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    Winchester, 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
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    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
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    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
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    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 15 Potential Opportunities for your consideration. Besides 7 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, 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

    Winchester, CT Multifamily Properties Investment Opportunities Market Analysis

    Explore 7 multifamily properties for sale in Winchester, CT, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 16,553 square feet of properties for sale, with an estimated market value of $1,049,900.

    Sale prices for multifamily properties in Winchester, CT start at $299,900, averaging $524,950, and reaching up to $750,000 — 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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