Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida! This vibrant subdivision is perfect for those seeking a serene lifestyle combined with an active community atmosphere. Oakwood Estates is renowned for its lush landscapes, friendly neighbors, and well-maintained homes, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of Oakwood Estates is its commitment to promoting an active lifestyle. Residents here enjoy exclusive access to pickleball courts, a fantastic amenity that has taken the community by storm. Whether you’re a seasoned player or a beginner looking to learn, these courts provide the perfect setting for friendly matches and social gatherings. The sport fosters camaraderie and encourages an active lifestyle, making it easy to connect with fellow residents.

The homes in Oakwood Estates are thoughtfully designed, offering a variety of layouts and styles to suit every taste. Each residence is surrounded by beautifully landscaped yards, providing a peaceful retreat after a long day. With convenient access to local shopping, dining, and recreational activities, you’ll find that everything you need is just moments away.

Embrace the charm of Oakwood Estates, where community spirit thrives, and an active lifestyle awaits. Come and discover your new home in this delightful Winter Haven subdivision, where pickleball courts and friendly faces are just the beginning of what makes this community truly special!

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

Start Your Search