Oakwood Estates Homes with Pickleball Court(s) Amenities

Welcome to Oakwood Estates, a picturesque subdivision nestled in the heart of Winter Haven, Florida. This charming community in Polk County offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between. With its tree-lined streets and beautifully landscaped yards, Oakwood Estates embodies the essence of suburban bliss.

One of the standout features of Oakwood Estates is its commitment to an active lifestyle. Residents can enjoy the luxury of homes equipped with private pickleball courts, a sport that has taken the recreational world by storm. Whether you’re a seasoned player or a beginner, these courts provide a fantastic way to stay fit while having fun. Imagine stepping out of your beautifully designed home and onto your very own court, ready to challenge friends or enjoy a leisurely game with family.

Beyond the courts, Oakwood Estates is conveniently located near a variety of shopping, dining, and entertainment options. The vibrant city of Winter Haven boasts beautiful lakes, parks, and a welcoming community atmosphere. Spend your weekends exploring local farmers' markets, enjoying waterfront activities, or indulging in the culinary delights of nearby eateries.

In Oakwood Estates, you’re not just buying a home; you’re investing in a lifestyle that prioritizes wellness, community, and leisure. Discover the charm and convenience of this exceptional subdivision, where your dream home awaits amidst a backdrop of active living and serene surroundings. Come and see for yourself why Oakwood Estates is the perfect place to call 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

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