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    Winchester, CT
    Residential Income

    Winchester, CT Residential Income Properties for Sale

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    Turnkey Restaurant with Upstairs Bar
    Updated: Jun 23
    Turnkey Restaurant with Upstairs Bar

    380 Main Street, Winchester, CT 06098

    $999,000
    6,200 sqft 0.17 AC lot
    Spacious dining area seating up to 156 guests plus an upstairs 20‑seat bar
    Five apartments on‑site: three currently functioning units and two additional units ready for completion
    12–15 car dedicated parking lot with additional street parking
    Outdoor dining seating for approximately 24
    Basement area equipped for dough preparation with abundant storage for catering support
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    Two-Family Residential Income Property
    Updated: Jul 6
    Two-Family Residential Income Property

    120 E Lake Street, Winchester, CT 06098

    $325,000
    2,103 sqft 0.60 AC lot
    Two‑family home built in 1880 with 2 units, each offering 5 rooms, 2 bedrooms, and 1 full bath
    Both units feature hardwood flooring throughout and separate natural gas heating systems
    Upper unit includes an enclosed porch for additional seasonal living space
    0.66‑acre lot with seasonal views of Highland Lake
    Detached three‑car garage and ample outdoor space
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    Updated Two-Family Winchester Residence
    Updated Two-Family Winchester Residence

    77 Hubbard Street, Winchester, CT 06098

    $299,900
    2,699 sqft 0.28 AC lot

    Two-family residence with modern updates and income potential.

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    Newly Renovated Three-Family Triplex
    Newly Renovated Three-Family Triplex

    26 Elm Street, Winchester, CT 06098

    $398,000
    2,496 sqft

    Newly renovated three-family property with two fully renovated units and exterior improvements for reduced near-term maintenance.

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    Two-Family Home with Rear Lot
    Two-Family Home with Rear Lot

    68 Wetmore Avenue, Winchester, CT 06098

    $349,999
    2,555 sqft

    Well-maintained two-family property with a rear lot, large yard, 3-car garage, and off-street parking.

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    Two-Family Duplex Property
    Two-Family Duplex Property

    71-73 Wheeler Street, Winchester, CT 06098

    $450,000
    2,000 sqft

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

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    Winsted Multifamily Investment Opportunity
    Winsted Multifamily Investment Opportunity

    150 Oak St, Winchester, CT 06098

    $549,000

    Charming 5-unit apartment building in residential neighborhood. Fully rented.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    120 E Lake St, Winchester, CT 06098

    $325,000

    Two well-maintained units each offer 2 bedrooms and a full bath, with separate natural gas heating systems.

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    Multifamily and Office Space Opportunity
    Multifamily and Office Space Opportunity

    25 Center Street, Winchester, CT 06098

    $359,900
    2,754 sqft 0.11 AC lot

    Multifamily residential property with office space in central location.

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    Updated Duplex with Income Potential
    Updated Duplex with Income Potential

    77 Hubbard St, Winchester, CT 06098

    $299,900
    0.28 AC lot

    Two-family residence with modern updates and income potential.

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    MULTI_FAMILY - Winchester, CT
    MULTI_FAMILY - Winchester, CT

    77 Hubbard St, Winchester, CT 06098

    $299,900
    2,699 sqft 0.28 AC lot

    Two-family residence with modern updates and income potential.

    View details
    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.

    Three-Unit Residential Income Property
    Three-Unit Residential Income Property

    908 Main Street, Torrington, CT 06790

    $460,000
    3,178 sqft 0.19 AC lot

    Spacious, well-maintained three-family with two currently unoccupied units and recent updates ready for occupancy.

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    Two-Family Residential Income Home
    Two-Family Residential Income Home

    33 Terrace View, Norfolk, CT 06058

    $399,000
    2,596 sqft 0.82 AC lot

    Two separate apartments with dedicated parking and a large yard, offering a straightforward setup for residential income use.

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    Three-Family Residential Income Property
    Three-Family Residential Income Property

    908 Main Street, Torrington, CT 06790

    $450,000
    3,178 sqft

    A well-maintained three-family with two updated, currently unoccupied units for flexible occupancy or ownership options.

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    Two-Family Home Near Norfolk Center
    Two-Family Home Near Norfolk Center

    33 Terrace Vw, Norfolk, CT 06058

    $399,000

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

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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.

    Wooded Hunting and Recreation Land
    Wooded Hunting and Recreation Land

    32 Norfolk Road, Winchester, CT 06098

    $299,900
    63.00 AC lot

    Wooded acreage abuts Algonquin State Forest and is located on a state highway, with an existing cell tower.

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    Forested Residential/Recreation Land
    Forested Residential/Recreation Land

    393 Winchester Road, Winchester, CT 06098

    $295,000
    51.00 AC lot

    51 acres of gently rolling, forested land in RU-1 zoning with a former homesite and intermittent streams.

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    Winchester Land with Waterfront Access
    Winchester Land with Waterfront Access

    843-845 (lots - 10A,10 &1 E wakefield Boulevard, Winchester, CT 06098

    $158,000
    1.18 AC lot

    1.18 acre Winchester lot with potential for dream home.

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    Winchester Land Near Highland Lake
    Winchester Land Near Highland Lake

    105,107 Mountain Road, Winchester, CT 06098

    $59,900
    0.41 AC lot

    Contiguous parcels near Highland Lake with potential city sewer access.

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    Winchester, CT Residential Income Properties Market Trends and Statistics

    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 23,506 square feet of properties for sale, with an estimated market value of $3,481,699.

    Sale prices for residential income properties in Winchester, CT start at $299,900, averaging $435,212, and reaching up to $999,000 — 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

    Commercial property segments ranked by active listings on the market

    Multifamily properties 15
    Apartment buildings 6
    Duplexes 5

    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 average listing prices of real estate assets

    Neighborhood Average Price
    Winsted - 06098 $533K

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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