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    Winchester, CT Residential Income Properties for Sale

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    New Hartford, CT Canton, CT Torrington, CT
    11 results
    Victorian Two-Family Home, Winchester CT
    $399,000
    2,779 SF
    Victorian Two-Family Home, Winchester CT

    217 Walnut Street, Winchester, CT 06098

    Well-maintained Victorian two-family home in a prime location.
    • Prime in‑town location close to shopping, dining, schools, and major routes.
    • Two‑family home in exceptional condition with updated kitchens and bathrooms.
    • Versatile property suitable for investors, owner‑occupants, or multi‑generational living.
    • Each unit has a private entrance; one unit has 2 bedrooms, the other has 3 bedrooms, both with 1.5 baths.
    • Features a wrap‑around covered porch, detached 2‑car garage, and additional shed.
    Updated: Apr 29
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    Winsted Multifamily Investment Opportunity
    $579,000
    Winsted Multifamily Investment Opportunity

    150 Oak St, Winchester, CT 6098

    Charming 5-unit apartment building in residential neighborhood. Fully rented.
    • Fully rented 5‑family apartment home in a desirable residential neighborhood.
    • Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).
    • Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.
    • Includes a 4‑bay detached garage, with rental income potential.
    • Convenient location: walking distance to Northwestern CT Community College and Downtown Winsted.
    Updated: Apr 21
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    Well-Maintained Three-Family Home
    $475,000
    Well-Maintained Three-Family Home

    Rare, well-maintained three-family home with market rents.

    51 Hinsdale Ave, Winchester, CT 6098

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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

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    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

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    Victorian Two-Family Home
    $399,000
    Victorian Two-Family Home

    Well-maintained Victorian two-family home with updated kitchens and baths.

    217 Walnut St, Winchester, CT 6098

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    Two-Family Duplex Property
    $450,000
    2,000 SF
    Two-Family Duplex Property

    Four-unit multifamily on one parcel with good parking and a convenient residential setting.

    71-73 Wheeler Street, Winchester, CT 6098

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    Based on your search, we've compiled 19 Potential Opportunities for your consideration. Besides 11 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.

    Opportunities in Nearby Cities

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

    Norfolk Two-Family Home For Sale
    $425,000
    2,596 SF
    Norfolk Two-Family Home For Sale

    Two-family home with income potential near the heart of Norfolk.

    33 Terrace View, Norfolk, CT 06058

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    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

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    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

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    Two-Family Home Near Norfolk Center
    $425,000
    Two-Family Home Near Norfolk Center

    Two-unit property with income potential, close to Norfolk's heart.

    33 Terrace Vw, Norfolk, CT 6058

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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.

    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

    View details

    Winchester, CT Residential Income Properties Investment Opportunities Market Analysis

    Explore 11 residential income properties for sale in Winchester, CT, showcased through 11 active listings on our real estate platform. These investment opportunities span a total of 28,324 square feet of properties for sale, with an estimated market value of $3,493,800.

    Sale prices for residential income properties in Winchester, CT start at $299,900, averaging $499,114, 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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    Top Commercial Asset Segments

    Multifamily properties 31
    Apartment buildings 11
    Duplexes 6
    Triplexes 2
    Quadplexes 1

    Demographics Overview

    Population 14K
    Population Growth (5Y) -2.6%
    Median Household Income $85,212
    College Educated 77.5%

    High-Yield Neighborhoods for Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the median listing prices of real estate assets

    Neighborhood Average Price
    Winsted - 06098 $494.7K

    Listings Trend

    Total CRE Area on Market Trend

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