Winter Garden Homes with Racquetball Community Features

Winter Garden Homes with Racquetball Community Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County, where the warmth of Southern hospitality meets the vibrancy of modern living. Known for its picturesque landscapes and rich history, Winter Garden boasts a delightful blend of outdoor activities, cultural experiences, and a tight-knit community atmosphere. With its stunning parks, scenic lakes, and delightful downtown area filled with boutique shops and delicious eateries, it's no wonder that Winter Garden has become a sought-after destination for families and individuals alike.

One of the standout features of this remarkable city is its welcoming racquetball communities. If you’re an enthusiast of this fast-paced sport or simply enjoy an active lifestyle, you’ll find a variety of homes that cater to your interests. These communities are designed to foster a sense of camaraderie among residents, offering state-of-the-art racquetball courts and facilities that encourage both competition and recreation. Imagine stepping out of your front door and into a vibrant community where you can hone your skills, meet fellow sports lovers, and enjoy the benefits of an active lifestyle right at your doorstep.

In addition to the racquetball amenities, Winter Garden offers a variety of home styles, from charming single-family residences to modern townhomes, ensuring that there’s something for everyone. With excellent schools, convenient access to major highways, and a plethora of recreational activities, Winter Garden is not just a place to live—it's a place to thrive. Come discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Winter Garden Homes with Racquetball Community Features

1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
1349 Castleport Road, Winter Garden
$749,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

1349 Castleport Road, Winter Garden
341 Southern Pecan Circle Unit 202, Winter Garden
$220,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
WINTER GARDEN GEM! NEW KITCHEN • NEW APPLIANCES • NO CARPET • PRIVATE GARAGE • RESORT-STYLE AMENITIES! Welcome to 341 Southern Pecan Circle, Unit 202, Winter Garden, FL 34787! Discover this beautifully updated, move-in-ready 1-bedroom, 1-bathroom condo featuring modern upgrades, open-concept living, a private garage, and outstanding resort-style community amenities in desirable Winter Garden, Central Florida! Step inside to enjoy bright, inviting living and dining areas filled with natural light, fresh interior paint, and NO CARPET THROUGHOUT! Attractive wood-look flooring enhances the living areas and bedroom, complemented by easy-to-maintain tile flooring in the kitchen and bathroom. The NEW KITCHEN showcases beautiful cabinetry, attractive countertops, a spacious breakfast bar, stainless steel appliances, and a NEW REFRIGERATOR AND MICROWAVE! The open layout provides an inviting space for everyday living and entertaining. The spacious bedroom offers generous closet space, while the UPDATED BATHROOM features attractive tile finishes and a convenient vanity. Additional conveniences include an IN-UNIT WASHER AND DRYER and a PRIVATE GARAGE for parking and extra storage. ENJOY RESORT-STYLE LIVING! This amenity-rich community features a sparkling swimming pool, fitness center (gym), basketball court, tennis courts, sand volleyball court, playground, and car wash station. The COMMUNITY CLUBHOUSE also offers a community kitchen, computer room, nursery room, and meeting room, providing excellent spaces for recreation, convenience, and community activities. DESIRABLE WINTER GARDEN LOCATION! Enjoy convenient access to shopping, dining, entertainment, parks, major roadways, and the greater Orlando area. IDEAL FOR LOW-MAINTENANCE LIVING OR INVESTMENT! Whether you're seeking a primary residence, seasonal retreat, convenient home for work or studies, or a potential rental investment, this updated Winter Garden condo offers comfort, functionality, and lifestyle amenities. Rental opportunities are subject to association rules and restrictions. NEW KITCHEN • NEW APPLIANCES • UPDATED BATHROOM • NO CARPET • PRIVATE GARAGE • IN-UNIT LAUNDRY • RESORT-STYLE AMENITIES! SCHEDULE YOUR PRIVATE SHOWING TODAY!

341 Southern Pecan Circle Unit 202, Winter Garden
15193 Aqua Sol Lane, Winter Garden
$459,900
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Welcome to Del Webb Oasis in Winter Garden, where everyday living feels like a getaway. Located right next to the clubhouse, allowing residents to easily walk to the community amenities, this 3-bedroom, 2-bath home offers approximately 1,579 square feet of comfortable living space. The spacious kitchen features a gas stove and plenty of cabinet storage, while the primary suite includes a large walk-in closet and a walk-in shower. Two additional bedrooms provide flexibility for guests, a home office, or hobbies, and the second bathroom also features a walk-in shower. The two-car garage includes an electric vehicle charging outlet and a convenient utility sink. With flexible indoor and outdoor spaces, energy-efficient features, and gas heating, the home is designed for comfortable everyday living. Residents can enjoy the Del Webb Oasis clubhouse, fitness center, resort-style pool, pickleball and tennis courts, walking trails, and a variety of social activities, all conveniently located near Winter Garden shopping, dining, and Orlando attractions. Del Webb Oasis is a 55+ community, and occupancy is subject to community requirements.

15193 Aqua Sol Lane, Winter Garden
6158 Meriwether Crescent, Winter Garden
$719,999
4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Welcome to 6158 Meriwether Crescent in Winter Garden! This spacious 4-bedroom home offers a flexible floor plan with plenty of room to spread out, plus a private screened-in pool that makes Florida living easy. The main living areas feature an open layout with wood and tile flooring, while the kitchen offers granite countertops, stainless steel appliances, ample cabinetry and breakfast-bar seating. Large windows throughout bring in plenty of natural light, and multiple living and dining spaces provide flexibility for everyday living, entertaining or working from home. Step outside to the screened pool and patio overlooking a peaceful green setting, creating a great place to relax or entertain year-round. A detached garage with a brick-paver driveway adds even more functionality, while the covered front porch and mature landscaping give the home welcoming curb appeal. The surrounding community offers beautiful green space, walking paths, ponds and a neighborhood gazebo just steps from the home. Conveniently located in Winter Garden with easy access to shopping, dining, schools and everything the area has to offer, this home combines space, privacy and outdoor living in a great location.

6158 Meriwether Crescent, Winter Garden
16570 Barbours Creek Way, Winter Garden
$452,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
MOVE-IN READY! BRAND-NEW CONSTRUCTION, NEVER LIVED IN! Located in the highly desirable Waterleigh community in Winter Garden, this beautiful Ibis townhome offers 3 bedrooms, 2.5 bathrooms, a one-car garage, and a long driveway providing additional parking space. With modern finishes and a bright, open-concept design, this home is ready for its first owner! Step inside through the welcoming foyer and into an open living space where the kitchen, dining area, and living room flow seamlessly together. The kitchen features upgraded stainless steel appliances, quartz countertops, ample cabinetry, and convenient bar seating, making it ideal for everyday living and entertaining. The living area overlooks a covered patio, offering additional space to relax and enjoy the Florida lifestyle. A powder room and rear-entry garage complete the first floor. Upstairs, you’ll find all three bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite features a walk-in closet, double-sink vanity, and generously sized shower. Two additional bedrooms and a full guest bathroom provide flexibility for family, guests, or a home office. The home also includes a Smart Home technology package, allowing convenient control of compatible home features from your smart device whether you’re home or away. Located in Waterleigh, one of Horizon West’s sought-after master-planned communities, residents enjoy an exceptional lifestyle with resort-style amenities and convenient access to shopping, dining, entertainment, and major Central Florida destinations. SR-429 is nearby, providing easy connectivity throughout the Orlando area. With attractive curb appeal, modern finishes, newer construction, and a low-maintenance townhome lifestyle, this Ibis offers an excellent opportunity to own a move-in-ready home in Winter Garden. Schedule your private showing today!

16570 Barbours Creek Way, Winter Garden
1315 Eastern Pecan Place Unit 202, Winter Garden
$204,900
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
233 Southern Pecan Circle Unit 101, Winter Garden
$219,900
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
142 Southern Pecan Circle Unit 204, Winter Garden
$280,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Ready to move in, under market value, not a fixer upper. 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
200 Southern Pecan Circle Unit 104, Winter Garden
$290,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code
**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden
16625 Point Rock Drive, Winter Garden
$564,900
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Better than new! Move-in ready with premium upgrades and resort-style living in the highly sought-after Waterleigh community! This beautiful all-concrete block construction home offers 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan that perfectly blends comfort, style, and functionality. The spacious kitchen overlooks the dining and great room while offering views of the covered lanai, creating the perfect setting for everyday living and entertaining. Featuring a large center island with bar seating, abundant cabinetry, generous counter space, and stainless steel appliances, the kitchen is truly the heart of the home. The first floor also includes a versatile FLEX ROOM, ideal for a home office, playroom, or fitness space, along with a convenient half bath. A custom WINE CELLAR built beneath the staircase adds a unique touch for wine enthusiasts. Upstairs, the spacious primary suite features a large walk-in closet and an ensuite bathroom with dual vanities. Two additional bedrooms share a full bathroom, while the upstairs laundry room adds everyday convenience. A rear-entry TWO-CAR GARAGE with a practical drop zone completes the home. This property has been thoughtfully upgraded with premium features that truly set it apart, including LAMINATE FLOORING throughout the entire second floor, a built-in SAUNA in the primary bathroom, a SCREEN-ENCLOSED LANAI with an above-ground HOT TUB, and ENERGY-SAVING SOLAR PANELS. Located in the award-winning Waterleigh community, residents enjoy resort-style amenities including multiple pools, clubhouses, fitness centers, tennis and pickleball courts, playgrounds, scenic walking trails, dog parks, community gardens, and beautiful lakes throughout the neighborhood. Waterleigh is also known for its outstanding educational opportunities, with TWO A-RATED SCHOOLS inside the community, including an A-rated middle school ranked among the top-performing schools in Orange County. Conveniently located just minutes from Walt Disney World, Hamlin Town Center, Horizon West, shopping, dining, medical facilities, and major highways, this home offers the perfect combination of luxury, convenience, energy efficiency, and one of Central Florida's most desirable communities.

16625 Point Rock Drive, Winter Garden
Winter Garden
$212,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautiful 1BR/1BA condo with a bright open floor plan, spacious solarium/flex space, granite countertops, walk-in closet, and interior laundry. Located in the gated Southern Pines community featuring a resort-style pool, fitness center, indoor basketball and racquetball courts, tennis courts, playground, and clubhouse. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and entertainment. Northeast-facing unit with abundant natural light and excellent community amenities.

Winter Garden
Start Your Search