Winter Garden/Oakland Homes with Racquetball Community Features

Winter Garden/Oakland Homes with Racquetball Community Features

Welcome to Winter Garden and Oakland, a vibrant community nestled in the heart of Orange County, Florida. Known for its picturesque landscapes, charming historic downtown, and a strong sense of community, this region is a hidden gem that offers both tranquility and adventure. With its lush parks, scenic lakes, and beautiful walking trails, residents can enjoy the great outdoors while being just a short drive from the bustling attractions of Orlando.

Winter Garden is particularly renowned for its rich history, which is beautifully showcased in its restored downtown area filled with boutique shops, delightful restaurants, and lively farmers' markets. The community spirit thrives here, making it an ideal place for families, retirees, and everyone in between.

For those seeking an active lifestyle, the homes in Winter Garden and Oakland boast exceptional community features, including access to racquetball courts. Imagine having the opportunity to engage in a spirited game right in your neighborhood! These amenities cater to fitness enthusiasts and social butterflies alike, providing a perfect blend of leisure and competition.

The homes themselves are designed with modern living in mind, offering spacious layouts and contemporary finishes that cater to diverse tastes. Whether you're looking for a cozy family home or a stylish retreat, Winter Garden and Oakland have something to fit every lifestyle.

With its unique combination of community spirit, natural beauty, and recreational opportunities, Winter Garden and Oakland are not just places to live—they're places to thrive. Come discover your dream home in this enchanting part of Florida!

Newest Winter Garden/Oakland Homes with Racquetball Community Features

$290,500
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
$259,000
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
$295,000
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
$569,900
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
$217,500
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
$287,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautiful 3-bedroom, 2-bath condominium located in the highly desirable gated community of Southern Pines in Winter Garden. This spacious unit offers 1,453 square feet of living space with an open floor plan, abundant natural light, and a comfortable layout perfect for both homeowners and investors. Residents enjoy resort-style amenities including a community pool, heated spa, fully equipped fitness center, indoor basketball court, tennis and racquetball courts, sand volleyball court, movie theater, game room, business center, and playground. The community is conveniently located near major highways, shopping, dining, entertainment, and historic downtown Winter Garden. Experience maintenance-free living in one of Central Florida's most sought-after communities. Schedule your private showing today.

1300 Eastern Pecan Place Unit 208, Winter Garden
$258,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Seller Offering a CREDIT Toward Buyer Closing Costs! HOA fee includes cable, internet, water, sewer, trash, pool and exterior maintenance. Welcome to this well maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan is perfect for everyday living and entertaining, featuring granite countertops, spacious living areas, abundant natural light throughout, and a versatile den that is ideal for a home office, reading space, or additional flex area. The community features an outstanding selection of amenities, including a serene pool and spa, fitness center, indoor basketball court, racquetball court, playground, outdoor grilling areas, and a beautifully appointed clubhouse complete with a movie room, pool table, business workspace, and a children's play area for added convenience while working out. Ideally located just minutes from Winter Garden Village, Historic Downtown Winter Garden, and major highways, this condo offers the perfect combination of comfort, convenience, and easy access to everything the area has to offer. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!

200 Southern Pecan Circle Unit 206, Winter Garden
$279,900
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Stunning 2-bedroom, 2-Bath condo on the second floor, 1276 sq ft, with new carpet in the bedrooms and stairs. All Appliances updated in the last few years, and the A/C is just a little over a year old. Walk to the pool, enjoy views of the retention pond, and be close to all the community amenities. Don't miss this gem?

143 Southern Pecan Circle Unit 206, Winter Garden
$235,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines in the heart of Winter Garden. This well-maintained 1-bedroom, 1-bath upper-level condo offers a bright and functional layout with abundant natural light. The kitchen features granite countertops, ample cabinetry, and a practical layout that connects to the living and dining areas, creating a comfortable flow for everyday living. The open layout and high ceilings help maximize the space and give the unit an airy feel. The bedroom is comfortable and well-sized, offering a quiet and private retreat. This unit also includes an attached 1-car garage and additional storage, a valuable feature within the community. Southern Pines is a gated community with resort-style amenities including a pool, fitness center, tennis courts, basketball, racquetball, sand volleyball, playground, and clubhouse. The HOA covers lawn care, water, cable, and internet for added convenience. Ideally located near Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail, with easy access to SR-429, Florida Turnpike, SR-408, and SR-50. Daily conveniences are just minutes away, including Publix (approx. 3 minutes) and Costco (approx. 8 minutes). Make this property your home today.

131 Southern Pecan Circle Unit 201, Winter Garden
$725,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal sitting room ideal for entertaining or home office, and an open-concept layout filled with natural light. The upgraded kitchen showcases custom gray cabinetry, stainless steel appliances, designer backsplash, pendant lighting, and generous counter space, flowing seamlessly into the dining and family room. Large windows frame tranquil views of the conservation area and lake, creating a peaceful backdrop for everyday living and entertaining. A first-floor bedroom with full bathroom provides an ideal guest or multigenerational suite. Upstairs, the spacious primary retreat features a tray ceiling and spa-style bath with dual sinks, soaking tub, and separate shower. A large loft offers flexible space for media, office, or play area, also with serene backyard and water views. Two additional bedrooms and a full bath complete the upper level. Step outside to your private outdoor oasis featuring a covered brick-paver lanai with summer kitchen, perfect for entertaining, plus a fully fenced backyard with room to add a pool — all while enjoying the privacy of no rear neighbors and protected conservation behind the home. Waterleigh residents enjoy 3 resort-style pools, 2 clubhouses with fitness centers, walking trails, sand volleyball, dog park, fishing and observation pier, tennis courts, pickleball, playgrounds, and lawn maintenance included in HOA. Zoned for Water Spring Elementary, Water Spring Middle School, and Horizon High School. Prime location near Disney, shopping, dining, SR-429, I-4, SR-417, and Publix. With furniture, golf cart, seller credit, premium lot, outdoor kitchen, and EV-ready garage all included, this home offers outstanding value and an effortless move-in experience.Schedule your private showing today.

9611 Lost Creek Drive, Winter Garden
$345,000
1 Beds ⋅ 1 Baths ⋅ Grove Res & Spa Hotel Condo Iv SubDv. ⋅ 34787 Zip Code
Experience Orlando from a fresh perspective in this refined one-bedroom, one-bath condominium suite set inside, The Terraces at The Grove Resort & Waterpark, just minutes from Walt Disney World®. Nestled on a quiet rise above shimmering Lake Austin, the residence blends boutique-hotel with the comforts of a private retreat. Wake each morning to calming waterfront views, then step into interiors styled with crisp lines, contemporary finishes, and floor-to-ceiling glass that invites the Florida sunshine in. Owners enjoy full privileges at The Grove, including the thrilling Surfing Water Park with its wave pool and surf simulator, yet The Terraces preserves an upscale, adult-oriented ambiance all its own. Exclusive resident perks include: Secluded infinity pool reserved for Terraces guests only, Poolside bar for craft cocktails and light bites, State-of-the-art fitness studio that keeps wellness on track, Byte market for convenient grab-and-go meals and lounge, an intimate space to unwind with friends after a day of adventure Beyond the resort gates, world-class shopping, dining, and Orlando’s famed theme parks are a quick drive away placing endless entertainment at your doorstep while safeguarding the serenity of home. Whether you’re seeking a wonderful vacation rental or a personal escape from everyday routine, this condominium delivers a rare blend of luxury, location, and lifestyle. Secure your slice of paradise before someone else claims the view.

15695 Grove Resort Avenue Unit 4303, Winter Garden
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