Oakwood Estates Homes with Lake Front Water Frontage

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida. This charming subdivision is a true paradise for those seeking a tranquil lifestyle combined with the beauty of nature. Known for its picturesque landscapes and stunning lakefront properties, Oakwood Estates offers a unique opportunity to embrace the serene waterfront living that Florida is famous for.

Imagine waking up to breathtaking views of glistening waters right from your doorstep. The homes in Oakwood Estates are designed to complement the natural beauty of the surrounding area, featuring spacious layouts and modern amenities that cater to every lifestyle. With direct lakefront access, residents can indulge in a variety of water activities, from kayaking and fishing to simply enjoying peaceful sunsets over the water.

The community is not only about stunning homes; it also fosters a warm, welcoming atmosphere. Neighbors become friends, and the sense of community is palpable. Enjoy leisurely strolls along tree-lined streets, or gather with family and friends at one of the nearby parks. With Winter Haven’s vibrant culture, shopping, and dining just a stone's throw away, Oakwood Estates truly offers the best of both worlds—serenity and convenience.

Whether you’re looking for a family home, a vacation retreat, or a peaceful place to retire, Oakwood Estates is the perfect choice. Discover the beauty of lakefront living and make your dream home a reality in this enchanting community!

Newest Oakwood Estates Homes with Lake Front Water Frontage

$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

$139,900

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

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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