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    Winsted, CT Multifamily Properties for Sale

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    New Haven, CT Waterbury, CT Hartford, CT
    7 results
    Turnkey Restaurant with Apartments
    $750,000
    5,389 SF

    Turnkey Restaurant with Apartments

    436 Main Street, Winchester, CT 06098

    Thriving restaurant with apartments in Litchfield County.

    • Turnkey, award‑winning restaurant with a 10‑year track record and loyal customer base.
    • High‑traffic location in the heart of Litchfield County.
    • Includes 4 apartments in addition to the restaurant.
    • Restaurant is fully equipped with all infrastructure items included in the sale.
    • Restaurant features 65 indoor seats and 35 outdoor seats.
    Updated: Oct 27, 2025
    View details
    Updated Two-Family Winchester Residence
    $299,900
    2,699 SF

    Updated Two-Family Winchester Residence

    77 Hubbard Street, Winchester, CT 06098

    Two-family residence with modern updates and income potential.

    • Completely renovated first‑floor unit featuring a new kitchen, updated bath, hardwood floors, and new carpet.
    • Two‑family residence ideal for investors or multi‑generational living.
    • Each unit features three bedrooms and one full bath.
    • Newer siding and recently updated roof ensure low‑maintenance living.
    • Attached one‑car garage for added convenience.
    Updated: Nov 11, 2024
    View details
    Mixed-Use Building with Income Potential
    $540,000
    7,405 SF

    Mixed-Use Building with Income Potential

    Seven-unit brick building with residential and commercial spaces for sale.

    45 Elm Street, Winchester, CT 6098
    View details
    Restaurant and Apartments in Winchester
    $750,000
    5,389 SF

    Restaurant and Apartments in Winchester

    Turnkey restaurant with apartments in high-traffic Litchfield County location.

    436 Main Street, Winchester, CT 6098
    View details
    Multifamily and Office Space Opportunity
    $359,900
    2,754 SF

    Multifamily and Office Space Opportunity

    Multifamily residential property with office space in central location.

    25 Center Street, Winchester, CT 6098
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    Downtown Winsted Mixed-Use Building
    $395,000
    1,909 SF

    Downtown Winsted Mixed-Use Building

    Two-story building with commercial space and renovated apartment.

    720 Main Street, Winchester, CT 6098
    View details
    Restaurant and Apartments in Winchester
    $750,000
    5,389 SF

    Restaurant and Apartments in Winchester

    Turnkey restaurant with apartments in high-traffic Litchfield County location.

    436 Main Street, Winchester, CT 6098
    View details
    Based on your search, we've compiled 43 Potential Opportunities for your consideration. Besides 7 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.

    Explore Opportunities in Nearby Cities

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

    Two-Family Home with Income Potential
    $239,900
    2,621 SF

    Two-Family Home with Income Potential

    Spacious two-family home offering income potential and flexible living.

    409 Brightwood Avenue, Torrington, CT 06790
    View details
    Main Street Mixed-Use Investment
    $559,000
    2,699 SF

    Main Street Mixed-Use Investment

    Fully occupied mixed-use property with strong income and recent renovations.

    433 Main Street, New Hartford, CT 6061
    View details
    North End Two-Family Home
    $224,900

    North End Two-Family Home

    Two-family home in North End neighborhood with detached garage.

    60 Benham St, Torrington, CT 6790
    View details
    Downtown Office Building For Sale
    $349,900
    2,248 SF

    Downtown Office Building For Sale

    Well-maintained office building with potential for mixed-use or residential conversion.

    7 Church Street North, New Hartford, CT 6057
    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.

    Holmes, NY Development Land
    $750,000
    75.32 Acres

    Holmes, NY Development Land

    75.32 acres of R-3 zoned land for single-family homes.

    545 Grape Hollow Road, Holmes, NY 12531
    View details
    Southampton Village Multifamily Opportunity
    $2,300,000
    0.33 Acres

    Southampton Village Multifamily Opportunity

    Two-family home in the heart of Southampton Village.

    39 Halsey Avenue, Southampton, NY 11968
    View details
    Fort Edward Land Investment Opportunity
    $349,900
    15.16 Acres

    Fort Edward Land Investment Opportunity

    15+ acre parcel zoned for mobile home land-lease community.

    L1.1 Drifting Ridge Road, Fort Edward, NY 12828
    View details
    Flatbush Development Property with R6 Zoning
    $1,249,000
    1,407 SF

    Flatbush Development Property with R6 Zoning

    Development property with existing home and R6, C1-2 zoning.

    14 E 32nd Street lot: 13, Brooklyn, NY 11226
    View details

    Explore 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

    169 Prospect St

    APARTMENT HOUSE (UNDER 5 UNITS) • 4,848 SF
    Value Estimation
    $550,000
    169 Prospect St, Winsted, CT 06098-1956
    View details
    91 Torringford St

    91 Torringford St

    APARTMENT HOUSE (UNDER 5 UNITS) • 1.54 Acres
    Value Estimation
    $670,000
    91 Torringford St, Winsted, CT 06098-2000
    View details
    157 Prospect St

    157 Prospect St

    APARTMENT HOUSE (UNDER 5 UNITS) • 0.92 Acres
    Value Estimation by Request
    157 Prospect St, Winsted, CT 06098-1955
    View details
    69 Pleasant Vly Rd

    69 Pleasant Vly Rd

    APARTMENT HOUSE (UNDER 5 UNITS) • 5.01 Acres
    Value Estimation
    $2,450,000
    69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008
    View details
    217 Main St

    217 Main St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,388 SF
    Value Estimation by Request
    217 Main St, Winsted, CT 06098-1282
    View details
    175 Main St

    175 Main St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,823 SF
    Value Estimation by Request
    175 Main St, Winsted, CT 06098-1227
    View details
    7 Chestnut St

    7 Chestnut St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,172 SF
    Value Estimation by Request
    7 Chestnut St, Winsted, CT 06098-1604
    View details
    149 Mdw St, Unit 155

    149 Mdw St, Unit 155

    APARTMENT HOUSE (UNDER 5 UNITS) • 4,798 SF
    Value Estimation by Request
    149 Mdw St, Winsted, CT 06098-1015
    View details
    6 Brk St

    6 Brk St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,400 SF
    Value Estimation by Request
    6 Brk St, Winsted, CT 06098
    View details
    14 Wheeler St

    14 Wheeler St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,043 SF
    Value Estimation by Request
    14 Wheeler St, Winsted, CT 06098-1568
    View details
    12 Gay St

    12 Gay St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,750 SF
    Value Estimation by Request
    12 Gay St, Winsted, CT 06098-1609
    View details
    61 Holabird Ave

    61 Holabird Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,675 SF
    Value Estimation by Request
    61 Holabird Ave, Winsted, CT 06098-1692
    View details
    106 Elm St, Unit 112

    106 Elm St, Unit 112

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,712 SF
    Value Estimation by Request
    106 Elm St, Winsted, CT 06098-1637
    View details
    143 Main St

    143 Main St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,756 SF
    Value Estimation by Request
    143 Main St, Winsted, CT 06098-1281
    View details
    13 Greenwoods Ave

    13 Greenwoods Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,600 SF
    Value Estimation by Request
    13 Greenwoods Ave, Winsted, CT 06098-3001
    View details
    5 Home Pl

    5 Home Pl

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,952 SF
    Value Estimation by Request
    5 Home Pl, Winsted, CT 06098-1709
    View details
    19 Ctr St

    19 Ctr St

    APARTMENT HOUSE (UNDER 5 UNITS) • 0.18 Acres
    Value Estimation by Request
    19 Ctr St, Winsted, CT 06098-1611
    View details

    Winsted, CT Multifamily Properties Investment Opportunities Market Analysis

    Explore 35 multifamily properties for sale in Winsted, CT, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 756,202 square feet of properties for sale, with an estimated market value of $11,974,900.

    Sale prices for multifamily properties in Winsted, CT start at $105,000, averaging $427,675, and reaching up to $2,695,000 — 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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