Lana Ogrodnik
Showcase Realty, Inc.
(475) 263-4970
56 Total Sales
1 in Winchester
$325,000 Price
69 Prospect St Winsted, CT 06098
Winchester Area
7
Beds
3
Baths
2,204
Sq Ft
0.27
Acre Lot
About This Home
As of June 2026Opportunity 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.
Last Agent to Sell the Property
Coldwell Banker Realty Brokerage Phone: (203) 927-6042 License #RES.0808686 Listed on: 05/13/2026
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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
Ownership 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
Name
Owned For
Owner Type
Purchase Details
Closed on
Jul 10, 2017
Sold by
Gillotte Darryl R and Deutsche Bank Natl T C
Bought by
Purchase Details
Closed on
Sep 14, 2005
Sold by
Barbero Eugene
Bought by
Gillotte Darryl R
Purchase Details
Closed on
Jun 9, 1995
Sold by
Hazard Denise M
Bought by
Barbero Eugene J
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Winsted, CT
-
Lana Ogrodnik
-
Jim Treanor Jr
Jim Treanor Jr
ERA Treanor Real Estate
(475) 244-9541
214 Total Sales
1 in Winchester
$420,000 Price
-
Chris Callahan
Chris Callahan
Berkshire Hathaway NE Prop.
(860) 406-5726
116 Total Sales
1 in Winchester
$288,557 Price
-
Susan Hotchkiss
Susan Hotchkiss
Realty ONE Group Connect
(475) 241-7831
67 Total Sales
1 in Winchester
$185,000 Price
-
Amanda Nemense
Amanda Nemense
Showcase Realty, Inc.
(475) 285-3197
117 Total Sales
2 in Winchester
$266K - $380K Price Range
-
Karen Mendes
Karen Mendes
Berkshire Hathaway NE Prop.
(959) 245-9021
217 Total Sales
1 in Winchester
$470,000 Price
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 |
|---|---|---|---|
| Foreclosure Deed | -- | -- | |
| Warranty Deed | $159,000 | -- | |
| Warranty Deed | $30,000 | -- |
Source: Public Records
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 |
|---|---|---|---|---|---|
| 06/29/2026 06/29/26 | Sold | $274,900 | 0.0% | $125 / Sq Ft | |
| 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 |
Source: SmartMLS
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 |
Source: Public Records
Agents Affiliated with this Home
-
Adam Cannon
Seller's Agent in 2026
Adam Cannon
Coldwell Banker Realty
(203) 927-6042
217 Total Sales
-
David Sartirana
Buyer's Agent in 2026
David Sartirana
Northwest CT Realty
(860) 806-0225
339 Total Sales
-
Amanda Balaski
Seller's Agent in 2021
Amanda Balaski
Northwest CT Realty
(860) 605-6618
43 Total Sales
-
Kimone Vassell
Buyer's Agent in 2021
Kimone Vassell
eXp Realty
(203) 600-6819
71 Total Sales
-
JS
Seller's Agent in 2018
Johanna Stanko
Berkshire Hathaway Home Services
-
Lisa McCarthy
Seller's Agent in 2018
Lisa McCarthy
Coldwell Banker Realty
(860) 604-8723
114 Total Sales
Map
Source: SmartMLS
MLS Number: 24173658
APN: WINC-000110-000086-000017
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