Windham County, CT Real Estate | Windham County, CT 6+ Bedrooms Homes for Sale

6 Beds ⋅ 2 Baths ⋅ 24206557 MLS

Unlock the potential of 5.18 acres in Thompson! With substantial acreage and an existing residence already in place, 150 Wilsonville Road presents an exciting opportunity for investors, developers, or buyers looking to create something of their own. The land may offer potential for subdivision or additional development, subject to town approvals, zoning requirements, and buyer due diligence. The property features a character-filled 1800s farmhouse with a later addition, offering a spacious layout, hardwood flooring, built-ins, a large kitchen, first-floor laundry, and a distinctive two-story brick fireplace/chimney. The home is ready for renovation and provides an opportunity to restore, redesign, and add value while preserving some of its original character. Three storage structures located to the right of the home provide additional utility. Solar panels are present; ownership and terms are being verified. Conveniently located just minutes from I-395. A unique opportunity to combine acreage, an existing home, and potential future possibilities all in one property. Buyer and buyer's agent to perform due diligence regarding subdivision/development potential, property condition, solar, utilities, zoning, and permitting requirements. Sale contingent upon contract owners ability to take title.

150 Wilsonville Rd, Thompson

$309,900

6 Beds ⋅ 4 Baths ⋅ 24206012 MLS

Welcome to this well-maintained side-by-side two-family home, offering an excellent opportunity for both owner-occupants and investors! Each spacious unit features 3 bedrooms and 2 full bathrooms, providing comfortable and functional living spaces with plenty of room to grow. Whether you're looking to live in one unit while generating rental income from the other, or seeking a solid investment property, this versatile two-family offers a great opportunity. Conveniently located near major highways, shopping, dining, schools, and other local amenities, making commuting and everyday living a breeze. Don't miss your chance to own this fantastic income-producing property in a convenient location!

105-107 S Chestnut St, Plainfield

$267,000

6 Beds ⋅ 2 Baths ⋅ 24205724 MLS

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.

120 North St, Windham

$170,000

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.

11 Bellevue St, Windham

$449,900

6 Beds ⋅ 2 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

$299,000

6 Beds ⋅ 2 Baths ⋅ 24193499 MLS

This two-family property offers solid bones and strong potential. Each unit provides a functional layout with 3 bedrooms and ample space including finished walk-up attic. Home has been used as a single family for the last 20 year's second floor kitchen needs to be reinstated. Ideal for investors, contractors, or owner occupants looking to build equity, this home needs work but delivers a great opportunity to create long-term value. Conveniently located in the heart of Putnam near local amenities and major routes, this property is a chance to transform a multi-unit home into a reliable income producing asset.

57 Wilkinson 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

$445,000

7 Beds ⋅ 3 Baths ⋅ 24198253 MLS

61-63 Pomfret Street, Putnam, CT 06260 Excellent turnkey investment in the heart of Putnam. This true side-by-side townhouse-style duplex has been thoroughly renovated and finished to a high standard. Each unit has its own first and second floor, private basement, and private fenced-in rear lawn. The left side offers 4 bedrooms and 1 bath, currently rented at $1,600/month. The right side offers 3 bedrooms and 1.5 baths, currently rented at $1,400/month. Combined gross rents are $3,000/month ($36,000/year). Both tenants are month-to-month. Updates include newer cabinets and countertops, fully renovated bathrooms, freshly painted walls throughout, and flooring in good condition. The roof is only 2 years old with 30-year architectural shingles, furnaces are 3 years old, and the building has brand-new vinyl replacement windows.Conveniently located near downtown Putnam restaurants, shops, and events with easy access to I-395. Worcester is approximately 28 miles, Providence about 33 miles, and New London roughly 48 miles. A clean, low-maintenance duplex ideal for investors seeking cash flow or an owner-occupant.

61-63 Pomfret St, Putnam

$389,900

6 Beds ⋅ 2 Baths ⋅ 24196938 MLS

This well-maintained duplex offers an excellent opportunity for investors or owner-occupants looking to build equity while generating rental income. Each unit features 3 bedrooms, 1 full bathroom, and nearly 1,300 square feet of living space, providing spacious layouts and strong rental potential. One unit will be vacant at the time of purchase and has been recently renovated, allowing a new owner the flexibility to move in, secure a new tenant at current market rates, or utilize the unit as an owner-occupied residence. The second unit is currently tenant-occupied and generates $1,700 per month in rental income, providing immediate cash flow from day one. Both units feature individual basements, offering valuable storage space and additional potential. Conveniently located in Plainfield with easy access to local amenities, schools, shopping, and major roadways, this property is an ideal addition to any investment portfolio. Live in one unit, rent the other, or maximize the property's income potential-this is a great opportunity to own a spacious two-family property.

81-83 Community Ave, Plainfield

$249,900

6 Beds ⋅ 2 Baths ⋅ 24196730 MLS

Exceptional opportunity for investors and owner-occupants alike! This two-family home has one vacant unit and one occupied currently generating $1625 per month in gross rental income 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

$699,900

6 Beds ⋅ 5 Baths ⋅ 73558344 MLS

Step back in time while enjoying the comforts of modern living at this extraordinary circa-1770 three-unit property, where historic New England charm meets exceptional income-producing potential. Set on nearly 4 private acres, this one-of-a-kind estate offers the perfect opportunity for investors, owner-occupants, or those seeking a multi-generational family compound. The property features three separate living units, each offering its own unique character while showcasing the timeless craftsmanship of the 18th century. Thoughtful renovations and updates have preserved the home's rich history while providing the conveniences of today's lifestyle. Whether you choose to occupy one unit and generate rental income from the others or maximize the property's investment potential, the possibilities are endless.Beyond the residences, the property is loaded with amenities including your own private dock, multiple garage spaces, several barns, outbuildings, and charming sheds that are ideal for workshops, storage, entertaining, or hobby spaces. The nearly 4-acre setting provides privacy, open space, and room to garden, explore, or simply enjoy the peaceful countryside. Properties offering this combination of history, flexibility, and income potential are incredibly rare. Whether you're looking to expand your investment portfolio, create a multi-generational estate, or own a distinctive piece of New England history, this remarkable three-unit property is truly unlike anything else.

1530 Hartford Pike, Killingly

$699,900

6 Beds ⋅ 5 Baths ⋅ 24196318 MLS

Step back in time while enjoying the comforts of modern living at this extraordinary circa-1770 three-unit property, where historic New England charm meets exceptional income-producing potential. Set on nearly 4 private acres, this one-of-a-kind estate offers the perfect opportunity for investors, owner-occupants, or those seeking a multi-generational family compound. The property features three separate living units, each offering its own unique character while showcasing the timeless craftsmanship of the 18th century. Thoughtful renovations and updates have preserved the home's rich history while providing the conveniences of today's lifestyle. Whether you choose to occupy one unit and generate rental income from the others or maximize the property's investment potential, the possibilities are endless.Beyond the residences, the property is loaded with amenities including your own private dock, multiple garage spaces, several barns, outbuildings, and charming sheds that are ideal for workshops, storage, entertaining, or hobby spaces. The nearly 4-acre setting provides privacy, open space, and room to garden, explore, or simply enjoy the peaceful countryside. Properties offering this combination of history, flexibility, and income potential are incredibly rare. Whether you're looking to expand your investment portfolio, create a multi-generational estate, or own a distinctive piece of New England history, this remarkable three-unit property is truly unlike anything else.

1530 Hartford Pike, Killingly

$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

$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

$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.

260 Summit 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

$385,000

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

$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

$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

$275,000

7 Beds ⋅ 4 Baths ⋅ 24138836 MLS

Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety of permitted uses. B-1A zoning may allow for additional residential units, subject to municipal approvals. Additional income opportunities include four dedicated storage spaces, ideal for ECSU students or nearby tenants, two garage bays, and an on-site parking lot, all of which convey with the property. Property is being sold as-is.

129 Valley St, Windham

Windham County, CT 6+ Bedroom Homes for Sale

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