Weekly Community Focus! Welcome to Cypresswood!
Posted By David Shippey @ Jan 27th 2026 5:59pm In: Winter Haven Community Focus

​The Community was developed and primarily built by John Wood Homes. This Community includes over 1,000 homes comprised of Custom Single Family Homes, Villas, Condominiums, Patio Homes, and Townhomes to accommodate all lifestyles. The homes are mostly two, three, and four bedroom homes. The first homes were built in 1975. Most of the homes were built out by 2007. But, there are still some Custom Homes being built in 2025.

This community is in Southeast Winter Haven FL off Dundee Rd (Hwy 542). The location is close to shopping, restaurants, and downtown. There is easy and quick access to Highway 27 and to Orlando.

It is a Gated community with a full time security guard. The community does have a homeowner's association. They do not have a CDD (Community Development District) fee in the property taxes as some communities do.

The amenities include a Community Swimming Pool, Golf Course, Fitness Center, Tennis Courts, Clubhouse, and a Lounge & Restaurant. The 18-Hole Golf Course was designed by Ron Garl and is open to the public.

If you are looking for a Golf community in Winter Haven, consider Cypresswood. I believe you will enjoy the lifestyle that is offered in this community. If you are interested in seeing the homes currently available in this community, you can visit Cypresswood Homes For Sale. If you have any questions, please contact me.


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