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

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

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is renowned for its picturesque landscapes, rich history, and a charming small-town atmosphere that offers residents a perfect blend of tranquility and modern convenience. With its lush parks, scenic lakes, and a thriving downtown district, Winter Garden is an ideal place for families, retirees, and anyone seeking a serene lifestyle just minutes away from the bustling Orlando metropolitan area.

One of the standout features of homes in this region is the availability of properties with private tennis courts. Imagine stepping out of your beautifully designed home and onto your own pristine tennis court, where you can enjoy a match with friends or family at your leisure. These homes often come with expansive outdoor spaces, allowing for entertaining, relaxing, or simply soaking in the sunny Florida weather.

The architecture of Winter Garden and Oakland is as diverse as its residents, with charming historic homes mingling alongside contemporary designs. Many properties boast lush landscaping and outdoor amenities, making them perfect for those who appreciate an active lifestyle. Whether you’re a seasoned tennis player or just enjoy the occasional game, having a tennis court at home enhances not only your fitness but also your social life.

In Winter Garden and Oakland, you’re not just buying a home; you’re investing in a lifestyle filled with community spirit, recreational opportunities, and the beauty of Florida living. Discover your dream home with a tennis court today, and embrace the vibrant life that awaits you in this charming region!

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

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 04 SubDv. ⋅ 34787 Zip Code

Here is your opportunity to own a very nicely remodeled 2 Bedroom 2 Bath Downstairs Condominium located at Windtree Gardens in the sweet spot of bustling Winter Garden Florida. This is an ideal unit for first time buyers, a second home or long term investment rental property. The monthly HOA fee is very reasonable and the community is very well maintained. Within minutes you can be on Plant Street in the very popular downtown district and enjoy numerous shops, restaurants, the Crooked Can Brewery, the West Orange Trail and the Splash Pad for the little ones. Just to the south you will find fabulous shopping & dining options at The Winter Garden Village at Fowler Groves. Professional offices and ample medical facilities are all with minutes as well. Be sure to schedule a showing soon as these downstairs units do not come up often.

109 Windtree Lane Unit N, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Watermark Ph 2b SubDv. ⋅ 34787 Zip Code

Welcome to resort-style living in the highly sought-after Watermark community of Winter Garden! This stunning, 2019-built, 4-bedroom, 2.5-bathroom home effortlessly blends modern luxury with absolute convenience. Step inside to find a bright, open-concept floor plan highlighted by premium ceramic tile flooring, soaring high ceilings, and a chef-inspired kitchen featuring granite countertops, stainless steel appliances, a massive island for entertaining, and a sprawling walk-in pantry. Smart storage abounds, including a deep walk-in closet under the stairs. Upstairs, you are greeted by a versatile multi-purpose loft? perfect for a home office, gym, or game room. The palatial primary suite boasts dual walk-in closets and double vanities. Enjoy community tennis courts, an amazing playground, and immediate access to the Watermark clubhouse. Located moments from Horizon West shopping, top-rated schools, and major toll roads. Schedule your private tour today!

14704 Seton Creek Boulevard, Winter Garden

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

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

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

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 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

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