Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida – a charming city that beautifully blends small-town warmth with modern conveniences. Nestled in Orange County, just a short drive from the bustling heart of Orlando, Winter Garden offers residents a serene escape while keeping them connected to the excitement of city life. Known for its picturesque downtown area, vibrant farmers’ market, and lush parks, Winter Garden is a haven for families, outdoor enthusiasts, and anyone looking to embrace a laid-back lifestyle.

One of the standout features of this delightful community is its homes with sidewalks, which encourage a sense of community and promote an active lifestyle. Picture yourself strolling down tree-lined streets, greeting neighbors, and enjoying the fresh Florida air. The sidewalks are not just pathways; they are the veins of a vibrant neighborhood, perfect for morning jogs, evening walks, or leisurely bike rides with family and friends.

Winter Garden boasts a variety of housing options, from charming single-family homes to modern townhouses, all designed to enhance the quality of life for residents. The community is rich with amenities, including parks, playgrounds, and recreational facilities, making it an ideal place for families to grow and thrive.

With its unique blend of history, culture, and community spirit, Winter Garden is more than just a place to live; it’s a place to call home. Discover the magic of Winter Garden, where every day feels like a welcoming embrace. Come explore the homes with sidewalks and experience the vibrant lifestyle that awaits you in this enchanting city!

Newest Winter Garden Homes with Sidewalks Community Features

728 Garden West Terrace, Winter Garden
$1,749,000
5 Beds ⋅ 5 Baths ⋅ Garden West SubDv. ⋅ 34787 Zip Code
Welcome to this stunning custom home crafted by the renowned Pioneer Builders in 2022, nestled in one of Winter Garden's most coveted locations. Just steps from the beloved West Orange Trail and the charming Golf Cart District of Historic Downtown Winter Garden, this home offers the best of the Winter Garden lifestyle right at your doorstep. Whether you're pedaling the trail at sunrise or cruising downtown in your golf cart for dinner and live music, this location makes it easy to enjoy everything this vibrant community has to offer. From the moment you step inside, the quality and craftsmanship are undeniable. Engineered hardwood floors flow seamlessly throughout the home, while custom cabinetry adds timeless elegance to every space. The open living areas feature top-of-the-line Fisher & Paykel appliances, blending elevated design with everyday functionality. Plantation shutters throughout the main house add a classic, refined touch, while an automatic gate provides an added layer of privacy and convenience. The main level features a private ensuite bedroom and full bath, ideal for guests or multigenerational living, along with a convenient powder bath for visitors. Upstairs, the primary suite serves as a true retreat, complete with two oversized walk-in closets and a luxurious ensuite bath. Two additional bedrooms share a well-appointed Jack-and-Jill bathroom, while an upstairs laundry room adds everyday convenience. Added in 2024, the private apartment above the garage is a rare and exceptional bonus, complete with a kitchenette, dedicated office space, full bath, and in-unit laundry. Whether envisioned as a private guest suite, in-law quarters, a dedicated work-from-home retreat, or an income-producing rental, the possibilities are endless. Winter Garden's Golf Cart District is more than a novelty—it's a way of life. Residents enjoy cruising to the award-winning Farmers Market, exploring boutique shops and local restaurants, visiting breweries, and taking part in the community events that make Historic Downtown Winter Garden one of Central Florida's most vibrant destinations. The West Orange Trail, spanning more than 22 miles of scenic, paved pathways, is a paradise for cyclists, joggers, and walkers. With this home's prime proximity, outdoor recreation is always within easy reach. This is more than a home—it's a lifestyle. Don't miss the opportunity to own a distinctive property offering timeless finishes, versatile living spaces, added privacy, and an exceptional location in one of Central Florida's most sought-after communities.

728 Garden West Terrace, Winter Garden
3275 Buoy Circle, Winter Garden
$740,000
5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. SPACIOUS LUXURY LIVING + 5 BEDROOMS + 4.5 BATHROOMS + 2 FLEX SPACES + GATED COMMUNITY! Welcome to this stunning YORKSHIRE MODEL in the highly desirable LAKEVIEW PRESERVE community of Winter Garden! Designed with space, comfort, and versatility in mind, this beautifully appointed home offers an exceptional floor plan ideal for MULTIGENERATIONAL LIVING, WORKING FROM HOME, AND ENTERTAINING. Featuring 5 generously sized bedrooms, 4 full bathrooms, a half bath, TWO FLEX SPACES—ONE ON EACH LEVEL, and an oversized lot with an open green backyard, there's room for everyone to spread out and enjoy! From the moment you enter, you'll appreciate the thoughtfully designed layout, 8-foot interior doors, abundant natural light, and stylish designer finishes. The OPEN-CONCEPT FLOOR PLAN flows seamlessly from the spacious gathering room into the dining area and GOURMET KITCHEN, featuring QUARTZ COUNTERTOPS, 42-INCH SOFT-CLOSE CABINETRY, BUILT-IN APPLIANCES, a decorative wood canopy hood, designer tile backsplash, oversized center island, and walk-in pantry. Expansive POCKET SLIDING GLASS DOORS open to the impressive 22-FOOT COVERED LANAI, NOW SCREENED IN BY THE CURRENT OWNERS, creating the perfect setting for indoor-outdoor entertaining while overlooking the spacious backyard. One of this home's greatest advantages is its FLEXIBLE, MULTIGENERATIONAL-FRIENDLY FLOOR PLAN. The FIRST-FLOOR GUEST SUITE WITH PRIVATE EN-SUITE BATHROOM AND WALK-IN CLOSET provides an ideal retreat for extended family, overnight guests, or anyone seeking additional privacy. A versatile FIRST-FLOOR FLEX SPACE offers the perfect opportunity for a home office, playroom, or additional living area. Upstairs, a SECOND SPACIOUS FLEX SPACE provides even more possibilities for a media room, game room, study area, or separate gathering area, allowing everyone to enjoy their own space. The upstairs PRIMARY SUITE is a relaxing private retreat featuring a large walk-in closet and a beautifully appointed en-suite bathroom with DUAL QUARTZ-TOPPED VANITIES, AN OVERSIZED WALK-IN SHOWER, and a private water closet. Three additional upstairs bedrooms, including one with its own EN-SUITE BATHROOM, offer comfortable accommodations and generous closet space. The upgraded laundry room adds convenience with cabinetry, quartz countertops, and a utility sink. Additional highlights include PORCELAIN TILE FLOORING throughout the main first-floor living areas, designer bathroom finishes, ample storage throughout, outdoor kitchen pre-plumbing, and a 2-CAR GARAGE WITH NEWLY ADDED EPOXY FLOORING for a clean, finished look. Located within the sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE, residents enjoy RESORT-STYLE AMENITIES, including a sparkling pool with splash pad, clubhouse, fitness center, playground, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE. Even better, the community has NO CDD FEE! Just approximately 5 miles from charming DOWNTOWN WINTER GARDEN and minutes from SR 429, you'll enjoy convenient access to shopping, dining, entertainment, and major Central Florida roadways. Experience the space, flexibility, and lifestyle this exceptional Winter Garden home has to offer. Schedule your private showing today!

3275 Buoy Circle, Winter Garden
2199 White Feather Loop, Oakland
$489,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland
618 Sigler Drive, Winter Garden
$685,240
3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

618 Sigler Drive, Winter Garden
15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden
622 Sigler Drive, Winter Garden
$604,580
3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Gardenia floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, Calacatta countertops, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

622 Sigler Drive, Winter Garden
620 Sigler Drive, Winter Garden
$697,240
4 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

620 Sigler Drive, Winter Garden
13051 Spring Grove Way, Winter Garden
$588,000
4 Beds ⋅ 4 Baths ⋅ Encore At Ovation SubDv. ⋅ 34787 Zip Code
JUST remodeld !Wonderful home across the street from serene pond. Enjoy this 4-3 home only 1 year old, with front porch overlooking the wildlife along the waterfront and walking path. This home has a nice sized bedroom downstairs with its own private bath and a wonderful open layout with kitchen, dining, and living room together, great for entertaining. The kitchen has Mocha colored cabinets with crown molding, island kitchen sink and breakfast bar, accented with gorgeous white stone quartz counters and all stainless steel appliances. The deluxe chef gas stove has split ovens and gridle center top . The dining room has a large slider to the side yard covered patio. A half bath powder room is behind the kitchen off the drop room from the garage. The stairs have open beautiful railings that lead you to the loft area. The Master Bedroom has 2 very large walk-in closets, and nice large bath with two separate vanities with extra cabinet space, a walk-in shower, elegant stand alone tub, and private toilet. The Master has more privacy split away from the other bedrooms by the laundry room. Laundry room has extra space for an ironing board, and laundry sink next to the provided washer and dryer. Bedrooms 2, 3 are separated by a full bath with double sinks and shower/tub. Tankless water heater saves in efficiency and constant hot water. This home is in a great and quite community just a few miles off the 429 west of Disney. While this home sits across from nice long pond with activities such as Corn hole, Bocce Ball courts, and picnic tables and dog park, the clubhouse and pool area are a short walk about a block and half away. The community offers other areas of interest to explore and enjoy too with more open park areas with trails by scenic ponds currently under construction along with the back park which the playground should soon be built. Just a few miles off the major interchange of 429 and Western, just outside Disney West provides fast and easy access anywhere. Hospitals, restaurants and shopping are all close and many more are being built nearby. The builder states; Water Spring Elementary, Bridgewater Middle, and Windermere Highschool.

13051 Spring Grove Way, Winter Garden
15613 Boggy Oak Circle Unit 110A, Winter Garden
$299,900
2 Beds ⋅ 2 Baths ⋅ Tucker Oaks Condo SubDv. ⋅ 34787 Zip Code
MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!

15613 Boggy Oak Circle Unit 110A, Winter Garden
900 Allendale Lane, Oakland
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code
Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland
14743 Field Daisy Drive, Winter Garden
$654,718
3 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Loft | Balcony. New Construction - December Completion! Welcome to the Newberry at 14743 Field Daisy Drive in Harvest at Ovation! Welcome to this stunning two-story home. Thoughtfully designed for both comfort and flexibility, this spacious floor plan features three bedrooms, four-and-a-half bathrooms, a versatile loft, an expansive game room, and a two-car garage. The open-concept main living area seamlessly connects the great room, designer kitchen, casual dining space, and lanai, creating an inviting setting for everyday living and entertaining. Upstairs, the private primary suite offers a relaxing retreat with a spacious bath and generous walk-in closet, while the loft provides additional space for work, play, or gathering. A secondary bedroom and bath on the upper level, plus an oversized game room with its own bathroom on the top floor, provide privacy and flexibility for guests or multigenerational living. 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, tray ceiling package, wet bar at game room and shower in place of tub at bath 2. Photos are for representative purposes only. MLS#O6450084

14743 Field Daisy Drive, Winter Garden
12934 Harvest Rain Avenue, Winter Garden
$750,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | 3 Full Baths. New Construction - February Completion! Welcome to the Ozark at 12934 Harvest Rain Avenue in Harvest at Ovation! This thoughtfully designed one-story home offers three bedrooms, three and a half bathrooms, and a private study off the foyer. The open-concept layout centers around a spacious gathering room that flows seamlessly into the dining area and gourmet kitchen with a walk-in pantry, creating the perfect space for everyday living and entertaining. The private primary suite features a spacious bathroom and large walk-in closet, while the secondary bedrooms provide comfort and flexibility for guests or hobbies. Enjoy outdoor living on the covered extended lanai and the convenience of a two-car garage with tandem storage space. 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: pocket sliding glass door at great room, tray ceiling package, whole house 8' interior doors, quartz countertops, whole house blinds, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6450081

12934 Harvest Rain Avenue, Winter Garden
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