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, where picturesque landscapes meet vibrant community life. Known for its rich history and small-town charm, Winter Garden offers a delightful blend of modern amenities and a close-knit atmosphere. The city is characterized by its beautiful historic downtown, which boasts a variety of boutique shops, delicious eateries, and lively farmers' markets that draw residents and visitors alike.

One of the standout features of Winter Garden is its commitment to creating a family-friendly environment, particularly evident in its Homes with Sidewalks community. Imagine strolling through tree-lined streets, where sidewalks invite leisurely walks or bike rides with loved ones. This community-centric design encourages neighbors to connect, fostering a sense of belonging and camaraderie among residents. Whether you’re enjoying a morning jog or an evening stroll, these walkable neighborhoods enhance the quality of life, making it easy to explore local parks and recreational areas.

Winter Garden is also home to a variety of outdoor activities, from the scenic West Orange Trail to beautiful lakes and parks that provide ample opportunities for family outings and picnics. With its excellent schools, thriving arts scene, and a calendar full of community events, Winter Garden is not just a place to live; it’s a place to thrive.

Discover the charm of Winter Garden and experience the warmth of a community where sidewalks lead to friendships and memories that last a lifetime. Your dream home awaits in this enchanting city!

Newest Winter Garden Homes with Sidewalks Community Features

4 Beds ⋅ 3 Baths ⋅ O6439501 MLS

Virtually Staged. The appeal isn’t just the house—it’s the lifestyle that comes with the community. Welcome to 10625 Atwater Bay Drive, Winter Garden, FL 34787, where comfort, convenience, and resort-style living come together in the highly desirable Waterleigh community. The first floor features a private bedroom and full bathroom with a bathtub, ideal for guests, extended family, or convenient first-floor living. The kitchen offers a large center island, granite countertops, ample cabinetry, and a walk-in pantry, opening seamlessly to the living and dining areas. A rear lanai provides a relaxing outdoor space, while the alley-access garage helps maintain the home’s attractive streetscape. Upstairs, a spacious loft offers flexible space for a home office, media room, or playroom. The primary suite features an en-suite bath with dual sinks and a walk-in shower, while two additional bedrooms share another full bath. What truly sets this home apart is the Waterleigh lifestyle. Residents enjoy multiple resort-style pools, fitness centers, clubhouses, playgrounds, sports fields, tennis and pickleball courts, mini-golf, dog parks, walking trails, fishing areas, lakes, green spaces, and community activities. Conveniently located near SR 429, Waterleigh offers easy access to Disney, Orlando, shopping, dining, and entertainment—with Publix located right within the community. 10625 Atwater Bay Drive offers more than a home—it’s an opportunity to enjoy the resort-style lifestyle that makes Waterleigh such a desirable place to live.

10625 Atwater Bay Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6431061 MLS

Welcome home to this freshly painted, charming Craftsman- inspired residence offering 2193 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities! This beautifully maintained home features 3 spacious bedrooms, 2 1/2 baths and a versatile loft/bonus room- perfect for a home office, media room or play area. The heart of the home is the open-concept kitchen overlooking the dining and family room, complete with an EXTRAORDINARY walk-in pantry that provides exceptional storage. Tile flooring flows throughout the main living areas, while the primary suite features warm hardwood flooring. Upstairs, the loft and secondary bedrooms are finished with comfortable Berber carpet. Step outside to relax or entertain on the screened lanai, offering the perfect space to enjoy Florida's beautiful weather year-round. Residents enjoy outstanding community amenities, including a resort-style pool, clubhouse, tennis courts, zip line and a dog park. Summerlake also appreciates access to TOP-RATED "A" schools. Conveniently located with easy access to Disney, Universal, Sea World, shopping, dining, major highways and all that Central Florida has to offer, this home truly combines comfort, convenience and an exceptional lifestyle!

7921 Iceland Gull Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ O6435631 MLS

Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden

4 Beds ⋅ 3 Baths ⋅ O6437872 MLS

PRIVATE HEATED POOL & SPA with panoramic screen enclosure on premium pond front lot. Welcome home to 15526 Mango Isle Street, a stunning single-story home nestled in the highly sought-after, resort-style community of Waterleigh in Horizon West. Step inside this spacious 4-bedroom, 3-bathroom open-concept home designed for effortless living and entertaining. The Gourmet Kitchen features a grand island with breakfast bar seating, solid surface countertops, solid wood cabinetry, a walk-in pantry, and stainless steel appliances, including a built-in cooktop and oven. The bright kitchen seamlessly opens to a wide-open family room and dining area framed by large sliding glass doors that draw your eye straight to the water views. Primary Suite feels like a tranquil sanctuary featuring elegant tray ceilings, a large walk-in closet, and an en-suite bath with a double-sink vanity and walk-in shower. Layout offers a generous split-bedroom floorplan offering optimal privacy for family and guests, plus an inside utility room. Enjoy this backyard oasis and step out through the sliding glass doors into your private sanctuary. The custom HEATED pool and integrated spa sit under a picture-frame panoramic screen enclosure, giving you unobstructed, serene views of the peaceful pond. Brick pavers cover the expansive covered lanai and pool deck, offering plenty of space for outdoor dining, lounging, and soaking in Florida's famous sunsets. The Waterleigh Community is renowned for its unmatched resort-style amenities and vibrant neighborhood atmosphere. Amenities: Access to two massive lakefront clubhouses, multiple resort-style pools, splash pads, two fully equipped fitness centers, tennis and pickleball courts, beach volleyball, walking trails, dog parks, playgrounds, and a mini-golf putting course. Location is phenomenal just minutes from Walt Disney World, top-rated Horizon West schools, Hamlin Town Center dining, shopping, golf courses, and quick access to State Road 429 for easy commutes across Central Florida. This home perfectly blends luxury, comfort, and the ultimate Florida indoor-outdoor lifestyle. Schedule your private showing today!

15526 Mango Isle Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ S5156936 MLS ⋅ Mezzano BLDG.

Welcome to this modern two-story townhome in Winter Garden. 2,024 square feet of interior living space, this home features 3 bedrooms and 3 full bathrooms, including a primary suite on the upper level and a full bedroom with a full bathroom conveniently located on the main level. The open-concept layout seamlessly connects the kitchen, dining, and gathering areas, creating an inviting space for daily living and entertaining. The kitchen is outfitted with quartz countertops, 42-inch cabinetry with crown molding, and a multi-functional center island. Additional highlights include an upper-level loft, a dedicated laundry room, smart home technology, and a private paver courtyard connecting the residence to a detached two-car garage equipped with an electric vehicle charging outlet. Residents enjoy access to community amenities, including a swimming pool and playground, with convenient proximity to local shopping, dining, and major thoroughfares.

7025 Twilight Bay Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ O6439215 MLS ⋅ 431/101 BLDG.

PROFESSIONAL MEDIA COMING SOON! A one-year home warranty is available with a full-price offer! Welcome to this meticulously maintained and beautifully updated 3-bedroom, 2-bathroom first-floor condo in the gated Southern Pines community of Winter Garden. Featuring fresh interior paint, new fixtures, and a bright open-concept floor plan, this home is truly move-in ready. Southern Pines offers an impressive amenity package including a resort-style pool and spa, fitness center, tennis courts, indoor basketball and volleyball courts, playground, dog park, clubhouse, theater room, billiards room, BBQ area, and resident car wash station. HOA dues include internet, basic cable, trash service, recreational amenities, lawn care, and exterior maintenance, providing convenient, low-maintenance living. The gated Southern Pines community offers exceptional value just minutes from everything needed for a balanced lifestyle, including Historic Downtown Winter Garden, Winter Garden Village, the West Orange Trail, shopping, dining, entertainment, and major highways, with easy access to Orlando and area attractions. Perfect for a primary residence, seasonal home, or investment opportunity. Schedule your private showing today!

431 Southern Pecan Circle Unit 101, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6438910 MLS ⋅ 11156 BLDG.

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 ⋅ S5156892 MLS

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, 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 ⋅ O6438512 MLS

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 ⋅ O6437857 MLS ⋅ 1315 BLDG.

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 ⋅ O6437583 MLS

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 ⋅ O6438081 MLS

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

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