Winding Cypress, FL housing market

The median sale price in Winding Cypress, FL was $818K in May 2026, up 7.6% year over year, measured across homes that actually closed that month (Redfin). The twelve months through May 2026 averaged $764K, easing from $904K across the twelve months before that. That puts prices 19.5% below the strongest twelve-month stretch on record here, which ended in Jan 2024 at $949K.

Buyers had 9 homes to choose from in May 2026 (Redfin). 1 homes came to market in May 2026, against 6 closings. Homes that sold in May 2026 took a median of 70 days to go under contract, 12 days faster than this market's usual May pace.

Winding Cypress, FL is a small market: 48 homes sold in the twelve months through May 2026. A single closing moves the monthly median here, so the averages above run over twelve months rather than three, and months-of-supply and bidding-competition readings are left to the charts below rather than summarized as a market verdict.

This page tracks 9 monthly housing series for Winding Cypress, FL — median sale price, inventory (active), median days on market, months of supply, homes sold, new listings, and more — sourced from Redfin, running from Sep 2016 through May 2026. Chart any of them below, switch between levels and year-over-year change, or add nearby Florida markets to compare side by side.