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    Winchester, CT Residential Income Properties for Sale

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    New Haven, CT Waterbury, CT Hartford, CT
    9 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
    Mixed-Use Building in Downtown Winsted
    $395,000
    1,909 SF

    Mixed-Use Building in Downtown Winsted

    720 Main Street, Winchester, CT 06098

    Two-story mixed-use building with commercial space and residential apartment.

    • Prime mixed‑use property in a high‑visibility downtown location on Main Street.
    • First‑floor commercial space suitable for restaurant, cafe, retail, or service business with existing kitchen infrastructure.
    • Spacious, recently renovated 3‑bedroom apartment on the second floor with new roof, windows, deck, and on‑demand hot water.
    • Ideal for owner‑occupancy (live and work) or investment with separate gas and electric meters.
    • Excellent location near Highland Lake, Route 44, and downtown amenities.
    Updated: Nov 12, 2025
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    Mixed-Use Building in Downtown Winsted
    $395,000
    1,909 SF

    Mixed-Use Building in Downtown Winsted

    Two-story mixed-use building with commercial space and residential apartment.

    720 Main Street, Winchester, CT 06098
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    Updated Two-Family Winchester Residence
    $299,900
    2,699 SF

    Updated Two-Family Winchester Residence

    Two-family residence with modern updates and income potential.

    77 Hubbard Street, Winchester, CT 06098
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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 17 Potential Opportunities for your consideration. Besides 9 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.

    63 Acres Abutting State Forest
    $299,900
    63.00 Acres

    63 Acres Abutting State Forest

    63-acre wooded land parcel abutting Algonquin State Forest.

    32 Norfolk Road, Winchester, CT 06098
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    Forested Land in Winchester Center
    $295,000
    51.00 Acres

    Forested Land in Winchester Center

    51 acres of gently rolling, forested land in Winchester.

    393 Winchester Road, Winchester, CT 06098
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    Winchester Land with Waterfront Access
    $158,000
    1.18 Acres

    Winchester Land with Waterfront Access

    1.18 acre Winchester lot with potential for dream home.

    843-845 (lots - 10A,10 &1 E wakefield Boulevard, Winchester, CT 06098
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    Winchester Land Near Highland Lake
    $59,900
    0.41 Acres

    Winchester Land Near Highland Lake

    Contiguous parcels near Highland Lake with potential city sewer access.

    105,107 Mountain Road, Winchester, CT 06098
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    Winchester, CT Residential Income Properties Investment Opportunities Market Analysis

    Explore 9 residential income properties for sale in Winchester, CT, showcased through 9 active listings on our real estate platform. These investment opportunities span a total of 22,651 square feet of properties for sale, with an estimated market value of $1,839,900.

    Sale prices for residential income properties in Winchester, CT start at $299,900, averaging $459,975, 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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