Oakwood Estates Real Estate

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Florida! This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal location for families, retirees, and everyone in between. With its picturesque tree-lined streets and beautifully manicured lawns, Oakwood Estates exudes a welcoming atmosphere that invites you to call it home.

One of the standout features of Oakwood Estates is its diverse range of beautiful homes, each designed to cater to various lifestyles and preferences. From cozy single-family residences to spacious modern designs, there’s something for everyone in this vibrant community. Many homes boast spacious backyards perfect for entertaining, gardening, or simply soaking up the Florida sunshine.

Residents of Oakwood Estates enjoy easy access to a variety of amenities. The subdivision is conveniently located near shopping centers, top-rated schools, and recreational parks, ensuring that everything you need is just a stone’s throw away. For those who love the outdoors, nearby nature trails and parks provide ample opportunities for hiking, biking, and enjoying Florida's stunning natural beauty.

Community spirit thrives in Oakwood Estates, with regular neighborhood events and gatherings that foster connections among residents. Whether you’re enjoying a weekend barbecue or a seasonal festival, you’ll find that the sense of belonging here is second to none.

If you're looking for a place that combines comfort, community, and convenience, Oakwood Estates in Florida is the perfect choice. Discover your dream home in this idyllic subdivision today!

Newest Listings in Oakwood Estates

4332 Cherrywood Street, Winter Haven image

4332 Cherrywood Street, Winter Haven $115,000

Oakwood Estates 55+ Community | Fully Furnished Home with Over $19K in Upgrades | Winter Haven, FL Over $19,000 in recent major upgrades means the big-ticket items are...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

3418 Monarch Way, Green Cove Springs image

3418 Monarch Way, Green Cove Springs $433,900

Under Construction. Set within Oakwood Estates in Green Cove Springs, the Carlisle showcases an expansive two-story layout filled with refined finishes, upgraded features...

4 Beds
3 Baths
Oakwood Estates SubDv.
32043 Zip Code

4234 Rolling Oaks Drive, Winter Haven image

4234 Rolling Oaks Drive, Winter Haven $139,900

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. Th...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4807 Plumwood Street, Winter Haven image

4807 Plumwood Street, Winter Haven $110,000

Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious a...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4242 Cedarwood Street, Winter Haven image

4242 Cedarwood Street, Winter Haven $110,000 ▼

Pack your bags and move right into this fully furnished home. You won't find any carpet in this well maintained home with new vinyl plank flooring in the living room, di...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4146 Sprucewood Street, Winter Haven image

4146 Sprucewood Street, Winter Haven $140,000

You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfect for entertaining....

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4158 Rolling Oaks Drive, Winter Haven image

4158 Rolling Oaks Drive, Winter Haven $124,900

Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contains a large pantry for ...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4132 Sprucewood Street, Winter Haven image

4132 Sprucewood Street, Winter Haven $129,000

Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the la...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4212 Cedarwood Street, Winter Haven image

4212 Cedarwood Street, Winter Haven $129,900 ▼

Spacious living plan and Luxurious Kitchen just updated for the top Chef status. As you come in through the covered carport you'll notice the Newly installed flooring th...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4253 Cedarwood Street, Winter Haven image

4253 Cedarwood Street, Winter Haven $99,000

Move right into this fully furnished home. This home offers lots of space with walk in closets in both bedrooms and a new vanity in the primary bathroom. Plus the lanai...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4173 Rolling Oaks Drive, Winter Haven image

4173 Rolling Oaks Drive, Winter Haven $95,000 ▼

Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing cool blue paint and ...

2 Beds
2 Baths
Oakwood Estates SubDv.
33880 Zip Code

4155 Sprucewood Street, Winter Haven image

4155 Sprucewood Street, Winter Haven $115,000 ▼

Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, pe...