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    Winchester, CT
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    Winchester, CT Multifamily Properties for Sale

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    Restaurant with Five Apartments
    Updated: Jun 23
    Restaurant with Five Apartments

    380 Main Street, Winchester, CT 06098

    $999,000
    6,200 sqft 0.17 AC lot
    6,200 SF restaurant property on 0.17 acres
    Dining room seats up to 156 guests
    Upstairs bar with 20‑seat capacity
    Five apartments; three functioning units and two ready for completion
    12‑15 car parking lot plus ample street parking
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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
    Two-Unit Duplex with Barn

    50 High Street, Winchester, CT 06098

    $324,900
    3,044 sqft 0.56 AC lot

    Two separately serviced apartments include porches and access to a two-story barn.

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    Turnkey Restaurant with Apartments
    Turnkey Restaurant with Apartments

    380 Main Street, Winchester, CT 06098

    $999,000
    6,200 sqft

    Turnkey restaurant with dining, upstairs bar seating, outdoor dining, and five apartments, plus dedicated parking.

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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 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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    Historic 5-Unit Apartment Building
    Historic 5-Unit Apartment Building

    150 Oak Street, Winchester, CT 06098

    $579,000
    5,233 sqft

    Fully rented 5-family apartment building with a detached 4-bay garage, updated roof and multiple heating systems.

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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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    Triplex with Two Driveways
    Triplex with Two Driveways

    69 Prospect Street, Winchester, CT 06098

    $274,900
    2,204 sqft

    Three separate residences include off-street parking and laundry hookups in Unit 1.

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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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    Mixed-Use Investment Property For Sale
    Mixed-Use Investment Property For Sale

    45 Elm St, Winchester, CT 06098

    $540,000
    0.17 AC lot

    Seven-unit brick building with residential and commercial spaces.

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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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    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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    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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    Renovated Three-Family Property
    Renovated Three-Family Property

    26 Elm Street, Winchester, CT 06098

    $398,000
    2,496 sqft

    Legally converted triplex with two renovated units and additional rental income potential.

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    Mixed-Use Retail and Apartments
    Mixed-Use Retail and Apartments

    430 Main St, Winchestr Ctr, CT 06098

    Contact for pricing
    9,508 sqft

    First-floor retail features parking and a rear loading dock, with apartments on the second and third floors.

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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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    Mixed-Use Building with Loft Plans
    Mixed-Use Building with Loft Plans

    35 Willow St, Winchester, CT 06098

    Contact for pricing
    27,000 sqft

    Nearly 27,000 square feet with approved plans for apartments and ground-floor commercial space.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 21 Active Listings in Winchester, CT

    Winchester, CT Multifamily Properties Market Trends and Statistics

    Explore 21 multifamily properties for sale in Winchester, CT, showcased through 21 active listings on our real estate platform. These investment opportunities span a total of 88,197 square feet of properties for sale, with an estimated market value of $8,346,499.

    Sale prices for multifamily properties in Winchester, CT start at $274,900, averaging $439,289, 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 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 $472.1K

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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