Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a premier subdivision nestled in the heart of Winter Haven, Florida, within the picturesque Polk County. This charming community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone in between.

Oakwood Estates is renowned for its beautifully designed homes that cater to various lifestyles and preferences. Each residence is thoughtfully crafted, showcasing modern amenities and spacious layouts that provide both comfort and style. One of the standout features of this community is its commitment to an active lifestyle, highlighted by the presence of private pickleball courts. Whether you’re a seasoned player or a newcomer to the sport, these courts offer the perfect setting to enjoy friendly matches with neighbors or hone your skills in a vibrant, engaging environment.

Beyond the courts, residents of Oakwood Estates can take advantage of the stunning Florida weather with ample outdoor spaces, parks, and walking trails that encourage an active lifestyle. The community is also conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away.

With its welcoming atmosphere, top-notch amenities, and prime location, Oakwood Estates is more than just a place to live; it’s a community where you can create lasting memories. Discover the charm of Winter Haven and make Oakwood Estates your new home 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 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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