Winter Garden Homes with Golf Carts OK Community Features

Winter Garden Homes with Golf Carts OK Community Features

Winter Garden, located in Orange County, Florida, is a vibrant city known for its charming historic downtown, beautiful lakes, and family-friendly community. With its small-town atmosphere and convenient proximity to Orlando, Winter Garden offers residents the best of both worlds.

One of the unique features of Winter Garden is its Homes with Golf Carts OK community. This community is perfect for those who love golf and enjoy the convenience of using a golf cart to get around. Whether you're heading to the golf course or simply exploring the neighborhood, having a golf cart makes it easy to navigate the area and enjoy the outdoors.

In addition to the golf cart-friendly community, Winter Garden offers a range of amenities and recreational opportunities for residents. The city boasts numerous parks, trails, and lakes where you can enjoy activities such as boating, fishing, and picnicking. The West Orange Trail, a popular 22-mile paved trail, is perfect for walking, jogging, or cycling.

Winter Garden is also home to a thriving downtown area, filled with unique shops, restaurants, and entertainment options. From art galleries to live music venues, there is always something happening in downtown Winter Garden. The city also hosts various events and festivals throughout the year, bringing the community together and creating a sense of camaraderie.

With its picturesque surroundings, friendly community, and Homes with Golf Carts OK community, Winter Garden is a sought-after destination for those looking for a relaxed yet active lifestyle. Whether you're a golf enthusiast or simply want to enjoy the beauty of Florida, Winter Garden is the perfect place to call home.

Newest Winter Garden Homes with Golf Carts OK Community Features

480 W Plant Street, Winter Garden
$785,000
2 Beds ⋅ 3 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
In the heart of Historic Downtown Winter Garden, this three-story townhome in Park Place offers a rare blend of architectural character, flexible living spaces, and an exceptional walkable lifestyle. Step inside and discover this well-executed floor plan that lives much larger than its square footage suggests. Soaring 20-foot ceilings, expansive windows, open stair railings, and a custom loft create an impressive sense of space and natural light with an airy feel. The second-floor living area is the centerpiece anchoring the home, featuring custom German Schmear limewashed brick, detailed trim work, a built-in entertainment center, and sliding glass doors that open to a Juliet balcony overlooking downtown. The thoughtfully designed kitchen offers an oversized island with dine-in seating, white wood cabinetry with glass insets, stainless steel Samsung appliances, designer lighting, plantation shutters, and a convenient built-in workspace. Only two of these Park Place floor plans exist. One of the home's most unique features is the custom loft overlooking Plant Street and the West Orange Trail. Complete with a built-in ladder and bench seating, it's an inviting space to read, work, or simply enjoy the view. The first floor offers a private guest suite or study with an en-suite bath and walk-in closet. With special-use permits issued for select Park Place Plant St units, commercial zoning on this level lets you add a professional workspace. Upstairs, the third-floor owner's retreat provides privacy, a spacious walk-in closet, walk-in shower, and additional storage. Lovingly maintained by its original owner for seven years, this home offers low-maintenance, lock-and-leave living in one of Downtown Winter Garden's most desirable locations. The location is hard to beat. Step outside and you're in the heart of what makes Downtown Winter Garden special. Walk to the Saturday farmers market, enjoy the restaurants and shops along Plant Street, hop on the West Orange Trail, or meet friends for dinner without ever getting in your car. Rare in character, remarkable in design, and irreplaceable in location, 480 W. Plant Street is more than a beautiful home. It’s an invitation to fall in love with where you live.

480 W Plant Street, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
16773 Broadwater Avenue, Winter Garden
$2,575,000
7 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury lakefront living in this exceptional 7-bedroom Mansfield floor plan, offered for sale for the first time by its original owner. Perfectly positioned along nearly 100 feet of shoreline on the spectacular 2,600-acre Johns Lake, this remarkable residence offers approximately 6,300 heated square feet of thoughtfully designed living space, breathtaking panoramic water views, and a rare walkout basement ideal for multigenerational living. Impressive curb appeal and a welcoming courtyard entrance set the stage for soaring ceilings, expansive living areas, and unforgettable lake views from the moment you enter. The magnificent great room is flooded with natural Florida sunshine, featuring an electric fireplace and sweeping views of Johns Lake. The recently renovated gourmet kitchen is a showpiece, boasting an oversized center island, freestanding natural gas range, and separate full-size refrigerator and freezer. The main level features a luxurious owner's suite, dedicated home office, and additional ensuite bedroom. Upstairs, an expansive bonus room complements three generously sized bedrooms and two full bathrooms, providing exceptional flexibility for family and guests. What truly distinguishes this extraordinary lakefront estate is the enormous walkout basement, offering endless possibilities for a home theater, fitness center, entertainment lounge, game room, or custom bar. A SECOND OWNER'S SUITE provides an incredible opportunity for an in-law retreat, extended family accommodations, or private multigenerational living quarters. Thoughtful planning by the original owners includes future pool connections, natural gas stub-outs for additional coach lighting, preplumbing and gas connections for an outdoor summer kitchen, and numerous additional ceiling fan locations. Additional enhancements include plantation shutters, custom closets, and a whole-home natural gas backup generator. Step outside to an expansive backyard showcasing breathtaking 180-degree panoramic views of Johns Lake. Your private covered boat dock with low-maintenance composite decking and boat lift creates the ultimate waterfront lifestyle, with boating, fishing, watersports, and sunset cruises right from your backyard. Spanning Orange and Lake counties, Johns Lake is renowned for its expansive open waters, scenic shoreline, and exceptional fishing. Located within the gated community of Waterside on Johns Lake, residents enjoy resort-style amenities including a beautiful clubhouse, state-of-the-art fitness center, community swimming pool, and playground. This highly desirable Clermont and Winter Garden corridor offers access to sought-after K–12 schools & Foundation Academy, Montverde Academy, and Windermere Prep School. Ideally situated along Marsh Road, this exceptional location places you minutes from outstanding shopping, dining, and entertainment in both Clermont and Winter Garden. Enjoy convenient access to Walt Disney World, SR 429, SR 408, Florida's Turnpike, and Downtown Orlando. Historic Downtown Winter Garden is just minutes away, offering charming boutiques, acclaimed restaurants, the West Orange Trail, community festivals, and its famous Saturday Farmers Market. Combining extraordinary square footage, a rare walkout basement, dual owner's suites, private boating access, and nearly 100 feet of pristine Johns Lake frontage, this remarkable property delivers an unparalleled opportunity to embrace the Florida lakefront lifestyle.

16773 Broadwater Avenue, Winter Garden
9662 Waterway Passage Drive, Winter Garden
$515,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code
SELLER IS OFFERING 5K IN UPGRADE CONCESSIONS for whatever your heart desires. BEST Price in the neighborhood! Premium CORNER lot w/ community green space (play areas for the little ones). This is one of the few larger lots (7,809 sq ft) in the community. You won't find a better deal in Waterleigh! ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This 3/2.5 + LOFT home is the perfect buy. NEW exterior paint! You know the old saying, buy the smaller house in the big expensive neighborhood. Some neighbors' homes are valued at over a million dollars. Your property will benefit from the increasing value. Well, this is it. Offering 2,014 square feet of living space, it is the perfect size for a growing family without all the heavy cleaning! -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- As an added bonus, the HOA includes landscaping, allowing for truly low-maintenance living. Beyond the home itself, you'll fall in love with the incredible resort-style amenities this sought-after community has to offer, including multiple pools, fitness centers, tennis courts, sand volleyball court, mini golf course, playgrounds, scenic walking trails, community dock and a vibrant calendar of community events throughout the year. Everyday conveniences are just a golf cart ride away, including Publix, Jersey Mike's, a nail salon & Kiddie Academy. --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This golf cart-friendly community was designed to make life easy, fun, and connected. Located in the highly desirable Horizon West area and zoned for Atwater Bay Elementary, you'll be just minutes from shopping, dining, entertainment, and outdoor recreation. Enjoy the charm of historic Downtown Winter Garden, the scenic West Orange Trail, and easy access to Orlando's world-famous attractions and theme parks. This home offers more than just beautiful living spaces, it offers a lifestyle. Why wait months to build when you can move right into a highly upgraded, turnkey home today?

9662 Waterway Passage Drive, Winter Garden
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
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
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
9849 Lost Creek Drive, Winter Garden
$949,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to 9849 Lost Creek Drive, a beautifully appointed 5-bedroom, 4-bathroom home in Winter Garden’s sought-after Waterleigh community. Built in 2021, this impressive residence offers 3,910 square feet of living space, a 3-car garage, and a thoughtful blend of timeless architectural details and modern functionality—all complemented by peaceful lake views. From the meticulously maintained landscaping to the welcoming front porch, the home makes a wonderful first impression. Inside, arched doorways and thoughtfully designed living spaces create a warm, inviting atmosphere. The foyer opens to a formal living room, while the separate formal dining room features sliding doors leading directly to the covered lanai, making entertaining effortless. At the heart of the home, the spacious kitchen overlooks the family room, creating a natural gathering place for everyday living and special occasions. White quartz countertops, 42-inch cabinetry, built-in ovens, a cooktop, stainless steel appliances, and an oversized island are paired with an abundance of cabinetry and generous countertop workspace. There’s room for everything, whether preparing weeknight meals or hosting a crowd. The first-floor primary suite offers a peaceful retreat with tranquil lake views and elegant coffered ceilings. The oversized walk-in closet features custom organization, while the ensuite bath delivers a spa-inspired experience with dual vanities and a spacious walk-in shower featuring shower fixtures on both walls. Upstairs, a generous loft provides flexible space for a media room, game room, or additional gathering area, while the well-proportioned secondary bedrooms offer room for family and guests. A convenient upstairs storage closet, thoughtfully lined with shelving, adds even more practical storage. The large laundry room is equally well designed, with a utility sink, abundant cabinetry, and an expansive work surface to keep household tasks organized. Step outside to the spacious pavered lanai, complete with retractable screens that let you enjoy Florida’s beautiful weather in comfort. Overlooking the lake, this inviting outdoor space is perfect for morning coffee, weekend gatherings, or relaxing at the end of the day while watching the sunset—and, on the right evenings, catching Disney fireworks in the distance. Life in Waterleigh extends beyond your front door, with resort-style amenities that include community pools, fitness facilities, walking trails, a clubhouse, playgrounds, and more. Conveniently located in the Horizon West area of Winter Garden, the community offers access to nearby shopping, dining, parks, and everyday essentials, with Walt Disney World and other Central Florida attractions within easy reach. Beautifully maintained, thoughtfully designed, and ideally situated to enjoy the best of Central Florida living, this home offers the space, comfort, and setting to make every day feel a little more special. Schedule your private showing and discover all that this exceptional Waterleigh home has to offer!

9849 Lost Creek Drive, Winter Garden
1349 Castleport Road, Winter Garden
$749,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

1349 Castleport Road, Winter Garden
251 N Plant Street, Winter Garden
$699,000
4 Beds ⋅ 4 Baths ⋅ J L Dillard Sub SubDv. ⋅ 34787 Zip Code
Prime Winter Garden Duplex in the Golf Cart District | Updated | Income-Producing!! Discover a rare opportunity to own a duplex in the heart of Winter Garden, ideally positioned within the coveted Golf Cart District and directly off the West Orange Trail. Both units are currently leased, offering immediate rental income and an attractive investment opportunity in one of Central Florida’s most sought-after communities. ROOF 2022 & whole duplex REPIPE in 2024. The location is truly the standout feature—enjoy easy access to the West Orange Trail for biking, walking, and outdoor recreation, while the golf-cart-friendly setting makes it convenient to cruise to nearby shopping, dining, entertainment, and the charming downtown Winter Garden area. Located in the heart of the vibrant Winter Garden community, residents can enjoy local restaurants, boutique shopping, weekend events, farmers markets, and the area's popular downtown atmosphere, all while being surrounded by established neighborhoods and recreational amenities. With convenient access to major roadways, the property also provides an easy commute to Orlando and the surrounding attractions. Whether you're looking to expand your investment portfolio or secure a well-positioned income-producing property in Winter Garden, this duplex offers an exceptional combination of location, lifestyle, and rental potential. Both sides are currently tenant occupied—an excellent opportunity to own a turnkey duplex in a highly desirable area. Please do not disturb tenants.

251 N Plant Street, Winter Garden
939 Kylee Alley, Winter Garden
$648,500
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. GOLF CART ACCESS to Downtown Winter Garden! Welcome to this gorgeous, exceptionally well-maintained, MOVE-IN READY home in the highly sought-after Oakland Park community. Featuring modern finishes, a functional open-concept floor plan, and a cute, charming front porch, this beautiful home offers the perfect combination of comfort, style, and convenience in one of Central Florida’s most desirable communities. Step inside to discover 9-foot ceilings and a bright, spacious open-concept living area designed for everyday living and entertaining. Luxury vinyl plank flooring extends throughout the first and second floors, with carpet reserved for the bedrooms. The stunning kitchen features beautiful finishes, ample cabinetry, and a functional layout perfect for hosting family and friends. A new tankless water heater adds modern efficiency and convenience. Enjoy the sought-after Winter Garden lifestyle in the WINTER GARDEN GOLF CART DISTRICT, with convenient access to Downtown Winter Garden, Plant Street Market, the West Orange Trail, and Winter Garden Village. Oakland Park is known for its tree-lined streets, green spaces, playgrounds, community amenities, and charming neighborhood atmosphere. Conveniently located near shopping, restaurants, local breweries, boutiques, parks, and entertainment, this home also offers easy access to major roadways and popular Central Florida attractions. Flexible showings available! Don’t miss your opportunity to see this beautifully cared-for home with its inviting front porch and desirable Winter Garden location. Schedule your private showing today!

939 Kylee Alley, Winter Garden
Start Your Search

How much is your home worth?

Get instant property value now!