#73386306, Katherine Waters Clark, Listing office: Compass
Winchester Housing Market Report May 2025•Middlesex County, Massachusetts
Housing Prices in Winchester, MA
How much do homes in Winchester, MA cost?
Housing Market Conditions
Is Winchester, MA a buyer’s or seller’s market?
Seller'sMarket
Buyer'sMarket
Winchester is a Seller's Market
Difference Since May 2024
Since last year, Winchester has remained a Seller's Market.
Winchester is a Sellers Housing Market, which means prices tend to be higher and homes sell faster.
Median Sold Price
Based on all homes sold in the last 12 months
Homes in Winchester have sold for 13.6% more than they did a year ago.
Summary: The median home sold price in Winchester was $1,564,000 in May 2025, up 13.6% from last year, and the median price per square foot was $543.
Median Sold Price By Bedrooms
Beds | May 2024 | May 2025 | Change YoY |
---|---|---|---|
11 Bedroom | $361.2K | $370K | +2.4% |
22 Bedrooms | $757K | $755K | -0.3% |
33 Bedrooms | $1.1M | $1.2M | +7.0% |
44 Bedrooms | $1.4M | $1.6M | +9.6% |
55+ Bedrooms | $1.9M | $2.2M | +17.3% |
Summary: Winchester housing price by bedroom type for May 2025, compared to the previous year. The home price for 1 bedroom homes increased by +2.4%. The home price for 2 bedroom homes decreased by -0.3%. The home price for 3 bedroom homes increased by +7.0%. The home price for 4 bedroom homes increased by +9.6%. The home price for 5 bedroom homes increased by +17.3%.
How does Winchester, MA compare with other places?
Market comparison tool
Data and numbers shown are subject to change and may vary based on different timeframes.
Winchester, MA
Housing supply in Winchester, MA
How many homes are available in Winchester, MA?
Number of Homes For Sale
Last Month | 2 months ago | Change MoM |
---|---|---|
104Last MonthMay 2025 | ||
842 months agoApr 2025 | +23.8 % Change MoMApr – May |
Summary: The Winchester real estate market had 104 homes for sale in May 2025, a 23.8 % increase compared to Apr 2025.
Number of Homes Sold
Last Month | 2 months ago | Change MoM |
---|---|---|
18Last MonthMay 2025 | ||
102 months agoApr 2025 | +80.0 % Change MoMApr – May |
Homes For Sale By Bedroom Count
Beds | Apr 2025 | May 2025 | Change MoM |
---|---|---|---|
11 Bedroom | 1 | 2 | +100.0% |
22 Bedrooms | 7 | 12 | +71.4% |
33 Bedrooms | 21 | 25 | +19.0% |
44 Bedrooms | 20 | 24 | +20.0% |
55+ Bedrooms | 35 | 41 | +17.1% |
Summary: Winchester housing inventory by bedroom type for May 2025, compared to the previous month. The inventory for 1 bedroom homes increased by +100.0%. The inventory for 2 bedroom homes increased by +71.4%. The inventory for 3 bedroom homes increased by +19.0%. The inventory for 4 bedroom homes increased by +20.0%. The inventory for 5 bedroom homes increased by +17.1%.
Asking Price vs. Sold Price
How much do homes in Winchester, MA cost?
Over Asking Price6 Homes
At Asking Price5 Homes
Under Asking Price7 Homes
If you're buying a home in Winchester, you may be able to get a good deal. 38.9% of homes here sold below asking price last month.
Summary: A total of 18 homes were sold or pending in Winchester in May 2025, up by 80.0% month-over-month. Of the 18 sold homes, 39% were sold under asking, 28% were sold at asking, and and 33% were sold over asking.
Days on Market for Winchester, MA
How long does it take to sell a home in Winchester, MA?
Breakdown of Home Sale Times
Under 30 Days13 Homes
30 – 90 Days4 Homes
Over 90 Days1 Home
Many homes in Winchester are selling fast, if you're buying plan to act quickly.
Summary: During May 2025, 18 homes were sold in Winchester; 72% of homes were sold within 30 days, 22% of homes were sold within 30 to 90 days, and 6% of homes were sold over 90 days.
Average Sale Time
This Year | 1 year ago | Change YoY |
---|---|---|
27 DaysThis YearMay 2025 | ||
20 Days1 year agoMay 2024 | +31.1 % Change YoYMay 2024 – May 2025 |
Summary: Homes in Winchester had an average listing age of 27 days in May 2025, up by 31.1% compared to the previous year.
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Newest Listings in Winchester, MA
What homes are available in Winchester, MA?
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MLS Disclaimers and Copyright
Based on information from MLS Property Information Network Inc., for the period 06/01/2023 - 06/01/2025

Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 6/5/2025, 3:45:27 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.