Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Nestled in the heart of Orange County, Florida, Winter Garden is a charming city known for its rich history, vibrant community, and family-friendly atmosphere. This picturesque city offers a perfect blend of small-town charm and modern amenities, making it an ideal place to call home.

One of the standout features of Winter Garden is its Homes with Sidewalks Community. True to its name, this community boasts well-maintained sidewalks that not only enhance the aesthetic appeal of the neighborhood but also promote a healthy and active lifestyle among residents. Whether you enjoy a leisurely stroll, a brisk jog, or a bike ride, the sidewalks provide a safe and convenient way to explore the beauty of the neighborhood.

Living in a Homes with Sidewalks Community in Winter Garden offers residents the opportunity to connect with neighbors, enjoy outdoor activities, and create lasting memories in a welcoming environment. With easy access to parks, schools, shopping, and dining options, Winter Garden truly embodies the essence of Florida living at its finest.

Newest Winter Garden Homes with Sidewalks Community Features

231 Tbd Drive, Winter Garden
$973,550
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Griffin by Toll Brothers at Westhaven at Ovation in Winter Garden, with estimated completion by the end of 2027! This beautifully designed home features an impressive foyer, formal dining room, and spacious kitchen overlooking the breakfast area and great room. The great room opens to a covered lanai, creating the perfect space for everyday living and entertaining. Upstairs, the primary suite offers a large walk-in closet and a private bath with a separate shower and private water closet. A spacious loft and generously sized secondary bedrooms provide additional flexibility. Experience the quality craftsmanship and thoughtful design of Toll Brothers. Model home available for walkthrough!

231 Tbd Drive, Winter Garden
233 Tbd Drive, Winter Garden
$867,555
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Winter Garden's Horizon West, with estimated completion by the end of 2027! Welcome home to this beautifully designed open-concept residence featuring a sought-after first-floor primary suite. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtfully designed with generous room sizes and abundant natural light, this home offers the perfect blend of comfort, style, and functionality for everyday living and entertaining.

233 Tbd Drive, Winter Garden
13011 Sunset Garden Lane, Winter Garden
$1,034,940
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Griffin by Toll Brothers at Westhaven at Ovation in Winter Garden! This beautifully designed home features an impressive foyer, formal dining room, and spacious kitchen overlooking the breakfast area and great room. The great room opens to a covered lanai, creating the perfect space for everyday living and entertaining. Upstairs, the primary suite offers a large walk-in closet and a private bath with a separate shower and private water closet. A spacious loft and generously sized secondary bedrooms provide additional flexibility. Experience the quality craftsmanship and thoughtful design of Toll Brothers. Model home available for walkthrough!

13011 Sunset Garden Lane, Winter Garden
15126 Flannan Lane, Winter Garden
$534,170
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Kelly bungalow by Toll Brothers at Westhaven at Ovation in Winter Garden! This thoughtfully designed home offers an inviting open-concept layout with a spacious great room, beautifully appointed kitchen, and dining area perfect for everyday living and entertaining. The private primary suite provides a relaxing retreat, while additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the charm of bungalow living with the quality craftsmanship and modern design Toll Brothers is known for. Conveniently located near shopping, dining, entertainment, and major roadways in desirable Horizon West.

15126 Flannan Lane, Winter Garden
15162 Flannan Street, Winter Garden
$702,570
5 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Winter Garden's Horizon West. Estimated completion Summer 2027. The Montpelier Bungalow features a covered entry leading to a spacious foyer and an expansive guest suite. The main living area offers a dining room, breakfast bar, great room, and access to the private courtyard. The second-floor features two bedrooms and a spacious primary suite with a large walk-in closet and private bath featuring dual vanities, a separate shower, and private water closet. An additional bedroom, loft, and full bathroom are located above the detached garage, offering flexible space for guests or family.

15162 Flannan Street, Winter Garden
14501 Grove Resort Avenue Unit 1516, Winter Garden
$283,800
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
GREAT NEW LISTING: PRICE $283,800.00. MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 3 BEDROOM/2 BATHROOM JASMINE DESIGN CONDO HAS GREAT WATER VIEWS FROM THE SCREENED BALCONY ON THE 5TH FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1516, Winter Garden
15530 Sunquat Dr, Winter Garden
$599,999
4 Beds ⋅ 4 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this stunning 4-bedroom, 3.5-bath home located in the highly desirable Hamlin Reserve community in Horizon West, Winter Garden! Thoughtfully designed with spacious living areas, modern finishes, and a versatile floor plan, this home offers the perfect setting for comfortable everyday living and effortless entertaining. Upon entering, you are greeted by an inviting foyer featuring soaring volume ceilings and stylish vinyl flooring throughout the entire first floor. A versatile flex room just off the entry provides endless possibilities and can be customized to suit your needs as a home office, den, formal living room, or additional dining space. The open-concept layout seamlessly connects the spacious family room, kitchen, and dining area, creating a warm and welcoming atmosphere. The well-appointed kitchen is sure to impress with its oversized island with seating, granite countertops, solid wood cabinetry, gas range, stainless steel appliances, and beautiful decorative backsplash. Conveniently located nearby are a half bath, a dedicated mudroom area with access to the garage, and sliding glass doors that open to the covered rear patio, offering the perfect spot to unwind or enjoy outdoor gatherings. Upstairs, you'll discover a spacious loft that provides additional flexible living space, ideal for a media room, playroom, or secondary family gathering area. The thoughtfully designed split-bedroom floor plan offers added privacy and functionality. The generously sized primary suite serves as a peaceful retreat, featuring a private en-suite bathroom with dual sinks, a standalone shower, and a walk-in closet. The second floor is completed by a conveniently located laundry room just off the loft, a private en-suite bedroom with its own standalone shower, two additional spacious bedrooms, and a full bathroom. For added convenience and modern appeal, all four bathrooms feature smart toilets. Residents of Hamlin Reserve enjoy wonderful community amenities, including a community pool, playground, and clubhouse. Ideally situated in the heart of Horizon West, this home is within walking distance of local dining and everyday conveniences, with Cinepolis, PopStroke, an exciting variety of restaurants, breweries, shopping, and entertainment just minutes away. Experience the best of the Horizon West lifestyle with this beautiful home offering space, comfort, community amenities, and an unbeatable location. Schedule your private showing today!

15530 Sunquat Dr, Winter Garden
925 Butter Oaks Court, Winter Garden
$619,000
3 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Timeless Craftsman Charm Meets the Best of Winter Garden Living! Welcome to this inviting Craftsman-style home in the highly desirable Winter Oaks community, where small-town charm meets the convenience of modern Florida living. Located in a golf-cart-friendly neighborhood and within minutes of Historic Downtown Winter Garden, this home provides an opportunity to enjoy everything this sought-after area has to offer and more! From the welcoming double front porches to the spacious, thoughtfully designed interior, this home combines character, comfort, and functionality. The kitchen features beautiful quartz countertops, wood cabinetry, stainless steel appliances, a gas range, and a versatile island with additional storage and seating. Absolutely perfect for everyday living and entertaining! The first-floor's open concept, high ceilings and abundant natural light is an ideal way to be welcomed inside. The primary suite, also located on the first floor, is a private retreat, complete with a walk-in closet and an en-suite bathroom featuring dual vanities, a jetted soaking tub, and a separate shower. The second story, also full of character and charm, is an amazing space for loved ones and/or valued guest. Step outside to enjoy the screened lanai, fenced backyard, and separate patio ideal for friends and family gatherings, weekend barbecues or simply relaxing in the Florida sun. Residents of Winter Oaks enjoy community activities & amenities including a swimming pool, cabana, and playground. The location is equally impressive, offering convenient access to the West Orange Trail, shopping, dining, and the unique shops, restaurants, and year-round activities of Historic Downtown Winter Garden. Hurry, as this opportunity has too many amenities to list! Call today before it's gone tomorrow!

925 Butter Oaks Court, Winter Garden
17316 Melogold Way, Winter Garden
$530,047
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a two-car garage, perfectly located in the heart of Winter Garden. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This popular Walden plans features finishes from the AW Collection Milan with clean, modern touches. The kitchen boards 42" cabinets, quartz countertops and tiled backsplash. Additional highlights include a detached two-car garage with private fenced courtyard space and upgraded 8' doors. Ideally situated, you’re just 37 minutes from Orlando International Airport, 20 minutes from world-famous Disney theme parks, and 30 minutes from Celebration. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17316 Melogold Way, Winter Garden
13151 Calming Breeze Way, Winter Garden
$489,900
3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
NEWER CONSTRUCTION. SHOWS LIKE A MODEL HOME + BUILT IN 2024 + SCREENED LANAI + FULLY FENCED BACKYARD + MINUTES FROM DISNEY! Welcome to 13151 Calming Breeze Way, a beautifully maintained 3-BEDROOM, 2.5-BATH HOME offering 2,096 SQ FT of stylish living space in the desirable SERENADE AT OVATION community of Horizon West in Winter Garden! With its modern finishes, thoughtfully designed OPEN-CONCEPT FLOOR PLAN, and exceptional attention to detail, this home offers the appeal of newer construction with valuable upgrades already completed by the current owners! Inside, experience the bright, inviting atmosphere created by HIGH CEILINGS, LUXURY VINYL FLOORING, and spacious living areas designed for both everyday comfort and entertaining. The beautiful GOURMET-STYLE KITCHEN is the heart of the home, featuring STONE COUNTERTOPS, A LARGE CENTER ISLAND, generous cabinetry, and an effortless connection to the dining and gathering areas. The open bungalow-style layout creates a welcoming space for hosting friends or simply relaxing at home. Upstairs, the spacious PRIMARY SUITE offers a comfortable private retreat with a walk-in closet and en-suite bathroom. Two additional generously sized bedrooms provide flexibility for guests, a HOME OFFICE, or additional living space. One of this home's standout features is its beautifully enhanced outdoor living area! Unlike many newer homes where these improvements are still on the wish list, the current owners have already invested in a SCREENED-IN COVERED LANAI AND PRIVACY FENCING, creating an inviting backyard retreat. Enjoy morning coffee, outdoor dining, or relaxing evenings in your own private space. Additional upgrades include WINDOW BLINDS AND CEILING FANS, adding comfort and convenience from day one. LOCATION, LOCATION, LOCATION! Situated in the thriving HORIZON WEST / WINTER GARDEN area, this home offers exceptional convenience to WALT DISNEY WORLD, with Disney's theme parks, resorts, dining, and entertainment just a short drive away. Enjoy easy access to FL-429, nearby shopping, restaurants, and everyday essentials, along with the charm of Historic Downtown Winter Garden. Even better, SERENADE AT OVATION OFFERS A LOW HOA AND NO CDD FEE, making this an attractive opportunity for buyers seeking newer construction in one of Central Florida's most desirable and growing locations. Why wait for new construction when you can enjoy a beautifully finished, MOVE-IN READY HOME with the outdoor upgrades already in place? SELLER OFFERING $10,000 TOWARDS BUYERS CLOSING COSTS. Schedule your private showing and see for yourself why this home truly shows like a model! Mortgage savings may be available for buyers of this listing. Ask for details.

13151 Calming Breeze Way, Winter Garden
15316 Oak Apple Court Unit B, Winter Garden
$285,000
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks SubDv. ⋅ 34787 Zip Code
MOTIVATED SELLER! ALL OFFERS WILL BE CONSIDERED! Imagine coming home to a quiet corner of Winter Garden, where your backyard view is filled with greenery instead of another row of homes. Tucked inside the gated community of Tucker Oaks, this 3 bedroom, 2.5 bathroom townhome offers 1,544 square feet of living space, a thoughtfully designed floor plan, and something that's becoming increasingly difficult to find: privacy with no rear neighbors. Being a corner unit overlooking a conservation area makes this home feel a little different from the typical townhome. There's more natural light, a peaceful backdrop, and a sense of separation from the homes around you. Inside, the main living area brings everything together. Tall ceilings, recessed lighting, and an open layout connect the kitchen, dining, and living spaces, making it just as comfortable for a quiet night at home as it is for having friends over. The kitchen features stainless steel appliances, crown molding on the cabinetry, generous counter space, and a breakfast bar that will probably become your favorite spot for morning coffee. Head upstairs, and you'll find all three bedrooms, including a spacious primary suite with a private bathroom and large closet. The additional bedrooms offer flexibility for guests, a home office, or whatever life calls for next. But what makes this property particularly appealing is everything waiting outside the front door. Living in Tucker Oaks in Winter Garden, Florida, means access to a community pool, playground, dog park, and neighborhood sidewalks. You're also a short drive from Historic Downtown Winter Garden, where weekends can mean grabbing coffee on Plant Street, browsing the farmers market, or spending an afternoon exploring the local shops and restaurants. The West Orange Trail is nearby for biking, running, or enjoying the outdoors, while convenient highway access keeps the rest of Central Florida within reach. Walt Disney World and Universal Orlando are approximately 25 minutes away, depending on traffic. Whether you're purchasing your first home, relocating to Central Florida, or simply looking for a low maintenance lifestyle in a gated Winter Garden community, this property deserves a closer look. Sometimes finding the right home isn't about having the most square footage. It's about finding the right combination of location, privacy, convenience, and everyday comfort. This one brings all four together. With a motivated seller ready to consider offers, now is the time to explore this Winter Garden opportunity. Schedule your private showing today!

15316 Oak Apple Court Unit B, Winter Garden
1414 Portmoor Way, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Video is virtually staged. Enjoy the best of both worlds in this beautiful pool home overlooking the Stoneybrook West Golf Course, where peaceful surroundings, beautiful views, and an abundance of community amenities create the perfect lifestyle. With NO REAR NEIGHBORS and a location OVERLOOKING THE GOLF COURSE on quiet Portmoor Way, you can relax while having plenty of opportunities to stay active, socialize, and connect with neighbors. The curb appeal is welcoming as is the spacious foyer, tall ceilings, and WOOD FLOORS. The well-appointed kitchen features QUARTZ countertops, tile backsplash, stainless steel appliances, and a WALK-IN PANTRY. Enjoy the breakfast nook that opens to the family room, creating a comfortable gathering space with beautiful views of the SCREENED-IN POOL and golf course. The spacious primary suite is conveniently located downstairs and offers a large walk-in closet, an updated vanity with double sinks, a garden tub, separate shower, and linen closet. Upstairs, you'll find AIRY LOFT, laundry room with cabinet storage, three additional bedrooms, and a hall bathroom with double sinks. Additional interior highlights include a formal dining room, a PRIVATE OFFICE with stylish barn doors, and an attractive staircase with iron railing and an accent wall. The home also offers valuable updates, including a NEW ROOF (2022), AC (2019), upgraded light fixtures, tile flooring in the garage, and rain gutters. One of the greatest benefits of living in Stoneybrook West is the incredible lifestyle included with your HOA! SPECTRUM CABLE AND INTERET ARE INCLUDED IN THE HOA DUES. Spend sunny afternoons at the Olympic-sized COMMUNITY POOL and splash pad, meet neighbors at the clubhouse and FITNESS CENTER, or enjoy friendly competition on the BASKETBALL, PICKELBALL, VOLLEYBALL and TENNIS courts. For those who love the water and outdoors, the community also offers a BOAT RAMP, limited BOAT STORAGE, and a FISHING pier. Stoneybrook West is conveniently located near highly regarded schools, restaurants, shopping, major roadways including the 429, Turnpike and 408, historic downtown Winter Garden, and Central Florida's world-famous theme parks.

1414 Portmoor Way, Winter Garden
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