Winter Garden/Oakland Homes with Tennis Court(s) Amenities

Winter Garden/Oakland Homes with Tennis Court(s) Amenities

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where charming small-town vibes meet modern conveniences. Nestled in Orange County, this picturesque area is renowned for its lush landscapes, vibrant community, and rich history. With its stunning sunsets and abundant recreational opportunities, Winter Garden and Oakland offer an idyllic lifestyle for families, retirees, and everyone in between.

One of the standout features of this beautiful region is its commitment to outdoor living. Residents enjoy access to an array of parks, trails, and waterways, making it a haven for nature lovers and adventure seekers alike. The historic downtown Winter Garden boasts delightful shops, delicious dining options, and a lively farmers’ market, ensuring that there’s always something to explore.

For those seeking an active lifestyle, homes with tennis court amenities are a perfect match. Imagine waking up to the sun-drenched Florida mornings and stepping outside to your private tennis court, where you can enjoy a friendly match or practice your serves right at home. These properties not only offer the luxury of having a personal sports facility but also promote a healthy, active lifestyle for you and your family.

Whether you’re a seasoned player or just looking to enjoy a leisurely game with friends, having a tennis court at your residence enhances the quality of life in this vibrant community. Experience the perfect blend of relaxation and recreation in Winter Garden and Oakland, where your dream home awaits. Embrace the Florida sunshine and make this charming region your own!

Newest Winter Garden/Oakland Homes with Tennis Court(s) Amenities

3 Beds ⋅ 3 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail. Link to interactive floor plan: https://www.zillow.com/view-imx/6a573be4-fd0d-4649-9df8-88349b2426f6?initialViewType=pano

263 Deer Isle Drive, Winter Garden

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

Situated in the sought-after Waterleigh community, one of the most popular communities in Horizon West/Winter Garden this stunning 3-bedroom, 2-bathroom home offers the perfect blend of comfort, style, and convenience. This home is perfect for those seeking a tranquil and inviting living environment. Upon entering, you'll be greeted by a warm and inviting atmosphere that flows throughout the entire home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a space that is perfect for both everyday living and entertaining. The kitchen features modern appliances, ample counter space, and a great circulation area. You will love cooking in the well-appointed kitchen with stainless steel appliances, a walk-in pantry, and an ample island w/ bar top seating that is perfect for gatherings. The kitchen has a WATER FILTRATION SYSTEM; system running to the fridge and a separate water faucet on the island. Whether you're preparing a quick meal or hosting a dinner party, this kitchen is sure to impress. The adjacent dining area is spacious and offers a lovely backdrop for enjoying meals with family and friends. The master suite offers privacy as it is separate from the other rooms located in the home, complete with a spacious bedroom, a walk-in closet, and an In-suite bathroom. The additional bedrooms are well-appointed, providing comfort and convenience for family members or guests. The home offers a large laundry room and a drop zone area situated next to the two-car garage perfect for your keys, tools, shoes…etc…. Located just minutes from DISNEY, in a family-friendly, GOLF CART FRIENDLY community, The owners of this home have access to a range of RESORT STYLE amenities, including 2 clubhouses with 2 beautiful large pools, a splash pad, 2 fitness centers with play area, miniature golf, beach volleyball, tennis, lake view BBQ/picnic area, dog-park, community dock, water-view walking trails. Location benefits include conveniently at the entrance of the community a new Publix shopping center, near Highway 429, and Highway 192, restaurants, and shopping at Flamingo Crossings, Hamlin, and Winter Garden Village. All lawn maintenance is provided through the community..... THE HOUSE HAS SOLAR PANELS. The seller will pay on the day of closing the debt he currently has with the solar panel financier. In this way, the Buyer has an ADDITIONAL DISCOUNT on the purchase of the property.

9456 Komika Lane, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Waterleigh Phase 4a SubDv. ⋅ 34787 Zip Code

WELCOME TO WATERLEIGH – RESORT-STYLE LIVING IN WINTER GARDEN! “TENANT-OCCUPIED – START GENERATING RENTAL INCOME FROM DAY ONE” Discover this beautiful 3-bedroom, 2-bathroom single-family home located at 16704 Point Rock Drive in the highly desirable Waterleigh community of Winter Garden. This well-designed home features a bright OPEN-CONCEPT FLOOR PLAN that seamlessly connects the living, dining and kitchen areas, creating a comfortable space for everyday living and entertaining. The home also offers a 2-CAR GARAGE and a functional single-story layout. What truly sets this property apart is the WATERLEIGH LIFESTYLE. Residents enjoy access to an impressive collection of resort-style amenities, including multiple community pools and amenity centers, fitness centers, playgrounds, sports fields, mini-golf, beach volleyball, community garden, walking and nature trails, scenic lakes and ponds, and beautiful outdoor spaces throughout the community. Waterleigh offers the perfect combination of residential comfort and resort-style living in one of Winter Garden's most desirable areas. Conveniently located near shopping, dining, schools, entertainment and Central Florida's world-famous attractions, with easy access to major roadways connecting you to the greater Orlando area. Whether you're looking for your primary residence or a home where you can enjoy the Florida lifestyle every day, this property offers much more than a house—it's an opportunity to become part of the Waterleigh lifestyle. Schedule your private showing today!

16704 Point Rock Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decorative tile backsplash. The Whirlpool stainless steel appliances—including a built-in natural gas cooktop and a refrigerator—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 zero-corner sliding glass door leads to the extended covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a rain shower head and a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. The additional spare bedroom and bathroom, along with the enclosed flex room, provide ample space for everyone. The upgraded laundry room with built-in cabinetry, quartz countertop, utility sink, and a Whirlpool washer and dryer make daily tasks a breeze. Designer-curated finishes elevate every corner of this home, including wood-look tile flooring throughout, pendant light pre-wire and under cabinet lighting in the kitchen, 2” faux wood blinds, and brushed nickel hardware and plumbing fixtures. The 2-car garage offers extra tandem storage space with an epoxy finish on the floor, ensuring that every part of your home is both beautiful and practical. With its stunning design and thoughtful touches, the Mystique home provides the perfect blend of luxury and functionality for today’s lifestyle.

13056 Sandcastle Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to Waterleigh! This beautiful 2023-built, 4-bedroom, 3-bath home sits on a spacious lot with a peaceful natural lake view from the backyard. Featuring an open-concept layout, modern kitchen, versatile loft, and private owner’s suite. Enjoy resort-style pools, clubhouses, fitness centers, tennis courts, trails, and playgrounds. Publix is conveniently located at the community entrance, with schools, shopping, dining, SR-429, and Walt Disney World nearby. Enjoy space, views, convenience, and the best of the Horizon West lifestyle

17882 Adrift Road, Winter Garden

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

Virtually Staged. The appeal isn’t just the house—it’s the lifestyle that comes with the community. Welcome to 10625 Atwater Bay Drive, Winter Garden, FL 34787, where comfort, convenience, and resort-style living come together in the highly desirable Waterleigh community. The first floor features a private bedroom and full bathroom with a bathtub, ideal for guests, extended family, or convenient first-floor living. The kitchen offers a large center island, granite countertops, ample cabinetry, and a walk-in pantry, opening seamlessly to the living and dining areas. A rear lanai provides a relaxing outdoor space, while the alley-access garage helps maintain the home’s attractive streetscape. Upstairs, a spacious loft offers flexible space for a home office, media room, or playroom. The primary suite features an en-suite bath with dual sinks and a walk-in shower, while two additional bedrooms share another full bath. What truly sets this home apart is the Waterleigh lifestyle. Residents enjoy multiple resort-style pools, fitness centers, clubhouses, playgrounds, sports fields, tennis and pickleball courts, mini-golf, dog parks, walking trails, fishing areas, lakes, green spaces, and community activities. Conveniently located near SR 429, Waterleigh offers easy access to Disney, Orlando, shopping, dining, and entertainment—with Publix located right within the community. 10625 Atwater Bay Drive offers more than a home—it’s an opportunity to enjoy the resort-style lifestyle that makes Waterleigh such a desirable place to live.

10625 Atwater Bay Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 1b-A Rep SubDv. ⋅ 34787 Zip Code

Welcome home to this freshly painted, charming Craftsman- inspired residence offering 2193 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities! This beautifully maintained home features 3 spacious bedrooms, 2 1/2 baths and a versatile loft/bonus room- perfect for a home office, media room or play area. The heart of the home is the open-concept kitchen overlooking the dining and family room, complete with an EXTRAORDINARY walk-in pantry that provides exceptional storage. Tile flooring flows throughout the main living areas, while the primary suite features warm hardwood flooring. Upstairs, the loft and secondary bedrooms are finished with comfortable Berber carpet. Step outside to relax or entertain on the screened lanai, offering the perfect space to enjoy Florida's beautiful weather year-round. Residents enjoy outstanding community amenities, including a resort-style pool, clubhouse, tennis courts, zip line and a dog park. Summerlake also appreciates access to TOP-RATED "A" schools. Conveniently located with easy access to Disney, Universal, Sea World, shopping, dining, major highways and all that Central Florida has to offer, this home truly combines comfort, convenience and an exceptional lifestyle!

7921 Iceland Gull Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b-3d SubDv. ⋅ 34787 Zip Code

PRIVATE HEATED POOL & SPA with panoramic screen enclosure on premium pond front lot. Welcome home to 15526 Mango Isle Street, a stunning single-story home nestled in the highly sought-after, resort-style community of Waterleigh in Horizon West. Step inside this spacious 4-bedroom, 3-bathroom open-concept home designed for effortless living and entertaining. The Gourmet Kitchen features a grand island with breakfast bar seating, solid surface countertops, solid wood cabinetry, a walk-in pantry, and stainless steel appliances, including a built-in cooktop and oven. The bright kitchen seamlessly opens to a wide-open family room and dining area framed by large sliding glass doors that draw your eye straight to the water views. Primary Suite feels like a tranquil sanctuary featuring elegant tray ceilings, a large walk-in closet, and an en-suite bath with a double-sink vanity and walk-in shower. Layout offers a generous split-bedroom floorplan offering optimal privacy for family and guests, plus an inside utility room. Enjoy this backyard oasis and step out through the sliding glass doors into your private sanctuary. The custom HEATED pool and integrated spa sit under a picture-frame panoramic screen enclosure, giving you unobstructed, serene views of the peaceful pond. Brick pavers cover the expansive covered lanai and pool deck, offering plenty of space for outdoor dining, lounging, and soaking in Florida's famous sunsets. The Waterleigh Community is renowned for its unmatched resort-style amenities and vibrant neighborhood atmosphere. Amenities: Access to two massive lakefront clubhouses, multiple resort-style pools, splash pads, two fully equipped fitness centers, tennis and pickleball courts, beach volleyball, walking trails, dog parks, playgrounds, and a mini-golf putting course. Location is phenomenal just minutes from Walt Disney World, top-rated Horizon West schools, Hamlin Town Center dining, shopping, golf courses, and quick access to State Road 429 for easy commutes across Central Florida. This home perfectly blends luxury, comfort, and the ultimate Florida indoor-outdoor lifestyle. Schedule your private showing today!

15526 Mango Isle Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

ONE-YEAR HOME WARRANTY AVAILABLE WITH A FULL-PRICE OFFER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom FIRST-FLOOR condo in the gated Southern Pines community of Winter Garden. Featuring a FRESH INTERIOR REPAINT (2026), UPDATED FIXTURES, a bright, open-concept layout, and NO CARPET THROUGHOUT FOR EASY MAINTENANCE, this home is truly move-in ready. Step inside to a spacious open living area offering a dedicated dining room and breakfast nook just off the kitchen. The kitchen features STAINLESS STEEL APPLIANCES, GRANITE COUNTERTOPS, NEUTRAL CABINETRY, and a pantry offering additional storage. The desirable split-bedroom floor plan provides added privacy, with the primary suite positioned on one side of the home and two additional bedrooms with a guest bathroom on the opposite side. All three generously sized bedrooms feature walk-in closets, providing plenty of storage throughout the home. Ideal as a primary residence or investment property, this low-maintenance condo offers excellent rental potential in a desirable Winter Garden location. HOA dues include internet and basic cable, adding further value and convenience. Southern Pines offers an impressive collection of resort-style amenities, including a pool and spa, fitness center, tennis courts, indoor basketball and volleyball courts, playground, dog park, clubhouse, theater room, billiards room, BBQ area, resident car wash station, and on-site management. Conveniently located near highly regarded public schools, Publix, Winter Garden Village, the West Orange Trail, and vibrant Downtown Winter Garden, with easy access to SR-429, Florida’s Turnpike, and major Orlando attractions. Whether you're searching for a comfortable primary residence or a great investment opportunity, this well-located Winter Garden condo delivers space, convenience, amenities, and value.

431 Southern Pecan Circle Unit 101, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a fully equipped kitchen and grilling area. The community also offers a park and playground, providing something for everyone to enjoy. This 1bed/1 bathroom with a flex room boast commercial grade luxury vinyl plank flooring, crown molding throughout, granite counter tops throughout the kitchen and bathroom, dedicated dining room, indoor laundry room with washer and dryer included, neutral interior wall paint, excellent natural light, ensuite bathroom, ample size primary suite walk-in closet, and more. Conveniences to be noted in the association fees are: Water, Cable, Trash, Pest Control, Roof, Exterior Building Maintenance, and Pool. Live just minutes from Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail. Getting around Central Florida is easy with quick access to SR-429, the Florida Turnpike, SR-408, and SR-50. Everyday shopping is also close by, with Publix and Costco Just minutes away. Low maintenance living at it's finest. Come see this condo today.

1315 Eastern Pecan Place Unit 202, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-2 & 2c-3 SubDv. ⋅ 34787 Zip Code

WATER & CONSERVATION VIEW | NO REAR NEIGHBORS | THREE-CAR TANDEM GARAGE | POOL READY, FENCED YARD | NEW CARPET & FRESH PAINT | MOVE IN READY -- Located in Winter Garden's sought-after Waterleigh community, minutes from Walt Disney World. The home sits on a premium oversized homesite backing to conservation, with pond views and no rear neighbors. It is part of D.R. Horton's luxury Emerald Collection, built with upgrades like a concrete tile roof and an extended tandem garage. New carpet and fresh interior paint throughout. The flexible floor plan offers four bedrooms, a first-floor bonus room, and a spacious upstairs loft. A first-floor bedroom and full bath make an ideal setup for guests, multigenerational living, or a private home office. The gourmet kitchen offers quartz counters, a built-in oven, an induction cooktop, a range hood vented outside, a butler's pantry, and a walk-in pantry. It opens to the living room and a dining room with water views. Upstairs, the primary suite features a tray ceiling, a pond-view sitting area, a garden tub, and a walk-in shower. Outside, the screened lanai with brick pavers overlooks a fully fenced backyard with room to design your own custom pool. The 38-foot tandem garage adds an epoxy floor and a Tesla EV charger that conveys. Best of all, this is maintenance-free living: the HOA handles the lawn and landscaping for you, along with resort-style amenities including community pools, clubhouse, fitness center, parks, playgrounds, and a dog park. Close to Horizon West and Hamlin shopping and dining, with easy access to SR-429. Zoned for Atwater Bay Elementary, Water Spring Middle, and Horizon High School. Seller is a licensed Florida real estate sales associate.

9982 Beach Port Drive, Winter Garden

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