Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida. This charming subdivision is not just a neighborhood; it’s a vibrant community where luxury meets leisure. With its picturesque landscapes and beautifully designed homes, Oakwood Estates offers a serene lifestyle that perfectly balances comfort and recreation.

One of the standout features of this subdivision is its commitment to active living. Residents of Oakwood Estates enjoy exclusive access to pickleball courts, an amenity that has become a favorite pastime for many. Whether you’re a seasoned player or just looking to pick up a new hobby, these courts provide the perfect setting for friendly matches with neighbors or intense games with friends. The environment is welcoming and encourages social interaction, making it easy to forge lasting friendships.

The homes in Oakwood Estates are thoughtfully designed, blending modern aesthetics with functionality. Spacious interiors, gourmet kitchens, and lush outdoor spaces create an inviting atmosphere for families of all sizes. Many homes also feature private backyards, perfect for entertaining or simply enjoying the beautiful Florida weather.

Located in the charming city of Winter Haven, Oakwood Estates is conveniently situated near shopping, dining, and recreational opportunities, including the stunning Chain of Lakes. With a strong sense of community and an array of amenities, Oakwood Estates is not just a place to live; it's a place to thrive. Come discover your dream home in this enchanting subdivision 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 & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & 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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