Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a charming subdivision nestled in the heart of Winter Haven, Florida, within the picturesque Polk County. This vibrant community is the perfect blend of tranquility and convenience, offering residents a serene lifestyle while being just minutes away from the bustling amenities of city life.

Oakwood Estates is renowned for its stunning homes, each thoughtfully designed to provide comfort and style. One of the standout features of this community is its dedication to an active lifestyle. Residents can take advantage of the exclusive pickleball courts, perfect for both seasoned players and those looking to learn a new sport. This engaging amenity fosters a sense of camaraderie among neighbors, making it easy to forge lasting friendships while enjoying the Florida sunshine.

The homes in Oakwood Estates boast spacious layouts, modern finishes, and lush landscaping, creating a welcoming atmosphere for families and individuals alike. With a variety of floor plans to choose from, prospective buyers are sure to find the perfect fit for their needs.

Beyond the pickleball courts, residents also have access to scenic walking trails and beautifully maintained parks, ideal for leisurely strolls or family picnics. The community is conveniently located near shopping centers, restaurants, and recreational facilities, ensuring that everything you need is just a stone's throw away.

Discover the charm of Oakwood Estates, where an active lifestyle meets the comforts of home, and experience the vibrant community spirit that makes Winter Haven a truly special place to live. Come join us in this idyllic Florida haven!

Newest Oakwood Estates Homes with Pickleball Court(s) Amenities

$114,995

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven

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