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    Winchester, CT Multifamily Properties for Sale

    10 results
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    Turnkey Restaurant with Apartments
    $750,000
    5,389 SF

    Turnkey Restaurant with Apartments

    436 Main St, Winchester, CT 06098

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

    • Turnkey, award‑winning restaurant with a 10‑year track record and loyal customer base.
    • Prime location in the heart of Litchfield County with high traffic.
    • Includes 4 apartments in addition to the restaurant.
    • Restaurant recognized in top publications including the New York Times and Wall Street Journal.
    • Fully equipped restaurant with all infrastructure items included (valued over $100k).
    Updated: Oct 27, 2025
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    Mixed-Use Building in Downtown Winsted
    $395,000
    1,909 SF

    Mixed-Use Building in Downtown Winsted

    720 Main St, Winchester, CT 06098

    Two-story building with commercial space and renovated apartment.

    • Prime mixed‑use property in a high‑visibility downtown location on Main Street.
    • Spacious, recently renovated 3‑bedroom apartment on the second floor with new roof, windows, deck, kitchen, and on‑demand hot water.
    • First‑floor commercial space with existing kitchen area, suitable for restaurant, cafe, retail, or service business.
    • Separate gas and electric meters for the commercial and residential units, ideal for owner‑occupier or investment.
    • Excellent location near Highland Lake, Route 44, and downtown amenities with strong walkability.
    Updated: Nov 14, 2025
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    Mixed-Use Building in Downtown Winsted
    $395,000
    1,909 SF

    Mixed-Use Building in Downtown Winsted

    Two-story building with commercial space and renovated apartment.

    720 Main St, Winchester, CT 06098
    View details
    Updated Two-Family Home, Winchester, CT
    Pending
    $299,900
    2,699 SF

    Updated Two-Family Home, Winchester, CT

    Two-family residence with updated first-floor unit and classic second-floor.

    77 Hubbard St, Winchester, CT 06098
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    Multifamily with Office Space Opportunity
    $319,900
    2,754 SF

    Multifamily with Office Space Opportunity

    Multifamily with office space in central Winchester location.

    25 Center St, Winchester, CT 06098
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    Three-Unit Multifamily Property in Winchester
    Pending
    $299,900
    1,874 SF

    Three-Unit Multifamily Property in Winchester

    Three-unit property with long-term tenants and a vacant unit.

    106 Rockwell St, Winchester, CT 06098
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    Restaurant and Apartments For Sale
    $750,000
    5,389 SF

    Restaurant and Apartments For Sale

    Mixed-use property with restaurant and apartments in Winchester, Connecticut.

    436 Main St, Winchester, CT 06098
    View details
    Litchfield County Two-Family Home
    $225,000

    Litchfield County Two-Family Home

    Two-family home in Litchfield County with income potential.

    30 Rock St, Winchester, CT 06098
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    Well-Maintained Two-Family Home
    $349,900

    Well-Maintained Two-Family Home

    Two-family home with detached garage, convenient location.

    135 Elm St, Winchester, CT 06098
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    Multifamily Home Near Transportation
    $259,000

    Multifamily Home Near Transportation

    Multifamily home with spacious rooms, storage, and convenient transportation.

    10 Crescent St, Winchester, CT 06098
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    Based on your search, we've compiled 14 Potential Opportunities for your consideration. Besides 10 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

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

    Torrington, CT 6-Unit Apartment Building
    $1,195,000
    5,000 SF

    Torrington, CT 6-Unit Apartment Building

    Brand new, 6-unit apartment complex, ready March 2025.

    775 Main St, Torrington, CT 06790
    View details
    Renovated Duplex with Garage Bays
    $469,900

    Renovated Duplex with Garage Bays

    Side-by-side duplex renovated in 2022 with modern amenities.

    25 Margerie St, Torrington, CT 06790
    View details
    Two-Family Home in Collinsville
    $419,900
    2,096 SF

    Two-Family Home in Collinsville

    Two-unit property near Farmington River Trail, ideal for investment.

    67 Torrington Ave, Canton, CT 06019
    View details
    Income Property with River Views
    $550,000

    Income Property with River Views

    Four-family home in Collinsville with Farmington River views.

    9 Maple Ave, Canton, CT 06019
    View details

    Winchester, CT Multifamily Properties Investment Opportunities Market Analysis

    Explore 10 multifamily properties for sale in Winchester, CT, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 39,640 square feet of properties for sale, with an estimated market value of $3,209,700.

    Prices for multifamily properties in Winchester, CT start at $299,900, averaging $458,528, and reaching up to $750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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