Winter Garden/Oakland Homes with Tennis Court(s) Exterior Features

Winter Garden/Oakland Homes with Tennis Court(s) Exterior Features

Welcome to the charming communities of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant atmosphere, these areas offer an idyllic blend of suburban tranquility and modern conveniences. Winter Garden, with its historic downtown district, is a hub of activity featuring delightful shops, delicious eateries, and a lively farmers market that brings the community together every Saturday. Just a stone's throw away, the quaint town of Oakland boasts a rich history and a welcoming small-town feel, making it an ideal spot for families and retirees alike.

One of the standout features of homes in this region is the presence of properties equipped with tennis courts. Imagine stepping outside your back door to find a private oasis where you can practice your serves or enjoy friendly matches with family and friends. These homes not only cater to tennis enthusiasts but also enhance the overall lifestyle, providing ample space for outdoor activities and social gatherings. The beautifully landscaped exteriors, often adorned with lush gardens and serene patios, create the perfect backdrop for relaxation and entertainment.

Living in Winter Garden and Oakland means embracing an active lifestyle, with numerous parks, trails, and recreational facilities just moments away. Whether you’re exploring the scenic West Orange Trail or enjoying a sunny day at Lake Apopka, this region offers endless opportunities for adventure. Discover your dream home with a tennis court in these delightful communities, where every day feels like a vacation!

Newest Winter Garden/Oakland Homes with Tennis Court(s) Exterior Features

$779,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
NEW PRICE — An Incredible Opportunity in Horizon West! Imagine coming home to more space, more flexibility, and the lifestyle you’ve been looking for—now at an even better value. This stunning, move-in-ready Toll Brothers home offers 4 bedrooms, 3.5 baths, and 3,304 sq. ft. of beautifully designed living space in one of Horizon West’s most desirable communities. From the Tuscan-inspired architecture and welcoming front porch to the bright, open-concept interior, this home makes an impression from the moment you arrive. The spacious chef’s kitchen features a large center island and flows effortlessly into the family room and covered lanai, creating the perfect setting for entertaining, family gatherings, or relaxing at home. One of the home’s standout features is its two primary suites, including one conveniently located on the first floor—ideal for multigenerational living, visiting family, guests, or anyone looking for additional privacy and flexibility. Step outside and discover an oversized backyard with plenty of room for a future pool, outdoor kitchen, play area, or your own private Florida retreat. The lifestyle continues beyond your front door with resort-style amenities, including lawn care, clubhouse, fitness center, parks, playgrounds, and a beautiful lakeside swimming pool overlooking Panther Lake. And the location is hard to beat. You’re just minutes from Hamlin Town Center, shopping, dining, top-rated schools, Disney, major roadways, and everything that makes Horizon West one of Central Florida’s most sought-after communities. The price has changed. The lifestyle hasn’t. Luxury. Space. Location. And now an even better opportunity to make this Toll Brothers home yours. Don’t wait for new construction when your next home is already here.

15149 Canoe Place, 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
$270,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time Residency Investor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large balcony, modern kitchen, and in-unit washer/dryer. High occupancy potential through the on-site rental program. Resort Amenities (included for guests): Surfari Water Park, surf simulator, water slides, laser river. Multiple resort-style pools, hot tubs & cabanas. Lake Austin access with fishing and water sports. Fitness center, arcade, full-service spa, on-site restaurants, bars, market, and conference center, 24/7 front desk, concierge, and gated community security. Prime Location, located in Winter Garden, FL, just minutes to Walt Disney World® and major Orlando attractions. Close to shopping, dining, and major highways. This unit is part of a condo-hotel program: no full-time residency allowed. Short-term rentals only. SHORT SALE – priced to sell fast! A great chance to secure a unit below market value in a high-demand tourist location. Ideal for investors looking for short-term rental income with professional management available on-site. Not suitable for full-time occupancy. Contact us today to schedule a showing and take advantage of this exceptional income-generating property!

14501 Grove Resort Avenue Unit 2527, Winter Garden
$298,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this amazing unit, nestled within the gated community of Southern Pines in the sought after area of Winter Garden , Florida; this beautiful 3 bedrooms 2 bathrooms condo is located in the second floor and has an open concept kitchen with a Dinning- living combo area, also an additional space for an office or a play area , the unit also has a split bedroom plan , with a spacious primary bedroom and an ensuite, also two additional bedroom at the other side of the unit, with an additional full bathroom . This incredible community has a so much in amenities; a real lifestyle for the residents , such as community pool and spa , a very well equipped fitness center, a club house with many areas for family entertainment, tennis court, playground, a car wash area and an indoor basketball / racquetball court. This condominium is located a short drive from the Winter Garden Village shopping area , as well as Downtown Winter garden, with easy access to all main Highways making the commute easier. The Disney World parks are just 9 miles away; this community is definitely a place where families will experience great enjoyment; don't miss the chance to call this unit your NEW HOME!!

330 Southern Pecan Circle Unit 208, Winter Garden
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code
Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural zoning designation). Very quiet. Very private. No HOA and close to Winter Garden and Windermere amenities as well as all theme parks.

13377 Lake Butler Boulevard, 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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