Winter Garden Homes with Tennis Court(s) Amenities

Winter Garden Homes with Tennis Court(s) Amenities

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County, where picturesque landscapes meet vibrant community living. Known for its rich history and small-town charm, Winter Garden boasts a blend of modern amenities and a quaint downtown area filled with boutique shops, delightful eateries, and lively farmers' markets. With its close proximity to Orlando, residents enjoy easy access to world-renowned attractions while savoring the tranquility of suburban life.

For those who appreciate an active lifestyle, Winter Garden is a haven for tennis enthusiasts. Imagine waking up in a stunning home equipped with your very own tennis court, where you can practice your serves and enjoy friendly matches with family and friends right in your backyard. Homes featuring tennis court amenities are not just about the sport; they offer a unique opportunity for outdoor entertaining, fitness, and relaxation all in one place.

The real estate market in Winter Garden is diverse, with properties ranging from charming single-family homes to luxurious estates, many of which come with private tennis courts. These homes provide the perfect setting for a healthy lifestyle and a welcoming environment for gatherings. With year-round sunshine and a supportive community, Winter Garden is the ideal place to invest in a home that aligns with your active lifestyle.

Whether you’re a seasoned player or just looking to enjoy the space, Winter Garden’s tennis court homes offer an exceptional way to embrace the Florida lifestyle. Explore the possibilities today and discover your dream home in this delightful city!

Newest Winter Garden Homes with Tennis Court(s) Amenities

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 ⋅ 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 ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, 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

6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code

Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden

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

Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden

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

Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden

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

Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden

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

Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden

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