Oakwood Estates Homes with Lake Front Water Frontage

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida. This picturesque subdivision offers a serene lifestyle surrounded by the natural beauty of the Sunshine State. Oakwood Estates is renowned for its stunning lakefront properties, providing residents with breathtaking views and direct access to the tranquil waters that define this charming community.

Imagine waking up each morning to the gentle sounds of nature, with the shimmering lake just steps from your door. The homes in Oakwood Estates boast exquisite waterfront frontage, allowing you to indulge in a variety of water activities right from your backyard. Whether you enjoy fishing, kayaking, or simply soaking in the sun, this community offers the perfect backdrop for your outdoor adventures.

The architecture in Oakwood Estates reflects a harmonious blend of modern elegance and classic charm, with spacious layouts and high-quality finishes. Each home is thoughtfully designed to maximize natural light and enhance the stunning lake views, creating a warm and inviting atmosphere for families and individuals alike.

Beyond the beauty of the homes and the lake, Oakwood Estates is conveniently located near Winter Haven's vibrant downtown area, where you can explore local shops, dining, and recreational activities. With its friendly community spirit and picturesque surroundings, Oakwood Estates is not just a place to live—it's a lifestyle.

Discover the tranquility and charm of lakefront living in Oakwood Estates, where your dream home awaits amidst the splendor of Florida's lakeside paradise. Come and experience the magic of this exceptional community today!

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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