Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a vibrant and welcoming subdivision nestled in the heart of Winter Haven, Florida, in beautiful Polk County. This charming community is designed for those who appreciate a blend of modern living and a laid-back Florida lifestyle. With its picturesque tree-lined streets and beautifully landscaped yards, Oakwood Estates offers a serene environment that feels like home from the moment you arrive.

One of the standout features of Oakwood Estates is its commitment to active living. For pickleball enthusiasts, this community is a dream come true! With dedicated pickleball courts on-site, residents can enjoy friendly matches and socialize with neighbors, fostering a sense of camaraderie and community spirit. Whether you’re a seasoned player or just looking to learn a new sport, the courts provide the perfect backdrop for fun and fitness.

The homes in Oakwood Estates are thoughtfully designed, offering a variety of layouts to suit different lifestyles and family sizes. Many residences feature spacious open-concept designs, modern kitchens, and inviting outdoor spaces perfect for entertaining or relaxing. With the Florida sun shining bright, you’ll find plenty of opportunities to enjoy your private backyard or take a leisurely stroll through the neighborhood.

Located just minutes from Winter Haven’s vibrant downtown, residents have easy access to shopping, dining, and recreational activities. Whether you’re exploring local parks, enjoying a day at the lake, or indulging in the culinary delights of the area, Oakwood Estates places you in the heart of it all.

Discover your new home in Oakwood Estates, where active living meets community charm!

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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