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    Winchester, CT
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    Winchester, CT Multifamily 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 two separate units, each with 5 rooms, 2 bedrooms, and 1 full bath
    Hardwood flooring throughout both apartments
    Separate natural gas heating systems for each unit
    Upper‑level unit includes an enclosed porch for additional seasonal living space
    Detached three‑car garage plus a generous 0.66‑acre lot
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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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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    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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    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.

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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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    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.

    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.

    Expansive Land Parcel in Holmes
    Expansive Land Parcel in Holmes

    545 Grape Hollow Road, Holmes, NY 12531

    $750,000
    2,480 sqft 75.32 AC lot

    75+ acre land parcel with garage near I-84.

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    89 Acres Vacant Land Catskill
    89 Acres Vacant Land Catskill

    300 Game Farm Road, Catskill, NY 12414

    $899,900
    89.06 AC lot

    89 acres of vacant land near Catskill Game Farm.

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    Two-Family Home with Detached Garage
    Two-Family Home with Detached Garage

    39 Halsey Avenue, Southampton, NY 11968

    $2,300,000
    0.33 AC lot

    Vacant two-family residence on a 0.33-acre lot with a detached two-bay car garage and long driveway.

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    Flatbush Development Property For Sale
    Flatbush Development Property For Sale

    14 E 32nd Street lot: 13, Brooklyn, NY 11226

    $1,249,000
    1,407 sqft 0.09 AC lot

    40 x 100 lot with R6, C1-2 zoning.

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    Winchester, CT Multifamily Properties Market Trends and Statistics

    Explore 9 multifamily properties for sale in Winchester, CT, showcased through 9 active listings on our real estate platform. These investment opportunities span a total of 21,234 square feet of properties for sale, with an estimated market value of $3,132,700.

    Sale prices for multifamily properties in Winchester, CT start at $299,900, averaging $447,528, 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

    Apartment buildings 6
    Duplexes 6

    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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