Capt. Josiah Locke House · Photo: User:Magicpiano · CC BY-SA 4.0274 homes sold in Winchester in the last year, at a typical $1.5M
About one sale in 4 is a condo. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Winchester homes are listed.
Every place Winchester homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Winchester.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
9% of Winchester’s sales are condos, at $1M less than a house
203 houses and 26 condos sold in the year to May 2026. Houses sell faster and draw more bidding wars.
typical sale · 203 sold in 12 months
- Per square foot
- $565MA $368
- Days to sell
- 22
- Sold over asking
- 43%
- Listings with a price cut
- 26%
typical sale · 26 sold in 12 months
- Per square foot
- $612MA $562
- Days to sell
- 30
- Sold over asking
- 27%
- Listings with a price cut
- 35%
Multi-family (2–4 units): 8 sold, typical $1.3M
Townhouses: 37 sold, typical $1.1M
Too few sales in 12 months for reliable figures.
About as many homes sell as usual, at 1.6 times the 2016 price
274 sales in the last year, against 348 in 2021 and a low of 206 in 2023. The typical sale went from $886K in 2016 to $1.5M.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $1.5M buys in Winchester
Check a listing against what Winchester homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Winchester are back to pre-pandemic levels, but a quarter fewer homes come up for sale
We read every month of Winchester’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to May 2026, 274 sales.
If you’re buying in Winchester
- Shop in March. It brings about 41 new listings a month, close to the busiest month, with fewer bidding wars (48% over asking).
- Less room to haggle. Only 24% of listings cut their price, against 29% before the pandemic.
- Bid near asking. Buyers paid 100.6% of the list price on average; 43% paid over.
- Move fast on good ones. 55% of homes are under contract within two weeks.
Spring brings both the most homes and the most bidding wars
May has the most new listings (about 48 a month), and the most competition: 54% close over asking. March and April offer nearly as much choice with fewer homes bid up (48%). January has the least competition (27%) but only about 18 new listings.
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and about like Massachusetts as a whole
| Winchester now | 2017–19 | 2021 peak | MA now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 43% | 39% | 51% | 45% |
| Gone within two weeksShare of homes under contract within 14 days | 55% | 51% | 63% | 49% |
| Listings with a price cutShare of homes for sale that cut their price | 24% | 29% | 21% | 25% |
| Price paid vs. askingAverage sale price ÷ list price | 100.6% | 99.9% | 102.1% | 100.4% |
| Days to sellMedian days from listing to contract | 21 | 19 | 21 | 27 |
41 homes for sale on a typical day
That’s 1.3 times the 2022 low (33), 23% fewer than in 2017–19 and well under 2012’s 107.
1 in 4 listings has cut its price
24% in the last year, against 29% in 2017–19 and 25% across Massachusetts.
Since 2019, houses are up 48%, condos 32%
A house typically sold for $1.6M in the last year (203 sales), a condo for $640K (26).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Winchester ranks 132nd of 206 busy Massachusetts markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Winchester is in the middle of the pack.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Five things worth knowing
New listings in May
The month with the most choice. December has the fewest, about 6.
Best time to buySchools
The schools grade for Winchester, from test results, graduation and how much students grow.
Schools in WinchesterTypical commute
The average one-way trip to work for people who live in Winchester.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Woburn, Medford, Stoneham and Melrose sell for less a square foot
The busier markets within 25 miles of Winchester, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Arlington | 461 | $1.1M | $610 | 53% | 16 |
| Medford | 452 | $873K | $496 | 48% | 26 |
| Woburn | 336 | $748K | $440 | 51% | 23 |
| Lexington | 311 | $1.8M | $574 | 48% | 22 |
| Winchester | 274 | $1.5M | $565 | 43% | 21 |
| Melrose | 272 | $902K | $478 | 66% | 17 |
| Stoneham | 223 | $717K | $440 | 61% | 20 |
Redfin Data Center, June 2025 to May 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Winchester, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Winchester. People who follow the town see it, and so do people comparing Winchester with their own town. No commission, no listing fee.
Questions about buying a home in Winchester
What do homes sell for in Winchester, MA?
274 homes sold in the year to May 2026 at a typical $1.5M, $565 a square foot. Houses sold for about $1.6M, condos for about $640K.
Is Winchester a buyer’s or seller’s market?
A seller’s market: 52 homes were for sale in May 2026 and 29 sold, about 1.8 months of supply. Buyers paid 100.6% of asking on average, and 24% of listings cut their price.
When is the best time to buy in Winchester?
May brings the most new listings. The sales history shows which months have fewer bidding wars.
Where can I see homes for sale in Winchester?
Zillow, Redfin, Realtor.com and Homes.com all carry Winchester’s MLS listings; the search links above open each one filtered to Winchester.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).