By Kevin Hoang · Published October 20, 2026 · Sales through September 30, 2026
14 homes sold in Winchester in September 2026: 12 single-family homes and 2 multi-families — the fewest in twelve months. The median single-family home sold for $2,021,000, up 4% on August and up 15% against the twelve-month median of $1,765,000. 25% sold above their final asking price, and the median sold at 97.5% of it.
Winchester in September 2026: the numbers
Single-family
12 sold
- Median price
- $2,021,000up 4% on August
- Sale-to-asking
- 97.5%
- Over asking
- 25%
Multi-family
2 sold
- Median price
- —
- Sale-to-asking
- —
- Over asking
- —
Homes sold each month in Winchester, all types
How September compared in Winchester
September 2026 beside the month before, the last three months (July–September 2026) and the last twelve (October 2025–September 2026). One month’s median moves with which homes happened to close — a few large houses one month, smaller ones the next — so the three- and twelve-month columns are the steadier read.
Single-family
| September 2026 | August 2026 | 3 months | 12 months | |
|---|---|---|---|---|
| Homes sold | 12 | 12 | 51 | 182 |
| Median price | $2,021,000 | $1,950,000 | $2,025,000 | $1,765,000 |
| Median per sq ft | $571 | $601 | $578 | $565 |
| Median sale-to-asking | 97.5% | 97.3% | 100.0% | 100.0% |
| Sold over asking | 25% | 33% | 43% | 43% |
| Typical amount over asking | — | — | $34,500 | $51,000 |
Condos
| September 2026 | August 2026 | 3 months | 12 months | |
|---|---|---|---|---|
| Homes sold | 0 | 6 | 9 | 58 |
| Median price | — | $1,180,000 | $729,000 | $894,000 |
| Median per sq ft | — | $515 | $523 | $538 |
| Median sale-to-asking | — | 100.6% | 100.4% | 100.0% |
| Sold over asking | — | 67% | 56% | 50% |
| Typical amount over asking | — | — | $25,000 | $37,000 |
Multi-family
| September 2026 | August 2026 | 3 months | 12 months | |
|---|---|---|---|---|
| Homes sold | 2 | 2 | 5 | 14 |
| Median price | — | — | $1,368,000 | $1,245,000 |
| Median per sq ft | — | — | $435 | $447 |
| Median sale-to-asking | — | — | 98.1% | 97.8% |
| Sold over asking | — | — | 20% | 21% |
| Typical amount over asking | — | — | — | — |
What changed since August
- Single-family: 12 closed, against 12 in August; the median price was up 4% at $2,021,000; the share selling over asking fell from 33% to 25%.
- Multi-family: 2 closed, against 2 in August.
Winchester going into October: homes for sale
On October 20, 2026, 60 homes were for sale in Winchester and 22 were under agreement — about 2.8 months of supply at the past year's pace.
| 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 |
Rents signed in Winchester in September 2026
12 leases were recorded in September 2026. The median monthly rent by bedrooms, beside the last twelve months:
| September 2026 | 12 months | |
|---|---|---|
| Studio | — | $1,8008 leases |
| 1 bedroom | — | $2,12516 leases |
| 2 bedrooms | — | $3,12522 leases |
| 3 bedrooms | — | $4,00020 leases |
| 4 or more | — | $6,84828 leases |
What September means for Winchester buyers and sellers
If you are buying
- 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.
If you are selling
- 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.
September 2026 in other towns
Sources for the Winchester September 2026 report
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.