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 not just a collection of homes; it's a lifestyle designed for those who cherish both comfort and recreation. Oakwood Estates boasts an array of beautifully crafted homes, each showcasing modern designs and spacious layouts, perfect for families, retirees, and everyone in between.

One of the standout features of Oakwood Estates is its commitment to an active lifestyle, highlighted by the presence of pickleball courts within the community. Whether you're a seasoned player or new to the game, these courts provide a fantastic opportunity to engage with neighbors, stay fit, and enjoy the Florida sunshine. Pickleball, known for its friendly competition and social atmosphere, is just one of the many ways residents can bond and create lasting friendships.

Surrounded by lush landscapes and serene views, Oakwood Estates offers a peaceful retreat while still being conveniently located near shopping, dining, and recreational activities. With Winter Haven’s renowned lakes and parks just a stone's throw away, outdoor enthusiasts will find plenty of opportunities for boating, fishing, and hiking.

In Oakwood Estates, you’re not just purchasing a home; you’re investing in a community that prioritizes wellness, connection, and fun. Experience the perfect blend of relaxation and activity in this delightful subdivision. Come and discover why Oakwood Estates is the ideal place to call home in sunny Florida!

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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