The Winding Cypress housing market is not very competitive. The median sale price of a home in Winding Cypress was $760K last month, down 1.9% since last year. The median sale price per square foot in Winding Cypress is $341, down 14.3% since last year.
What is the housing market like in Winding Cypress today?
In May 2025, Winding Cypress home prices were down 1.9% compared to last year, selling for a median price of $760K.
All Home Types
Median Sale PriceAll Home Types
Median Sale Price
(All Home Types)
$760,000
-1.9% YoY | May 2025
Based on Redfin calculations of home data from MLS and/or public records.
Location
Data
May 2025
Growth
% YoY
Winding Cypress, FL
$760,000
-1.9%
United States
To compare other locations to the Winding Cypress and U.S. housing market, enter a city, neighborhood, state, or zip code into the search bar. Learn which home features in Winding Cypress add value to a home.
How much is your home worth? Track your home’s value and compare it to nearby sales.
Work with the best agents in Winding Cypress
Redfin agents are among the most experienced in the industry, so we know how to help you win in today's market.
How hot is the Winding Cypress housing market?
Winding Cypress is not very competitive. Homes sell in 64 days.
0
100
27
Not Very Competitive
Redfin Compete Score™
The Redfin Compete Score rates how competitive an area is on a scale of 0 to 100, where 100 is the most competitive.
Calculated over the last 9 months
Multiple offers are rare.
The average homes sell for about 3% below list price and go pending in around 64 days.
Hot homes
can sell for about 2% below list price and go pending in around 26 days.
Based on Redfin calculations of home data from MLS and/or public records.
Location
Data
May 2025
Growth
% YoY
Winding Cypress, FL
96.4%
-1.3 pt
United States
Winding Cypress Migration & Relocation Trends
In Feb '25 - Apr '25, 40% of Winding Cypress homebuyers searched to move out of Winding Cypress, while 60% looked to stay within the metropolitan area.
Where are people moving to Winding Cypress from?
Across the nation, 1% of homebuyers searched to move into Winding Cypress from outside metros.
Miami homebuyers searched to move into Winding Cypress more than any other metro followed by Chicago and New York.
Where are people from Winding Cypress moving to?
60% of Winding Cypress homebuyers searched to stay within the Winding Cypress metropolitan area.
Sarasota was the most popular destination among Winding Cypress homebuyers followed by Knoxville and Greenville.
This data does not reflect actual moves. The latest migration analysis is based on a sample of about two
million Redfin.com users who searched for homes across more than 100 metro areas. To be included in this dataset, a Redfin.com user
must have viewed at least 10 homes in a three month period. This dataset excludes all rentals data.
School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.
Climate's impact on Winding Cypress housing
Learn about natural hazards and environmental risks, such as floods, fires, wind, and heat that
could impact homes in Winding Cypress.
Flood Factor - Major
95% of properties are at risk of severe flooding over the next 30 years
Flood Factor
Winding Cypress has a major risk of flooding. 469 properties in Winding Cypress are likely to be
severely affected
by flooding over the next 30 years. This represents 95% of all properties in Winding Cypress. Flood risk is increasing faster than the national average.
99% of properties are at risk of wildfire over the next 30 years
Fire Factor
Winding Cypress has a moderate risk of wildfire. There are 825 properties in Winding Cypress that have some risk of being affected by wildfire over the next 30 years. This represents 99% of all properties in Winding Cypress.
100% of properties are at extreme
risk of a severe wind event over the next 30 years
Wind Factor
Winding Cypress has an Extreme Wind Factor® risk based on the projected likelihood and speed of hurricane, tornado, or severe storm winds impacting it. Winding Cypress is most at risk from hurricanes. 826 properties in Winding Cypress have some risk of being in a severe wind event within the next 30 years.
Wind likelihood over time
If an exceedingly rare windstorm
(a 1-in-3,000 year storm event)
occurred today, it could cause wind gusts of up to 174 mph. In 30 years, an event of this same likelihood would show increased wind gusts of up to 189 mph.
100% of properties are at extreme
risk of heat over the next 30 years
Heat Factor
Winding Cypress has an extreme risk from heat. This is due to
"feels like" temperatures
increasing, and because 100% of homes in Winding Cypress have an Extreme Heat Factor®.
Winding Cypress is expected to see a 300% increase in the number of days over 108ºF over the next 30 years. Winding Cypress is expected to experience 7