Windham County, CT Real Estate Search

Windham County, CT 6+ Bedroom Homes for Sale

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Newest Windham County, CT 6+ Bedrooms Homes for Sale

$1,100,000
6 Beds ⋅ 5 Baths ⋅ 24194248 MLS
The Fenner-Matthewson Mansion-an extraordinary piece of Connecticut history. Built circa 1855 for prominent mill owner Arnold Fenner, this magnificent Italian Villa is a distinguished contributing property within the National Register-listed Central Village Historic District. Nearly 6,000 SF of timeless grandeur offers 12 rooms, 6 bedrooms and 4.5 baths, with soaring 12' ceilings and exquisite period detail throughout. A grand foyer and sweeping staircase make an unforgettable first impression, complemented by 2 additional staircases, original black walnut doors and millwork, red pine floors, mercury glass doorknobs and beautiful built-ins. An incredible 9 working fireplaces, many with distinctive Italian marble surrounds, grace the home-including fireplaces in the updated kitchen and primary suite. The kitchen blends historic character with modern function, featuring a Sub-Zero refrigerator, pantry and butler's pantry. The primary suite offers a private full bath with soaking tub and fireplace. Recent improvements include a new roof and new central air. Set on 2.65 acres with an inviting front porch, stone courtyard and charming stucco outbuilding. More than a home-this is architecture, history and legacy, awaiting its next steward.

40 Main St, Plainfield
$850,000
9 Beds ⋅ 7 Baths ⋅ 24191809 MLS
Turnkey multifamily investment opportunity in the heart of Putnam, CT. This 7-unit building offers immediate cash flow with a strong unit mix and meaningful recent capital improvements. The property comprises five (5) one-bedroom/one-bath units and two (2) two-bedroom/one-bath units across 5,402 square feet on a 6,500 SF lot. All units have been updated and the building has seen significant reinvestment, including a new roof (2024) and a new rear deck and staircase (2024). All utilities are separately metered, with tenants responsible for their own heat, hot water, and electric. Shared laundry in the basement provides an additional amenity without utility burden to ownership, and each tenant enjoys dedicated basement storage. Current 8.6% cap rate with room to improve.

34 Marshall St, Putnam
$474,900
8 Beds ⋅ 2 Baths ⋅ 24190300 MLS
Side by side two family home, perfect for owner-occupants or investors. Each unit offers a functional layout. One unit features all 4 bedrooms on the second floor with the convenience of a first floor laundry room, while the second unit offers a desirable first-floor bedroom and a similar layout. Recent improvements include new flooring on the second floor bedrooms in unit on the left. Situated on a generous lot, this property presents an excellent opportunity for multi-generational living, rental income, or expanding your investment portfolio.

232 Ballouville Rd, Killingly
$359,000
6 Beds ⋅ 2 Baths ⋅ 24189472 MLS
Excellent duplex style home in move-in ready condition! This home has been owned by the same family for 40 years, and has been well maintained and cared for. With both sides available for occupancy, it lends itself to owner/occupant, extended family, or investor ownership. Unit 31 has 3 bedrooms, one full bath, lots of living space on the main level, and oil fired steam heat. It is move-in ready, having been occupied just a few months ago, but it could use some cosmetics updates from a new owner. Unit 33 also has 3 bedrooms, one full bath, kitchen, living room, and dining room on first floor, and oil fired baseboard heat. This side has more cosmetic updates, and was also occupied until recently. Each side has a private basement area with a concrete floor, washer and dryer hookup, and separate heating systems and electrical panels. The home is set on a large lot, has a one car garage, a shed, and plenty of off-street parking. There is also a lovely private yard which would be perfect for gardening and outdoor enjoyment. There is a private well with a new well pump, and city sewer. Convenient location, with easy access to RI and to the highway for commuting. A great opportunity to purchase an excellent investment property! Conventional financing or cash would be best for this property.

31-33 Brunswick Ave, Plainfield
$220,000
6 Beds ⋅ 3 Baths ⋅ 24189860 MLS
This listing is for 383 Putnam Pike Only - However, a single family (same owner) is available next door at 385 Putnam Pike, Dayville, CT New roof 2025! 1st Floor: 3BR/1.5BA (potential 4BR reconfiguration), forced hot air heat 2nd Floor: 3BR/1BA, hot water baseboard heat Large walkout basement with expansion potential Newer roof and some replacement windows Needs: flooring, plumbing, kitchen/bath updates, paint, cosmetics; possible HVAC LOCATION: Close to I-395, approx. 5 minutes to Putnam and 10 minutes to Killingly Commons. Large unit sizes offer excellent value-add opportunity. NOTES: Subject to professional inspection and due diligence. Strong cash flow or BRRRR candidate if inspection confirms numbers

383 Putnam Pike, Killingly
$400,000
6 Beds ⋅ 2 Baths ⋅ 24187717 MLS
Exceptional investment opportunity! This well-maintained two-family property is business zoned, offering endless possibilities for investors, business owners, or those seeking a live/work opportunity. Each spacious unit features approximately 1,500 square feet with 3 bedrooms, providing strong rental appeal and excellent income potential. Whether you're looking to continue its use as a multi-family rental, explore commercial possibilities (subject to local zoning regulations), or add to your investment portfolio, this property offers flexibility and long-term value. Conveniently located with excellent visibility and easy access to major routes, this is an opportunity you won't want to miss. Agent related

78 S Main St, Brooklyn
$299,900
6 Beds ⋅ 3 Baths ⋅ 24187426 MLS
Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive. Whether you're looking to expand your investment portfolio, live in one unit and rent the other, or accommodate extended living arrangements, this multi-family home offers versatility, functionality, and long-term value. Sold as is where is. Needs work

14 Carey St, Windham
$649,900
6 Beds ⋅ 6 Baths ⋅ 24181170 MLS
Welcome to 9 East Franklin St, where modern comfort meets thoughtful design in this beautifully rebuilt side by side two-family home. The owner's unit feels like a private retreat, offering 3 spacious bedrooms, 2 beautifully updated full baths with heated floors, a convenient half bath, and gleaming hardwood floors throughout. A new 2022 roof adds peace of mind along with the home being fully insulated which saves each month on utility costs. The show stopping stone patio complete with a built-in stove, refrigerator, and sink creates the perfect outdoor living space for entertaining or relaxing. The attached rental unit is equally inviting, featuring 2 bedrooms, 1.5 baths, and a well designed two-level layout ideal for tenants seeking comfort and privacy. This unit also includes its own small private yard area, giving tenants outdoor space that feels separate and exclusive. With the side-by-side configuration, both owner and tenant enjoy their own privacy, making the property feel more like two individual homes than a traditional multifamily. Both units benefit from forced hot air and central A/C, ensuring year-round climate control. This is more than a home-it's an opportunity to live comfortably while generating income in a beautifully updated property, with privacy preserved for both households.

9 E Franklin St, Killingly
$529,900
7 Beds ⋅ 3 Baths ⋅ 24184050 MLS
Welcome to the Albert C. Luke home in the heart of Putnam. This Queen Anne Victorian home has been well maintained. It's everything you'd expect in a restored Victorian home. Beautiful wood flooring, build-ins, four fireplaces all with custom carved mantels, and an updated kitchen that's modern with quartz countertops and a marble backsplash, while complimenting the era of the home. The first floor offers plenty of space including a foyer that is used as a sitting room and a library that could be a first floor bedroom. There's also a full bathroom. You'll appreciate the ceiling medallions in some of the rooms with gas-replica light fixtures to mimic the time period. The staircase with a detailed railing leads to the second floor where the home continues to shine. Four bedrooms. One with a balcony and two that have water views or the Quineboag River. There's also a full bathroom on this floor that connects to the hallway and the primary bedroom. Need more living space? When you head up the stairs to the third floor, it's spacious. It has 2 bedrooms and a full bathroom. The heating system and hot water heater are 5 years old. Outside has a variety of plants and fruit trees. In addition, the property has a greenhouse and a shed for all of your lawn and yard needs. This home is close to the river trail and downtown with restaurants, shops and entertainment. Another great feature of this home is it's minutes away from I-395.

110 Church St, Putnam
$398,900
9 Beds ⋅ 3 Baths ⋅ 24182846 MLS
Exceptional opportunity to own this well-maintained 1895 three-family up/down property ideally situated near downtown Putnam. The charming property offers comfortable and spacious three bedroom units filled with character. The first floor unit has been tastefully updated throughout, and the property features both garage storage and off-street parking. A solid investment with timeless appeal and strong income potential.

176 S Main St, Putnam
$639,777
10 Beds ⋅ 5 Baths ⋅ 24177946 MLS
Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio.

120 North St, Windham
$6,950,000
12 Beds ⋅ 9 Baths ⋅ 24101484 MLS
Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799 Main Residence, a 7,577 SF, 5-bedroom, 5.2-bathroom masterpiece of timeless architecture. Ideal for grand-scale entertaining, the butler's pantry flows seamlessly from the exquisite dining room into a spacious eat-in kitchen, complete with a Viking Professional stove. Additional structures include a 1900 Caretaker's Residence (4 bedrooms) & a 1948 14-stall barn with a 3-bedroom apartment above-ideal for a barn manager or rental income, it also offers great potential for a remote home office. Car collector enthusiasts & woodworking hobbyists will love the ultra-spacious garage, complete with a large workshop, a walk-in laundry/tack room, & a powder room. Amenities abound: 2 inground pools, an enchanting pool house with a potting room, raised-bed gardens, & a tranquil bass pond. Enjoy direct access to the Air Line Trail for riding/hiking. The estate directly abuts the CT Audubon Society land, with its beautiful trails located just a half-mile down the road, while the prestigious Pomfret & Rectory Schools are a mere 1.5 miles away. Conveniently accessible to Hartford, Providence/RI

433 Wrights Crossing Rd, Pomfret
$1,150,000
6 Beds ⋅ 5 Baths ⋅ 24172480 MLS
At the end of a long private drive on six rolling acres sits the 1880 Clark Cottage at Wintergreen, a Pomfret estate on the National Register of Historic Places. It's a rare antique that asks nothing of you: 19th-century craftsmanship paired with a fully renovated chef's kitchen and a spa-inspired primary bath, impeccably maintained throughout. Approximately 5,000 square feet span three finished levels and six bedrooms. The remodeled kitchen features custom quartz countertops and sink, a butler's pantry, and a sunlit breakfast nook opening to a living room and sunroom. Formal and casual living rooms, a formal dining room, and an expansive porch handle everything from quiet nights to large gatherings. The primary suite offers a sitting area, balcony, walk-in closet, and renovated bath. A bonus room over the garage and a finished top floor add flexibility for guests, offices, or multi-generational living. Outside is real seclusion: open lawn, mature trees, and room for gardens, set well back from the road yet minutes from Putnam, Woodstock, and the area prep schools, with Hartford, Providence, and Boston within easy reach. Move-in ready and genuinely private.

354 Pomfret St, Pomfret
$264,900
6 Beds ⋅ 2 Baths ⋅ 24171757 MLS
Exceptional opportunity for investors and owner-occupants alike! This fully rented two-family home generates $3,025 per month in gross rental income ($36,300 annually) while being offered at just $265,000. Opportunities to acquire a property with this level of income at this price point are becoming increasingly difficult to find. This Putnam two-family is located on a quiet dead-end street just a short walk from downtown's restaurants, shops, and amenities. Each unit offers three bedrooms and one full bath, providing spacious layouts that remain highly desirable to tenants. With nearly 2,000 square feet of living space on a manageable 0.14-acre lot, the property delivers strong rental performance without the burden of extensive grounds maintenance. Putnam's ongoing downtown revitalization continues to attract residents seeking a walkable lifestyle, helping support strong demand for well-located rental housing. Whether you're looking to add a cash-flowing asset to your portfolio or offset your mortgage with rental income, 21 George Street represents an affordable entry into investment property ownership with income already in place from day one.

21-23 George St, Putnam
$849,900
14 Beds ⋅ 7 Baths ⋅ 24166823 MLS
4 UNITS PLUS A 3 FAMILY ALL ON ONE PROPERTY, PLENTY OF OFF STREET PARKING, FULLY RENTED AND SOME LONG TERM TENANTS IN PLACE. CONVIENT LOCATION. TENANTS PAY ALL THERE OWN UTILITIES. CALL FOR MORE INFORMATION AND TO VIEW THE PROPERTY.

129 Woodstock Ave, Putnam
$350,000
6 Beds ⋅ 2 Baths ⋅ 24160273 MLS
Well-maintained two-family home located in a convenient area of Killingly, Connecticut. Each unit offers three spacious bedrooms and one full bathroom, with plenty of windows throughout allowing for abundant natural light. Both units include in-unit washer and dryer for added convenience. Unit 36A is equipped with a Navien propane system and mini-split heating and cooling, while Unit 36B features a Navien propane system. Both systems have been recently serviced, with records available through March 2026. Off-street parking adds additional ease for residents. The property also includes outbuildings, which are unheated and without electricity; contents will be removed prior to closing. Ideally located near the Danielson area with easy access to local shops, restaurants, and everyday amenities. Convenient to Interstate 395 and Route 6, with nearby access to Putnam, Connecticut and the Quinebaug River.

36 Church St, Killingly
$267,000
6 Beds ⋅ 2 Baths ⋅ 24117898 MLS
Price Improved.... Seller says Sell Sell Sell.. Looking for your next investment property?? Look no further. This home has been under agreement several times, but not because of inspection issues- the previous transactions couldn't move forward due to owner- occupied requirements from the solar. If you been searching for a home that's move in ready, while allowing you to update it at your own pace, this is it! With solid bones and only cosmetic improvements needed, this is a fantastic opportunity to create instant equity. While generating income at same time...

144 Prospect Ave, Killingly
$267,000
6 Beds ⋅ 2 Baths ⋅ 73422970 MLS
Price Improved.... Seller says Sell Sell Sell.. Looking for your next investment property?? Look no further. This home has been under agreement several times, but not because of inspection issues- the previous transactions couldn't move forward due to owner- occupied requirements from the solar. If you been searching for a home that's move in ready, while allowing you to update it at your own pace, this is it! With solid bones and only cosmetic improvements needed, this is a fantastic opportunity to create instant equity. While generating income at same time...

144 Prospect Avenue, Killingly
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