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 designed for those who appreciate a blend of tranquility and active living, making it an ideal place for families, retirees, and everyone in between.

Oakwood Estates boasts a variety of beautifully crafted homes that reflect modern design and comfort. Each residence is thoughtfully laid out, providing ample space for relaxation and entertainment. One of the standout features of this community is its commitment to an active lifestyle, highlighted by the inclusion of pickleball courts. Whether you're a seasoned player or new to the game, these courts offer a fantastic opportunity to engage with neighbors and enjoy the Florida sunshine.

The subdivision is surrounded by lush greenery and scenic landscapes, creating a serene environment that enhances your living experience. Residents can take advantage of nearby parks, walking trails, and recreational facilities, making it easy to stay active and connected with nature.

In addition to its amenities, Oakwood Estates is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. With its welcoming atmosphere and community spirit, Oakwood Estates offers not just a home, but a lifestyle. Come discover the charm of this delightful neighborhood and find your perfect slice of paradise in Winter Haven, Florida!

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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