Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida, a vibrant city that perfectly blends small-town charm with modern conveniences. Nestled just a short drive from Orlando, Winter Garden boasts a rich history and an inviting atmosphere that attracts families, retirees, and everyone in between. With its picturesque downtown area, lined with quaint shops, delicious eateries, and a lively farmers market, residents enjoy a sense of community that is truly special.

One of the standout features of Winter Garden is its commitment to creating pedestrian-friendly neighborhoods. Homes with sidewalks are a common sight here, making it easy for residents to stroll through the community, enjoy evening walks, or bike ride with the family. The well-planned communities emphasize connectivity, encouraging an active lifestyle while fostering neighborly interactions.

Imagine living in a home where you can step outside and take a leisurely walk along tree-lined streets, greet friendly neighbors, and explore nearby parks. The sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote a sense of safety and accessibility for residents of all ages.

Winter Garden is also renowned for its outdoor recreational opportunities, with numerous parks and trails to explore. Whether you're enjoying a weekend picnic at the local park or participating in seasonal events, there's always something happening in this lively city.

If you're seeking a home in a community that prioritizes walkability and fosters a strong sense of belonging, Winter Garden is the perfect place for you. Experience the charm of this delightful city and discover the joys of living in a community that truly feels like home.

Newest Winter Garden Homes with Sidewalks Community Features

$1,249,990
5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, four full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior crisp and cool while keeping utility costs in check. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a sophisticated lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Lake Apopka Sound Ph 1 SubDv. ⋅ 34787 Zip Code
Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, and calming bird watching right from the backyard. Highlights of this home from outside to inside are wide paver driveway with parking pad, spacious 3 car garage, covered front and rear porches, fully fenced in backyard, extended rear concrete patio, large flex room, mother in law suite with private entrance and kitchenette, and incredible kitchen to love at the center of an open floorplan. Floorplan: Triple split layout puts the primary suite, the secondary bedrooms, and the mother in law suite each in their own private area of the home. The mother in law suite has its own private exterior entrance, kitchenette, bedroom, and full bath. Large flex room for a home gym, office, studio, gaming room, or playroom. Kitchen: Cabinets to the ceiling, stone counters, beveled subway tile, farmhouse sink, island with seating for four, built-in wall oven and microwave, stainless vented hood, pot filler above the cooktop, spacious pantry, open to the living and dining space. Interior: Tray ceilings in the dining room, living room, and primary suite, wood slat accent wall, crown molding, upgraded lighting, ceiling fans, window treatments installed. Primary suite with walk in closet, corner tub, double sinks, and glass shower. Ceramic tile in main living areas, carpet in secondary bedrooms, inside laundry room. Exterior: Wide paver driveway with large paved parking pad, spacious three car garage, covered front porch, covered rear porch, extended full width concrete patio, fully fenced backyard with gates on both sides, sprinkler system throughout, tile roof. Recreation: Killarney Station trailhead five minutes out with bike rentals, repairs, and supplies center. West Orange Trail runs 20 plus miles into historic downtown Winter Garden. Lake Apopka Wildlife Drive and Lake Louisa State Park both an easy drive. Convenience: Downtown Wintergarden 25 minutes, Costco 8 minutes, Disney 25 minutes, Downtown Orlando 30 minutes, MCO Airport 35 minutes.

17854 Hither Hills Circle, Winter Garden
$219,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
**Beautiful 3-bedroom/2-bathroom Jasmine floorplan available for sale at The Grove Resort and Water Park! This first floor apartment is fully-furnished and has everything you need for a wonderful vacation condo! This spacious unit has 14-foot ceilings in the main living space, giving a light, airy feel, and opens to an enclosed balcony where you can enjoy views of gardens and pond. Full kitchen has everything you need for cooking breakfasts, to family dinners, with a full washer and dryer in a room just off the kitchen. The living room also has a sleeper sofa for extra guests if needed. A short stroll brings you to either the central front desk area where you will find The Marketplace, the well-stocked convenience store, and the gift shop and concierge desk, or to the Springs Pools area where you can choose from three beautiful pools and the hot tub. The Valencia Restaurant, with additional outside seating, is open for breakfast, lunch, and dinner, 7 days a week, and is next to the 24/7 gym. Take a walk down to Lake Austin and try some fishing, or paddle a swan boat! From there you can visit the Surfari water park with its large pool, lazy river, water slides, and splash area! Try out the Flowrider surfing experience, or just watch while enjoying food and drinks from the Longboard Bar and Grill! Flip Flops is the 6000sf games arcade with glow-in-the-dark mini golf, so don't miss that! Free daily shuttles to the Disney parks are available for all owners and guests! This truly is a great place to own a vacation condo while the onsite management company rent out your unit when you are not there! Call for more details!!**

14501 Grove Resort Avenue Unit 2119, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Luxurious upgraded TOLL BROTHERS Townhome located in coveted Lakeshore Preserve! As you enter this Immaculate 3-bedroom, 2.5-bathroom townhouse the living area offers a bright spacious open floor plan with 10' ceilings and upgraded kitchen area perfect for entertaining or simply bringing out your inner chef! The large center island provides plenty of space for multiple people to enjoy and an additional generous sized counter invites guests to join all activities centered in the kitchen. Featuring 42" upgraded cabinets, stainless steel appliances and a natural gas range, the area has sliding glass doors that open up to the private patio so that enjoying the outdoors becomes effortless. Outside, a covered walkway leads to the 2-car garage located across the beautifully paved patio. Moving upstairs, the primary bedroom is a tranquil retreat with a generous sized walk-in closet and an ensuite bathroom with dual sinks and at private water closet. From the relaxing bedroom you can enjoy beautiful sunsets in the evening without leaving the comfort of your home. Located on the other side of the second floor are two comfortable bedrooms that share a spacious bathroom across the hall. In addition, the home offers a whole house water filtration system, tankless water heater and above head storage racks in the garage. If you are ready to enjoy resort style living, Lakeshore Preserve also offers plenty of activities with a beautiful clubhouse with fitness center, outdoor community pool and playgrounds nestled along the shores of Panther Lake. Whether you enjoy going for a stroll along one of the walkways or grabbing a seat in one of the beautifully landscaped park areas, you are sure to find a quiet place with views. Best of all, your HOA dues cover not only all the amenities, but also exterior maintenance of your townhome, exterior painting, roof cleaning, and basic cable and internet. This well-maintained townhome in Horizon West is close to top rated schools, Disney attractions, shopping, dining, and has easy access to HWY 429.

8932 Bismarck Palm Drive, Winter Garden
$179,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
**Beautiful Palm model 2-bedroom/2-bathroom condo for sale at The Grove Resort and Water Park! This fully-furnished unit has a lovely view over the central fountain and is bright and airy. This floorplan has the desirable two double beds in the second bedroom, providing extra sleeping accommodation for owners and guests. A sleeper sofa in the living room gives extra sleeping space if required. A full kitchen provides all you need for cooking a quick breakfast, or family dinner, and a laundry room is also conveniently situated just off the kitchen. The dining area and living room give plenty of seating for guests, or enjoy a quiet coffee out on the screened balcony. The unit is central to the resort, so all amenities are just a few minutes stroll away. You can enjoy the Surfari water park with its large pool, lazy river, water slides, and splash zone! The Longboard Bar and Grill are also inside the water park, along with the Flowrider surfing experience!! Don't forget to visit Flip Flops, the 6000sf games arcade, with glow-in-the-dark mini golf, or go down to the Springs Pools where you have your choice of three further pools, or relax in the hot tub! You can enjoy a meal at the Valencia Restaurant, or at the outdoor bar, or walk down to Lake Austin and try your hand at fishing, kayaking, or paddling a swan boat! The Front Desk is where you will find the Marketplace convenience store and gift shop, and the concierge for all your theme park tickets or excursions! The Grove Resort also provides FREE daily transportation to the Disney theme parks. Don't miss out on owning a wonderful vacation condo at The Grove, where you can enjoy your vacations, then let the onsite management company rent out your unit for income when you are not using it. Call for more details!!**

14501 Grove Resort Avenue Unit 3406, Winter Garden
$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

93 Windtree Lane Unit 102, Winter Garden
$520,000
3 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to Longleaf at Oakland by Pulte! Built in 2020, this move-in-ready three-bedroom, 2.5-bath home offers 1,811 square feet of stylish living space featuring brand-new luxury vinyl plank flooring throughout, fresh interior paint, quartz countertops, stainless steel appliances and an open-concept layout designed for comfortable everyday living and effortless entertaining. Located less than five minutes from the new Oakland Town Center, you’ll be close to an exciting new lifestyle destination featuring chef-driven restaurants, boutique shopping, fitness and wellness concepts, medical services, outdoor gathering spaces and everyday conveniences. Historic Downtown Winter Garden, the West Orange Trail and major highways are also just minutes away. Residents of Longleaf at Oakland enjoy a community pool, playground and beautifully maintained green spaces, all within one of West Orange County’s most desirable communities. Don’t miss the opportunity to own this beautifully updated, move-in-ready home in one of Oakland’s most sought-after neighborhoods. Schedule your private showing today!

2766 Bobcat Chase Boulevard, Winter Garden
$1,030,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden
$550,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code
Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!

16130 Wind View Lane, Winter Garden
$435,000
3 Beds ⋅ 3 Baths ⋅ Hickory Hammock Phase 2b SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained end-unit townhome in the highly sought-after Hickory Hammock at Johns Lake! Filled with natural light from additional windows and offering extra green space rarely found with townhome living, this move-in-ready home combines comfort, style, and an unbeatable Winter Garden location. The open-concept floor plan features a spacious great room, dining area, and a well-appointed kitchen with granite countertops, stainless steel appliances, and abundant cabinet space—perfect for everyday living and entertaining. Upstairs, the private primary suite provides a relaxing retreat, while two additional bedrooms and an upstairs laundry room offer comfort and convenience for family and guests. Enjoy peaceful mornings or relaxing evenings on the covered patio overlooking lush green space. Hickory Hammock is a gated, virtual guard community surrounded by Johns Lake, Lake Burnett, and Lake Claire, offering resort-style amenities including a community pool, clubhouse, fitness center, tennis courts, sand volleyball, dog park, playgrounds, parks, and a community fishing pier. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, the Florida Turnpike, top-rated schools, shopping, dining, and Central Florida's world-famous attractions, this home offers the perfect blend of convenience and lifestyle. Don't miss this exceptional opportunity—schedule your private showing today!

15190 Sunrise Grove Ct, Winter Garden
$775,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay Ph 3 SubDv. ⋅ 34787 Zip Code
Beautifully upgraded home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home over 2,100 square feet of comfortable living space with modern finishes and an open floor plan filled with natural light. The spacious kitchen is truly the heart of the home, featuring a large quartz island, built-in oven and microwave, gas cooktop, stainless steel appliances, plenty of cabinet space, and a walk-in pantry.  Master Bedroom Suite offers a spa-like bathroom with dual vanities, a large walk-in shower, and a custom walk-in closet. The dedicated office with built-in cabinetry provides an ideal work-from-home space. The backyard offers your own private retreat with a heated saltwater pool, covered lanai, outdoor kitchen, pergola, and a fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. Additional features include solar panels, luxury laminate flooring throughout the main living areas, a custom wood panel for the TV, a spacious laundry room with built-in cabinets and utility sink, an irrigation system, and a two-car garage with storage racks and an EV charger. Winding Bay enjoy resort-style amenities including a community pool, playground, dog park, and scenic walking paths, all conveniently located near Disney, Horizon West, shopping, dining, and top-rated schools.

15009 Lebeau Loop, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
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