Windham County, CT 6+ Bedroom Homes for Sale

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Newest Windham County, CT 6+ Bedrooms Homes for Sale

$329,000

7 Beds ⋅ 2 Baths ⋅ 24215520 MLS

Explore the possibilities at this townhome-style duplex in Killingly. Offering two separate units, the property features a four-bedroom, one-bath unit and a three-bedroom, one-bath unit currently occupied by month-to-month tenants. With seven bedrooms in total and ample off-street parking, this property presents an appealing opportunity for an owner-occupant looking to offset housing costs or an investor seeking a versatile addition to their portfolio. Conveniently located at 4 Church Street, this duplex offers flexibility, space, and income potential.

4 Church St, Killingly

$340,000

6 Beds ⋅ 2 Baths ⋅ 24207270 MLS

Multiple Offers: Highest and Best Offer Deadline 5PM Tuesday Oct 27 2026. Quiet Corner ease! 2 Units for an extended family or live in one unit; let the other unit's rent pay most if not all the mortgage. Big 2 family, 2766 sq feet heated, on 0.66 grassy acre with 2 car garage, large shed, and above ground pool. 1st floor unit: 3 bedrooms, full bath with pocket door, kitchen, dining area, living room, mudroom with lots of storage and washer hookup, enclosed unheated sunporch, and breezeway to 2 car garage. 2nd floor unit: 3 bedrooms, 1 oversized full bath with washer hookup (a perfect spot for stackables), large kitchen, living room, walkup attic for storage or more liveable space if you finish it. See floorplans in photos. Quiet road, large paved driveway in excellent shape, recently resealed. Lovely old large, flat granite block for front stoop. Full unfinished basement has big workbench that will convey. Newer vinyl windows throughout! Both units share the septic and share the well; unknown which unit's elec meter has the well pump on it. Generator hookup in garage. Oil, radiators, one furnace currently, but there were two: concrete pad and oil line for 2nd furnace in basement. Same family for 100 years. Well maintained, but in need of cosmetic updates; unknown if hardwood floors under carpeting. Roof 20 years old with 50 year shingles and looks great. Deck at pool is mahogany. Staircase to 2nd floor mahogany with stair treads pressure treated wood.

114 Green Hollow Rd, Killingly

$499,900

6 Beds ⋅ 3 Baths ⋅ 24212211 MLS

Beautifully charming and beaming with character is this very spacious 2-family duplex; a rare find in Woodstock! This home is not your typical duplex and has a great floor plan in each unit. Perfect for an owner that wants to occupy a lovely home in a great location. Also nice for investors because the nicely updated and generously-sized units, each with their own laundry on the main floors, brings a higher rental income! The very large main house has attractive character, 4 large bedrooms, 2 full bathrooms, a dreamy updated kitchen with open floor plan to living room and dining areas. A first floor 4th bedroom and a laundry room on the main floor is large enough to be a 5th bedroom or office space! The second floor has three large bedrooms and a very large open den/craft room/office/home or college school area and a 2nd full bath! This unit has more space than you can dream to fill! The second unit is also generously-sized and nicely updated with 2 large bedrooms and a laundry room large enough to be a 3rd bedroom or office. Large living room leads to the updated open kitchen with an island and separate dining room. The home has a 3-car detached garage and peacefully landscaped grounds with room to garden. All separate utilities. Well water and public sewer. Listing Agent related to Seller. Come see this hidden gem before its gone!

9 Ellen Ln, Woodstock

$449,900

7 Beds ⋅ 4 Baths ⋅ 24210750 MLS

Great two family opportunity in downtown Putnam featuring a rare to find, 4 bay garage & commercial/industrial shop space with separate electric & sewer connections. The existing large duplex, believed to be two single families that have been long ago connected, features architectural singled roof, vinyl siding, replacement windows, updated boilers, electrical & oil tanks. Two stable tenants in both units which are very large with many potential bedrooms setups and both units featuring multiple bathrooms. The large covered front porch is a great feature. The shop/garage has tons of potential. Shop has two floors (main & cold storage basement). Great for contractors! This investment is more like a 3 unit investment or a commercial owner occupant with residential income.

291-293 School St, Putnam

$349,999

9 Beds ⋅ 4 Baths ⋅ 24210190 MLS

HISTORIC CHARM MEETS VALUE ADD POTENTIAL in Connecticut's Quiet Corner! This distinctive multi family property offers 3 residential units plus a fourth space with commercial potential, and a fascinating history as Kenney's Store, a post office and train depot. Units 1, 2 and 3 feature spacious layouts, beautiful hardwood floors and timeless character. Two units offer 3 bedrooms, while the third offers 2 bedrooms. Unit 1 is currently configured as a 1-bedroom but can be converted back to a 2 or 3 bedroom layout. The property is ready to be repositioned, with one or two residential units requiring significant renovation and the former commercial space offering a true blank canvas for its next use. The commercial space includes two large rooms and a half bath. For the investor, owner occupant or entrepreneur with vision, this is an opportunity to transform a historic property and unlock its potential. Conveniently located near Acme Pond, the Air Line North State Park Trail, local vineyards and breweries, antique shops and scenic country roads. Bring your vision and create the next chapter of this unique property! CASH BUYER ONLY

6 Old Rte 12, Thompson

$895,000

12 Beds ⋅ 12 Baths ⋅ 24209225 MLS

Rare six-family investment opportunity featuring six townhouse-style units! Built in 1981, this exceptionally clean and well-maintained property offers 5,400 square feet of living space with six identical, turnkey 2-bedroom, 1.5-bath layouts. Each unit features main-level living space with a convenient half bath, two bedrooms and a full bath upstairs, private laundry hookups, and its own private basement offering additional storage and utility space. Designed with investment ownership in mind, the property features public water and sewer, individually metered electricity, and tenant-paid electric baseboard heat-helping limit owner-paid utility expenses. A private paved driveway and parking area, along with a 0.55-acre lot, complete the property. All occupied units are currently month-to-month, offering flexibility for the next owner. Purpose-built six-family properties with townhouse-style layouts like this are a rare find. A compelling opportunity to acquire a clean, turnkey multifamily asset with existing income and meaningful potential for future growth.

82 Hutchins St, Killingly

$365,000

8 Beds ⋅ 2 Baths ⋅ 24208553 MLS

Excellent opportunity to own a spacious two-family home offering flexibility for owner-occupants or investors. Each unit features 4 bedrooms and 1 full bath. Both units have their own utilities. Outdoors, each unit enjoys its own backyard area separated by fencing, creating defined outdoor spaces for each residence. A detached 2-car garage provides additional parking and storage, adding even more value. Whether you're looking to live in one unit while generating rental income from the other or add a multi-unit property to your investment portfolio, this two-family home is well worth a look!

137-139 S Chestnut St, Plainfield

$464,900

8 Beds ⋅ 2 Baths ⋅ 24205633 MLS

A wonderful opportunity for owner-occupants seeking additional income, or extended families looking for separate yet conveniently connected living spaces. This spacious side-by-side two-family offers four bedrooms in each unit, providing an abundance of room and flexibility. Each unit features its own separate entrance, along with newer plumbing, electrical and renovated bathrooms. Outside, you'll love the generous, flat and level yard, offering plenty of space for outdoor entertaining, gardening, or recreation.

235 Ballouville Rd, Killingly

$975,000

6 Beds ⋅ 5 Baths ⋅ 24206911 MLS

Fairytale living isn't just imagined-it actually exists. At the end of a private drive, surrounded by six rolling acres, sits an extraordinary Pomfret Estate. Professionally designed & impeccably maintained, old-world charm blends beautifully with modern luxury, with something unexpected around every corner.A grand entry introduces architectural delights throughout, from hardwood floors and detailed crown molding to six stunning fireplaces adding warmth and character. The main level unfolds through a formal dining room, gracious living room, sunroom, half bath, and beautifully renovated chef's kitchen with custom quartz, butler's pantry, sun-filled eat-in area, and heated floors. A second entrance with mudroom adds everyday function. The second level offers three additional bedrooms, including two luxurious primary suites, plus an additional full bath. The third floor reveals 3 more bedrooms, a full bath -an unexpected retreat all its own. Even the two-car garage surprises with a finished great room above, wrapped in windows and natural light. An updated roof, generator-ready setup, walkout basement, expansive porches, rolling lawns, and mature trees complete the setting. With 6 bedrooms, 4.5 baths, and three finished levels, this is proof that fairytale living truly exists.

354 Pomfret St, Pomfret

$475,000

7 Beds ⋅ 3 Baths ⋅ 24206870 MLS

Step inside and you'll immediately understand what makes this home so unique. Beautiful wood floors, custom built-ins, intricate details, and four fireplaces with hand-carved mantels are reminders of an era when homes were built to be admired. Look up and you'll discover decorative ceiling medallions paired with gas-replica light fixtures that add warmth and authenticity to the home's historic character. The Albert C. Luke House, a captivating Queen Anne Victorian in the heart of Putnam where craftsmanship, character, and modern comfort come together beautifully. The updated kitchen blends old and new with quartz countertops and a marble backsplash while complementing the home's historic charm. The spacious first floor includes a welcoming foyer currently used as a sitting room, a library that could serve as a first-floor bedroom or office, and a full bath. A beautifully detailed staircase leads to four second-floor bedrooms, including one with a balcony and two with views of the Quinebaug River, plus a full bath with access from the hallway and primary bedroom. The third floor adds two more bedrooms and a full bath, offering incredible flexibility. Outside, enjoy established plantings, fruit trees, a greenhouse, and shed. The heating system and hot water heater are approximately five years old. Close to the river trail, downtown Putnam's restaurants, shops and entertainment, and minutes from I-395, this is more than a home, it's a piece of history ready for its next chapter

110 Church St, Putnam

$499,900

6 Beds ⋅ 3 Baths ⋅ 24206136 MLS

ONE of a KIND property close to the mass line! INVESTORS take notice! There are 3 single-family RANCH homes on this 1 ACRE property!! One is rented and the other 2 you can make your own rent and leases! 2 bedrooms each 2 of the homes are on a slab and the 3 rd one has a dirt basement. Mini splits, electric baseboard, and SOLAR! Built in 1953, 1968 and 1974.

1-5 Mountain Hill Rd, Thompson

$262,000

6 Beds ⋅ 2 Baths ⋅ 24205724 MLS

ASK ABOUT SELLER OFFERING A 1-0 BUY DOWN... Looking to get into an already affordable house and get a good interest rate??? Inquire today...Seller says Sell Sell Sell.. Looking for your next investment property?? Look no further. 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... Solar on property is not owned Buyer and buyer agents to do due diligence on solar. bank requires owner occupied borrowers for solar loan.

144 Prospect Ave, Killingly

$634,900

10 Beds ⋅ 5 Baths ⋅ 24204552 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. One of the parties to the LLC has an active real estate license.

120 North St, Windham

$159,999

6 Beds ⋅ 2 Baths ⋅ 24201036 MLS

Bring your vision to this six-bedroom home in Willimantic's Hill Section. With approximately 1,948 square feet of living space, the property features generously sized rooms, hardwood flooring, tall windows, original woodwork, and period details throughout. A brand-new roof has already been installed, providing a great start for future improvements. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 15 Bellevue Street, located at the front of the property, creating the possibility of a package purchase. One of the parties to the LLC has an active real estate license.

11 Bellevue St, Windham

$444,900

6 Beds ⋅ 4 Baths ⋅ 24198642 MLS

19-21 Mohegan Street, Putnam, CT. Spacious double-lot 3-family property featuring an in-ground pool, fully fenced yard, and multiple sheds. The right side unit spans the basement, first, and second floors with 4 bedrooms and 1.5 baths. The lower left unit is a 1 bedroom 1 bath, and the top left unit with a sliding glass door is also a 1 bedroom 1 bath. Conveniently located just minutes from downtown Putnam amenities, shopping, and services. Easy commute to Worcester in about 25 minutes, Providence in about 45 minutes, and both New London and Hartford in under an hour. Currently occupied by tenants. 5 minutes to I-395 and major shopping with solid outdoor space and strong regional accessibility.

19-21 Mohegan St, Putnam

$749,900

7 Beds ⋅ 4 Baths ⋅ 24198629 MLS

Step back in time while enjoying the comforts of today in this exceptional Antique Colonial, built in 1830 and proudly situated on historic Thompson Hill. From the moment you arrive, the home makes a lasting impression with its welcoming wrap-around front porch, tastefully landscaped grounds, and classic circular driveway. The property also features a sizeable barn, offering abundant storage and endless possibilities. There is even an original "privy"! Inside, the 5-bedroom main residence offers generous closet space, 2 full baths, a thoughtfully designed updated kitchen, both formal and informal dining spaces, and beautifully updated bathrooms.A convenient first-floor laundry adds to the functionality of this spacious home, while the property's original character provides the warmth and charm that only an antique Colonial can offer. A standout feature is the spacious two-story in-law apartment, complete with a private entrance and rear deck. With 2 bedrooms and 1 1/2 baths, this versatile space is perfect for extended family, guests, a home office, or other living arrangements. The property has been thoughtfully improved with updated mechanical systems and a brand-new septic system, providing modern peace of mind while maintaining the home's historic character. This home is ideally located just minutes from the Massachusetts and Rhode Island state lines and major commuter routes allowing quick and easy access to the Arts, Dining, Shopping, Medical facilities and Airports

362 Thompson Rd, Thompson

$995,000

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 with great income potential! 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 had been occupied until spring 2026, with all mechanical systems functional, but it could use some cosmetics updates. 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

$350,000

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

$479,000

9 Beds ⋅ 4 Baths ⋅ 24185574 MLS

Opportunity awaits with this multi-family property in Willimantic. Featuring multiple residential units with a mix of layouts, this property offers flexibility for both investors and owner-occupants seeking rental income. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks, public transportation, and major commuter routes. Separate living spaces provide privacy for occupants while the property's central location adds to its long-term appeal. Whether you're looking to expand your investment portfolio or offset your housing costs with rental income, this property presents a versatile opportunity in a convenient location. One of the parties to the LLC has an active real estate license.

260 Summit St, Windham

$6,450,000

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

$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

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Windham County, CT 6+ Bedroom Homes for Sale

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