Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a delightful subdivision nestled in the heart of Winter Haven, Florida, in the picturesque Polk County. This charming community offers an idyllic blend of modern living and serene surroundings, making it a perfect haven for families, retirees, and everyone in between.

Oakwood Estates stands out with its beautifully designed homes that cater to a variety of lifestyles. Each residence is thoughtfully crafted, boasting spacious layouts, contemporary finishes, and lush landscaping. One of the highlights of this community is its unique amenity: private pickleball courts. Whether you're a seasoned player or just looking to enjoy some friendly competition, these courts provide the perfect setting for socializing and staying active.

Imagine stepping outside your door to enjoy a game with neighbors or family, fostering a sense of community and camaraderie. The courts are designed for players of all skill levels, ensuring that everyone can join in on the fun. Beyond pickleball, Oakwood Estates is conveniently located near parks, shopping, and dining options, making it easy to enjoy all that Winter Haven has to offer.

With its perfect blend of leisure and convenience, Oakwood Estates is more than just a neighborhood; it’s a lifestyle. Come discover your dream home in this vibrant community where happiness and activity await at every corner. Experience the charm of Oakwood Estates, and let the good times roll on the pickleball courts!

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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