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 offers a perfect blend of suburban tranquility and active living, making it an ideal place to call home. With its lush landscapes and well-maintained streets, Oakwood Estates is designed for those who appreciate both comfort and convenience.

One of the standout features of Oakwood Estates is its commitment to promoting an active lifestyle. Residents can enjoy exclusive access to pickleball courts, a beloved sport that combines elements of tennis, badminton, and ping-pong. Whether you’re a seasoned player or new to the game, these courts provide a fantastic opportunity to engage with neighbors, stay fit, and enjoy the Florida sunshine. Imagine sunny afternoons spent perfecting your serve or friendly matches with friends and family just steps from your front door.

The homes in Oakwood Estates are thoughtfully designed to cater to a variety of lifestyles, featuring spacious layouts and modern amenities that ensure comfort and convenience. With a range of styles and sizes, there’s a perfect home waiting for everyone. The community is also conveniently located near shopping centers, dining options, and recreational parks, making everyday errands a breeze.

In Oakwood Estates, you’re not just buying a home; you’re investing in a lifestyle. Embrace the warmth of a friendly neighborhood, the thrill of pickleball matches, and the beauty of Winter Haven. Come discover your new home in Oakwood Estates today!

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 & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & 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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