Winter Garden/Oakland Homes with Racquetball Amenities

Winter Garden/Oakland Homes with Racquetball Amenities

**Discover the Charm of Winter Garden and Oakland, Florida**

Nestled in the heart of Orange County, Winter Garden and its neighboring community of Oakland offer a unique blend of small-town charm and modern convenience. Known for its picturesque landscapes and vibrant downtown area, this region is a haven for families, retirees, and anyone seeking a tranquil lifestyle with easy access to urban amenities. With its lush parks, scenic lakes, and a rich history reflected in the beautifully preserved historic district, Winter Garden is a place where community spirit thrives.

One of the standout features of homes in this area is the availability of properties with racquetball amenities. Imagine stepping out of your beautifully designed home and into your own private racquetball court! These homes cater to sports enthusiasts and fitness lovers alike, providing a fantastic way to stay active while enjoying the comforts of home. Whether you're playing a competitive game with friends or enjoying a casual match with family, having a racquetball court right at your doorstep enhances your lifestyle.

Winter Garden is also known for its excellent schools, diverse dining options, and easy access to major highways, making it a convenient location for commuters. The nearby West Orange Trail offers miles of scenic pathways for walking, biking, or jogging, adding to the region's appeal for outdoor lovers.

In Winter Garden and Oakland, you’re not just buying a home; you’re investing in a vibrant community where every day feels like a vacation. Explore the possibilities and discover your dream home with racquetball amenities in this enchanting part of Florida!

Newest Winter Garden/Oakland Homes with Racquetball Amenities

$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
$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
$1,295,000
Briley Farm SubDv. ⋅ 34787 Zip Code
LAST DEVELOPER OWNED LOT IN BILEY PHASE 1. Lakefront homesite with the ability to add your own private dock. Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a classic Southern estate, or a luxurious lakeside residence. You’ll have the option to work with one of our three trusted builders, each known for their exceptional craftsmanship and personalized approach: Pioneer Builders, J&J Building, and Element Home Builders. Each of these professionals brings years of experience and a dedication to turning your vision into reality. This lot is situated within a peaceful, beautifully maintained community that combines the tranquility of lakeside living with convenient access to local shops, dining, and major roadways. With utilities already in place and minimal site preparation required, you're ready to get started on building the home you’ve always dreamed of. As a lakefront property owner, you'll also have the opportunity to add a private dock—perfect for boating, fishing, or simply soaking in the stunning sunsets over Lake Apopka. This is a rare opportunity to become part of the Briley Farm lifestyle—where quality, nature, and community come together. Don’t miss your chance to build in Briley Farm, Okland's newest custom home community. Reach out today for more information or to schedule a private tour.

556 Walker Street, Oakland
$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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