Crossroads at Lake Region
Homes for Sale in Winter Haven, FL

Crossroads at Lake Region market snapshot (as of August 2, 2026): the median sale price is about $489K ($180 per sq ft over the trailing 12 months of closed sales), and a median 104 days on market for closed sales.

In ZIP 33881 (Winter Haven), 406 homes closed in the last 12 months at a median of $308K ($163/sq ft), down 3.3% year over year, with a median 68 days on market. Right now 1 active and 1 pending listings put supply at about 3.0 months - a balanced market. See the live ZIP 33881 housing market and the Polk County market.

Crossroads at Lake Region is a community of 108 homes in Winter Haven, Polk County, built between 2006 and 2020 (median 2007), with a median living area of about 3,846 square feet. 90% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Crossroads at Lake Region is a small, built-out enclave of 108 large homes in Winter Haven, with construction running from 2006 to 2020 and a homestead share near 90% - a stable, owner-occupied pocket where listings are scarce.

• Polk County Public Schools (verify by address) · Public
• Confirm zoned elementary, middle, and high · By address
• Magnet and choice options may apply · Choice

Zoned schools reflect the assignments reported on recent Crossroads at Lake Region listings and can change; always confirm with Polk County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Crossroads at Lake Region address.

The housing stock is consistent: roughly 108 homes built between 2006 and 2020, with the median year built at 2007, so most of the community dates to the earlier end of that window. Living areas are generous, with a median near 3,846 square feet. The high homestead share, close to 90%, points to long-term ownership rather than frequent flipping.

No community amenities surfaced in current MLS listings, so judge this on the homes and the location, not on shared facilities. With zero active listings and a median of 104 days on market across a narrow recent closing window, inventory is the limiting factor. When a home does list, the per-square-foot math and condition will set the number far more than any neighborhood amenity story.

In a thin, low-turnover market with no active inventory, timing and comp discipline matter more than marketing noise. We track this pocket closely, read the per-square-foot and condition signals behind each sale, and advise on realistic pricing and patience whether you are listing a large home or trying to be first in line when one comes up.