Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a charming subdivision nestled in the picturesque city of Winter Haven, Florida, within the heart of Polk County. This vibrant community is designed for those who appreciate a blend of serene living and active lifestyles. With its lush landscapes and friendly atmosphere, Oakwood Estates is not just a place to live; it’s a place to thrive.

One of the standout features of Oakwood Estates is its commitment to fostering an active community spirit, exemplified by the inclusion of pickleball courts. Whether you’re a seasoned player or a curious newcomer, these courts provide the perfect setting for friendly competition and social gatherings. Pickleball, known for its fun and engaging nature, is a fantastic way to meet neighbors and build lasting friendships while enjoying the Florida sunshine.

The homes in Oakwood Estates are thoughtfully designed, offering a variety of styles and sizes to suit different lifestyles and preferences. Each residence is crafted with modern amenities, spacious layouts, and beautiful outdoor spaces, ideal for family gatherings or quiet evenings under the stars. Many homes feature private backyards, perfect for barbecues or simply unwinding after a long day.

Located conveniently close to shopping, dining, and recreational opportunities, Oakwood Estates is a haven for those who enjoy both tranquility and convenience. Embrace the Florida lifestyle in this welcoming community, where your dream home awaits amidst the charm and warmth of Oakwood Estates!

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