The Winchester housing market is somewhat competitive. The median sale price of a home in Winchester was $249K last month, down 30.8% since last year. The median sale price per square foot in Winchester is $229, up 102.7% since last year.
What is the housing market like in Winchester today?
In May 2025, Winchester home prices were down 30.8% compared to last year, selling for a median price of $249K.
$249K
Sale Price
-30.8% since last year
$229
Sale $/Sq. Ft.
+102.7% since last year
Under List Price
1.7%
Days on Market
27
Down Payment
—
Total Homes Sold
2
To compare other locations to the Winchester and U.S. housing market, enter a city, neighborhood, state, or zip code into the search bar. Learn which home features in Winchester 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 Winchester
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 Winchester housing market?
Winchester is somewhat competitive. Homes sell in 27 days.
0
100
60
Somewhat 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 12 months
Some homes get multiple offers.
The average homes sell for about 2% below list price and go pending in around 27 days.
Hot homes
can sell for about 2% above list price and go pending in around 9 days.
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 Winchester housing
Learn about natural hazards and environmental risks, such as floods, fires, wind, and heat that
could impact homes in Winchester.
Flood Factor - Severe
34% of properties are at risk of severe flooding over the next 30 years
Flood Factor
Winchester has a severe risk of flooding. 162 properties in Winchester are likely to be
severely affected
by flooding over the next 30 years. This represents 34% of all properties in Winchester. Flood risk is increasing slower than the national average.
99% of properties are at risk of wildfire over the next 30 years
Fire Factor
Winchester has a moderate risk of wildfire. There are 606 properties in Winchester that have some risk of being affected by wildfire over the next 30 years. This represents 99% of all properties in Winchester.
100% of properties are at moderate
risk of a severe wind event over the next 30 years
Wind Factor
Winchester has a Moderate Wind Factor® risk based on the projected likelihood and speed of hurricane, tornado, or severe storm winds impacting it. Winchester is most at risk from hurricanes. 608 properties in Winchester 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 65 mph. In 30 years, an event of this same likelihood would show increased wind gusts of up to 77 mph.