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$324,900 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 4 Total Beds
  • 2 Car Garage
  • Updated 1 day ago
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Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

Full Property Details for 50 High St

General

  • Price: $324,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24199721
  • Updated: 8/17/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 12
  • Fireplace: Yes
  • Number of Fireplaces: 1

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Exterior

  • Exterior Features: Porch-Wrap Around, Porch-Enclosed, Porch, Barn
  • Color: Blue

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking: Barn, Detached Garage, Off Street Parking

Location

  • County: Litchfield
  • Neighborhood: Winsted
  • Driving Directions: 50 High St

School Information

  • Elementary School: Per Board of Ed
  • High School: Gilbert

Community

  • Community Name: Winsted

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Water, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Upright Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Units on different Floors
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,044
  • Above Ground: 3,044 Sq. Ft.
  • Year Built: 1900

Unit Information

Unit 1

  • Square Feet: 1620
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 2

  • Square Feet: 1424
  • Total Bathrooms: 1
  • Bedrooms: 2

Lot Features

  • Lot Size (Acres): 0.56
  • Zoning: R-3
  • Lot Description: Level Lot

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $77,350
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 927736

Listed by Northwest CT Realty, David Sartirana

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Listing agent

— 50 High St —

  • David Sartirana

    Northwest CT Realty

Agent Contact: (860) 806-0225 Office Contact: (860) 379-7245

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 50 High St

School District:Winchester School District
NameGradesDistance
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-60.4 mi
Batcheller Early Education Center
201 Pratt Street, Winsted, CT 06098
PK-20.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 50 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/17/2026
Listed
$324,900
549.8%
MLS
8/01/2014
Sold
$50,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 50 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,256
7%
$77,350
—
2023
$2,107
3%
$77,350
—
2023
$2,041
6%
$77,350
34%
2022
$1,932
—
$57,610
—
2021
$1,932
—
$57,610
—
2020
$1,932
-41%
$57,610
-41%
2019
$3,289
—
$98,070
—
2018
$3,289
-1%
$98,070
-1%
2017
$3,334
—
$99,400
—
2016
$3,334
3%
$99,400
—
2015
$3,250
3%
$99,400
1%
2014
$3,150
2%
$98,700
—
2013
$3,079
—
$98,700
—
2011
$3,079
—
$98,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Northwest CT Realty, David Sartirana

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50 High Street, Winchester, CT 06098 (MLS# 24199721) is a Multi-Family property with 2 units containing 4 bedrooms and 2 full bathrooms. 50 High Street is currently listed for $324,900 and was received on August 17, 2026. Want to learn more about 50 High Street? Do you have questions about finding other Multi-Family real estate for sale in Winsted? You can browse all Winsted real estate or contact a Coldwell Banker agent to request more information.

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