Photo: Dougtone · CC BY-SA 2.0129 homes sold in Winchester in the last year, at a typical $295K
Redfin reports Winchester’s sales by ZIP code, so these figures are for ZIP 06098, which takes in Winchester and the area around it. Almost every sale is a house. 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.
11% of Winchester’s sales are condos, at $134K less than a house
98 houses and 14 condos sold in the year to May 2026. Condos sell faster and draw more bidding wars.
typical sale · 98 sold in 12 months
- Per square foot
- $203CT $273
- Days to sell
- 53
- Sold over asking
- 42%
typical sale · 14 sold in 12 months
- Per square foot
- $174CT $256
- Days to sell
- 41
- Sold over asking
- 52%
About as many homes sell as usual, at 2.2 times the 2016 price
129 sales in the last year, against 231 in 2021 and a low of 75 in 2012. The typical sale went from $131K in 2016 to $295K.
Source: Redfin Data Center, MLS sales; for ZIP 06098, which takes in Winchester and the area around it (each month is a 3-month rolling window, its counts divided by 3). Typical price and $/sq ft are the monthly medians, weighted by sales.
What $300K 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 more common than before the pandemic, but three quarters fewer homes come up for sale
We read every month of home sales in ZIP 06098 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, 129 sales.
If you’re buying in Winchester
- Shop in April. It brings about 18 new listings a month, close to the busiest month, with fewer bidding wars (26% over asking).
- Bid near asking. Buyers paid 100.7% of the list price on average; 44% paid over.
- You’ll usually have time. Only 42% of homes go under contract within two weeks; the typical one takes 49 days.
Summer brings the homes; winter brings the bidding wars
July has the most new listings (about 22 a month), but December is the most competitive: 31% of December sales close over asking. April and May offer nearly as much choice with fewer homes bid up (26%). April has the least competition (26%).
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and calmer than Connecticut
| Winchester now | 2017–19 | 2021 peak | CT now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 44% | 15% | 37% | 56% |
| Gone within two weeksShare of homes under contract within 14 days | 42% | 11% | 47% | 47% |
| Listings with a price cutShare of homes for sale that cut their price | — | — | — | 18% |
| Price paid vs. askingAverage sale price ÷ list price | 100.7% | 93.8% | 98.5% | 102.2% |
| Days to sellMedian days from listing to contract | 49 | 104 | 61 | 39 |
26 homes for sale on a typical day
That’s 73% fewer than in 2017–19 and well under 2012’s 127.
Since 2019, houses are up 100%, condos 131%
A house typically sold for $313K in the last year (98 sales), a condo for $179K (14).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Source: Redfin Data Center, ZIP code tracker; for ZIP 06098, which takes in Winchester and the area around it (each month is a 3-month rolling window, its counts divided by 3), January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winchester home costs about $2,010 a month
Price: Winchester’s typical sale, last 12 months. Property tax at Winchester’s 1.9% (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.
Six things worth knowing
New listings in July
The month with the most choice. January has the fewest, about 12.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $295K home, about $5,640 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
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 | |
|---|---|---|---|---|---|
| Torrington | 468 | $301K | $186 | 52% | 47 |
| Winchester (ZIP 06098) | 129 | $295K | $188 | 44% | 49 |
| Winsted | 105 | $297K | $187 | 47% | 46 |
| Northwest Harwinton | 42 | $494K | $217 | 48% | 57 |
| Collinsville | 41 | $429K | $217 | 68% | 31 |
| New Hartford Center | 36 | $378K | $228 | 56% | 55 |
| Canton Valley | 22 | $385K | $226 | 68% | 49 |
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, CT?
129 homes sold in the year to May 2026 at a typical $295K, $188 a square foot. Houses sold for about $313K, condos for about $179K.
Is Winchester a buyer’s or seller’s market?
A seller’s market: 27 homes were for sale in May 2026 and 8 sold, about 3.4 months of supply. Buyers paid 100.7% of asking on average.
When is the best time to buy in Winchester?
July brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winchester?
About 1.9% of a home’s value a year. On a $295K home that’s near $5,640.
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; for ZIP 06098, which takes in Winchester and the area around it (each month is a 3-month rolling window, its counts divided by 3)). 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).