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For sale
    • Price cut: $30K (6/23)
    $549,000

    150 Oak Street, Winchester, CT 06098

    11beds
    5,233sqft
    : 
    $3,715/mo
    Get pre-qualified
    Multi Family
    Built in 1924
    -- sqft lot
    $-- Zestimate®
    $105/sqft
    $-- HOA

    What's special

    High ceilingsSpacious roomsMostly hardwood floors
    *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! 48 HOURS Notice needed for all showings. Please do not disturb tenants or enter the property without showing agent present. Property being sold "As Is". Conventional Financing or cash. Not all units have been photographed. Each apartment has separate utilities.
    129 days
    |
    203
    |
    10
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Pamela Silvestri (959)799-1696,

    Turning Point Realty, LLC 860-909-1162,

    Suzie Larson 860-601-3730,

    Turning Point Realty, LLC

    Source: Smart MLS,MLS#: 24166332MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 11
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Heating
      • Hot Water, Electric, Natural Gas
      Cooling
      • None
      Appliances
      • Included: Gas Water Heater, Electric Water Heater, Water Heater
      • Laundry: In Basement, In Unit
      Features
      • Basement: Full,Unfinished,Storage Space,Concrete
      • Attic: None
      • Has fireplace: No
      Interior area
      • Total structure area: 5,233
      • Total interior livable area: 5,233 sqft
      • Finished area above ground: 5,233

      Property

      Parking
      • Total spaces: 8
      • Parking features: Detached, On Street, Off Street, Unassigned
      • Garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Porch
      Lot
      • Size: 8,276 Square Feet
      • Features: Sloped
      Details
      • Parcel number: 926977
      • Zoning: R-3

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Units are Side-by-Side,Other
      • Property subtype: Multi Family
      • Attached to another structure: Yes
      Materials
      • Stucco
      • Foundation: Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1924

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Features: Library, Medical Facilities, Park, Playground, Public Rec Facilities, Shopping/Mall, Tennis Court(s), Near Public Transport
      • Subdivision: Winsted
      HOA
      • Has HOA: No
      Location
      • Region: Winsted

      Financial & listing details

      • Price per square foot: $105/sqft
      • Tax assessed value: $229,880
      • Annual tax amount: $6,896
      • Date on market: 4/20/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/23/2026Price change$549,000-5.2%$105/sqft
        Source: Smart MLS #24166332 Report a problem
        5/1/2026Listed for sale$579,000+69.8%$111/sqft
        Source: Smart MLS #24166332 Report a problem
        8/13/2021Sold$341,000-14.5%$65/sqft
        Source: Smart MLS #170383932 Report a problem
        6/1/2021Contingent$399,000$76/sqft
        Source: Smart MLS #170383932 Report a problem
        3/26/2021Listed for sale$399,000+4887.5%$76/sqft
        Source: Smart MLS #170383932 Report a problem
        7/30/2020Sold$8,000-96.5%$2/sqft
        Source: Smart MLS #170265834 Report a problem
        6/28/2007Sold$230,000$44/sqft
        Source: Smart MLS #A980233 Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 06098

        Getting around

        62 / 100
        Somewhat Walkable
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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