variable-speed, high-efficiency system, offering enhanced performance and energy efficiency. INTEGRATED POOL LIGHTING within the screen enclosure adds the perfect ambiance for evening swims and outdoor entertaining. The SCREEN-ENCLOSED REAR PATIO with BRICK PAVERS overlooks the peaceful conservation area, providing PRIVACY lighting to enclosed screen. Additional highlights include STONE ELEVATION, COVERED FRONT PORCH, FRESHLY EPOXIED TANDEM 3-CAR GARAGE FLOOR, ALARM SYSTEM, POOL SAFETY GATE, and NO DIRECT REAR NEIGHBORS. WATER FILTRATION & EXTRAS INCLUDED! The CULLIGAN WATER SYSTEM, WHOLE-HOUSE FILTRATION SYSTEM, WATER SOFTENER, and REVERSE OSMOSIS SYSTEM FOR DRINKING WATER all STAY WITH THE HOME! Plus, the POOL TABLE IS INCLUDED WITH THE PURCHASE. Enjoy RESORT-STYLE COMMUNITY AMENITIES including a clubhouse with fitness center and monthly activities, RESORT-STYLE POOL, PLAYGROUNDS, and DOG PARK, with the MONTHLY HOA FEE INCLUDING LAWN CARE. Ideally located just minutes from HORIZON WEST’S RESTAURANTS, SHOPPING, CINÉPOLIS LUXURY DINE-IN MOVIE THEATERS, CRAFT AND FARMERS MARKETS, WINTER GARDEN VILLAGE, and DISNEY, with easy access to SR 429, FLORIDA’S TURNPIKE, SR 408, and DOWNTOWN ORLANDO. TOP-RATED SCHOOLS add even more appeal to this incredible location.

14567 Cedar Hill Drive, Winter Garden

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