Active Under Contract
Multi family home for sale at 150 Oak St, Winsted, CT 06098 | MLS# 24166332 | Listing updated on 2026-10-29
Photo 1 of Multi family home for sale at 150 Oak St, Winsted, CT 06098 | MLS# 24166332 | Listing updated on 2026-10-29
Photo 2 of Multi family home for sale at 150 Oak St, Winsted, CT 06098 | MLS# 24166332 | Listing updated on 2026-10-29
Photo 3 of Multi family home for sale at 150 Oak St, Winsted, CT 06098 | MLS# 24166332 | Listing updated on 2026-10-29
Photo 4 of Multi family home for sale at 150 Oak St, Winsted, CT 06098 | MLS# 24166332 | Listing updated on 2026-10-29
15+
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Street View

$549,000

Monthly Est:$2,733

  • Beds Icon11 Beds
  • Beds Icon
    6 Baths
  • Beds Icon5,233sqft

150 Oak St, Winsted, CT 06098

$2,733/moEst:

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  • Multi Family

  • Built in 1924

  • $-- HOA

  • 8,276.4 sqft lot

  • $105/sq.ft

Description

*PRICE REDUCTION* 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, mostly 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 3-4 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!

  • Houzeo last checked: 7 minutes ago
  • Listing updated: October 29, 2026 at 1:28 pm
  • Listing Provided by: Pamela Silvestri | Turning Point Realty, LLC
  • Source: SMART MLS-CT | MLS#: 24166332 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Litchfield County

  • City

    Winsted

  • Neighborhood

    --

  • Year Built

    1924

  • HOA Fees

    -

  • Finished Area

    5,233 sqft

  • Lot Size

    8,276.4 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24166332

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    197

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 11

    Bathrooms: 6

Interior

  • Heating

    Hot Water, Natural Gas, Electric

  • Cooling

    None

  • Exterior Features

    Porch

  • Sewer

    Public Sewer Connected

Construction

  • Year Built

    Year Built: 1924

  • Home type

    Multi Family

  • Architectural Style

    Units Are Side By Side, Other

  • Roof

    Asphalt Shingle

  • Foundation Details

    Stone

Utilities & Energy

  • Laundry Features

    Basement Hook Up(s), Washer/dryer Some Units

  • Parking Features

    Detached Garage, On Street Parking, Off Street Parking, Unassigned Parking

  • Water Source

    Public Water Connected

  • Basement

    Full, Unfinished, Storage, Concrete Floor

Other Features

  • Lot Features

    Sloping Lot

  • Subdivision Name

    Winsted

Price History

DateEventPrice

10/29/2026

Source: mls_logoSMART MLS-CT #24166332

Contingent (Active Under Contract)

$549,000

$105/sqft

06/23/2026

Source: mls_logoSMART MLS-CT #24166332

Price Decreased

$549,000 -5.18%

$105/sqft

05/01/2026

Source: mls_logoSMART MLS-CT #24166332

Listed for Sale

$579,000

$111/sqft

04/20/2026

Source: mls_logoSMART MLS-CT #24166332

Coming Soon

$579,000 +69.79%

$111/sqft

08/18/2021

Source: mls_logoSMART MLS-CT #170383932

Price Increased

$341,000 +30900.00%

$65/sqft

Show more

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Nov 04, 2026, 10:45AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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