Winter Garden/Oakland Homes with Golf Carts OK Community Features

Winter Garden/Oakland Homes with Golf Carts OK Community Features

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant atmosphere, these areas offer a unique blend of suburban tranquility and lively urban amenities. With lush greenery and scenic views, Winter Garden and Oakland are perfect for those who appreciate the beauty of nature while enjoying the conveniences of modern living.

One of the standout features of this region is its golf cart-friendly community. Imagine cruising through the sun-kissed streets in your golf cart, making your way to local shops, restaurants, and parks with ease. The homes in Winter Garden and Oakland are designed to embrace this lifestyle, with many properties featuring spacious layouts and inviting outdoor spaces that are perfect for entertaining. Whether you're a golf enthusiast or simply enjoy the leisurely pace of life, this community offers a unique charm that is hard to resist.

In addition to its golf cart-friendly environment, Winter Garden boasts a rich history and a vibrant downtown area filled with boutique shops, delightful eateries, and a bustling farmer's market. Residents can enjoy a variety of recreational activities, from hiking and biking trails to nearby lakes for fishing and kayaking. The warm Florida sunshine and friendly community spirit make Winter Garden and Oakland an ideal place to call home.

Explore the possibilities of living in this enchanting region, where golf carts are not just a mode of transport but a way of life. Experience the perfect blend of relaxation and recreation in Winter Garden and Oakland – your new home awaits!

Newest Winter Garden/Oakland Homes with Golf Carts OK Community Features

$849,988
4 Beds ⋅ 3 Baths ⋅ Lake Cove Pointe 46/58 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully maintained custom home located in the gated community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Conveniently located just minutes from Historic Downtown Winter Garden, this home offers easy access to dining, shopping, theater, entertainment, and local avente. A paver driveway and path lead to the charming front porch and welcoming entry. Inside, this nearly 2, 400-square-foot home features 4 bedrooms, 3 full baths, and a spacious three-way split floor plan designed for comfort and privacy. The main living areas feature attractive wood-look ceramic tile, with carpet in the family room and bedrooms. The well-appointed kitchen offers white cabinetry, beautiful countertops, and glass-pane display cabinets for added character and storage. The spacious Owner's Suite includes custom closets, a comfortable sitting area, and French doors leading to the screened-in patio. The Owner's Bath features a large shower and freestanding soaking tub. Enjoy Florida outdoor living from the screened-in patio, complete with a convenient wet bar and sink, making it an ideal space for entertaining or relaxing. The property also offers an immaculate two-car garage with new epoxy flooring, plus a separate third golf cart garage/workshop combination, providing excellent flexibility for golf cart storage, hobbies, or additional workspace. Recent updates include a 2019 roof, 2019 A/C, a Rheem 60-gallon hybrid water heater installed approximately nine months ago, and lifetime garage door springs !installed approximately last summer. Located in a desirable gated community and close to Historic Downtown Winter Garden, this well-maintained home combines a thoughtful floor plan, attractive updates, excellent garage space, and convenient access to all that Winter Garden has to offer.

427 Tierra Verde Lane, Winter Garden
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden
$580,000
4 Beds ⋅ 2 Baths ⋅ Covington Park A B D E F G & J SubDv. ⋅ 34787 Zip Code
Welcome to 618 Bainbridge Loop, where thoughtful updates, flexible living space, and the Winter Garden lifestyle come together. This 4-bedroom, 2-bath home PLUS a dedicated office features a desirable split-bedroom floor plan, while maintaining an open-concept layout that’s perfect for entertaining and everyday living. The renovated kitchen serves as the heart of the home, while the updated guest bathroom and renovated patio add even more move-in-ready appeal. The office features brand-new flooring, creating the perfect space for working from home, a playroom, or additional flex space. Major updates have already been taken care of with a 2023 roof, 2022 A/C, 2025 water heater, and 2024 appliances. Step outside to the refreshed patio, ready for morning coffee, weekend gatherings, or unwinding at the end of the day. Located within the Winter Garden golf cart district and near highly regarded local schools, this home offers a location that’s just as appealing as the home itself. With its combination of updates, functional layout, and sought-after Winter Garden lifestyle, 618 Bainbridge Loop is ready to welcome you home.

618 Bainbridge Loop, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$758,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this stunning 3-bedroom, 3-full-bathroom residence boasting 2,976 square feet of beautifully designed living space, plus a dedicated office, spacious loft, and versatile bonus room. Perfectly positioned on a premium lakeview homesite, this exceptional property offers tranquil water views and the spectacular bonus of enjoying Disney fireworks from your own backyard. Step outside into your private backyard oasis, where a sparkling pool creates the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. The fully fenced backyard provides both privacy and space, while the premium lot offers a picturesque backdrop that truly sets this home apart. Inside, the home is thoughtfully appointed with upscale details throughout. The gourmet-inspired kitchen features 42-inch cabinetry, complemented by upgraded light fixtures and designer-style ceiling fans throughout the home. The spacious bonus room, enclosed by elegant frosted-glass doors, offers a flexible space ideal for a media room, home office, entertaining, or additional living space. The dedicated office and generous loft provide even more versatility for today’s lifestyle. Additional highlights include a 2024 A/C, 2025 water heater, and an impressive 25-foot extended garage offering exceptional storage and flexibility for vehicles, recreational equipment, or hobbies. Adding to the ease of Florida living, the HOA includes landscaping and hedge trimming, allowing you to spend more time enjoying your home and less time maintaining it. From the premium lakefront setting and private pool oasis to the thoughtful upgrades, expansive floor plan, and unforgettable Disney fireworks views, this is a home that delivers an exceptional blend of luxury, comfort, and lifestyle.

14735 Snowy Egret Street, Winter Garden
$975,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home!

9566 Bolero Road, Winter Garden
$611,610
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
$1,137,150
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
$1,100,000
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
$710,000
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
$574,900
4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Better Than New – Why Wait to Build? NO CDD FEE! Welcome to this meticulously maintained Ellison floor plan, perfectly positioned on a fully fenced corner lot in the highly sought-after Silverleaf Reserve community of Horizon West, Winter Garden. Less than two years old and within walking distance of A-rated elementary and middle schools, this move-in-ready home offers all the benefits of new construction without the wait. The property can also be purchased with a tenant already in place, creating an outstanding investment opportunity with immediate rental income. From the moment you arrive, you'll appreciate the exceptional curb appeal with professional landscaping, a covered front porch, and an extended brick paver driveway and walkway. Inside, the bright open-concept layout seamlessly connects the spacious great room, dining area, and gourmet kitchen. The kitchen features 42-inch cabinetry, quartz countertops, stainless steel appliances, an upgraded backsplash to the ceiling, abundant storage, and a dedicated coffee station—perfect for everyday living and entertaining. A convenient half bath completes the first floor. Upstairs, a versatile loft with a built-in office provides the ideal work-from-home space or second living area. The spacious owner's suite features a tray ceiling, dual vanities, a frameless glass walk-in shower, private water closet, and a custom walk-in closet. Three additional bedrooms, a full guest bath, ample storage, and an upstairs laundry room provide plenty of space for family and guests. The two-car garage is finished with epoxy floors and LED Hex lighting, making it perfect for a home gym, workshop, or car enthusiast. Thoughtfully upgraded beyond builder standards, the home includes custom closet systems throughout, an extended driveway completed in 2025, professionally finished epoxy garage floors, and a fresh exterior repaint in 2026. Boasting over $47,000 in builder upgrades, this home includes 8-foot interior doors on the main level, upgraded bronze hardware and plumbing fixtures, designer finishes, and numerous premium selections throughout. Built by Meritage Homes, this energy-efficient home features spray foam insulation, a Climate-Sealed® building envelope, high-efficiency HVAC, Low-E windows, ENERGY STAR® appliances, and smart home technology for year-round comfort and lower utility costs. Silverleaf Reserve offers resort-style amenities including a community pool, pickleball, tennis and basketball courts, playgrounds, a turf sports field, scenic walking trails, and green spaces. Families will appreciate being able to walk to highly rated schools while enjoying one of Horizon West's most desirable neighborhoods. Ideally located less than two miles from Hamlin Town Center, you'll enjoy premier shopping, dining, Orlando Health, Publix, entertainment, and quick access to SR 429. You're also just minutes from Historic Downtown Winter Garden, the Winter Garden Farmers Market, Winter Garden Village, the future Olympus Sports & Entertainment District, Walt Disney World, and major roadways including Florida's Turnpike, SR 408, and I-4. Why wait to build when you can own a better-than-new home today? Combining premium upgrades, exceptional energy efficiency, resort-style amenities, and one of Central Florida's most desirable locations, this home offers an incredible opportunity for both homeowners and investors.

4981 Coral Bean Alley, Winter Garden
$549,500
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
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