Oakwood Estates Homes with Pickleball Court(s) Amenities

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

Oakwood Estates features beautifully designed homes that cater to a variety of lifestyles, with options ranging from cozy single-family residences to spacious multi-bedroom layouts. Each home is thoughtfully crafted, boasting contemporary finishes and spacious layouts that encourage both comfort and elegance. The community is enhanced by lush landscaping and well-maintained common areas, providing a warm and inviting atmosphere for residents and visitors alike.

One of the standout features of Oakwood Estates is its commitment to an active lifestyle, highlighted by the inclusion of pickleball courts within the community. Pickleball has rapidly become one of the most popular sports, and residents here enjoy the convenience of having dedicated courts right at their doorstep. Whether you're a seasoned player or new to the game, these courts provide a fantastic opportunity to socialize, stay fit, and enjoy the Florida sunshine.

In addition to the recreational amenities, Oakwood Estates is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. With its perfect blend of community spirit, recreational amenities, and prime location, Oakwood Estates is truly a hidden gem in Winter Haven, FL. Come explore the possibilities and make Oakwood Estates your new home!

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

Start Your Search