Winter Garden Homes with Tennis Court(s) Community Features

Winter Garden Homes with Tennis Court(s) Community Features

Welcome to Winter Garden, Florida—a charming city nestled in Orange County that perfectly blends small-town warmth with modern conveniences. Known for its picturesque landscapes and vibrant community spirit, Winter Garden boasts a rich history, beautiful parks, and a thriving downtown area filled with delightful shops, restaurants, and entertainment options. The city’s commitment to preserving its heritage is evident in its historic buildings and the scenic West Orange Trail, which invites outdoor enthusiasts to explore its natural beauty.

For those seeking an active lifestyle, Winter Garden is home to exquisite homes featuring tennis courts, perfect for both casual players and serious enthusiasts. Imagine stepping out of your beautifully designed residence and right onto your private court, ready for a friendly match or an invigorating practice session. These communities are thoughtfully designed to foster a sense of camaraderie among residents, offering not just a home, but a lifestyle enriched by sports and recreation.

In addition to tennis courts, many of these neighborhoods offer a wealth of amenities, including swimming pools, fitness centers, and walking trails that encourage a healthy and active lifestyle. The welcoming atmosphere and strong community ties make Winter Garden an ideal place for families, retirees, and anyone looking to enjoy the Florida sunshine.

With its perfect blend of outdoor activities, community spirit, and beautiful homes, Winter Garden is not just a place to live—it's a place to thrive. Come discover your dream home in this delightful city, where every day feels like a vacation!

Newest Winter Garden Homes with Tennis Court(s) Community Features

4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code

Motivated seller! Located in the community of Johns Lake Pointe, this beautifully designed 4-bedroom, 2.5-bath home offers a desirable split floor plan and a spacious 2-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private fenced backyard, creating the perfect setting for relaxing or entertaining. The kitchen features chestnut cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. The primary suite includes a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. The back porch is protected by a screen. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities, including a clubhouse with a pool and kitchen, fitness center, yoga room, tennis courts, and playground. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable house your home!

745 Marsh Reed Drive W, Winter Garden

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

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

Beautifully refreshed and ready to move in today, this charming 2-bedroom, 1-bath corner condo offers an inviting combination of modern updates, natural light, and exceptional community amenities. The bright, crisp interior is filled with loads of natural light and features fresh paint throughout, brand-new carpet, new door handles, and stylish modern finishes. All appliances are included, making this home truly move-in ready. The attached garage has also been washed and painted, creating a clean and functional space for parking and storage. And when it comes to value, this one is hard to beat. This is currently the most aggressively priced 2-bedroom condo with an attached garage on the market, making it a rare opportunity for a buyer looking for the combination of price, updates, and convenience. The A/C system was newly installed in June 2026, adding another significant update and valuable peace of mind. The community offers an impressive lineup of amenities designed to enhance everyday living, including a resort-style pool and relaxing hot tub, fully equipped fitness center, indoor basketball and racquetball courts, tennis court, and a convenient car wash area. Conveniently located near 429 and the Florida Turnpike, this home provides easy access to shopping, dining, major roadways, and a short drive to Orlando's theme parks and either coastline. With its desirable corner-unit location, attached garage, extensive updates, incredible amenities, and unmatched price point, this is a rare find that won't be easy to duplicate. If you're looking for a move-in-ready 2-bedroom with an attached garage at the best value currently available, this one deserves a look!

233 Southern Pecan Circle Unit 101, Winter Garden

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

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

Welcome to this beautifully maintained home in the highly sought after Watermark at Horizon West community! This spacious two story residence offers 3 bedrooms, 2.5 bathrooms, and over 2,000 square feet of thoughtfully designed living space. The open concept floor plan is perfect for both everyday living and entertaining, featuring wood tile flooring throughout the main level, abundant natural light, and a modern kitchen complete with built in appliances, ample cabinetry, generous counter space, and a large island overlooking the living and dining areas. Upstairs, you'll find a versatile loft that makes an ideal home office, media room, or play area, along with a spacious primary suite featuring a walk in closet and an en-suite bath. Two additional bedrooms, a full bath, and an upstairs laundry room complete the second floor. Enjoy Florida living from the welcoming front porch while taking advantage of the home's rear entry two car garage and low maintenance yard. Residents of Watermark enjoy resort style amenities including a community pool, fitness center, tennis courts, playground, parks, walking trails, and beautifully maintained common areas. You’re also within close distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move in ready home in a great location with a strong lifestyle, this one checks all the boxes!

14543 Golden Harbor Lane, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Watermark Ph 2b SubDv. ⋅ 34787 Zip Code

Stunning Winter Garden Home for Sale – Modern Comfort, Resort-Style Amenities & Solar Energy! Welcome to this beautiful Winter Garden home, offering the perfect combination of comfort, style, functionality, and modern living. Featuring a spacious open floor plan, this home is designed for easy living and entertaining, with abundant natural light flowing throughout the main living areas. The spacious primary suite provides a private retreat, complete with an en-suite bathroom featuring modern cabinetry and quality finishes. The gourmet kitchen is the heart of the home, featuring modern appliances, ample cabinetry, and a large center island—perfect for preparing meals while entertaining family and friends. Large windows bring in plenty of natural light and create a bright, welcoming atmosphere throughout the home. Step outside to enjoy the outdoor living area and take advantage of Florida's beautiful weather. The home is equipped with solar panels, and the seller will pay off the solar system in full at closing, providing the new owner with the benefit of solar energy without assuming the existing solar financing. Located in a desirable Winter Garden community, residents enjoy access to excellent amenities, including a resort-style pool, fully equipped fitness center, and a multi-purpose sports court. The community provides an ideal setting for an active and enjoyable lifestyle. Conveniently located near restaurants, shopping, major roads, entertainment, and everything Winter Garden and the surrounding area have to offer, this home is an excellent opportunity for those seeking comfort, convenience, and modern Florida living. Don't miss this opportunity! Schedule your private showing today and experience all that this beautiful home has in store.

14739 Glade Hill Park Way, Winter Garden

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

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

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

Virtually Staged. LOCATION, LOCATION, LOCATION! Welcome to the highly sought-after Watermark at Horizon West, one of Winter Garden's premier communities. Whether you're searching for your next home or a smart investment opportunity, this beautifully maintained 3-bedroom, 2.5-bath home with a 2-car garage checks all the boxes. Built in 2020, this thoughtfully designed home features an open-concept floor plan with ceramic tile throughout the main living areas, creating the perfect space for everyday living and entertaining. The gourmet kitchen overlooks the spacious living and dining areas, while upstairs you'll find a versatile loft/game room that can easily serve as a home office, media room, or additional living space. Enjoy added peace of mind with the original roof, HVAC system, and water heater, all just a few years old. Watermark is known for its outstanding resort-style amenities, including multiple community pools, tennis and basketball courts, fitness center, playgrounds, parks, walking trails, and beautifully maintained green spaces. Just minutes from Hamlin Town Center, SR-429, Walt Disney World, shopping, dining, entertainment, and top-rated schools, this home offers exceptional convenience in one of Central Florida's fastest-growing communities. Investor opportunity! The home is currently tenant occupied, providing the potential for immediate rental income, making it an excellent addition to an investment portfolio. Buyers looking for future occupancy can also take advantage of owning in one of Winter Garden's most desirable communities.

10301 Austrina Oak Loop, 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

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

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