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    Winsted, CT Residential Income 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
    View details
    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
    View details
    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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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    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 Enclosed Porch
    Two-Unit Duplex with Enclosed Porch

    120 E Lake Street, Winchester, CT 06098

    $325,000
    2,103 sqft 0.60 AC lot

    Two-unit duplex in R-3 zoning with separate natural gas heat and an upper enclosed porch, served by public water and sewer.

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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 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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    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.

    View details
    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 17 Active Listings in Winsted, CT, we suggest to view alternatives - similar 28 Off-Market properties to explore as potential leads.

    Off-Market Properties in Winsted, CT

    Consider similar Off-Market properties in Winsted, CT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    169 Prospect St
    APARTMENT HOUSE (UNDER 5 UNITS)

    169 Prospect St, Winsted, CT 06098-1956

    $550,000
    Estimated value
    4,848 sqft 0.56 AC lot
    View details
    91 Torringford St
    APARTMENT HOUSE (UNDER 5 UNITS)

    91 Torringford St, Winsted, CT 06098-2000

    $730,000
    Estimated value
    1.54 AC lot
    View details
    157 Prospect St
    APARTMENT HOUSE (UNDER 5 UNITS)

    157 Prospect St, Winsted, CT 06098-1955

    $410,000
    Estimated value
    0.92 AC lot
    View details
    69 Pleasant Vly Rd
    APARTMENT HOUSE (UNDER 5 UNITS)

    69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

    $2,695,000
    Estimated value
    5.01 AC lot
    View details
    217 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    217 Main St, Winsted, CT 06098-1282

    $365,000
    Estimated value
    2,388 sqft 1.13 AC lot
    View details
    175 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    175 Main St, Winsted, CT 06098-1227

    $355,000
    Estimated value
    3,823 sqft 0.91 AC lot
    View details
    7 Chestnut St
    APARTMENT HOUSE (UNDER 5 UNITS)

    7 Chestnut St, Winsted, CT 06098-1604

    $210,000
    Estimated value
    3,172 sqft 0.10 AC lot
    View details

    Winsted, CT Residential Income Properties Market Trends and Statistics

    Explore 45 residential income properties for sale in Winsted, CT, showcased through 17 active listings on our real estate platform. These investment opportunities span a total of 54,240 square feet of properties for sale, with an estimated market value of $7,348,599.

    Sale prices for residential income properties in Winsted, CT start at $299,000, averaging $459,287, 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 25
    Apartment buildings 13
    Duplexes 9

    Demographics Overview

    Population 13K
    Population Growth (5Y) -7.4%
    Median Household Income $82,614
    College Educated 57.2%

    Taxes & Financing

    Tax Rate (average for all types) 2.65%
    Property Tax per SF $43.14 per SF
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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