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 that seamlessly blends small-town charm with modern convenience. Known for its picturesque landscapes and vibrant downtown area, Winter Garden is a delightful place to call home. With its rich history, friendly community, and an array of recreational activities, residents enjoy a lifestyle that is both relaxed and engaging.

One of the standout features of Winter Garden is its commitment to creating walkable neighborhoods, particularly in homes with sidewalks. Imagine taking leisurely strolls along tree-lined streets, where friendly neighbors greet you, and children play safely in their front yards. These community-oriented features not only enhance the aesthetic appeal of the neighborhood but also foster a sense of connection among residents.

Winter Garden boasts a variety of parks, trails, and outdoor spaces, perfect for family outings or quiet afternoons spent enjoying nature. The West Orange Trail, a popular destination for walkers, runners, and cyclists, runs through the heart of the city, providing easy access to the area's stunning scenery. Additionally, the historic downtown area is filled with unique shops, delightful dining options, and vibrant community events, making it a hub of activity for residents of all ages.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Garden offers a diverse selection of properties, many of which feature inviting sidewalks that enhance neighborhood interactions. Experience the warmth of community living in Winter Garden, where every day feels like a walk in the park!

Newest Winter Garden Homes with Sidewalks Community Features

1396 Roxy Lane, Winter Garden

1396 Roxy Lane, 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 offers an open-concept floor plan with a great blend of functionality and living space. The first floor features the great room that 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, 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.

1396 Roxy Lane, Winter Garden

14791 Field Daisy Drive, Winter Garden

14791 Field Daisy Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Dedicated Study | Close to Amenities | Flat Lot. New Construction - January Completion! Welcome to the Ashwood at 14791 Field Daisy Drive in Harvest at Ovation! This beautiful new home blends open-concept living with flexible spaces for today’s lifestyle. The inviting foyer leads to a private study, while the spacious great room flows seamlessly into the kitchen featuring a large island and walk-in pantry. Enjoy indoor-outdoor living with the covered lanai just off the main living area. Upstairs, the private primary suite offers a relaxing retreat with a generous bathroom and walk-in closet, while two secondary bedrooms sharing a full bathroom, and a laundry room are nearby. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: 8' interior doors, single exterior door at kitchen, oak treads and painted risers, sink at laundry room, and whole house blinds. Photos are for representative purposes only. MLS# O6447800

14791 Field Daisy Drive, Winter Garden

17332 Wild Daisy Drive, Winter Garden

17332 Wild Daisy Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The BISCAYNE floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With three bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your needs. The open-concept design flows seamlessly from the dining room into the expansive great room, making it perfect for entertaining. A covered patio extends your living space outdoors, ideal for relaxing or hosting gatherings. The second floor offers all four bedrooms, including an extended primary suite with a walk-in closet and private bath, ensuring a peaceful retreat. An extended bonus room on this level provides additional versatility, perfect for a playroom or media space. Laundry is conveniently located upstairs to make daily chores easier. This floorplan is designed to accommodate diverse lifestyles, giving you the perfect combination of open spaces and private retreats. With options to add an additional bedroom.

17332 Wild Daisy Drive, Winter Garden

Winter Garden

Winter Garden

4 Beds ⋅ 3 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and three bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality in a layout that truly works for today’s lifestyle.

Winter Garden

8649 Flagship Alley, Winter Garden

8649 Flagship Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful one-story home located in the highly desirable Waterleigh community of Winter Garden! This charming 3-bedroom, 2-bath home offers a thoughtfully designed, open and inviting floor plan. The spacious kitchen features stone countertops, solid wood cabinetry, stainless steel appliances, a walk-in pantry, and a large center island overlooking the family room—perfect for everyday living and entertaining. The split-bedroom layout provides added privacy, while the primary suite features a walk-in closet and comfortable ensuite bath. Enjoy Florida living from the covered lanai and the added privacy of a corner lot. A two-car attached garage provides plenty of parking and storage. Waterleigh offers an exceptional resort-style lifestyle with community pools, clubhouses, fitness centers, tennis courts, playgrounds, parks, and more. Conveniently located in the sought-after Horizon West area of Winter Garden, near shopping, dining, entertainment, and Central Florida attractions. Don’t miss the opportunity to make this wonderful home yours!

8649 Flagship Alley, Winter Garden

14501 Grove Resort Avenue Unit 3636, Winter Garden

14501 Grove Resort Avenue Unit 3636, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

Welcome to effortless resort living and an incredible SHORT-TERM RENTAL OPPORTUNITY at The Grove Resort & Water Park! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2-bath condo-hotel is TURNKEY READY and already part of the resort’s rental pool with onsite management, making ownership especially convenient. Owners are permitted PERSONAL USE for up to 179 days per year, offering the flexibility to enjoy the property yourself while also taking advantage of its VACATION-RENTAL POTENTIAL. Set within the GATED RESORT COMMUNITY, this condo is located in a high-rise building with ELEVATOR ACCESS and puts an incredible array of amenities right outside your door. Step inside to find a bright, inviting interior with LUXURY VINYL PLANK FLOORING throughout the main living areas. The open Kitchen features QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES and a convenient breakfast bar, all overlooking the spacious Living Room with plenty of room for a Dining Area. Sliding glass doors extend the living space outdoors to a SCREENED, COVERED BALCONY, creating a relaxing spot to enjoy your morning coffee or unwind after a day at the parks. The AC WAS UPDATED in 2017, adding to the home's appeal as a well-maintained vacation property.The SPLIT-BEDROOM FLOOR PLAN provides privacy for owners and guests alike. The generous PRIMARY SUITE features a walk-in closet, an en suite Bath, and a COMFORTABLE SITTING AREA with its own PRIVATE ACCESS to the balcony. The en suite Bath offers dual sinks with QUARTZ COUNTERTOPS, a garden tub, step-in shower and private water closet. On the opposite side of the condo, the spacious SECOND BEDROOM offers a walk-in closet and its own EN SUITE BATH. A dedicated Laundry Room with washer and dryer adds everyday convenience.The Grove Resort & Water Park is a 106-acre destination with an IMPRESSIVE COLLECTION OF AMENITIES, including SURFARI WATER PARK, featuring a 695-foot lazy river, dual water slides, a FlowRider surf simulator, kids' activity pool and ZERO-ENTRY POOL. The resort also offers MULTIPLE POOLS including the lakefront Springs Pools with three full-size pools, hot tub and children's splash area, along with a 24-hour FITNESS CENTER, restaurants, family activities, LAKE AUSTIN ACCESS and more. CABLE AND INTERNET are also included, while resort transportation provides SHUTTLE SERVICE to Walt Disney World, Universal Orlando and SeaWorld. Lake Austin provides another way to enjoy the outdoors, with a LAKESIDE PIER offering beautiful nature views, catch-and-release fishing and resort watersports. When it is time to venture out, the resort is just SIX MILES FROM WALT DISNEY WORLD, putting Orlando's WORLD-FAMOUS ATTRACTIONS within easy reach. Beyond the resort, enjoy the growing Horizon West area with FLAMINGO CROSSINGS TOWN CENTER, Historic Downtown Winter Garden, the West Orange Trail and Plant Street offering opportunities for dining, shopping, entertainment and enjoying the FLORIDA LIFESTYLE. Families will appreciate the access to A-RATED SCHOOLS, including WATER SPRING ELEMENTARY, WATER SPRING MIDDLE and HORIZON HIGH SCHOOL.Whether you're looking for a vacation home, a personal getaway or a TURNKEY SHORT-TERM RENTAL INVESTMENT, this furnished Grove Resort condo provides an EXCEPTIONAL OPPORTUNITY to own a piece of the Orlando vacation lifestyle—with onsite management, RESORT AMENITIES, and the flexibility to enjoy it yourself. Come discover the possibilities at The Grove!

14501 Grove Resort Avenue Unit 3636, Winter Garden

15302 Honeybell Drive, Winter Garden

15302 Honeybell Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code

Welcome a beautifully maintained home in the highly sought-after Hamlin Reserve community of Horizon West! From the moment you step inside, you’ll notice the thoughtful design, spacious layout, and beautiful finishes throughout.One of the standout features is the gorgeous front flex space, complete with custom built-ins, offering the perfect opportunity for a home office, study, reading room, playroom, or additional living space. The open-concept main living area provides an inviting space for everyday living and entertaining, with a seamless flow between the living, dining, and kitchen areas.The spacious primary suite offers a relaxing retreat, while the additional bedrooms provide flexibility for family, guests, or a dedicated workspace. Step outside to enjoy your private backyard and Florida outdoor living.Located in the heart of Horizon West, Hamlin Reserve offers an exceptional lifestyle with community amenities, parks, playgrounds, nature trails, and convenient access to Hamlin Town Center, where shopping, dining, and entertainment are just minutes away. Enjoy everything Winter Garden has to offer, including top-rated schools, beautiful neighborhoods, and easy access to major roadways including SR-429.Beautiful, flexible, and ideally located, this home is a wonderful opportunity to experience the best of Hamlin and Horizon West living!

15302 Honeybell Drive, Winter Garden

15231 Groveside Road, Winter Garden

15231 Groveside Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code

Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex room. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath. The photos shown are of a previously built home. For more details or to schedule a visit, please contact our sales team.

15231 Groveside Road, Winter Garden

12511 Gold Honeysuckle Street, Winter Garden

12511 Gold Honeysuckle Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code

Under Construction. .

12511 Gold Honeysuckle Street, Winter Garden

10114 Salt Point Drive, Winter Garden

10114 Salt Point Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code

Welcome to this inviting 3-bedroom, 2.5-bathroom townhome in the desirable Waterleigh community in Winter Garden! The thoughtfully designed two-story layout offers comfortable living spaces for everyday enjoyment and entertaining. Enjoy Waterleigh’s resort-style amenities, including community pools, clubhouses, fitness centers, playgrounds, and scenic walking trails. Conveniently located near shopping, dining, Walt Disney World, and major highways, this home offers an appealing combination of comfort and convenience. Schedule your private showing today!

10114 Salt Point Drive, Winter Garden

939 Kylee Alley, Winter Garden

939 Kylee Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this gorgeous, exceptionally well-maintained home in the highly sought-after Oakland Park community of Winter Garden! Practically brand new, this beautiful residence features 9-foot ceilings, a charming front porch, and a bright, open-concept layout designed for both everyday living and entertaining. The first and second floors feature beautiful luxury vinyl plank flooring, with carpet reserved only for the bedrooms. The stunning kitchen is a true centerpiece of the home, offering beautiful finishes, ample cabinetry, and a functional layout perfect for gatherings. A new tankless water heater adds modern efficiency and convenience.Enjoy the best of the Winter Garden lifestyle, located within the Winter Garden Golf Cart District, with convenient access to nearby shopping, dining, parks, and entertainment. Oakland Park features beautiful tree-lined streets, green spaces, playgrounds, community amenities, and a charming neighborhood atmosphere. The home is just minutes from Downtown Winter Garden, Plant Street Market, the West Orange Trail, Winter Garden Village, and an array of restaurants, breweries, boutiques, and local events. With easy access to major roadways and Central Florida attractions, this beautifully cared-for home offers an exceptional combination of style, comfort, and location.

939 Kylee Alley, Winter Garden

16387 Taliesin Street, Winter Garden

16387 Taliesin Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Located in the heart of Winter Garden’s desirable Hawksmoor community, this beautifully appointed one-story Derby floor plan offers 3 bedrooms, 2.5 baths, and a 2-car garage, thoughtfully designed for comfortable everyday living and effortless entertaining. A welcoming foyer leads into the bright, open-concept main living area, where the dining room, gathering room, and kitchen come together to create a warm and connected space for family and guests. The kitchen features upgraded white cabinetry, contrasting countertops, upgraded flooring, along with a huge walk-in pantry offering exceptional storage. Tray ceilings and double crown molding reflect the upgraded finishes you will see throughout the home. The spacious owner’s suite provides a private retreat, complete with a generous walk-in closet and a versatile sitting room. Whether used as a home office, workout area, reading nook, or nursery, this flexible space adds a level of functionality that is hard to find in many one-story homes. Two generously sized secondary bedrooms are located at the front of the home and share a dedicated full bathroom, while a separate powder room provides added convenience for guests without requiring access to the private bedroom areas. A large laundry room and convenient owner’s entry from the garage with a practical stop and drop zone make daily routines even easier. At the rear of the home, beautiful sliding glass doors open to a spacious lanai, seamlessly extending the living space and POOL outdoors and creating an inviting setting for morning coffee, relaxing evenings, or entertaining friends and family. Beyond the home itself, Hawksmoor offers an exceptional community lifestyle. Residents can enjoy a large playground, expansive green spaces, a community park, walking trails, a resort-style pool, fitness center, and clubhouse—providing plenty of opportunities to stay active, unwind, and connect with neighbors. Thoughtfully designed from front to back, this home brings together stylish upgrades, exceptional functionality, flexible living spaces, and an inviting community atmosphere in the heart of Winter Garden. WELCOME HOME!

16387 Taliesin Street, Winter Garden

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