Oakwood Estates Homes with Lake Front Water Frontage

Welcome to Oakwood Estates, a serene and picturesque subdivision nestled in the heart of Winter Haven, Florida. This enchanting community offers a perfect blend of tranquility and luxury, making it an ideal choice for families, retirees, and anyone seeking a peaceful lakeside lifestyle.

Oakwood Estates is renowned for its stunning homes that boast breathtaking lakefront properties. Imagine waking up each morning to the gentle sound of water lapping at the shore and enjoying spectacular views from your own backyard. These beautifully designed residences feature spacious layouts, modern amenities, and expansive outdoor spaces, perfect for entertaining or simply soaking in the natural beauty that surrounds you.

Living in Oakwood Estates means embracing a lifestyle rich in outdoor activities. With direct access to the serene lakes of Winter Haven, residents can enjoy fishing, kayaking, and leisurely strolls along the water’s edge. The community is also conveniently located near parks, walking trails, and recreational facilities, ensuring that there’s always something to do.

In addition to its natural beauty, Oakwood Estates is ideally situated near shopping, dining, and entertainment options. Whether you’re looking for a cozy café, a vibrant shopping district, or family-friendly attractions, everything is just a short drive away.

Discover the charm of Oakwood Estates, where lakefront living meets modern convenience. Experience the joy of calling this beautiful community home, where every day feels like a vacation. Your dream home awaits in this idyllic Florida paradise!

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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