Jim Treanor Jr
ERA Treanor Real Estate
(475) 244-9541
216 Total Sales
1 in Winchester
$420,000 Price
In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a 2-bedroom apartment, the other a 3-bedroom apartment. Both units include 1.5 baths, updated kitchens with appliances, and tastefully renovated bathrooms. Gleaming hardwood floors run throughout, adding warmth and timeless character. Enjoy the charm of a classic wrap-around covered porch-perfect for relaxing or entertaining. The property also includes a detached 2-car garage and an additional shed for storage. Centrally located close to shopping, dining, schools, and major routes, this home is ideal as a strong rental investment or an in-law setup. Meticulously cared for and in extraordinary condition-this is a must-see property!
Last Agent to Sell the Property
Northwest CT Realty Brokerage Phone: (860) 485-3508 License #REB.0158950 Listed on: 04/29/2026
Last Buyer's Agent
Northwest CT Realty Brokerage Phone: (860) 485-3508 License #REB.0158950 Listed on: 04/29/2026
Jim Treanor Jr
ERA Treanor Real Estate
(475) 244-9541
216 Total Sales
1 in Winchester
$420,000 Price
Chris Callahan
Berkshire Hathaway NE Prop.
(860) 406-5726
114 Total Sales
1 in Winchester
$288,557 Price
Susan Hotchkiss
Realty ONE Group Connect
(475) 241-7831
66 Total Sales
1 in Winchester
$185,000 Price
Amanda Nemense
Showcase Realty, Inc.
(475) 285-3197
114 Total Sales
2 in Winchester
$266K - $380K Price Range
Karen Mendes
Berkshire Hathaway NE Prop.
(959) 245-9021
219 Total Sales
1 in Winchester
$470,000 Price
Jennifer Petron
Berkshire Hathaway NE Prop.
(959) 230-0845
220 Total Sales
1 in Winchester
$470,000 Price
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 07/15/2026 07/15/26 | Sold | $420,000 | +5.3% | $151 / Sq Ft |
| 05/19/2026 05/19/26 | Pending | -- | -- | -- |
| 04/29/2026 04/29/26 | For Sale | $399,000 | -- | $144 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $5,942 | $203,700 | $32,900 | $170,800 |
| 2024 | $5,549 | $203,700 | $32,900 | $170,800 |
| 2023 | $5,376 | $203,700 | $32,900 | $170,800 |
| 2022 | $4,663 | $139,020 | $23,870 | $115,150 |
| 2021 | $4,663 | $139,020 | $23,870 | $115,150 |
| 2020 | $4,663 | $139,020 | $23,870 | $115,150 |
| 2019 | $4,663 | $139,020 | $23,870 | $115,150 |
| 2018 | $4,663 | $139,020 | $23,870 | $115,150 |
| 2017 | $4,599 | $137,130 | $23,870 | $113,260 |
| 2016 | $4,599 | $137,130 | $23,870 | $113,260 |
| 2015 | $4,484 | $137,130 | $23,870 | $113,260 |
| 2014 | $4,376 | $137,130 | $23,870 | $113,260 |
Seller's Agent in 2026
David D'Amore
Northwest CT Realty
(860) 485-3508
43 Total Sales
Source: SmartMLS
MLS Number: 24168016
APN: WINC-000107-000020-000026
Ask me questions while you tour the home.