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    Winsted, CT
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    Winsted, 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
    View details
    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
    View details
    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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    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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    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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    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-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.

    View details
    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
    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.

    View details
    Based on your search, we've compiled 50 Potential Opportunities for your consideration. Besides 14 Active listings in Winsted, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 28 Off-Market properties to explore as potential leads, 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.

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

    44 Bird Street, Torrington, CT 06790

    $398,000
    4,324 sqft 0.21 AC lot

    Duplex with two apartments, separate gas heat, off-street parking, and a detached two-car garage.

    View details
    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.

    View details
    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.

    View details
    Charming Multi-Family Property
    Charming Multi-Family Property

    682 Main St, Torrington, CT 06790

    $275,000

    Well-maintained multi-family property listed for sale in Torrington, CT.

    View details

    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.

    View details
    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.

    View details
    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.

    View details
    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.

    View details

    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

    $670,000
    Estimated value
    1.54 AC lot
    View details
    157 Prospect St
    APARTMENT HOUSE (UNDER 5 UNITS)

    157 Prospect St, Winsted, CT 06098-1955

    Value Estimation by Request
    0.92 AC lot
    View details
    69 Pleasant Vly Rd
    APARTMENT HOUSE (UNDER 5 UNITS)

    69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

    $2,450,000
    Estimated value
    5.01 AC lot
    View details
    217 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    217 Main St, Winsted, CT 06098-1282

    Value Estimation by Request
    2,388 sqft 1.13 AC lot
    View details
    175 Main St
    APARTMENT HOUSE (UNDER 5 UNITS)

    175 Main St, Winsted, CT 06098-1227

    Value Estimation by Request
    3,823 sqft 0.91 AC lot
    View details
    7 Chestnut St
    APARTMENT HOUSE (UNDER 5 UNITS)

    7 Chestnut St, Winsted, CT 06098-1604

    Value Estimation by Request
    3,172 sqft 0.10 AC lot
    View details
    149 Mdw St, Unit 155
    APARTMENT HOUSE (UNDER 5 UNITS)

    149 Mdw St, Winsted, CT 06098-1015

    Unit 155
    Value Estimation by Request
    4,798 sqft 0.50 AC lot
    View details
    6 Brk St
    APARTMENT HOUSE (UNDER 5 UNITS)

    6 Brk St, Winsted, CT 06098

    Value Estimation by Request
    3,400 sqft 0.12 AC lot
    View details
    14 Wheeler St
    APARTMENT HOUSE (UNDER 5 UNITS)

    14 Wheeler St, Winsted, CT 06098-1568

    Value Estimation by Request
    3,043 sqft 0.07 AC lot
    View details

    Winsted, CT Multifamily Properties Market Trends and Statistics

    Explore 42 multifamily properties for sale in Winsted, CT, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 34,939 square feet of properties for sale, with an estimated market value of $5,059,699.

    Sale prices for multifamily properties in Winsted, CT start at $299,900, averaging $505,969, 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 7
    Duplexes 5

    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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