Windham County, CT 5 Bedroom Homes for Sale

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Newest Windham County, CT 5 Bedroom Homes for Sale

$324,900

5 Beds ⋅ 3 Baths ⋅ 24216555 MLS

Fantastic Opportunity for Investors or Owner-Occupants! This three-family property offers versatility, income potential, and a great opportunity to build equity! Two of the three units have been updated, making this an appealing option for both investors and buyers looking to offset their mortgage with rental income. Live in one unit while renting out the others, or add this property to your investment portfolio. Off-street parking adds convenience for residents. Additional Investment Opportunity! The neighboring mixed-use property, featuring both commercial and residential units, is also available for sale mls # 24216499 The owner is looking to sell both properties together, presenting a unique opportunity to acquire multiple income-producing units and expand your investment portfolio. Whether you're looking for a multi-family home to call your own or an investment with multiple income streams, these properties offer plenty of possibilities. Don't miss out on this opportunity!

24 Railroad Ave, Plainfield

$900,000

5 Beds ⋅ 5 Baths ⋅ 24215278 MLS

Welcome to this extraordinary contemporary masterpiece, where architectural elegance meets a semi secluded natural paradise. Perfectly situated on a private wooded lot complete with picket fence that lines driveway. This beautiful 5-bedroom, 4-bathroom home offers the ultimate retreat for modern living and sophisticated entertaining. Step inside to a dramatic, floor plan highlighted by soaring vaulted ceilings and an exquisite stone fireplace that anchors the main living space. Loads of natural light that seamlessly bring the outdoors in. The gourmet, beautifully updated kitchen is a chef's dream, featuring a massive built-in pantry, sleek countertops, and stainless steel appliances. Just above the main living area, a spectacular open loft provides a flexible space ideal for a home office, library, or studio. With five generously sized bedrooms and four completely remodeled bathrooms, there is no shortage of space or comfort. The luxurious primary suite serves as a private oasis within the home, complete with elegant soaking tub and peaceful views of the surrounding tree line. The massive, finished basement expands your living space exponentially. It boasts a massive rec room, offering the perfect setup for a home theater, game room, or private gym. Step outside into your large yard with a pool and large deck. Surrounded by nature and tranquility. A wonderful retreat that is close to major highway. Come see for yourself.

Plainfield

$169,900

5 Beds ⋅ 2 Baths ⋅ 24214541 MLS

Do not miss out on the opportunity to own this Mansard style Victorian in Putnam for ONLY $169,900! Currently zoned as a single family but has the possibility of changing use back to a duplex for income producing opportunities. 3 Stories featuring 2,767 square feet consisting of 5 bedrooms and 2 full baths with room to expand the square footage even more. This property is in need of extensive renovation, but offers tremendous potential for the right buyer. With vision, effort, and the right improvements, there is a great opportunity to build significant sweat equity and transform the property into something truly special. Cross posted, all listed under MLS# 24210829. Call today for private tour!

20 Bradley St, Putnam

$799,000

5 Beds ⋅ 4 Baths ⋅ 24211775 MLS

Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. Formerly used as a two-family home it provides options for single family, multi-generational living, farm staff, owner occupancy, or rental income. The home has been professionally cleaned, with major improvements already completed including a new roof, windows, garage doors, repointed chimney, serviced furnace, new dishwasher in the upper unit, refinished upstairs floors, repainted porch, and rebuilt deck. Kitchens and bathrooms offer an opportunity for additional cosmetic updating and personalization. Equestrian amenities are extensive, including a 12-stall main barn with multiple tack, feed and storage areas, lounge, bathrooms, water, and an approximately 2,000-bale hay loft. The lower barn offers 7 additional stalls with room to expand, plus storage. Two accessory buildings include a garage-style structure ideal for equipment storage. A 50' x 100' indoor arena provides year-round riding, while five fenced grass pastures with automatic waterers offer excellent turnout. With substantial infrastructure, multiple buildings, established fencing, and 19 acres - this property is ready for its next chapter. A rare opportunity for an equestrian estate, boarding or training operation, or simply the space to create your ideal multi-generational property.

91 Church St, Thompson

$209,900

5 Beds ⋅ 1 Baths ⋅ 24211639 MLS

The potential is endless in this classic 1890 conventional style home which sits on a spacious .69 acre open level corner lot, offering strong curb appeal and plenty of outdoor usability. The property features 5 bedrooms, providing excellent space for larger households or flexible room arrangements. With its old-world charm and traditional layout, the home presents a solid foundation for buyers looking to update and personalize to their own taste. The structure, lot size, and location create meaningful long term value, and buyers will appreciate the opportunity to restore this well situated Plainfield property into a comfortable and character filled residence. Hurry to book a viewing, simply too good to be true. Don't miss this diamond in the rough.

31 Depot Rd, Plainfield

$169,900

5 Beds ⋅ 2 Baths ⋅ 24210829 MLS

Do not miss out on the opportunity to own this Mansard style Victorian in Putnam for ONLY $169,900! Currently zoned as a single family but has the possibility of changing use back to a duplex for income producing opportunities. 3 Stories featuring 2,767 square feet consisting of 5 bedrooms and 2 full baths with room to expand the square footage even more. This property is in need of extensive renovation, but offers tremendous potential for the right buyer. With vision, effort, and the right improvements, there is a great opportunity to build significant sweat equity and transform the property into something truly special. More photos coming soon. Call today for private tour!

20 Bradley St, Putnam

$349,900

5 Beds ⋅ 2 Baths ⋅ 24210038 MLS

Spacious two-family home offering 5 bedrooms, 2 baths, a large basement, detached garage, covered front porch, and flexible space throughout. Great opportunity for an owner-occupant or investor. Unit 1 offers approximately 1,453 sq. ft. with 3 bedrooms and 1 full bath. The first floor features a large bedroom, spacious living room, kitchen, and full bath, with two additional bedrooms upstairs. The unit also has access to an approximately 1,201 sq. ft. unfinished basement with washer and dryer and plenty of storage space. Unit 2 offers approximately 1,026 sq. ft. with 2 bedrooms and a 3/4 bath. It includes a living room, kitchen, large bedroom with balcony, second bedroom, and approximately 216 sq. ft. of additional attic/storage space on the third floor. The property also includes a 462 sq. ft. detached garage and off-street parking. Convenient opportunity to live in one unit while renting the other, or add a two-family property to your investment portfolio. Furniture shown in the photos can be included with the sale at no additional cost.

19 Bellevue St, Windham

$424,900

5 Beds ⋅ 2 Baths ⋅ 24209915 MLS

Over 2,100 SF of beautifully updated living space awaits at 990 Riverside Drive! A welcoming farmer's porch adds to the curb appeal, while the home itself has been extensively renovated over the past approximately 10 years, including plumbing, electrical, HVAC with central air, insulation, kitchen, baths, flooring, paint and more. The spacious first floor offers a gorgeous kitchen with granite counters, abundant cabinetry, a new slider to the oversized deck and stairway leading to the upper level. An oversized dining room provides plenty of room for gatherings and entertaining, while the pellet stove offers an economical supplemental heat source. The enormous foyer offers incredible flexibility as an office, playroom, sitting area or additional living space as well as the second access to the upper level. A separate first-floor bedroom, office or flex room with access to the deck adds even more versatility. Upstairs are 4 generously sized bedrooms all completely updated. The second-floor bath is a standout with a whirlpool tub, double vanity, solid-surface counters, separate tiled shower, tile flooring and generous built-in storage. A walk-up attic and full basement provide excellent additional storage. Outside, enjoy the oversized deck, farmer's porch and detached 2-car garage. Conveniently located near the MA and RI borders with easy highway access, making commuting throughout the region a breeze. This is as turnkey as you are going to get with tons of space!!

990 Riverside Dr, Thompson

$2,500,000

5 Beds ⋅ 6 Baths ⋅ 24198180 MLS

Welcome to Ufton Estate, a remarkable 41-acre private estate where historic character, exceptional craftsmanship and modern luxury come together in an extraordinary setting. Originally built in 1850 and thoughtfully reimagined in the early 1900s, the residence is filled with distinctive architectural details. Intricate hand-carved woodwork, elegant millwork and grandly proportioned rooms reflect the artistry of another era. Each space offers a sense of history while remaining comfortable, inviting and well suited to modern living. The home provides an impressive backdrop for both everyday life and memorable gatherings. Gracious entertaining spaces flow throughout the residence, complemented by intimate rooms that invite relaxation. Abundant windows frame views of the surrounding landscape and fill the interiors with natural light. Outside, the estate unfolds across 41 private acres with a heated pool, greenhouse, established gardens and expansive lawns. The beautifully layered grounds provide a timeless setting with endless opportunities for personalization. Reimagine the gardens and greenhouse, introduce an equestrian or agricultural component, enhance the outdoor entertaining spaces or simply enjoy the privacy and natural beauty of the estate as it is.

357 Wrights Crossing Rd, Pomfret

$779,000

5 Beds ⋅ 4 Baths ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$379,900

5 Beds ⋅ 2 Baths ⋅ 24209326 MLS

Discover the possibilities at 8 Dyer St in Killingly, a versatile two-unit property offering a unique combination of residential space, parking, and flexible layouts. One of the two units has been fully converted from a former commercial storefront, creating a distinctive living space with an open and adaptable floor plan. The property features two generously sized bedrooms on the first floor, while the second-floor unit offers three bedrooms, providing plenty of room for residents, guests, a home office, or additional living space. Additional highlights include a two-car garage with convenient interior access and off-street parking, adding valuable storage, convenience, and functionality. Whether you're looking for an investment property, owner-occupied multifamily, or a property with flexible residential possibilities, 8 Dyer St offers a unique opportunity in Killingly

8 Dyer St, Killingly

$489,000

5 Beds ⋅ 3 Baths ⋅ 24204645 MLS

3 Family well maintained for sale in Willimantic with extra large lot size, .53 ac. and extra large out building for garage, storage and workbench area with power. 2 units on first floor with one unit on second floor. close and convenient to Main Street and bus line. Historical home been in family for generations. see agent remarks

28 Pleasant St, Windham

$749,900

5 Beds ⋅ 3 Baths ⋅ 24202466 MLS

Set on nearly 25 private acres in Pomfret, this well maintained and upgraded 3,343 sq ft home offers space, privacy and incredible recreational potential. Features include a 3-car attached garage with an attached workspace, primary suite w/private balcony & jetted tub, central air, ducted heat, a whole-house generator and a heated/cooled basement offering an easy path to additional finished space and extra bedroom potential. Inside, enjoy a beautiful stone fireplace with wood-stove insert, while a screened porch off the dining room overlooks a wooded setting. Extensive covered deck space provides even more outdoor living, including the current hot tub, which is included. A detached, fully insulated and heated garage/workshop with a full 16' door provides exceptional space for vehicles, equipment, hobbies or storage. Established riding and walking trails wind throughout the acreage. The property also features a former in-ground pool with potential for restoration and a former ice rink/tennis/pickleball court ready to be brought back to life. An ideal setting for a private retreat or a horse farm, with abundant space for recreation, equipment, toys and outdoor living. Ideal for anyone seeking a serious workshop, trail riding, outdoor entertaining and room to spread out. A rare combination of acreage, recreation, storage, privacy and flexible space. Conveniently located under 30 miles from Providence, 34 miles from Foxwoods and Mohegan Sun with easy access to I-395.

40 Searles Rd, Pomfret

$699,900

5 Beds ⋅ 3 Baths ⋅ 24204013 MLS

Looking for a large home with character and charm. This property offers a beautiful single family home that could be a great place for a multi generational family. If you are looking to expand your imagination, consider creating a lovely Air BNB or a traditional Bed and Breakfast for those travelers visiting our historic, scenic rural area. A drive along the 36 mile highway of Route 169 takes you right through the heart of New England's "Quiet Corner". Perhaps with the 10+ acres you could create a venue for destination weddings or a place family retreats. The historic character of this wonderful old home remains but with many modern amenities. The home was built in 1704 and includes 5 Bedrooms, 2.5 Baths, 2 Fireplaces, and 2 Woodstoves. The attached heated workshop is state of the art and offers many uses. There is a very cool walkup attic, and several outbuildings. Set just off the main road offers a peace and quiet setting. So many possibilities, so much potential. It is a must see.

26 Beecher Rd, Brooklyn

$799,000

5 Beds ⋅ 4 Baths ⋅ 24203344 MLS

EXCEPTIONAL EQUESTRIAN PROPERTY WITH 19 ACRES & TWO-FAMILY HOME! Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. The two-family home provides options for multi-generational living, farm staff, owner occupancy, or rental income. The home has been professionally cleaned, with major improvements already completed including a new roof, windows, garage doors, repointed chimney, serviced furnace, new dishwasher in the upper unit, refinished upstairs floors, repainted porch, and rebuilt deck. Kitchens and bathrooms offer an opportunity for additional cosmetic updating and personalization. Equestrian amenities are extensive, including a 12-stall main barn with multiple tack, feed and storage areas, lounge, bathrooms, water, and an approximately 2,000-bale hay loft. The lower barn offers 7 additional stalls with room to expand, plus storage. Two accessory buildings include a garage-style structure ideal for equipment storage. A 50' x 100' indoor arena provides year-round riding, while five fenced grass pastures with automatic waterers offer excellent turnout. With substantial infrastructure, multiple buildings, established fencing, and 19 acres - this property is ready for its next chapter. A rare opportunity for an equestrian estate, boarding or training operation, or simply the space to create your ideal multi-generational property.

91 Church St, Thompson

$525,000

5 Beds ⋅ 4 Baths ⋅ 24198620 MLS

Set on nearly 4 private acres, 21 Linkkila Lane offers the space, flexibility, and peaceful setting that make country living feel special. Start your morning with coffee on the deck while taking in the surrounding landscape and watching the horses at the neighboring horse farm. Inside, this beautifully updated log home strikes the perfect balance between cozy character and clean, modern updates. An abundance of natural light keeps the home feeling bright and airy, while wide plank floors add warmth and charm throughout. A gorgeous brick fireplace anchors the living room, creating an inviting gathering space. The main house features 3 spacious bedrooms, 3 full bathrooms, an extensively renovated kitchen, updated baths, new windows throughout, and a spacious walk-in pantry. Screened-in porches along the back offer additional space to relax and enjoy the peaceful surroundings. A separate in-law suite adds even more versatility with its own kitchen, 2 bedrooms, full bathroom, and separate utilities. Recent improvements include 2 updated kitchens, 4 renovated full bathrooms, new windows in 2025, 2 new water heaters, and refinished decks in 2026. A partially finished basement provides additional usable space and storage. Conveniently located near local schools, UConn, Eastern Connecticut State University, and surrounding towns, this home offers a unique combination of privacy, character, modern comfort, and flexible living.

21 Linkkila Ln, Chaplin

$625,000

5 Beds ⋅ 4 Baths ⋅ 24198311 MLS

Here's your opportunity to have the feeling of a little piece of Vermont while being in Connecticut. About 7 minutes to the highway and 10 minutes to UConn. 17.3 acres creating such a unique setting. Knowlton Brook Runs through the property feeding a beautiful pond. The property is surrounded by treed areas with a lot of nature's feeling integrated into the living areas of the property. Tranquil is an understatement. First floor of this home has three bedrooms, primary bedroom has private bath, Main bath, living room, dining room, kitchen and family room. There is a lower-level rec room and an additional half bath. The Lower-level In-law apartment has private entry, 2 bedrooms, living room, kitchen and a full bath. Two car garage. Two-story barn.

97 Cushman Rd, Ashford

$325,000

5 Beds ⋅ 2 Baths ⋅ 24198176 MLS

Fantastic 2 family with both units recently renovated. 3 bedrooms in one unit. 2 bedrooms in other with a formal dining room. Each unit has a washer and a dryer. Each unit has its own parking area.

983 Riverside Dr, Thompson

$435,000

5 Beds ⋅ 3 Baths ⋅ 24196439 MLS

Excellent opportunity to own a versatile 3-family property in the heart of Putnam! This well-located multi-family home offers an outstanding opportunity for both investors and owner-occupants. Live in one unit while generating rental income from the others, or add a solid income-producing property to your portfolio. Situated on a 0.31-acre level lot, the property features three residential units, a detached 3-car garage, ample paved parking, and public water and sewer. Conveniently located just minutes from vibrant Downtown Putnam, you'll enjoy easy access to restaurants, shops, parks, schools, and local amenities, making this an attractive location for tenants and homeowners alike.

31 Mill St, Putnam

$685,000

5 Beds ⋅ 3 Baths ⋅ 24191051 MLS

SELLER IS OFFERING A $10,000 RATE BUY DOWN OR CREDIT TOWARDS BUYERS CLOSING COSTS!! Welcome to this beautifully renovated home in desirable Pomfret CT! Offering the perfect blend of modern updates, flexible living space, and country charm, this impressive property is ready for its next owners. Inside, you'll find five spacious bedrooms and three full bathrooms, providing plenty of room for family, guests, or multi-generational living. The massive dining and flex space, offers endless possibilities for entertaining, hosting holiday gatherings, creating a home office, playroom, or additional living area. A convenient mudroom helps keep everyday life organized, and a large storage room provides abundant space for seasonal items, hobbies, and more. Comfort and efficiency are top priorities with mini-split systems throughout the home and a cozy pellet stove that creates a warm and inviting atmosphere during New England winters. Car enthusiasts, hobbyists, and those in need of extra workspace will appreciate the detached three-car garage with ample room for vehicles, equipment, and storage. Whether you're looking for room to grow, space to entertain, or a property with exceptional flexibility and future possibilities, this turnkey Pomfret home delivers it all. Don't miss your opportunity to own this rare offering in one of Northeastern Connecticuts most desirable communities.

250 Killingly Rd, Pomfret

$450,000

5 Beds ⋅ 3 Baths ⋅ 24189873 MLS

This charming multi-family home located at 23 Mechanic St in Killingly, CT offers a perfect blend of historic charm and modern convenience. Built in 1900, this two-story property boasts a spacious finished area of 2,411 sq.ft. with three bathrooms. The lot size is 8,712 sq.ft., providing plenty of outdoor space for relaxation and entertaining. The home features a classic design with a welcoming atmosphere and is perfect for families or investors looking for a versatile property. With its central location and ample living space, this property is a fantastic opportunity for those seeking a charming and well-maintained home in a desirable neighborhood. There is 3 apartments rented...2 Bedrooms apartments and 1 bedroom at the basement...4.400.00 Monthly income from rent...Two bay garages and 1 room that can be turned to another small bay enough for a car.

23 Mechanic St, Killingly

$425,000

5 Beds ⋅ 3 Baths ⋅ 24190726 MLS

WATERFRONT 3 Family ON ONECO POND! LIVE IN ONE UNIT AND COLLECT RENT FROM THE OTHER TWO UNITS or Rent out All Three Units! Take the side steps down to the big back yard with a large Firepit. Almost 1/2 acre lot is mostly in the back of the home abutting the water! Take in all the views of the Pond and Wildlife!! In the Summertime enjoy Kayaking, Canoeing, Fishing and possibly Swimming from your back yard!!! Or just sit and enjoy the Beautiful Views of the Pond from the deck. In the Winter enjoy Ice Skating or Ice Fishing. Home has 3 units. Two units have 2 Bedrooms and 1 Full Bath and 1 unit has 1 Bedroom and 1 Full Bath. Updates include Two Oil Furnaces for two units which are only about 6 years young, upstairs unit has electric heat, Shared drilled well, Newer shared septic, most Windows and some Flooring. One of the first-floor units has beautiful hardwood flooring and a stone Fireplace! All 3 Units are Rented at this time. Close to RI line! Only 30 minutes to Mass Line And approximately 30 minutes to casinos!

1147 Plainfield Pike, Sterling

$399,900

5 Beds ⋅ 3 Baths ⋅ 24179982 MLS

Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra bedrooms, a home office, playroom, gym, or guest space - perfect for today's flexible lifestyle needs. Tucked away in a truly special setting, this home is surrounded by federal land, offering direct access to scenic hiking and horseback riding trails just steps from your door. Enjoy the peace and privacy of nature while still having the convenience of recent updates, including a newer boiler and porch. A seldom-available gem with room to grow both inside and out! Enjoy the space, charm, and opportunity this beautiful property provides with peaceful surroundings while still being in close proximity to Mansfield Hollow State Park, as well as nearby shopping and dining options. A rare opportunity to own acreage, space, and convenience all in one - schedule your showing today!

13 Bates Rd, Chaplin

$325,000

5 Beds ⋅ 2 Baths ⋅ 24156729 MLS

Charming Victorian 2-family set up high and framed by a classic stone wall, situated on a spacious .45-acre lot and fully occupied with strong cash flow from day one. Both tenants are in yearly leases, providing stability and consistent income, and each unit features separate utilities with individual boilers, with tenants paying their own heat and electric to help maximize returns. The first-floor unit offers 2 bedrooms, while the second-floor unit features 3 bedrooms, and both include washer and dryer hookups for added convenience. With plenty of paved parking, city water, city sewer, and natural gas, this property offers efficiency and ease of ownership. Located close to all the amenities Putnam has to offer - including shopping, dining, parks, and everyday conveniences - this is a versatile opportunity ideal for investors seeking immediate, reliable income or owner-occupants looking to live in one unit while benefiting from rental income in the other. Recent work done on the property is as follows: Main sewer line replaced, both water heaters replaced, electrical panel main breaker replaced, furnaces replaced, and general painting and cleaning.

70 Walnut St, Putnam

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Windham County, CT 5 Bedroom Homes for Sale

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