Winter Garden Homes with Golf Carts OK Community Features

Winter Garden Homes with Golf Carts OK Community Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant downtown area, Winter Garden offers a unique blend of small-town charm and modern conveniences. With its rich history dating back to the early 1900s, the city has transformed into a thriving community that appeals to families, retirees, and everyone in between.

One of the standout features of Winter Garden is its commitment to outdoor living and recreational activities. The city is home to numerous parks, trails, and the stunning West Orange Trail, perfect for walking, biking, and enjoying the beautiful Florida sunshine. The downtown area is a delightful mix of boutique shops, cafes, and restaurants, making it a great spot for leisurely strolls and community events.

For golf enthusiasts and those who appreciate a laid-back lifestyle, Winter Garden boasts several neighborhoods where golf carts are welcomed. Imagine cruising through the scenic streets in your golf cart, easily accessing local shops, dining, and recreational facilities. Homes in these golf cart-friendly communities often come with spacious layouts, modern amenities, and beautifully landscaped yards, creating the perfect setting for relaxation and entertainment.

Whether you're looking for a family home or a cozy retreat, Winter Garden has something to offer everyone. Experience the warmth of this community and discover why so many are choosing to call Winter Garden home. With its inviting atmosphere, excellent schools, and recreational opportunities, you’ll find that life here is truly a hole-in-one!

Newest Winter Garden Homes with Golf Carts OK Community Features

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West Unit 3 Rep SubDv. ⋅ 34787 Zip Code

Located in the highly desirable Stoneybrook West community of Winter Garden, this 3-bedroom, 2-bath home offers over 1,600 square feet of living space in a 24-hour manned, Guard-Gated Golf community. The home features vaulted ceilings, a built-in closet system in the primary bedroom, and a spacious covered and screened-in back patio overlooking a fully fenced backyard with lush landscaping. Recent updates include an A/C replaced in December 2024, a 2023 water heater, and a NEW roof scheduled to be installed in approximately two weeks. The combination of these major updates provides added peace of mind for the next owner. Stoneybrook West offers an incredible array of amenities, including a resort-style Olympic-sized pool, children's splash area, clubhouse, fitness center, tennis, pickleball, basketball and volleyball courts, playground, fishing pier, private boat ramp and access to Black Lake, along with numerous community activities. The community also features 24-hour guarded security, and the low HOA fee includes cable and internet. Zoned for highly desirable Whispering Oak Elementary, SunRidge Middle School and West Orange High School, this home is conveniently located near Winter Garden Village, Fowler's Grove, Historic Plant Street and downtown Winter Garden, offering an abundance of shopping, dining and entertainment. Easy access to major roadways including State Road 429 makes commuting throughout Central Florida convenient. A great opportunity to own a well-maintained home with valuable updates in one of Winter Garden's most sought-after gated golf communities!

2250 Oakington Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

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. Land, Site, and Tax Infor

636 Sigler Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. 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.

642 Medora Way, Winter Garden

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

Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom built in closets, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. Don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh provides!

10043 Little Alcove Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3a SubDv. ⋅ 34787 Zip Code

Welcome HOME to this beautifully upgraded Bellake floorplan located in the HIGHLY sought-after Waterleigh community in the heart of Horizon West! From the moment you walk through the front door, you'll be welcomed by a bright, open-concept layout designed for both everyday living and effortless entertaining. Just off the entry, the ENCLOSED FLEX ROOM offers the perfect space for a home office, playroom or media room. The heart of the home is the kitchen, where you'll find stainless steel appliances, a stylish subway tile backsplash, an updated faucet, upgraded lighting, and elegant crown molding throughout. Overlooking the spacious dining and living areas, this inviting space makes it easy to stay connected whether you're hosting family gatherings or enjoying a quiet evening at home. Upstairs, escape to your spacious primary suite, thoughtfully designed to feel like your own private retreat. Custom touches including a MODERN ACCENT WALL, CROWN MOLDING, and a custom walk-in closet with built-in shelving. Two additional bedrooms provide flexibility for family, guests, or hobbies, while the upgraded laundry room features added cabinets and shelving for exceptional organization. Step outside to your EXTENDED COVERED LANAI with an ALUMINUM ROOF, creating the perfect outdoor living space for morning coffee, weekend barbecues, or relaxing Florida evenings. The home has been beautifully updated with FRESH EXTERIOR PAINT completed in MAY 2026 and a professionally repainted interior, offering a modern, MOVE-IN-READY feel from the moment you arrive! Additional upgrades include GUTTERS, upgraded ceiling fixtures, NO CARPET DOWNSTAIRS or on the lower portion of the staircase, and a garage featuring EPOXY FLOORS and overhead storage racks. Living in Waterleigh means enjoying more than just a beautiful home, it's a lifestyle. This community offers the convenience of NO CDD and HOA-maintained landscaping! Residents enjoy access to FOUR resort-style amenity centers featuring pools, fitness centers, clubhouses, playgrounds, sports courts, scenic walking trails, community events, and a GOLF CART FRIENDLY atmosphere. You'll even enjoy views of Walt Disney World fireworks and NASA rocket launches from within the community. Located just minutes from Walt Disney World, you'll also be close to shopping, dining, major highways, the newly opened Horizon West Regional Park, the new Horizon West Library opening soon, and the highly anticipated Lifetime Fitness coming soon. This home has been thoughtfully upgraded, meticulously maintained, and is ready for its next owners to make lasting memories. Schedule your private showing TODAY and discover why so many families love calling Waterleigh home!

9462 Komika Lane, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Oak Park At Winter Garden SubDv. ⋅ 34787 Zip Code

Located in the desirable charming golf cart community of Oak Park within a couple blocks of walking distance (or golf cart) to historical Winter Garden vibrant downtown with dining, boutique shopping and entertainment featuring a theatre and an award-winning farmers market. This well built cement block Maronda home offers a blend of charm and convenience with low HOA dues, and can be easily updated. Step out of this home into a wonderful screened heated pool and covered lanai for year-round enjoyment. The almost third acre lot is fenced on 3 sides and easily fenced and gated on each side for privacy. Within the wooded area in the back of the lot is an attractive storage shed. Veterans Memorial Park borders on the rear of the property featuring several acres of a variety of sports, including ten pickleball courts, picnic areas and playgrounds for families and pets. Hop on the scenic West Orange Trail just minutes from this home for a walk, run or bike ride. Commuting via the 429 and the Florida Turnpike gives easy access to all of Central Florida and its theme parks.

665 Stevelynn Circle, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

**Virtual staging in formal living and dining rooms. Video available.** Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code

Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Crooked Can Brewery, Plant Street Market, The Garden Theater & the West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Refined outdoor living abounds on the back porch with a custom summer kitchen. Just a short golf cart ride to Pickle Ball at Veterans, Splash Pad on Plant, a swim at Farnsworth Pool or exploring nature at Newton Park. Don't miss this one-of-a-kind opportunity!

412 N Boyd Street, Winter Garden

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

Welcome to 10439 Austrina Oak Loop, a beautifully upgraded 3-bedroom, 2.5-bath home with over 2,080 square feet of thoughtfully designed living space in the highly sought-after Watermark community. From the moment you step inside, you'll appreciate the luxury vinyl flooring throughout the first floor, upgraded 8-foot interior doors, designer hardware, and abundant natural light that enhances the home's bright, open-concept layout. The spacious main room flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for everyday living and entertaining. The kitchen features stainless steel appliances, upgraded cabinetry lighting above and below the cabinets, modern stairs with wire handrails, and stylish finishes that blend beauty with functionality. Upstairs, a versatile loft provides the ideal space for a home office, media room, fitness area, or playroom. All three bedrooms are conveniently located on the second floor, offering privacy and comfort. The spacious primary suite features an elegant tray ceiling, oversized walk-in closets, and a luxurious ensuite bath with dual vanities, a large walk-in shower, and plenty of natural light. The secondary bathroom also offers dual sinks, providing added convenience for family and guests. The upstairs laundry room is both practical and well-appointed with upgraded cabinetry and a large utility sink. For those who work remotely, the dedicated office area includes hard-wired internet for reliable high-speed connectivity. The oversized two-car garage is equipped with a 240-volt outlet, making it ready for electric vehicle charging. Enjoy the added benefit of a professional installed whole-water treatment system with dual treatment tanks and pre-filter, helping provide cleaner, conditioned water throughout the home while protecting plumbing and appliances. Enjoy relaxing on the inviting covered front porch, and each evening step outside to catch views of the spectacular Magic Kingdom fireworks. Residents of Watermark enjoy exceptional resort-style amenities, including a clubhouse, resort pool, splash pad, fitness center, tennis courts, playgrounds, scenic walking trails, and beautifully maintained green spaces. The home is just minutes from The Mark at Watermark, featuring Starbucks, Walgreens, New York Beer Project, restaurants, and everyday conveniences. You'll also enjoy close proximity to Orange County National Golf Center, Winter Garden Village, Walt Disney World Resort, highly rated local schools, and convenient access to State Road 429. Offering an exceptional combination of premium upgrades, an unbeatable location, and outstanding community amenities, this move-in-ready home presents an incredible opportunity to enjoy the very best of Central Florida living.

10439 Austrina Oak Loop, Winter Garden

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

Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Waterleigh community in Winter Garden. Built in 2021, this move-in ready home features an open-concept floor plan with a spacious living area, a modern kitchen with stainless steel appliances, granite countertops, and a large island perfect for entertaining. Upstairs, the primary suite offers a walk-in closet and a private en-suite bathroom, while two additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy a private patio, attached one-car garage, and low-maintenance living. Waterleigh offers resort-style amenities including multiple pools, fitness center, clubhouse, playgrounds, walking trails, tennis courts, beach volleyball, mini golf, and scenic lakes. Conveniently located near Hamlin Town Center, shopping, dining, top-rated schools, major highways, and Walt Disney World. Don't miss this incredible opportunity to own a home in one of Winter Garden's most desirable communities!

10108 Salt Point Drive, Winter Garden

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

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