Housing · Winchester
Winchester, CT housing market
The typical Winchester home is worth about $402,000, up 1.4% in a year, 11% below the Connecticut typical home.
Home values, sales, trends and how Winchester compares with the towns next door — updated as new data is published.
The market right now
Winchester at a glance
Typical home value
$402K
▲ 1.4% in a year · Zillow
Ten-year trend
Typical home value, 2016–2026
WinchesterConnecticut
Show as a table
| January | Winchester | Connecticut |
|---|---|---|
| 2017 | $199,000 | $248,000 |
| 2018 | $209,000 | $256,000 |
| 2019 | $213,000 | $258,000 |
| 2020 | $218,000 | $264,000 |
| 2021 | $256,000 | $293,000 |
| 2022 | $291,000 | $326,000 |
| 2023 | $326,000 | $357,000 |
| 2024 | $365,000 | $395,000 |
| 2025 | $394,000 | $420,000 |
| 2026 | $395,000 | $438,000 |
| August 2026 | $402,000 | $451,000 |
Next door
Winchester and its neighbors
The towns that share a border. Tap one to see its housing page.
| Town | Typical value | 1-yr change | Days on market | Median income |
|---|---|---|---|---|
| Winchester | $402K | +1.4% | — | $66,519 |
| Torrington | $302K | +4% | 59 | $70,856 |
| Colebrook | $407K | +5.5% | — | $111,250 |
| Barkhamsted | $444K | +3.1% | — | $123,544 |
| Winsted | $286K | +1.2% | 38 | $64,871 |
Affordability
6 years of income
The typical Winchester home costs about 6 years of the town's median household income, more than across Connecticut (4.7 years).
How Winchester ranks on affordability →
Home value ÷ ACS median household income.
The homes
Owners, rent & taxes
Homeownership
65.8%
Connecticut: 66.5%
Median tax bill
$4,780
Connecticut: $6,643
Median rent
$1,174
Connecticut: $1,488
Typical home built
1955
Connecticut: 1967
U.S. Census Bureau, ACS 2020-2024.
Home values: Zillow Home Value Index (ZHVI), Zillow Research, August 2026. Sales, days on market and supply: Redfin Data Center. Income, ownership, taxes and rent: U.S. Census Bureau, American Community Survey. Listings link to their publishers.