69 Prospect St Winsted, CT 06098
Estimated payment $1,829/month
About This Home
Opportunity awaits with this versatile 3-family property located at 69 Prospect Street in Winchester, perfect for both investors and owner-occupants alike. Whether you're looking to expand your investment portfolio or offset your mortgage with rental income, this multi-family offers flexibility, functionality, and strong potential in a convenient location. The property features 3 separate units with spacious layouts and off-street parking made easy with two driveways. Unit 1 includes in-unit laundry hookups, adding everyday practicality and additional appeal for renters. A newer roof offers peace of mind, while the layout of the property provides opportunities for long-term rentals, owner occupancy, or future value-add potential. Located just minutes from downtown Winsted, tenants can enjoy close proximity to local restaurants, coffee shops, grocery stores, and everyday conveniences. Outdoor enthusiasts will appreciate being near Highland Lake, the Sue Grossman Still River Greenway, and scenic hiking trails throughout the Litchfield Hills region. The property also offers easy access to Route 8 for commuting to Torrington, Canton, and surrounding towns. With strong rental demand, multiple income-producing units, and a location that blends small-town charm with convenience, this is a fantastic opportunity.
Listing Agent
Coldwell Banker Realty Brokerage Phone: (203) 927-6042 License #RES.0808686 Listed on: 05/13/2026
Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $4,078
Year Built
- Built in 1900
Lot Details
- 11,761 Sq Ft Lot
- Partially Wooded Lot
Home Design
- Side-by-Side
- Stone Foundation
- Frame Construction
- Asphalt Shingled Roof
- Vinyl Siding
Interior Spaces
- 2,204 Sq Ft Home
- Unfinished Basement
- Basement Fills Entire Space Under The House
Bedrooms and Bathrooms
- 7 Bedrooms
- 3 Full Bathrooms
Outdoor Features
- Rain Gutters
Utilities
- Cooling System Mounted In Outer Wall Opening
- Window Unit Cooling System
- Baseboard Heating
- Heating System Uses Natural Gas
Community Details
- 3 Units
Listing and Financial Details
- Assessor Parcel Number 927781
Map
Home Values in the Area
Average Home Value in this Area
Tax History
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 | $4,078 | $139,790 | $27,930 | $111,860 |
| 2024 | $3,808 | $139,790 | $27,930 | $111,860 |
| 2023 | $3,689 | $139,790 | $27,930 | $111,860 |
| 2022 | $2,996 | $89,320 | $20,230 | $69,090 |
| 2021 | $2,996 | $89,320 | $20,230 | $69,090 |
| 2020 | $2,996 | $89,320 | $20,230 | $69,090 |
| 2019 | $2,996 | $89,320 | $20,230 | $69,090 |
| 2018 | $2,996 | $89,320 | $20,230 | $69,090 |
| 2017 | $3,036 | $90,510 | $20,230 | $70,280 |
| 2016 | $3,038 | $90,580 | $20,230 | $70,350 |
| 2015 | $2,962 | $90,580 | $20,230 | $70,350 |
| 2014 | $2,890 | $90,580 | $20,230 | $70,350 |
Property History
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 | Prior Sale |
|---|---|---|---|---|---|
| 05/18/2026 05/18/26 | Pending | -- | -- | -- | |
| 05/13/2026 05/13/26 | For Sale | $274,900 | +39.2% | $125 / Sq Ft | |
| 07/19/2021 07/19/21 | Sold | $197,500 | +1.3% | $90 / Sq Ft | View Prior Sale |
| 05/14/2021 05/14/21 | Pending | -- | -- | -- | |
| 04/23/2021 04/23/21 | Price Changed | $194,900 | -2.5% | $88 / Sq Ft | |
| 03/11/2021 03/11/21 | For Sale | $199,900 | 0.0% | $91 / Sq Ft | |
| 05/10/2018 05/10/18 | Rented | $695 | 0.0% | -- | |
| 05/05/2018 05/05/18 | Under Contract | -- | -- | -- | |
| 04/18/2018 04/18/18 | For Rent | $695 | 0.0% | -- | |
| 03/28/2018 03/28/18 | Sold | $51,700 | -13.7% | $23 / Sq Ft | View Prior Sale |
| 02/27/2018 02/27/18 | Pending | -- | -- | -- | |
| 02/21/2018 02/21/18 | Price Changed | $59,900 | -20.0% | $27 / Sq Ft | |
| 01/30/2018 01/30/18 | Price Changed | $74,900 | -11.8% | $34 / Sq Ft | |
| 01/10/2018 01/10/18 | Price Changed | $84,900 | -15.0% | $39 / Sq Ft | |
| 12/10/2017 12/10/17 | Price Changed | $99,900 | -9.9% | $45 / Sq Ft | |
| 11/08/2017 11/08/17 | Price Changed | $110,900 | -5.5% | $50 / Sq Ft | |
| 10/06/2017 10/06/17 | For Sale | $117,300 | -- | $53 / Sq Ft |
Purchase History
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 | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $197,500 | None Available | |
| Warranty Deed | $197,500 | None Available | |
| Warranty Deed | $197,500 | None Available | |
| Warranty Deed | $51,700 | -- | |
| Warranty Deed | $51,700 | -- | |
| Warranty Deed | $51,700 | -- | |
| Foreclosure Deed | -- | -- | |
| Foreclosure Deed | -- | -- | |
| Warranty Deed | $159,000 | -- | |
| Warranty Deed | $159,000 | -- | |
| Warranty Deed | $30,000 | -- | |
| Warranty Deed | $30,000 | -- |
Mortgage History
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 | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $148,125 | Purchase Money Mortgage | |
| Closed | $148,125 | Purchase Money Mortgage | |
| Previous Owner | $112,000 | Adjustable Rate Mortgage/ARM | |
| Previous Owner | $68,053 | Purchase Money Mortgage |
Source: SmartMLS
MLS Number: 24173658
APN: WINC-000110-000086-000017
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