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.
Under contract
$274,900
69 Prospect Street, Winchester, CT 06098
7beds
2,204sqft
Multi Family
Built in 1900
-- sqft lot
$-- Zestimate®
$125/sqft
$-- HOA
What's special
In-unit laundry hookupsNewer roof
- 46 days |
- 46 |
- 0 |
Zillow last checked:
Listing updated:
Listed by:
Adam Cannon (203)927-6042,
Coldwell Banker Realty 860-231-2600
Source: Smart MLS,MLS#: 24173658
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Baseboard, Electric, Natural Gas
Cooling
- Wall Unit(s), Window Unit(s)
Appliances
- Laundry: In Basement, In Unit
Features
- Basement: Full,Unfinished
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 2,204
- Total interior livable area: 2,204 sqft
- Finished area above ground: 2,204
- Finished area below ground: 0
Property
Features
- Exterior features: Rain Gutters
Lot
- Size: 0.27 Acres
- Features: Few Trees
Details
- Parcel number: 927781
- Zoning: R-3
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units on different Floors,Units are Side-by-Side
- Property subtype: Multi Family
- Attached to another structure: Yes
Materials
- Vinyl Siding
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $125/sqft
- Tax assessed value: $139,790
- Annual tax amount: $4,078
- Date on market: 5/13/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/18/2026 | Pending sale | $274,900$125/sqft |
Source:  Smart MLS #24173658 Report a problem | ||
| 5/13/2026 | Listed for sale | $274,900+39.2%$125/sqft |
Source: Smart MLS #24173658 Report a problem | ||
| 7/19/2021 | Sold | $197,500+282%$90/sqft |
Source: Smart MLS #170379418 Report a problem | ||
| 5/6/2018 | Listing removed | $695 |
Source: The D'Amore Agency, LLC #170073573 Report a problem | ||
| 4/18/2018 | Listed for rent | $695 |
Source: The D'Amore Agency, LLC #170073573 Report a problem | ||
| 3/28/2018 | Sold | $51,700-13.7%$23/sqft |
Source: Smart MLS #170022212 Report a problem | ||
| 2/21/2018 | Price change | $59,900-20%$27/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 1/30/2018 | Price change | $74,900-11.8%$34/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 1/10/2018 | Price change | $84,900-15%$39/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 12/10/2017 | Price change | $99,900-9.9%$45/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 11/8/2017 | Price change | $110,900-5.5%$50/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 10/8/2017 | Listed for sale | $117,300+62.9%$53/sqft |
Source: Coldwell Banker Residential Brokerage - West Hartford Office #170022212 Report a problem | ||
| 5/1/2017 | Listing removed | $72,000$33/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 9/2/2016 | Listed for sale | $72,000$33/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 6/11/2016 | Listing removed | $72,000$33/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 5/6/2016 | Price change | $72,000-19.1%$33/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 3/24/2016 | Pending sale | $89,000$40/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 3/4/2016 | Price change | $89,000-10.1%$40/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 2/10/2016 | Listed for sale | $99,000-37.7%$45/sqft |
Source: The D'Amore Agency, LLC #L10108623 Report a problem | ||
| 9/14/2005 | Sold | $159,000+430%$72/sqft |
Source: Public Record Report a problem | ||
| 6/9/1995 | Sold | $30,000$14/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,078 +10.5% | $139,790 |
| 2024 | $3,689 | $139,790 |
| 2023 | $3,689 +23.1% | $139,790 +56.5% |
| 2022 | $2,996 | $89,320 |
| 2021 | $2,996 | $89,320 |
| 2020 | $2,996 | $89,320 |
| 2019 | $2,996 | $89,320 |
| 2018 | $2,996 -1.3% | $89,320 -1.3% |
| 2017 | $3,036 -0.1% | $90,510 -0.1% |
| 2016 | $3,038 +2.6% | $90,580 |
| 2015 | $2,962 +2.5% | $90,580 |
| 2014 | $2,890 +2.3% | $90,580 |
| 2013 | $2,826 +0.7% | $90,580 -17.9% |
| 2012 | $2,805 | $110,320 |
| 2011 | $2,805 | $110,320 |
| 2010 | $2,805 +3% | $110,320 |
| 2009 | $2,722 | $110,320 |
| 2008 | $2,722 +9.6% | $110,320 +52.3% |
| 2007 | $2,483 +2.8% | $72,450 |
| 2006 | $2,415 +1.1% | $72,450 |
| 2005 | $2,389 +9.5% | $72,450 |
| 2003 | $2,182 | $72,450 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06098
Nearby schools
GreatSchools rating
- NABatcheller Early Education CenterGrades: PK-2Distance: 0.5 mi
- NAPearson AcademyGrades: Distance: 0.5 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 0.5 mi
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A local lender can help you make sure your offer is ready when you are.
- Connecticut
- Litchfield County
- Winsted
- 06098
- 69 Prospect Street
Nearby cities
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