Market report · September 2026
Winchester, MA Housing Market
Sales over the last 12, 6 and 3 months, what is for sale now, and what rents — from MLS data through September 30, 2026. Updated on the 3rd of every month.
- Brokerage
- LPT Realty
- Licensed
- MA Broker
- Towns covered
- 17
- Languages
- English · Tiếng Việt
Is it a buyer’s or a seller’s market in Winchester?
Over the three months to September 2026, Winchester's single-family homes sold for a median $2,025,000 — 100.0% of the final asking price, with 43% going over. Condos sold for a median $788,000 — 101.1% of the final asking price, with 64% going over. 43 single-family homes were for sale on October 20, 2026 — about 2.8 months of supply at the past year's pace — and 17 more were under agreement.
Single-family
Close to balanced
- Sold over asking
- 43%
- Median sale-to-asking
- 100.0%
- Months of supply
- 2.8
51 sales over the last three months (July–September 2026); supply as of October 20, 2026.
Condos
Sellers have the edge
- Sold over asking
- 64%
- Median sale-to-asking
- 101.1%
- Months of supply
- 3.3
28 sales over the last six months (April–September 2026); supply as of October 20, 2026.
Multi-family
Buyers have room to negotiate
- Sold over asking
- 21%
- Median sale-to-asking
- 97.8%
- Months of supply
- 0.9
14 sales over the last twelve months (October 2025–September 2026); supply as of October 20, 2026.
How we call it: see how these numbers are calculated.
Winchester home prices over 12, 6 and 3 months
The same measures over three spans, each ending with September 2026. Read them as a set: the three months hold fewer sales and a single season, and the season changes which homes sell, so a gap between the columns is partly the calendar. Comparisons with the same months a year earlier appear here as the sales archive behind these reports reaches back far enough.
Single-family
| 12 monthsOctober 2025–September 2026 | 6 monthsApril–September 2026 | 3 monthsJuly–September 2026 | |
|---|---|---|---|
| Homes sold | 182 | 102 | 51 |
| Sold per month | 15.2 | 17.0 | 17.0 |
| Median price | $1,765,000 | $1,878,000 | $2,025,000 |
| Middle half of prices | $1.33M–$2.38M | $1.4M–$2.55M | $1.66M–$2.41M |
| Median price per sq ft | $565 | $571 | $578 |
| Median sale-to-asking | 100.0% | 100.0% | 100.0% |
| Sold over asking | 43% | 46% | 43% |
| Sold under asking | 49% | 47% | 49% |
| Typical amount over asking | $51,000 | $51,000 | $34,500 |
| Median size (sq ft) | 3,267 | 3,341 | 3,474 |
Condos
| 12 monthsOctober 2025–September 2026 | 6 monthsApril–September 2026 | 3 monthsJuly–September 2026 | |
|---|---|---|---|
| Homes sold | 58 | 28 | 9 |
| Sold per month | 4.8 | 4.7 | 3.0 |
| Median price | $894,000 | $788,000 | $729,000 |
| Middle half of prices | $665k–$1.38M | $680k–$1.2M | $620k–$1.2M |
| Median price per sq ft | $538 | $522 | $523 |
| Median sale-to-asking | 100.0% | 101.1% | 100.4% |
| Sold over asking | 50% | 64% | 56% |
| Sold under asking | 34% | 25% | 22% |
| Typical amount over asking | $37,000 | $36,500 | $25,000 |
| Median size (sq ft) | 1,598 | 1,700 | 1,431 |
Multi-family
| 12 monthsOctober 2025–September 2026 | 6 monthsApril–September 2026 | 3 monthsJuly–September 2026 | |
|---|---|---|---|
| Homes sold | 14 | 8 | 5 |
| Sold per month | 1.2 | 1.3 | 1.7 |
| Median price | $1,245,000 | $1,130,000 | $1,368,000 |
| Middle half of prices | $1.02M–$1.6M | $980k–$1.37M | $1.2M–$1.46M |
| Median price per sq ft | $447 | $414 | $435 |
| Median sale-to-asking | 97.8% | 98.8% | 98.1% |
| Sold over asking | 21% | 13% | 20% |
| Sold under asking | 64% | 63% | 80% |
| Typical amount over asking | — | — | — |
| Median size (sq ft) | 3,041 | 2,727 | 3,360 |
Winchester sales month by month
Homes sold each month, all types
Share of single-family homes sold over asking
A gap is a month with fewer than five sales.
The numbers behind the charts
| Month | Sold | Single-family median | Condos median | Multi-family median | Single-family over asking |
|---|---|---|---|---|---|
| September 2026 | 14 | $2,021,000 | — | — | 25% |
| August 2026 | 20 | $1,950,000 | $1,180,000 | — | 33% |
| July 2026 | 31 | $2,025,000 | — | — | 56% |
| June 2026 | 29 | $2,213,000 | $817,000 | — | 39% |
| May 2026 | 29 | $1,728,000 | $1,055,000 | — | 55% |
| April 2026 | 15 | $1,560,000 | — | — | 55% |
| March 2026 | 16 | $1,522,000 | $566,000 | — | 30% |
| February 2026 | 15 | $1,458,000 | $750,000 | — | 50% |
| January 2026 | 19 | $1,475,000 | — | — | 58% |
| December 2025 | 24 | $1,627,000 | — | — | 43% |
| November 2025 | 17 | $1,799,000 | $1,100,000 | — | 13% |
| October 2025 | 25 | $1,750,000 | $850,000 | — | 37% |
What is for sale in Winchester now
On October 20, 2026, 60 homes were for sale in Winchester and 22 were under agreement — about 2.8 months of supply at the pace homes sold over the past year.
| Single-family | Condos | Multi-family | |
|---|---|---|---|
| For sale | 43 | 16 | 1 |
| Under agreement | 17 | 5 | 0 |
| Share with a buyer | 28% | 24% | — |
| Months of supply | 2.8 | 3.3 | 0.9 |
| Median asking price | $1,749,000 | $693,000 | — |
| Asking per sq ft | $557 | $560 | — |
| Listed in the last 30 days | 13 | 3 | 0 |
| Price cut in the last 30 days | 13 (typically 3%) | 6 (typically 2%) | 0 |
Winchester by price range
Every type of home together, by what it sold for (or asks), over the last twelve months. A buyer shops by budget first, and competition is rarely the same across a town’s price ranges.
| Price range | Sold | Sale-to-asking | Over asking | For sale | Under agreement | Months of supply |
|---|---|---|---|---|---|---|
| Under $500k | 11 | 95.9% | 0% | 5 | 1 | 5.5 |
| $500k–$750k | 14 | 100.0% | 43% | 4 | 1 | 3.4 |
| $750k–$1M | 17 | 100.0% | 47% | 10 | 3 | 7.1 |
| $1M–$1.5M | 77 | 100.8% | 56% | 13 | 6 | 2.0 |
| $1.5M–$2M | 58 | 100.0% | 47% | 10 | 6 | 2.1 |
| $2M–$3M | 60 | 97.5% | 38% | 9 | 4 | 1.8 |
| $3M and up | 17 | 97.2% | 24% | 9 | 1 | 6.4 |
What a home costs in Winchester, by bedrooms
Single-family, last twelve months
| Bedrooms | Sold | Median | Per sq ft | Size |
|---|---|---|---|---|
| 2 bedrooms or fewer | 3 | — | — | — |
| 3 bedrooms | 46 | $1.32M | $610 | 2,142 |
| 4 bedrooms | 54 | $1.66M | $570 | 2,888 |
| 5 bedrooms | 47 | $2.17M | $520 | 4,591 |
| 6 or more | 32 | $2.52M | $534 | 4,930 |
Condos, last twelve months
| Bedrooms | Sold | Median | Per sq ft | Size |
|---|---|---|---|---|
| Studio or 1 bedroom | 9 | $340k | $630 | 606 |
| 2 bedrooms | 16 | $737k | $514 | 1,387 |
| 3 bedrooms or more | 33 | $1.2M | $526 | 2,303 |
Rents in Winchester
Median monthly rent on leases signed, by bedrooms, and what rentals on the market are asking now.
| 12 months | 6 months | 3 months | Asking now | |
|---|---|---|---|---|
| Studio | $1,8008 leases | — | — | — |
| 1 bedroom | $2,12516 leases | $2,1509 leases | $2,0756 leases | — |
| 2 bedrooms | $3,12522 leases | $2,90019 leases | $3,1009 leases | $3,20011 leases |
| 3 bedrooms | $4,00020 leases | $4,0009 leases | $3,9506 leases | $3,85010 leases |
| 4 or more | $6,84828 leases | $6,70019 leases | $6,74812 leases | $4,8505 leases |
Buying in Winchester: what the numbers say
- Single-family homes have sold close to asking over the last three months — a median 100.0% of the final asking price — with 43% going over, typically by $34,500. That varies from home to home and from one price range to the next.
- Expect competition for condos: over the last six months, 64% sold above their final asking price, typically by $36,500. On many of them, the asking price was not what it took.
- Competition depends on price. Over the last twelve months 56% of homes between $1M and $1.5M sold over asking; under $500k only 0% did, and there are 5.5 months of homes for sale there.
- Of the 43 single-family homes for sale on October 20, 2026, 30 have been listed for more than 30 days. 13 of the 43 cut their price in the last 30 days, typically by 3%. A listing that has sat is where an offer under asking is most often heard.
Selling in Winchester: what the numbers say
- Single-family homes sold at a median 100.0% of their final asking price over the last three months, and 49% sold below it. That is against the LAST asking price: a home cut before it sold is counted against the lower one, so the price you start at matters more than this number suggests.
- Your competition: 43 single-family homes for sale and 17 under agreement (28% of the market already has a buyer). At the past year's pace the homes for sale would take about 2.8 months to sell.
- Homes between $750k and $1M sell more slowly: 10 homes for sale against 17 sold in twelve months, or 7.1 months of supply. Expect a longer sale there.
- Timing: the most single-family homes closed in July 2026 (27) and the fewest in November 2025 (8). A closing follows the accepted offer by several weeks, so a busy month for closings reflects offers made the month or two before.
Winchester monthly market reports
How the Winchester numbers are calculated
Based on information from MLS Property Information Network, Inc. (MLS PIN) for closings from October 1, 2025 through September 30, 2026, and listings as of October 20, 2026. The figures are calculated by Kevin Hoang, LPT Realty, not by MLS PIN, and are believed accurate but not guaranteed. Sales that were never listed on MLS — some private and new-construction sales — are not included.
- Sale-to-asking
- The sale price divided by the final asking price, which is the only one MLS data carries. A home that cut its price and then sold at the lower figure reads as 100%.
- Sold over asking
- The share of sales that closed above the final asking price, by any amount.
- Months of supply
- Homes for sale now, divided by the average number sold per month over the past twelve months: how long the current listings would last if nothing new came on. It is lower in spring and higher in winter, as inventory is.
- Under agreement
- Listings with an accepted offer that has not closed, including contingent ones.
- Windows
- Whole calendar months ending with September 30, 2026. A closing reaches MLS a few days after it happens, so a window ending today would undercount its own last week.
- Medians
- The middle sale: half sold for more, half for less. A median needs at least five sales and is shown as a dash otherwise. A month’s median moves with which homes happened to close, so the three- and twelve-month figures are the steadier read.
- Listed in the last 30 days
- When this site first saw the listing. Tracking began on September 2, 2026; MLS data does not include days on market, so these pages do not report it.
- Rents
- Leases recorded in MLS, by bedroom count. Parking spaces, and anything under $500 or over $30,000 a month, are left out.
- Who has the edge
- We call it for sellers when 50% or more of homes sold above their final asking price, or the median sold above 101.0% of it; for buyers when the median sold at or below 98.0% and fewer than 25% went over. Anything between is close to balanced.
These figures describe a town, not a house. For what a particular home would sell for, ask for a written valuation.
Buying or selling in Winchester?
These numbers describe a whole town. What they mean for one home, one street or one budget is a conversation, and the first one costs nothing.