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 is more than just a collection of homes; it’s a lifestyle destination designed for those who appreciate the perfect blend of comfort, recreation, and community spirit.

Oakwood Estates boasts beautifully designed homes that cater to a variety of tastes and lifestyles. Each residence features modern amenities and spacious layouts that provide an inviting atmosphere for families and individuals alike. One standout feature of this community is the availability of homes with private pickleball courts, making it a haven for sports enthusiasts and those who enjoy an active lifestyle. Whether you're a seasoned player or a beginner looking to learn a new sport, having a pickleball court right in your backyard offers endless opportunities for fun and fitness.

In addition to the pickleball amenities, Oakwood Estates is surrounded by lush greenery and scenic landscapes, perfect for leisurely strolls and outdoor activities. The community fosters a friendly atmosphere, encouraging neighbors to connect and engage in various social events.

Living in Oakwood Estates means you’re just a stone’s throw away from Winter Haven’s vibrant downtown, where you can explore delightful shops, restaurants, and local attractions. With its ideal location, fantastic amenities, and a welcoming community, Oakwood Estates is the perfect place to call home. Come and experience the charm and excitement that awaits you in this lovely Florida enclave!

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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