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    Windham County, CT Duplexes for Sale

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    Side-by-Side Two-Family Home
    Updated: Jun 19
    Side-by-Side Two-Family Home

    9 E Franklin Street, Killingly, CT 06239

    $649,900
    4,134 sqft 0.21 AC lot
    Rebuilt side‑by‑side two‑family with private separation for the owner and rental unit
    Owner unit: 3 bedrooms, two updated full baths with heated floors, plus a half bath
    Rental unit: 2 bedrooms, 1.5 baths, two‑level layout with a small private yard area
    New 2022 roof plus full insulation
    Stone patio with built‑in stove, refrigerator, and sink, plus underground sprinkler
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    Duplex with Legal In-Law Apartment
    Updated: Jul 16
    Duplex with Legal In-Law Apartment

    48 Edmond Street, Putnam, CT 06260

    $400,000
    2,500 sqft 0.25 AC lot
    Legal in‑law apartment with both interior access and a private entrance
    Connecting bedroom between the main home and in‑law, plus 3 full and 1 half baths
    New kitchen with stainless appliances, butcher block counters, soft‑close cabinets and pantry cabinet
    Updates include new 100‑amp electrical panel, PEX water lines, and interconnected wireless smoke/CO detectors
    Heated space totals 2,891 SF (1,913 above grade, 978 below grade); finished walk‑out lower level
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    Duplex with Separate Heating Systems
    Duplex with Separate Heating Systems

    31-33 Brunswick Avenue, Plainfield, CT 06354

    $359,000
    2,383 sqft 0.51 AC lot

    Two 3-bedroom units with separate heating and electrical panels, zoned RA19, each with private basement and washer/dryer hookups.

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    Waterfront Land with Renovated Duplex
    Waterfront Land with Renovated Duplex

    25 Kennerson Reservoir Rd, Eastford, CT 06242

    $1,350,000
    2,700 sqft 158.00 AC lot

    158-acre waterfront offering with 3 contiguous parcels and a fully renovated 2-family dwelling.

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    Duplex with Four-Car Garage
    Duplex with Four-Car Garage

    19 Cady Street, Killingly, CT 06239

    $250,000
    1,200 sqft 0.69 AC lot

    Two-floor residential income property with a detached garage and an active first-floor lease.

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    Two-Family Home with Two-Car Garage
    Two-Family Home with Two-Car Garage

    14 Carey Street, Windham, CT 06226

    $299,900
    2,700 sqft 0.27 AC lot

    Two-family home in Windham on a 0.27-acre lot with a 2-car garage, steam heating, and public water and sewer.

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    Two-Family Waterfront Duplex
    Two-Family Waterfront Duplex

    13 Grove Street, Sterling, CT 06377

    $349,900
    2,496 sqft 0.22 AC lot

    Two-unit duplex on the Moosup River with a deck and public water and sewer service.

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    Single-Family with In-Law Apartment
    Single-Family with In-Law Apartment

    48 Edmond Street, Putnam, CT 06260

    $400,000
    2,891 sqft

    Fully remodeled single-family home offers a legal in-law apartment with private entrance and interior access.

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    Two-Unit Duplex With Separate Utilities
    Two-Unit Duplex With Separate Utilities

    11 Type Road, Windham, CT 06266

    $315,000
    1,890 sqft 0.42 AC lot

    Duplex on nearly a half-acre lot with separate utilities, two 2-bedroom units, and off-street parking.

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    Up-Down Duplex with Walk-Up Attic
    Up-Down Duplex with Walk-Up Attic

    27 Railroad Street, Putnam, CT 06260

    $349,900
    2,808 sqft 0.18 AC lot

    Up-down duplex in zoning NC with public utilities, hot-water heat, and a walk-up attic.

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    Business-Zoned Two-Family Duplex
    Business-Zoned Two-Family Duplex

    78 South Main Street, Brooklyn, CT 06234

    $400,000
    2,652 sqft

    Well-maintained two-family duplex with business zoning and two separate units, each with three bedrooms.

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    Duplex with Separate Driveways
    Duplex with Separate Driveways

    59-61 Gallup Street, Plainfield, CT 06374

    $339,900
    1,602 sqft 0.88 AC lot

    Two-unit duplex with separate driveways and laundry hookups, served by public sewer and a shared well.

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    Vacant Two-Family Home With Updates
    Vacant Two-Family Home With Updates

    29 Florence Street, Putnam, CT 06260

    $349,900
    1,892 sqft 0.13 AC lot

    Vacant two-family home in R-7 zoning with new roof, windows, siding, updated plumbing, and solar panels.

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    Two-Unit Duplex with Laundry
    Two-Unit Duplex with Laundry

    232 Ballouville Road, Killingly, CT 06241

    $474,900
    2,450 sqft

    Side-by-side duplex with two similar layouts, including first-floor laundry and recent second-floor flooring updates in one unit.

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    Legal Two-Family Duplex with In-Law Apartment
    Legal Two-Family Duplex with In-Law Apartment

    9 Carey Avenue, Plainfield, CT 06374

    $339,900
    2,576 sqft 0.36 AC lot

    Legal two-family duplex featuring a private in-law apartment, solar panels, and flexible space for multi-generational living.

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    Two-Family Residential Income Property
    Two-Family Residential Income Property

    63 School Street, Killingly, CT 06239

    $249,900
    1,536 sqft

    Two-family home offers separate utilities for each unit, plus off-street parking and a newer roof.

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    Two-Family Ranch Home
    Two-Family Ranch Home

    185 Chaplin Road, Eastford, CT 06242

    $499,000
    1,629 sqft 1.00 AC lot

    Ranch-style two-family residence on a level 1-acre lot, featuring a separate 2-bedroom unit with garage and a 1-bedroom unit.

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

    25-27 Pleasant Street, Plainfield, CT 06374

    $359,900
    2,248 sqft

    Two residential units with separate utilities, oversized corner-lot frontage on two streets, plus carport and storage sheds.

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    Up-and-Down Duplex with Attic
    Up-and-Down Duplex with Attic

    27 Railroad Street, Putnam, CT 06260

    $349,900
    2,808 sqft

    An up-and-down duplex with two renovated units and a walk-up attic ready for future finishing.

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    Two-Family Duplex Investment
    Two-Family Duplex Investment

    21-23 George Street, Putnam, CT 06260

    $319,900
    1,993 sqft 0.14 AC lot

    Built in 1890, this two-family duplex offers separate floor plans with three bedrooms and one full bath per unit.

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    MULTI_FAMILY - Windham, CT
    MULTI_FAMILY - Windham, CT

    14 Carey St, Windham, CT 06226

    $299,900
    2,700 sqft 0.27 AC lot

    Spacious two-family setup offers flexible living or rental configurations with a 2-car garage for parking and storage.

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    Spacious Duplex for Investors
    Spacious Duplex for Investors

    Windham, CT 06226

    $310,000
    2,781 sqft

    Income-generating duplex with potential for subdivision.

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

    185-187 Main Street, Plainfield, CT 06354

    $329,900
    3,211 sqft

    Duplex with three bedrooms and one bath per unit, plus a three-car detached garage and a newly installed roof.

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    Putnam Duplex Investment Opportunity
    Putnam Duplex Investment Opportunity

    236 Church Street, Putnam, CT 06260

    $275,000
    2,074 sqft

    Two-family property near downtown Putnam, ideal for investors or owner-occupiers.

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    Windham County, CT Duplexes Market Trends and Statistics

    Explore 32 duplexes for sale in Windham County, CT, showcased through 32 active listings on our real estate platform. These investment opportunities span a total of 59,746 square feet of properties for sale, with an estimated market value of $12,256,300.

    Sale prices for duplexes in Windham County, CT start at $220,000, averaging $395,364, and reaching up to $1,350,000 — 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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