Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a picturesque subdivision nestled in the heart of Winter Haven, Florida, in beautiful Polk County. This charming community is designed for those seeking a blend of comfort, luxury, and an active lifestyle. With its lush landscapes and inviting atmosphere, Oakwood Estates is more than just a neighborhood; it’s a place where memories are made and dreams come to life.

One of the standout features of Oakwood Estates is its dedication to wellness and recreation, highlighted by the inclusion of private pickleball courts. Perfect for both seasoned players and beginners, these courts offer a fantastic opportunity to engage in this rapidly growing sport, fostering a sense of community and camaraderie among residents. Imagine spending your afternoons perfecting your serve or enjoying friendly matches with neighbors just steps from your front door!

The homes in Oakwood Estates are beautifully designed, showcasing modern architecture and spacious layouts that cater to a variety of lifestyles. Each residence is thoughtfully crafted with high-quality finishes, ample natural light, and outdoor spaces perfect for entertaining or simply relaxing.

With a location that offers easy access to Winter Haven’s vibrant downtown area, shopping, dining, and recreational activities, Oakwood Estates truly embodies the ideal Florida lifestyle. Whether you’re seeking a family home, a retirement haven, or a seasonal retreat, this subdivision invites you to experience the warmth of community living paired with the thrill of an active lifestyle. Discover your dream home in Oakwood Estates today!

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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