Justin Guerrera
Regency Real Estate, LLC
(475) 285-4179
39 Total Sales
1 in Winchester
$180,000 Price
Owner Occupants take notice: Rare three family home with market rents (one three-bedroom unit vacant) building is in exceptional condition!! A new roof will be installed in May before closing. One unit, a three-bedroom with a kitchen, living room, dining room, and two full bathrooms, this unit is rented @ $2136. per month ($2221.00 for the June 30, 2026-May 31, 2027 lease).) A one-year lease for the one bed unit expires on 5-31-26. This unit, an efficiency one-bedroom with a living room, kitchen, and full bath, unit is rented for $1160 per month. Total income now/$ 3381! Potential income for INVESTORS $5831! All tenants are current. 2 months' security deposits held in savings. The vacant unit is a three-bedroom unit with a kitchen, living room, dining room, and two full baths, and it will be vacant as of April 30 2026. Landlord owns most appliances. Natural gas heating units and electric water heaters have all been updated (servicing scheduled. May 26). Separate utilities for everyone. Very well cared for. Rents are at market rate. Plenty of off street parking. Each tenant has secure basement storage. Landlord electric panel, resulting in a $9-10$ per month bill for common area lighting. Fire marshal inspected and approved in 2025. No open violations. After accepted offer, appointments will be scheduled to view the remaining two units with minimum 48 hours notice to the tenants and broker/owner who will be present during those showings. Due to the severe low inventory, multiple offers are anticipated. Please include escalation clauses if desired. Appraisal gap coverages will be required due to no three family sales in Winsted that are comparable (condition and rental income) for several years. Appraisers may need to think outside the box and use properties from Torrington for accurate comparables. For rent MLS#24160451 $2450.00 per month. Schedule C & Leases provided upon request. Broker prefers G H A R Contracts. DO NOT DISTURB TENANTS OWNER DOES NOT RESIDE THERE.
Last Agent to Sell the Property
Turning Point Realty, LLC Brokerage Phone: (860) 601-3730 License #REB.0790888 Listed on: 04/20/2026
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Justin Guerrera
Regency Real Estate, LLC
(475) 285-4179
39 Total Sales
1 in Winchester
$180,000 Price
Rob Rosa
Berkshire Hathaway NE Prop.
(860) 560-1786
289 Total Sales
1 in Winchester
$255,000 Price
David Sartirana
Northwest CT Realty
(959) 251-2063
342 Total Sales
161 in Winchester
$118 - $950K Price Range
Guillermo Araujo
Five Stars Realty
(860) 791-3396
203 Total Sales
1 in Winchester
$170,000 Price
Simonne Corriveau
KW Legacy Partners
(860) 855-3309
130 Total Sales
1 in Winchester
$227,000 Price
Jennifer Kamens
Berkshire Hathaway NE Prop.
(860) 385-6843
83 Total Sales
1 in Winchester
$199,900 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 | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $173,000 | -- |
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 |
|---|---|---|---|---|---|
| 06/22/2026 06/22/26 | Sold | $485,000 | +2.1% | $137 / Sq Ft | |
| 06/05/2026 06/05/26 | Pending | -- | -- | -- | |
| 04/20/2026 04/20/26 | For Sale | $475,000 | 0.0% | $134 / Sq Ft | |
| 06/20/2025 06/20/25 | Rented | $2,150 | 0.0% | -- | |
| 05/31/2025 05/31/25 | Under Contract | -- | -- | -- | |
| 05/07/2025 05/07/25 | For Rent | $2,150 | +16.2% | -- | |
| 07/18/2024 07/18/24 | Rented | $1,850 | 0.0% | -- | |
| 07/05/2024 07/05/24 | Under Contract | -- | -- | -- | |
| 06/28/2024 06/28/24 | For Rent | $1,850 | +15.6% | -- | |
| 09/23/2023 09/23/23 | Rented | $1,600 | 0.0% | -- | |
| 09/23/2023 09/23/23 | Under Contract | -- | -- | -- | |
| 09/11/2023 09/11/23 | Price Changed | $1,600 | -5.9% | $1 / Sq Ft | |
| 09/07/2023 09/07/23 | Price Changed | $1,700 | -5.5% | $1 / Sq Ft | |
| 08/27/2023 08/27/23 | Price Changed | $1,799 | -2.8% | $1 / Sq Ft | |
| 08/15/2023 08/15/23 | For Rent | $1,850 | 0.0% | -- | |
| 04/12/2021 04/12/21 | Sold | $210,198 | +5.1% | $59 / Sq Ft | View Prior Sale |
| 02/25/2021 02/25/21 | Pending | -- | -- | -- | |
| 02/25/2021 02/25/21 | For Sale | $199,999 | -4.9% | $57 / Sq Ft | |
| 02/17/2021 02/17/21 | Off Market | $210,198 | -- | -- | |
| 02/04/2021 02/04/21 | For Sale | $199,999 | 0.0% | $57 / Sq Ft | |
| 10/03/2020 10/03/20 | Rented | $1,200 | 0.0% | -- | |
| 10/02/2020 10/02/20 | Under Contract | -- | -- | -- | |
| 07/15/2020 07/15/20 | For Rent | $1,200 | +26.3% | -- | |
| 01/29/2019 01/29/19 | Rented | $950 | 0.0% | -- | |
| 01/16/2019 01/16/19 | Under Contract | -- | -- | -- | |
| 11/01/2018 11/01/18 | For Rent | $950 | +11.8% | -- | |
| 05/20/2016 05/20/16 | Rented | $850 | -29.2% | -- | |
| 05/20/2016 05/20/16 | Under Contract | -- | -- | -- | |
| 10/22/2015 10/22/15 | For Rent | $1,200 | 0.0% | -- | |
| 03/27/2015 03/27/15 | Sold | $55,299 | -6.0% | $16 / Sq Ft | View Prior Sale |
| 02/23/2015 02/23/15 | Pending | -- | -- | -- | |
| 02/15/2015 02/15/15 | For Sale | $58,800 | -- | $17 / 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 | $4,819 | $165,200 | $25,480 | $139,720 |
| 2024 | $4,500 | $165,200 | $25,480 | $139,720 |
| 2023 | $4,360 | $165,200 | $25,480 | $139,720 |
| 2022 | $4,099 | $122,220 | $18,480 | $103,740 |
| 2021 | $4,099 | $122,220 | $18,480 | $103,740 |
| 2020 | $4,099 | $122,220 | $18,480 | $103,740 |
| 2019 | $4,099 | $122,220 | $18,480 | $103,740 |
| 2018 | $4,099 | $122,220 | $18,480 | $103,740 |
| 2017 | $4,158 | $123,970 | $18,480 | $105,490 |
| 2016 | $4,158 | $123,970 | $18,480 | $105,490 |
| 2015 | $3,628 | $110,950 | $18,480 | $92,470 |
| 2014 | $3,540 | $110,950 | $18,480 | $92,470 |
Seller's Agent in 2026
Suzie Larson
Turning Point Realty, LLC
(860) 601-3730
112 Total Sales
Buyer's Agent in 2026
Meagan Albert
Tier 1 Real Estate
(860) 716-5012
133 Total Sales
A
Seller Co-Listing Agent in 2023
Ashley Church
Turning Point Realty, LLC
Buyer's Agent in 2023
Jessica Boswell
LPT Realty
(860) 777-0703
600 Total Sales
A
Buyer Co-Listing Agent in 2023
Ace Ricker
eXp Realty
Seller's Agent in 2021
Diane Carroll
The Washington Agency
(860) 485-8371
122 Total Sales
Source: SmartMLS
MLS Number: 24168665
APN: WINC-000106-000041-000001
Ask me questions while you tour the home.