Photo: User:Magicpiano · CC BY-SA 4.021 homes sold in Winchester in the last year, at a typical $264K
Almost every sale is a house. Below: what each kind of home sells for, what your budget buys, 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.
Houses are 81% of Winchester’s sales, at a typical $244K
21 homes sold in the year to March 2026.
typical sale · 17 sold in 12 months
- Per square foot
- $162NH $282
- Days to sell
- 125
- Sold over asking
- 41%
- Listings with a price cut
- 39%
Multi-family (2–4 units): 4 sold, typical $288K
Too few sales in 12 months for reliable figures.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $250K 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.
Owning the typical Winchester home costs about $1,859 a month
Price: Winchester’s typical sale, last 12 months. Property tax at Winchester’s 2.2% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Winchester is affordable on local pay is on Cost of living.
Five things worth knowing
Property tax, a year
Of a home’s value: the median bill over the median home value. On a $264K home, about $5,770 a year.
Taxes vs. neighborsSchools
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.
No busy market nearby sells for less a square foot; Keene, Turners Falls, Greenfield, Athol and Jaffrey for far more
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 | |
|---|---|---|---|---|---|
| Keene | 235 | $363K | $221 | 40% | 37 |
| Greenfield | 144 | $336K | $205 | 42% | 30 |
| Athol | 67 | $329K | $223 | 43% | 41 |
| Orange | 49 | $292K | $180 | 45% | 32 |
| Jaffrey | 37 | $402K | $235 | 35% | 82 |
| Turners Falls | 33 | $330K | $256 | 55% | 20 |
| Winchester | 21 | $264K | $144 | 33% | 111 |
Redfin Data Center, April 2025 to March 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, NH?
21 homes sold in the year to March 2026 at a typical $264K, $144 a square foot.
Is Winchester a buyer’s or seller’s market?
A seller’s market: 1 homes were for sale in March 2026 and 4 sold, about 0.3 months of supply. Buyers paid 96.4% of asking on average, and 39% of listings cut their price.
How much are property taxes in Winchester?
About 2.2% of a home’s value a year. On a $264K home that’s near $5,770.
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).