Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a premier subdivision nestled in the heart of Winter Haven, Florida. Known for its serene landscapes and vibrant community spirit, Oakwood Estates offers a perfect blend of comfort and luxury. This charming neighborhood is situated in Polk County, just a stone's throw away from the stunning lakes and recreational facilities that Winter Haven is famous for.

One of the standout features of Oakwood Estates is its commitment to an active lifestyle, highlighted by the presence of dedicated pickleball courts. Whether you’re a seasoned player or just looking to learn a new sport, these courts provide the perfect setting for friendly matches and community events. The pickleball courts are not just amenities; they are a hub for socializing and building lasting friendships with your neighbors.

The homes in Oakwood Estates are thoughtfully designed, featuring spacious layouts and modern finishes that cater to both families and retirees alike. With beautifully landscaped yards and access to community parks, residents can enjoy the outdoors while soaking up the Florida sunshine.

Living in Oakwood Estates means you’re never far from the action, with nearby shopping, dining, and entertainment options just minutes away. Plus, the scenic lakes and parks offer endless opportunities for outdoor adventures.

Join us in Oakwood Estates, where a vibrant lifestyle and a welcoming community await you. Experience the perfect blend of relaxation and recreation, all while enjoying the charm of Winter Haven, Florida. Your dream home is just around the corner!

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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