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    Winsted, CT
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    Winsted, CT Residential Income Properties for Sale

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    Turnkey Restaurant with Upstairs Bar
    Updated: Jun 23
    Turnkey Restaurant with Upstairs Bar

    380 Main Street, Winchester, CT 06098

    $999,000
    6,200 sqft 0.17 AC lot
    Spacious dining area seating up to 156 guests plus an upstairs 20‑seat bar
    Five apartments on‑site: three currently functioning units and two additional units ready for completion
    12–15 car dedicated parking lot with additional street parking
    Outdoor dining seating for approximately 24
    Basement area equipped for dough preparation with abundant storage for catering support
    View details
    Victorian Two-Family Home, Winchester CT
    Updated: Apr 29
    Victorian Two-Family Home, Winchester CT

    217 Walnut Street, Winchester, CT 06098

    $399,000
    2,779 sqft 0.28 AC lot
    Prime in‑town location close to shopping, dining, schools, and major routes.
    Two‑family home in exceptional condition with updated kitchens and bathrooms.
    Versatile property suitable for investors, owner‑occupants, or multi‑generational living.
    Each unit has a private entrance; one unit has 2 bedrooms, the other has 3 bedrooms, both with 1.5 baths.
    Features a wrap‑around covered porch, detached 2‑car garage, and additional shed.
    View details
    Two-Family Residential Income Property
    Two-Family Residential Income Property

    120 E Lake Street, Winchester, CT 06098

    $325,000
    2,103 sqft 0.60 AC lot

    Well-maintained two-family with separate gas heat, hardwood floors, enclosed porch, and detached three-car garage.

    View details
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    Winsted Multifamily Investment Opportunity
    Winsted Multifamily Investment Opportunity

    150 Oak St, Winchester, CT 06098

    $549,000

    Charming 5-unit apartment building in residential neighborhood. Fully rented.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    120 E Lake St, Winchester, CT 06098

    $325,000

    Two well-maintained units each offer 2 bedrooms and a full bath, with separate natural gas heating systems.

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    Updated Duplex with Income Potential
    Updated Duplex with Income Potential

    77 Hubbard St, Winchester, CT 06098

    $299,900
    0.28 AC lot

    Two-family residence with modern updates and income potential.

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    Victorian Two-Family Home
    Victorian Two-Family Home

    217 Walnut St, Winchester, CT 06098

    $399,000

    Well-maintained Victorian two-family home with updated kitchens and baths.

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    Two-Family Duplex Property
    Two-Family Duplex Property

    71-73 Wheeler Street, Winchester, CT 06098

    $450,000
    2,000 sqft

    Four-unit multifamily on one parcel with good parking and a convenient residential setting.

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    Multifamily and Office Space Opportunity
    Multifamily and Office Space Opportunity

    25 Center Street, Winchester, CT 06098

    $359,900
    2,754 sqft 0.11 AC lot

    Multifamily residential property with office space in central location.

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    MULTI_FAMILY - Winchester, CT
    MULTI_FAMILY - Winchester, CT

    77 Hubbard St, Winchester, CT 06098

    $299,900
    2,699 sqft 0.28 AC lot

    Two-family residence with modern updates and income potential.

    View details
    Based on your search, we've compiled 46 Potential Opportunities for your consideration. Besides 10 Active listings in Winsted, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 28 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Two-Family Residential Income Home
    Two-Family Residential Income Home

    33 Terrace View, Norfolk, CT 06058

    $399,000
    2,596 sqft 0.82 AC lot

    Two separate apartments with dedicated parking and a large yard, offering a straightforward setup for residential income use.

    View details
    Three-Family Residential Income Property
    Three-Family Residential Income Property

    908 Main Street, Torrington, CT 06790

    $450,000
    3,178 sqft 0.19 AC lot

    Well-maintained three-family with two updated, currently unoccupied units, offering flexible occupancy options.

    View details
    Three-Family Residential Income Property
    Three-Family Residential Income Property

    908 Main Street, Torrington, CT 06790

    $450,000
    3,178 sqft

    A well-maintained three-family with two updated, currently unoccupied units for flexible occupancy or ownership options.

    View details
    Two-Family Home Near Norfolk Center
    Two-Family Home Near Norfolk Center

    33 Terrace Vw, Norfolk, CT 06058

    $399,000

    Two-unit property with income potential, close to Norfolk's heart.

    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Wooded Hunting and Recreation Land
    Wooded Hunting and Recreation Land

    32 Norfolk Road, Winchester, CT 06098

    $299,900
    63.00 AC lot

    Wooded acreage abuts Algonquin State Forest and is located on a state highway, with an existing cell tower.

    View details
    Forested Residential/Recreation Land
    Forested Residential/Recreation Land

    393 Winchester Road, Winchester, CT 06098

    $295,000
    51.00 AC lot

    51 acres of gently rolling, forested land in RU-1 zoning with a former homesite and intermittent streams.

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    Winchester Land with Waterfront Access
    Winchester Land with Waterfront Access

    843-845 (lots - 10A,10 &1 E wakefield Boulevard, Winchester, CT 06098

    $158,000
    1.18 AC lot

    1.18 acre Winchester lot with potential for dream home.

    View details
    Winchester Land Near Highland Lake
    Winchester Land Near Highland Lake

    105,107 Mountain Road, Winchester, CT 06098

    $59,900
    0.41 AC lot

    Contiguous parcels near Highland Lake with potential city sewer access.

    View details

    Off-Market Properties in Winsted, CT

    Consider similar Off-Market properties in Winsted, CT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    169 Prospect St
    APARTMENT HOUSE (UNDER 5 UNITS)

    169 Prospect St, Winsted, CT 06098-1956

    $550,000
    Estimated value
    4,848 sqft 0.56 AC lot
    View details
    91 Torringford St
    APARTMENT HOUSE (UNDER 5 UNITS)

    91 Torringford St, Winsted, CT 06098-2000

    $670,000
    Estimated value
    1.54 AC lot
    View details
    157 Prospect St
    APARTMENT HOUSE (UNDER 5 UNITS)

    157 Prospect St, Winsted, CT 06098-1955

    Value Estimation by Request
    0.92 AC lot
    View details
    69 Pleasant Vly Rd
    APARTMENT HOUSE (UNDER 5 UNITS)

    69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

    $2,450,000
    Estimated value
    5.01 AC lot
    View details
    217 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    217 Main St, Winsted, CT 06098-1282

    Value Estimation by Request
    2,388 sqft 1.13 AC lot
    View details
    175 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    175 Main St, Winsted, CT 06098-1227

    Value Estimation by Request
    3,823 sqft 0.91 AC lot
    View details
    7 Chestnut St
    APARTMENT HOUSE (UNDER 5 UNITS)

    7 Chestnut St, Winsted, CT 06098-1604

    Value Estimation by Request
    3,172 sqft 0.10 AC lot
    View details
    149 Mdw St, Unit 155
    APARTMENT HOUSE (UNDER 5 UNITS)

    149 Mdw St, Winsted, CT 06098-1015

    Unit 155
    Value Estimation by Request
    4,798 sqft 0.50 AC lot
    View details
    6 Brk St
    APARTMENT HOUSE (UNDER 5 UNITS)

    6 Brk St, Winsted, CT 06098

    Value Estimation by Request
    3,400 sqft 0.12 AC lot
    View details
    14 Wheeler St
    APARTMENT HOUSE (UNDER 5 UNITS)

    14 Wheeler St, Winsted, CT 06098-1568

    Value Estimation by Request
    3,043 sqft 0.07 AC lot
    View details
    12 Gay St
    APARTMENT HOUSE (UNDER 5 UNITS)

    12 Gay St, Winsted, CT 06098-1609

    Value Estimation by Request
    2,750 sqft 0.12 AC lot
    View details
    61 Holabird Ave
    APARTMENT HOUSE (UNDER 5 UNITS)

    61 Holabird Ave, Winsted, CT 06098-1692

    Value Estimation by Request
    3,675 sqft 0.36 AC lot
    View details
    106 Elm St, Unit 112
    APARTMENT HOUSE (UNDER 5 UNITS)

    106 Elm St, Winsted, CT 06098-1637

    Unit 112
    Value Estimation by Request
    2,712 sqft 0.12 AC lot
    View details
    143 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    143 Main St, Winsted, CT 06098-1281

    Value Estimation by Request
    2,756 sqft 0.37 AC lot
    View details

    Winsted, CT Residential Income Properties Market Trends and Statistics

    Explore 38 residential income properties for sale in Winsted, CT, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 23,924 square feet of properties for sale, with an estimated market value of $3,582,800.

    Sale prices for residential income properties in Winsted, CT start at $299,900, averaging $511,828, and reaching up to $999,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Multifamily properties 17
    Apartment buildings 7
    Duplexes 6

    Demographics Overview

    Population 13K
    Population Growth (5Y) -7.4%
    Median Household Income $82,614
    College Educated 57.2%

    Taxes & Financing

    Tax Rate (average for all types) 2.65%
    Property Tax per SF $43.14 per SF
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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