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Windham County CT Multifamily Homes & Duplexes for Sale

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  • /29

    $179,925

    • 7 Beds
    • 3 Baths
    • 2,668 Sq Ft

    57 Chapman St, Willimantic, CT 06226

    Don't miss this exceptional investment opportunity at 57 Chapman Street in Willimantic, CT! This versatile 3-family property features one spacious 3-bedroom, 1-bath unit and two well-proportioned 2-bedroom, 1-bath units, making it an ideal choice for investors or owner-occupants seeking rental income. Each unit offers comfortable layouts with ample potential for updates and customization,

    Agent Photo

    Jason Kemp

    Five Stars Realty

    (860) 419-7674

    57 Chapman St, Willimantic, CT 06226
  • /19

    $299,000

    • 6 Beds
    • 2 Baths
    • 1,932 Sq Ft

    100 South St, Willimantic, CT 06226

    Discover 100 South Street in Willimantic-a great opportunity to own a fully occupied 2-family home with solid rental income and key updates already done. The first floor unit hasbeen remodeled, including fresh flooring and paint, and a brand-new furnace. The property also features a 2-year-old roof, offering long-term durability and reduced future expenses. With great tenants already in place,

    Agent Photo

    Amber Jones

    KW Legacy Partners

    (860) 831-4634

    100 South St, Willimantic, CT 06226
  • /21

    $289,000

    • 6 Beds
    • 2 Baths
    • 1,736 Sq Ft

    96 South St, Willimantic, CT 06226

    Welcome to 96 South Street in Willimantic-a solid investment opportunity with tenants already in place through February and April 2026. This well-maintained 2-family property offers reliable rental income from day one. Recent improvements include: New windows and flooring on the first floor. Updated electrical and mechanical systems. 1-year-old roof for peace of mind and reduced maintenance

    Agent Photo

    Amber Jones

    KW Legacy Partners

    (860) 791-3791

    96 South St, Willimantic, CT 06226
  • /8

    $225,000

    • 4 Beds
    • 2 Baths
    • 988 Sq Ft

    395 Hartford Pike, Dayville, CT 06241

    Welcome to this well-maintained 2-family home located in the heart of Dayville! Whether you're looking for an owner-occupied residence with rental income or a solid investment property, this one checks all the boxes. Each unit offers 2 bedrooms and 1 bath . Live in one side and rent the other unit With strong rental history and separate utilities, it's truly investor-friendly. Conveniently

    Courtney Ravenelle RE/MAX Bell Park Realty

    395 Hartford Pike, Dayville, CT 06241
  • /14

    $279,900

    • 4 Beds
    • 2.5 Baths
    • 1,520 Sq Ft

    10 Tiffany St, Brooklyn, CT 06234

    2-Family with one unit ready for occupancy! 2/3 bedrooms with living room, eat in appliance kitchen with breakfast bar, & 1/2 bath. Room could be dining room or bedroom. Staircase leads to full bathroom with glass shower and 2 spacious bedrooms with plenty of closet space. Porch to enjoy your evenings. City water, sewer and gas! Unit B is rented and has a large deck, 1 bedroom, large living room,

    Christine Johnson RE/MAX One

    10 Tiffany St, Brooklyn, CT 06234
  • /33

    $399,990

    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    190 Main St, Moosup, CT 06354

    Whether you're a seasoned investor or looking to make your first real estate purchase, 190 Main St, Moosup, CT is a smart and strategic opportunity you don't want to miss. This 4-family property is located in the heart of Plainfield, offering solid rental income with plenty of room to add value and boost returns. With an affordable price point, this property presents the perfect chance to

    Jonathan Santos William Raveis Real Estate

    190 Main St, Moosup, CT 06354
  • /40

    $279,900

    • 7 Beds
    • 2 Baths
    • 2,422 Sq Ft

    110 Franklin St, Danielson, CT 06239

    Charming 2-family home in Killingly, CT, offering strong investment potential or multi-generational living! The first unit features 4 spacious bedrooms and 1 full bath, while the second unit offers 3 bedrooms and 1 full bath-perfect for rental income or extended family. This property is brimming with potential and awaits your personal touch and TLC to truly shine. Located in an incredibly

    Kyle Seyboth Century 21 Limitless

    110 Franklin St, Danielson, CT 06239
  • /5

    $235,000

    • 4 Beds
    • 2 Baths
    • 2,259 Sq Ft

    434 Pleasant St, Willimantic, CT 06226

    This 2 story multi-family gem offers two spacious 2-bedroom, 1-bath units (approx. 1,100 sq ft each), one upstairs and one downstairs-both currently leased by long-term tenants with separate utilities, providing hassle-free rental income. Many upgrades have already been done here. Schedule a showing for a better look of this property. Check agent remarks

    Chad Saba I.M.A. Realty LLC

    434 Pleasant St, Willimantic, CT 06226
  • /36

    $484,999

    • 8 Beds
    • 4 Baths
    • 4,808 Sq Ft

    40 Elm St, Willimantic, CT 06226

    ATTENTION INVESTORS!!! This incredible 10 CAP investment Opportunity for 4 units across 2 2-family properties may be exactly what you're looking for!!! Discover the potential in this centrally located low overhead property. With strong rental demand from nearby ECSU, Uconn and in the general market, vacancy will not be a problem. Tenant amenities include large backyards, with privacy and gardens.

    Robyn Letourneau Berkshire Hathaway NE Prop.

    40 Elm St, Willimantic, CT 06226
  • /35

    $489,999

    • 8 Beds
    • 4 Baths
    • 3,828 Sq Ft

    389 Pleasant St, Windham, CT 06226

    Prime Investment Opportunity in Willimantic! Excellent potential in a high-demand, low vacancy location. With strong bones, proximity to ECSU, public transit and downtown this property is perfect for investors or house hackers looking to build equity fast. NEW ELECTRIC PANELS, NEW HEAT AND HOT WATER FURNACES. Combine with other listed Willimantic properties: Elm st., Jackson St., and Chapman St.

    Robyn Letourneau Berkshire Hathaway NE Prop.

    389 Pleasant St, Windham, CT 06226
  • /35

    $599,999

    • 12 Beds
    • 5 Baths
    • 4,466 Sq Ft

    136 Chapman St, Windham, CT 06226

    INVESTORS TAKE NOTE!! LOW VACANCY in Windham county. 5-unit Investment Property with Strong Cash Flow! Located in the heart of Willimantic, this fully occupied property offers easy maintenance, off street parking, and stable tenants. GOI: $82,560 Other income: $2400 Expenses: $71,628 NOI: $71,628 12 CAP Combine with other listed willimantic properties: Elm st., Jackson St., and Pleasant St. as a

    Robyn Letourneau Berkshire Hathaway NE Prop.

    136 Chapman St, Windham, CT 06226
  • /28

    $568,900

    • 7 Beds
    • 3 Baths
    • 2,115 Sq Ft

    51 Main St, North Grosvenordale, CT 06255

    Own your own beautiful property in Thompson Ct and have your mortgage paid. This property offers ample living space with large apartments. The huge back yard is private and offers shade and a beautiful tree line. This property has off street parking with ample of garage space. Enjoy your own workshop that is heated and offers plenty of extra room to work! The insulated garage is 18 x 36 ft and

    Tessa Stacy Brunet and Company Real Estate

    51 Main St, North Grosvenordale, CT 06255
  • /40

    $485,000

    • 9 Beds
    • 5 Baths
    • 5,134 Sq Ft

    4 Main St, Willimantic, CT 06226

    Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a

    Tammy Arute Arute Realty Group LLC

    4 Main St, Willimantic, CT 06226
  • /33

    $469,900

    • 6 Beds
    • 3.5 Baths
    • 2,684 Sq Ft

    34 2nd St Unit 36, Plainfield, CT 06374

    Amazing opportunity to own a 2-unit home offering 3 bedrooms, and 2 baths each side with its own laundry. The right side was completely gutted in 2024 and renovated from the ground up, with NEW insulation, sheetrock, vinyl plank flooring, Windows, splitters for heat & AC, Kitchen with 5 appliances and 2 full baths. Outside the home has a new roof, siding, asphalt driveways, porch and deck, and

    Pat Malek First Choice Realty

    34 2nd St Unit 36, Plainfield, CT 06374
  • /40

    $320,000

    • 6 Beds
    • 2 Baths
    • 2,981 Sq Ft

    87 North St, Willimantic, CT 06226

    TWO HOUSES ON ONE PROPERTY! This unique investment opportunity at 87-89 North Street in Willimantic, CT, presents a compelling proposition for investors. The property comprises TWO single-family homes situated on a single lot, each with its own driveway and access to a large garage located conveniently on the front house's driveway. The rear house, a charming 1,224 square-foot dwelling,

    Toni Iandoli William Pitt Sotheby's Int'l

    87 North St, Willimantic, CT 06226
  • /13

    $330,000

    • 5 Beds
    • 2 Baths
    • 2,200 Sq Ft

    9 Ann St, Willimantic, CT 06226

    2 family house on a quiet street. First floor is a 2 bed 1 bath with hardwood floors throughout. Direct access to their side of the basement. Front foyer, eat in kitchen, living room. Second unit is the 2nd floor & 3rd floor and open, perfect for owner occupied multifamily. 2 bedrooms on the upper level with new carpet. Kitchen, dining room, living room, bathroom and 1 bedroom on the second floor

    david breau eXp Realty

    9 Ann St, Willimantic, CT 06226
  • /9

    $499,995

    • 8 Beds
    • 8 Baths
    • 4,160 Sq Ft

    8 High St, Putnam, CT 06260

    "Exceptional Investment Opportunity in Putnum CT, 8-unit property featuring two separate buildings on a generously sized lot, offering both immediate income potential and exciting development prospects. Building 1 stands ready for immediate occupancy, featuring 4 vacant 1 bed units meticulously maintained and prepared for new tenants. while you explore options for the second building. Building 2,

    Karim Douich William Raveis Real Estate

    8 High St, Putnam, CT 06260
  • /39

    $695,000

    • 3 Beds
    • 3 Baths
    • 2,546 Sq Ft

    48 Wrights Crossing Rd, Pomfret Center, CT 06259

    Welcome to Wrights Crossing Road in picturesque Pomfret, where charm, nature, and opportunity meet. This fully remodeled circa-1890 three-family home offers the perfect blend of timeless character and 2021 modern upgrades-nestled along a majestic brook with peaceful, natural soundscapes, and the scenic Audubon sanctuary land and trails right up the road. Two units are currently rented at strong

    Jennie Kesselman Berkshire Hathaway NE Prop.

    48 Wrights Crossing Rd, Pomfret Center, CT 06259
  • /23

    $375,000

    • 7 Beds
    • 4.5 Baths
    • 2,926 Sq Ft

    25-27 Farrows St, Putnam, CT 06260

    Invest in your next multi family. With the high demand for multi families, this oversized TWO family is set to be a money maker. Entire property has been properly updated and maintained for many years. Stable tenants in place with potential to increase rents in the future. Newer asphalt roofing, vinyl siding, updated interior units all make this property low maintenance for many years. The two

    Mark Tetreault, II RE/MAX Bell Park Realty

    25-27 Farrows St, Putnam, CT 06260
  • /15

    $1,100,000

    • 6 Beds
    • 3 Baths
    • 1,800 Sq Ft

    18 Ware Rd, Dayville, CT 06241

    Approved Residential Development Opportunity - Dayville, Killingly, CT Prime development land approved for 14 duplex buildings in the Dayville section of Killingly. This exceptional opportunity sits on land currently generating rental income from three existing structures: a two 2-family home and a mobile home. The property offers dual access from Ware Road and Pineville Road, and the proposed

    Claudia Bergstrom RE/MAX Diverse

    18 Ware Rd, Dayville, CT 06241
  • /29

    $650,000

    • 6 Beds
    • 4 Baths
    • 3,240 Sq Ft

    223 Route 169, Woodstock, CT 06281

    A rare investment opportunity located in beautiful Woodstock, CT! This 4 unit property is a blank slate to set your own rents, procure your own tenants, or owner occupy. These completely remodeled units feature stunning floors, tiled bathrooms, granite counters, and all have appliances. 2 bed/ 1 bed set up. Coin op laundry available. Close to Woodstock Academy and the Hyde School. Sits on a

    Amy Brunet Brunet and Company Real Estate

    223 Route 169, Woodstock, CT 06281
  • /25

    $1,495,000

    • 19 Beds
    • 12 Baths
    • 11,775 Sq Ft

    29 Tiffany St, Brooklyn, CT 06234

    Attention Investors! Rare opportunity to own a 12-unit brick multifamily building in desirable Brooklyn, Connecticut. This well-maintained property features a diverse mix of units offering both ranch-style one-bedroom, one-bath units on the first floor and townhouse-style two-bedroom, one-bath units on the second floor, offering a total of 12 units to rent. The building is currently fully

    Anthony Chabot Chabot & Associates Real Estate

    29 Tiffany St, Brooklyn, CT 06234
  • /31

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 2,542 Sq Ft

    227 Pudding Hill Rd, Hampton, CT 06247

    This stunning 1775 Colonial home, set on 153 picturesque acres in scenic Scotland, Connecticut, gives a unique opportunity for those who appreciate the charm of farm life. Currently utilized for hay production, beef cattle, and horses, the property boasts an estimated 70 percent of its land dedicated to fields, with the remainder covered in beautiful woodlands. The mostly level fields are

    Peter Plourde Berkshire Hathaway NE Prop.

    227 Pudding Hill Rd, Hampton, CT 06247
  • /2

    $237,500

    • 5 Beds
    • 1 Bath
    • 2,548 Sq Ft

    33 MacHine Shop Hill Rd, South Windham, CT 06266

    Welcome to a unique chance to own a spacious multi-family property in the charming South Windham area. This home presents an outstanding opportunity for investors seeking rental income and invites a creative new owner to explore the renovation potential. With a total of five bedrooms and two bathrooms spread across 2,548 square feet, this property is ideal for offering flexibility to operate as a

    Franchesca Pescatello Prue Realty LLC

    33 MacHine Shop Hill Rd, South Windham, CT 06266
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