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    Winchester, CT
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    Winchester, CT Duplexes for Sale

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    Two-Unit Duplex
    Updated: Aug 26
    Two-Unit Duplex

    48 Center Street, Winchester, CT 06098

    $325,000
    2,257 sqft 0.08 AC lot
    Two‑unit duplex with 2,257 square feet of building area
    Each unit includes 5 rooms, 2 bedrooms, and 1 full bathroom
    Both units are currently rented
    CX zoning on a 0.08‑acre lot
    Built in 1900 with hot‑water heating
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    Two-Unit Duplex with Barn
    Updated: Aug 17
    Two-Unit Duplex with Barn

    50 High Street, Winchester, CT 06098

    $324,900
    3,044 sqft 0.56 AC lot
    3,044‑square‑foot duplex with two apartments
    First‑floor apartment measures approximately 1,620 square feet
    Second‑floor apartment measures approximately 1,424 square feet
    Each unit has its own natural gas boiler and hot water system
    Two‑story barn on a 0.56‑acre lot
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    Victorian Duplex with Barn
    Victorian Duplex with Barn

    64 Wheeler Street, Winchester, CT 06098

    $299,000
    2,270 sqft 0.33 AC lot

    Two-floor residential income property with hardwood interiors, separate heating systems, and a seasonal enclosed porch.

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    Two-Unit Duplex Investment Property
    Two-Unit Duplex Investment Property

    48 Center Street, Winchester, CT 06098

    $325,000
    2,257 sqft

    Downtown duplex with two leased residences, each offering a practical two-bedroom layout and one full bathroom.

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    Two-Unit Duplex with Garage
    Two-Unit Duplex with Garage

    120 E Lake Street, Winchester, CT 06098

    $325,000
    2,103 sqft 0.60 AC lot

    Two apartments feature hardwood floors and separate natural gas heating systems, with an enclosed porch on the upper level.

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    Two-Unit Duplex with Barn
    Two-Unit Duplex with Barn

    50 High Street, Winchester, CT 06098

    $324,900
    3,044 sqft 0.56 AC lot

    Two apartments provide separate utilities, covered porches, and access to downtown shopping and dining.

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    Victorian Two-Unit Duplex
    Victorian Two-Unit Duplex

    64 Wheeler Street, Winchester, CT 06098

    $299,000
    2,270 sqft

    Built in 1900, this two-family home features hardwood floors and separate natural gas heating systems for each unit.

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

    120 East Lake Street, Winchester, CT 06098

    $325,000
    2,103 sqft

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

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    Duplex with Carriage Barn
    Duplex with Carriage Barn

    160 Williams Avenue, Winchester, CT 06098

    $385,000
    3,302 sqft 1.25 AC lot

    Two-family residence with separate living areas, updated systems, fenced grounds, and substantial detached garage and workshop space.

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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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    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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    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.

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    Based on your search, we've compiled 16 Potential Opportunities for your consideration. Besides 12 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

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

    Two-Unit Duplex with Separate Parking
    Two-Unit Duplex with Separate Parking

    33 Terrace View, Norfolk, CT 06058

    $369,000
    2,596 sqft 0.82 AC lot

    Two residential units offer distinct layouts, a front porch, and designated parking areas for each occupant.

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

    33 Terrace View, Norfolk, CT 06058

    $369,000
    2,596 sqft

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

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    Two-Unit Duplex with Garage
    Two-Unit Duplex with Garage

    433 Torringford W Street, Torrington, CT 06790

    $380,000
    1,895 sqft 0.23 AC lot

    Corner-lot duplex with updated kitchens, a detached garage apartment, yard space, and off-street parking.

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    Two-Unit Residential Income Duplex
    Two-Unit Residential Income Duplex

    53 Calhoun Street, Torrington, CT 06790

    $339,900
    2,216 sqft

    Freshly painted two-family home with separate utilities, open layouts, and a large detached 2-car garage.

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    Winchester, CT Duplexes Market Trends and Statistics

    Explore 12 duplexes for sale in Winchester, CT, showcased through 12 active listings on our real estate platform. These investment opportunities span a total of 29,904 square feet of properties for sale, with an estimated market value of $4,032,699.

    Sale prices for duplexes in Winchester, CT start at $299,000, averaging $336,058, and reaching up to $450,000 — 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

    Apartment buildings 11
    Duplexes 11
    Triplexes 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 average listing prices of real estate assets

    Neighborhood Average Price
    Winsted - 06098 $379.8K

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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