Winter Garden Homes with Tennis Court(s) Community Features

Winter Garden Homes with Tennis Court(s) Community Features

Welcome to Winter Garden, Florida, a vibrant city nestled in the heart of Orange County. Known for its rich history, charming downtown area, and stunning natural beauty, Winter Garden is a hidden gem that offers an exceptional quality of life. With its picturesque landscapes, lush parks, and numerous recreational opportunities, this city is perfect for families, retirees, and everyone in between.

One of the standout features of Winter Garden is its beautiful homes with tennis court amenities. Imagine waking up each day in a stunning residence that not only offers luxurious living spaces but also provides the perfect setting for your active lifestyle. These communities are designed for those who appreciate the finer things in life, blending elegance with functionality. Whether you’re a seasoned player or just starting, having a tennis court right at your doorstep means you can enjoy a quick match or practice your serve whenever the mood strikes.

In addition to tennis courts, these communities boast a wealth of amenities. Residents can enjoy beautifully landscaped grounds, sparkling swimming pools, fitness centers, and social gathering spaces, making it easy to connect with neighbors and build lasting friendships. The sense of community is palpable, with regular events and activities that cater to all ages.

Winter Garden is also conveniently located near major highways, making it easy to access nearby attractions like Walt Disney World, Universal Studios, and the vibrant city of Orlando. With its blend of small-town charm and modern conveniences, Winter Garden is truly a place you’ll be proud to call home. Come discover the lifestyle that awaits you in this delightful city!

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

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

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

2250 Oakington Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ 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

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

Welcome to the highly desirable Waterleigh community in Winter Garden! This beautifully maintained 3-bedroom, 2.5-bath townhome features a bright open-concept floor plan designed for comfortable living and entertaining. The spacious kitchen offers granite countertops, stainless steel appliances, ample cabinet space, and A WHOLE-HOUSE WATER FILTRATION SYSTEM IS INCLUDED, providing added value and peace of mind for the new owner. Upstairs you'll find all three bedrooms, each equipped with ceiling fans, including a spacious primary suite with a walk-in closet and dual-sink vanity. Enjoy the private patio and rear-entry one-car garage for added convenience. Waterleigh offers exceptional resort-style amenities including multiple pools, fitness center, tennis and pickleball courts, walking trails, playgrounds, dog parks, beach volleyball, mini golf, and beautifully maintained green spaces. HOA includes lawn maintenance for a low-maintenance lifestyle. Conveniently located just minutes from Hwy 429, Disney, Flamingo Crossings, shopping, dining, and top-rated schools. Don't miss the opportunity to own this beautiful home in one of Central Florida's most sought-after communities!

16931 Reseda Alley, 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 with a distant golf course 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

5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

Luxurious Fully Furnished 5-Bedroom Home in Winter Garden Experience the perfect blend of elegance, comfort, and convenience in this stunning fully furnished two-story home located in the highly desirable Winter Garden area. Designed with both style and functionality in mind, this exceptional residence offers 5 spacious bedrooms, 4 full bathrooms, and 1 half bathroom, providing plenty of room for families of all sizes. The thoughtfully designed open-concept floor plan creates a seamless flow between the expansive living and dining areas, making it ideal for everyday living and entertaining. At the heart of the home is a beautifully appointed kitchen featuring solid wood cabinetry, stone countertops, and a full suite of included appliances, offering both timeless style and modern convenience. The luxurious primary suite serves as a private retreat with a generous walk-in closet and an elegant en-suite bathroom. The additional bedrooms are equally well-designed and include built-in closets, providing excellent storage and comfort for family members or guests. Upstairs, you'll also find a spacious loft that offers endless possibilities as a second living area, media room, home office, or playroom. Step outside to enjoy the convenience of a 2-car attached garage and the peace of mind that comes with owning a meticulously maintained, move-in-ready home. Being fully furnished, this property is perfect for buyers seeking a seamless transition without the hassle of furnishing an entire home. Ideally situated in Winter Garden, this home offers easy access to major highways, shopping, dining, entertainment, and highly rated schools, making it an outstanding choice for those seeking both convenience and an exceptional lifestyle. Don't miss this incredible opportunity to own a beautifully furnished home in one of Central Florida's most desirable communities. Schedule your private showing today and discover everything this remarkable property has to provide.

16091 Silver Brook Way, Winter Garden

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

Welcome to this newly updated 2 bedroom / 2 bathroom first floor condo in Winter Garden, where low-maintenance living meets comfort and convenience. This beautifully updated first-floor condo features fresh interior paint and new flooring, creating a bright, modern, and move-in-ready space. The open-concept floor plan offers comfortable living and dining areas, making it perfect for everyday living or entertaining. The well-designed layout provides a seamless flow, while large windows bring in an abundance of natural light. This condo hasa detached garage for easy parking near your home. Residents enjoy the outstanding amenities of this sought-after community, including a resort-style swimming pool, fitness center, clubhouse, playground, walking paths, and beautifully maintained green spaces. The HOA also provides low-maintenance living, allowing you more time to enjoy everything Winter Garden has to offer. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, shopping, dining, entertainment, major highways, and Orlando's world-famous attractions, this home offers an unbeatable combination of location and lifestyle. Whether you're a first-time homebuyer, seasonal resident, downsizing, or looking for an investment opportunity, this move-in-ready condo delivers exceptional value in one of Central Florida's most desirable communities.

130 Southern Pecan Circle Unit 103, 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

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