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$579,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 11 Total Beds
  • 4 Car Garage
  • Updated 14 hours ago
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150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, some hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since @between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

Full Property Details for 150 Oak St

General

  • Price: $579,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24166332
  • Updated: Today (5/1/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 26

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 11

Other Rooms

  • Laundry: Basement Hook-Up(s), Washer/Dryer Some Units

Exterior

  • Exterior Features: Porch
  • Color: grey

Parking

  • Garage: Yes
  • Garage Spaces: 4
  • Total Spaces: 8
  • Parking: Detached Garage, On Street Parking, Off Street Parking, Unassigned Parking

Location

  • County: Litchfield
  • Neighborhood: Winsted
  • Driving Directions: GPS friendly

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: Winsted

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Water, Electric, Natural Gas
  • Heating Fuel: Electric, Natural Gas
  • Water Heater: Natural Gas, Electric, 40 Gallon Tank

Utilities

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

Structural Information

  • Architectural Style: Units are Side-by-Side, Other
  • Construction Status: No/Resale
  • Exterior Const.: Stucco
  • Basement Desc.: Full, Unfinished, Storage, Concrete Floor
  • Roof: Asphalt Shingle
  • Square Feet: 5,233
  • Above Ground: 5,233 Sq. Ft.
  • Year Built: 1924

Unit Information

Unit 1

  • Square Feet: 1050
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 2

  • Square Feet: 1050
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 3

  • Square Feet: 1050
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 4

  • Square Feet: 1050
  • Total Bathrooms: 1
  • Bedrooms: 5

Unit 5

  • Square Feet: 1033
  • Total Bathrooms: 2
  • Half Baths: 1
  • Partial Bathrooms: 1
  • Bedrooms: 3

Lot Features

  • Lot Size (Acres): 0.19
  • Zoning: R-3
  • Lot Description: Sloping Lot

Financial Considerations

  • Assessment Amount: $229,880
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 926977

Listed by Turning Point Realty, LLC, Pamela Silvestri and Turning Point Realty, LLC, Suzie Larson

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Listing agents

— 150 Oak St —

  • Pamela Silvestri

    Turning Point Realty, LLC

  • Suzie Larson

    Turning Point Realty, LLC

Agent Contact: (959) 799-1696 Office Contact: (860) 909-1162

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 150 Oak St

School District:Winchester School District
NameGradesDistance
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-60.2 mi
Batcheller Early Education Center
201 Pratt Street, Winsted, CT 06098
PK-21 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 150 Oak St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$579,000
69.79%
MLS
7/28/2021
Sold
$341,000
—
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 150 Oak St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,706
7%
$229,880
—
2023
$6,262
3%
$229,880
—
2023
$6,067
5%
$229,880
33%
2022
$5,797
—
$172,830
—
2021
$5,797
—
$172,830
—
2020
$5,797
—
$172,830
—
2019
$5,797
—
$172,830
—
2018
$5,797
11%
$172,830
11%
2017
$5,245
—
$156,380
—
2016
$5,245
3%
$156,380
—
2015
$5,114
5%
$156,380
—
2011
$4,879
—
$156,380
—
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.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Turning Point Realty, LLC, Pamela Silvestri and Turning Point Realty, LLC, Suzie Larson

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150 Oak Street, Winchester, CT 06098 (MLS# 24166332) is a Multi-Family property with 5 units containing 11 bedrooms, 5 full bathrooms and 1 partial bathroom. 150 Oak Street is currently listed for $579,000 and was received on May 01, 2026. Want to learn more about 150 Oak 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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