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 serene living and active lifestyle, making it an ideal choice for families, retirees, and anyone looking to enjoy the Florida sunshine.

Oakwood Estates is known for its beautifully designed homes that boast modern amenities and spacious layouts. One of the standout features of this community is its dedication to promoting an active lifestyle, highlighted by the presence of pickleball courts. Whether you’re a seasoned player or a beginner looking to learn the ropes, these courts provide a fantastic space for residents to engage in friendly matches, socialize, and stay fit.

In addition to pickleball, Oakwood Estates is surrounded by lush landscaping and scenic views, ensuring that you can enjoy the great outdoors right from your doorstep. The community is conveniently located near shopping centers, dining options, and recreational parks, making it easy to access everything you need for a comfortable lifestyle.

With a strong sense of community and a variety of amenities, Oakwood Estates is more than just a place to live; it’s a place to thrive. Experience the warmth of friendly neighbors and the joy of an active lifestyle in this delightful Winter Haven subdivision. Come explore your dream home in Oakwood Estates today, where every day feels like a vacation!

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