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    Winchester, CT Residential Income Properties for Sale

    13 results
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    Updated Two-Family Winchester Residence
    Pending
    $299,900
    2,699 SF

    Updated Two-Family Winchester Residence

    77 Hubbard St, 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: Mar 3
    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 mixed-use building with commercial space and residential apartment.

    • Prime mixed‑use property in a high‑visibility downtown location on Main Street.
    • Spacious, recently renovated 3‑bedroom apartment on the second floor featuring a new roof, windows, deck, and kitchen, also includes on‑demand hot water.
    • First‑floor commercial space with existing kitchen area (oven range vents, fridge), bathroom, and open seating, suitable for restaurant, retail, or service business.
    • 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: Mar 2
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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
    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 St, Winchester, CT 06098
    View details
    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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    Winchester Multi-Family Investment Opportunity
    Pending
    $299,900
    1,874 SF

    Winchester Multi-Family Investment Opportunity

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

    106 Rockwell St, Winchester, CT 06098
    View details
    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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    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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    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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    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 St, Winchester, CT 06098
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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 St, Winchester, CT 06098
    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 St, Winchester, CT 06098
    View details
    Based on your search, we've compiled 20 Potential Opportunities for your consideration. Besides 13 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 3 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
    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 Ave, 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
    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 Rd, 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 Rd, Winchester, CT 06098
    View details
    Rare Multi-Parcel Land Opportunity
    $879,990
    131.50 Acres

    Rare Multi-Parcel Land Opportunity

    Five contiguous parcels in Winchester and Colebrook, Connecticut.

    000000 Norfolk Rd, Winchester, CT 06098
    View details

    Winchester, CT Residential Income Properties Investment Opportunities Market Analysis

    Explore 13 residential income properties for sale in Winchester, CT, showcased through 13 active listings on our real estate platform. These investment opportunities span a total of 42,689 square feet of properties for sale, with an estimated market value of $2,558,700.

    Sale prices for residential income properties in Winchester, CT start at $99,000, averaging $365,528, 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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