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    Windham County, CT Apartment Buildings for Sale

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    Mixed-Use Building on Main Street
    $369,900
    3,391 SF

    Mixed-Use Building on Main Street

    239 Main St, Killingly, CT 06239

    Mixed-use property with offices and apartments on Main Street.

    • Mixed‑use building with offices and apartments on Main Street, offering income potential and business visibility.
    • Recent major upgrades: 2021 roof, furnace, hot water heater, electrical service (200 amps), 2025 windows and exterior doors, and blown‑in insulation.
    • Potential for additional income: Unfinished room plumbed for a kitchen, suitable for 4 more offices or a 2‑bedroom apartment with laundry.
    • Includes a 1‑bedroom apartment with private entrance, and multiple office spaces.
    • City water, sewer, and gas connections.
    Updated: Dec 29, 2025
    View details
    Multi-Unit Property with Income Potential
    $450,000

    Multi-Unit Property with Income Potential

    4 Main St, Windham, CT 06226

    Well-maintained multi-unit property featuring three separate living spaces.

    • Multi‑unit property with three separate units offering strong income potential.
    • Separate 2‑bedroom unit ideal for extended family or additional rental income.
    • Detached 3‑car garage with a 2‑bedroom apartment above.
    • Main home benefits from a whole‑house generator.
    • Newer boiler and hot water heater.
    View details
    Based on your search, we've compiled 243 Potential Opportunities for your consideration. Besides 2 Active listings in Windham County, CT, we suggest exploring several alternatives: similar 241 Off-Market properties to explore as potential leads

    Explore Off-Market Properties in Windham County, CT

    Consider similar Off-Market properties in Windham County, 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.

    Riverside Dr & Azud Rd

    Riverside Dr & Azud Rd

    Multifamily properties • 12.82 Acres
    Value Estimation by Request
    0 Riverside Dr & Azud Rd, Thompson, CT 06277
    View details
    18 Cady St

    18 Cady St

    APARTMENT HOUSE (UNDER 5 UNITS) • 5.20 Acres
    Value Estimation
    $640,000
    18 Cady St, Killingly, CT 06239-3727
    View details
    347 Fox Rd

    347 Fox Rd

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,160 SF
    Value Estimation
    $370,000
    347 Fox Rd, Putnam, CT 06260-2729
    View details
    643 Riverside Dr

    643 Riverside Dr

    APARTMENT HOUSE (UNDER 5 UNITS) • 4,957 SF
    Value Estimation
    $340,000
    643 Riverside Dr, North Grosvenordale, CT 06255
    View details
    23 Sunnyside Ave

    23 Sunnyside Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,390 SF
    Value Estimation
    $265,000
    23 Sunnyside Ave, Putnam, CT 06260-1881
    View details
    24 Ml St, Unit 32

    24 Ml St, Unit 32

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,432 SF
    Value Estimation
    $295,000
    24 Ml St, Putnam, CT 06260-1504
    View details
    52 Ring St

    52 Ring St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,742 SF
    Value Estimation
    $490,000
    52 Ring St, Putnam, CT 06260-2153
    View details
    72 Reynolds St

    72 Reynolds St

    APARTMENT HOUSE (5+ UNITS) • 6,504 SF
    Value Estimation by Request
    72 Reynolds St, Killingly, CT 06239-2957
    View details
    7 Otis St

    7 Otis St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,784 SF
    Value Estimation
    $495,000
    7 Otis St, Killingly, CT 06241
    View details
    54 Aldrich Ave, Unit 60

    54 Aldrich Ave, Unit 60

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,248 SF
    Value Estimation
    $350,000
    54 Aldrich Ave, Moosup, CT 06354-1602
    View details
    68 Bolles St

    68 Bolles St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,024 SF
    Value Estimation
    $250,000
    68 Bolles St, Putnam, CT 06260
    View details
    11 Tiffany St

    11 Tiffany St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,889 SF
    Value Estimation
    $325,000
    11 Tiffany St, Brooklyn, CT 06234-3861
    View details
    38 Aldrich Ave, Unit 44

    38 Aldrich Ave, Unit 44

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,304 SF
    Value Estimation
    $465,000
    38 Aldrich Ave, Moosup, CT 06354-1602
    View details
    52 Dog Hl Rd

    52 Dog Hl Rd

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,584 SF
    Value Estimation
    $375,000
    52 Dog Hl Rd, Killingly, CT 06241
    View details
    190 Main St

    190 Main St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,288 SF
    Value Estimation
    $325,000
    190 Main St, Moosup, CT 06354-1225
    View details
    64-70 Chestnut St

    64-70 Chestnut St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,383 SF
    Value Estimation
    $255,000
    64-70 Chestnut St, Plainfield, CT 06374
    View details
    49 Bolduc Ln

    49 Bolduc Ln

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,614 SF
    Value Estimation
    $360,000
    49 Bolduc Ln, Chaplin, CT 06235-2120
    View details
    113 Riverside Dr

    113 Riverside Dr

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,024 SF
    Value Estimation
    $260,000
    113 Riverside Dr, Thompson, CT 06277-2715
    View details
    66 Reynolds St

    66 Reynolds St

    APARTMENT HOUSE (5+ UNITS) • 6,132 SF
    Value Estimation
    $1,110,000
    66 Reynolds St, Killingly, CT 06239-2943
    View details
    75-81 Chestnut St

    75-81 Chestnut St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,380 SF
    Value Estimation
    $310,000
    75-81 Chestnut St, Plainfield, CT 06374
    View details
    53 Smith St

    53 Smith St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,854 SF
    Value Estimation
    $250,000
    53 Smith St, Putnam, CT 06260-1275
    View details
    14 Windsor Ave

    14 Windsor Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,642 SF
    Value Estimation by Request
    14 Windsor Ave, Plainfield, CT 06374-1046
    View details

    Windham County, CT Apartment Buildings Investment Opportunities Market Analysis

    Explore 243 apartment buildings for sale in Windham County, CT on our real estate platform. These investment opportunities span a total of 10,270,205 square feet of properties for sale, with an estimated market value of $72,959,900.

    Prices for two-family homes in Windham County, CT start at $70,000, averaging $313,132, and reaching up to $1,265,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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