Oakwood Estates Homes with Lake Front Water Frontage

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida, within the picturesque Polk County. This charming subdivision offers a unique blend of serene lakefront living and modern convenience, making it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle.

Oakwood Estates boasts stunning homes with breathtaking lakefront properties, providing residents with direct access to the sparkling waters of the area’s pristine lakes. Imagine waking up to the gentle sounds of nature, sipping your morning coffee on a spacious deck while enjoying panoramic views of the shimmering lake. These homes are designed with outdoor living in mind, featuring expansive backyards perfect for gatherings, barbecues, or simply unwinding after a long day.

The community is not just about beautiful homes; it fosters a friendly atmosphere where neighbors become friends. Residents enjoy a variety of amenities, including walking trails, parks, and access to water activities like fishing, kayaking, and paddleboarding. With Winter Haven’s vibrant downtown just a short drive away, you’ll find an array of shopping, dining, and entertainment options to explore.

Whether you’re looking for a peaceful retreat or an active lifestyle, Oakwood Estates is the perfect place to call home. Discover the beauty of lakefront living and experience the warmth of this welcoming community. Come and see for yourself why Oakwood Estates is the ideal destination for your next chapter!

Newest Oakwood Estates Homes with Lake Front Water Frontage

$114,995

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.

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

$139,900

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.

Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The guest bedroom is attached to the guest bathroom offering privacy and convenience to your guests. The Lanai which is also air conditioned (vent behind the couch) offers a wonderful area to sit and enjoy your morning coffee where you can watch the world go by. Oakwood Estates offers many activities and amenities including two pools, two clubhouses, tennis courts, shuffle board, miniature golf and much more. You can stay as busy as you like or just sit back and enjoy the peaceful community. The golf cart is included in the sale of the home. The Sellers have a home warranty in place and with a reasonable offer will pay for three month to continue the plan. Make your appointment today to see this beautiful home.

4234 Rolling Oaks Drive, Winter Haven

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