3 hours on Rocket
$10,000 Closing Credit¹
#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.
Insight
Winchester is a Sellers Housing Market, which means prices tend to be higher and homes sell faster.
Median Sold Price
$1,564,000$543/SqFt
+$187,333
+13.6%
Based on all homes sold in the last 12 months
Insight
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
Insight
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
Insight
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?
6 hours on Rocket
$10,000 Closing Credit¹
#73386110, Ngoc Anh Goldstein, Listing office: Leading Edge Real Estate
7 hours on Rocket
$10,000 Closing Credit¹
#73386065, The Marrocco Group, Listing office: Coldwell Banker Realty - Lexington
9 hours on Rocket
$10,000 Closing Credit¹
#73385982, Joanne Hofmann, Listing office: Coldwell Banker Realty - Lexington
9 hours on Rocket
$10,000 Closing Credit¹
#73385985, The Pallotta Group, Listing office: Advisors Living - Winchester
22 hours on Rocket
$10,000 Closing Credit¹
#73385735, Andrew Martini, Listing office: Compass
23 hours on Rocket
$10,000 Closing Credit¹
#73385650, Santana Team, Listing office: Keller Williams Realty Boston Northwest
1 day on Rocket
$10,000 Closing Credit¹
#73385500, The Serrano Team, Listing office: Leading Edge Real Estate
1 day on Rocket
#73385326, Kim Covino & Co. Team, Listing office: Compass
1 day on Rocket
#73385211, Mark Donnellan, Listing office: Advisors Living - Winchester
1 day on Rocket
$10,000 Closing Credit¹
#73384905, Elena Langlois, Listing office: Compass
2 days on Rocket
$10,000 Closing Credit¹
#73384584, Andersen Group Realty, Listing office: Keller Williams Realty Boston Northwest
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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
Disclaimer: The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein. We may make use of information provided by users of this website - see our Terms of Use for more details on our privacy policy.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.