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    Winchester, CT Residential Income Properties for Sale

    12 results
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    Restaurant and Apartments For Sale
    $750,000
    5,389 SF

    Restaurant and Apartments For Sale

    436 Main St, Winchester, CT 06098

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

    • Turnkey, award‑winning restaurant with a 10‑year track record of success and loyal customer base, recognized in top publications.
    • Includes 4 apartments in addition to the restaurant, offering diverse income streams.
    • Prime location in the heart of Litchfield County with high traffic.
    • Restaurant is fully equipped with all infrastructure items included in the sale (valued over $100k).
    • Restaurant offers a warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats.
    Updated: Oct 28, 2025
    View details
    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 location on Main Street in downtown Winsted.
    • First‑floor commercial space suitable for restaurant, cafe, retail, or service business with existing kitchen area.
    • Spacious, renovated 3‑bedroom apartment on the second floor with new roof, windows, deck, kitchen, and on‑demand hot water system.
    • Separate gas and electric meters for the commercial and residential units, ideal for owner‑occupancy or investment.
    • Excellent location near Highland Lake, Route 44, and downtown amenities with strong walkability.
    Updated: Nov 14, 2025
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    Downtown Winchester Redevelopment Opportunity
    Pending
    $99,000
    4,679 SF

    Downtown Winchester Redevelopment Opportunity

    Redevelopment opportunity in downtown Winchester with retail and residential potential.

    508 Main St, Winchester, CT 06098
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    Multifamily and Office Space Opportunity
    $319,900
    2,754 SF

    Multifamily and Office Space Opportunity

    Multifamily residential property with office space in central 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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    Turnkey Restaurant with Apartments
    $750,000
    5,389 SF

    Turnkey Restaurant with Apartments

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

    436 Main St, Winchester, CT 06098
    View details
    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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    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
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    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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    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
    View details
    Based on your search, we've compiled 17 Potential Opportunities for your consideration. Besides 12 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 1 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.

    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
    Mixed-Use Property in Central Goshen
    $499,000
    6,944 SF

    Mixed-Use Property in Central Goshen

    Mixed-use property on over 3 acres in central Goshen.

    78 North St, Goshen, CT 06756
    View details
    Goshen, CT Residential Land - 294 Acres
    $4,450,000
    294.00 Acres

    Goshen, CT Residential Land - 294 Acres

    Prime Connecticut Land: Private Pond, Wooded

    0 Reservoir Rd, Goshen, CT 06756
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    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.

    Rare Land Opportunity in Winchester
    $879,990
    131.50 Acres

    Rare Land Opportunity in Winchester

    Five contiguous parcels with open fields and mature forest.

    000000 Norfolk Rd, Winchester, CT 06098
    View details

    Winchester, CT Residential Income Properties Investment Opportunities Market Analysis

    Explore 12 residential income properties for sale in Winchester, CT, showcased through 12 active listings on our real estate platform. These investment opportunities span a total of 51,836 square feet of properties for sale, with an estimated market value of $3,628,600.

    Prices for residential income properties in Winchester, CT start at $99,000, averaging $403,177, 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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    Browse Residential income properties for Sale Near Winchester, CT

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    Most Searched ZIP Codes in Winchester, CT

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