Windham County, CT Real Estate | Windham County, CT 5 Bedroom Homes for Sale

Step back in time while enjoying the comforts of today at this remarkable circa-1770 property, where timeless New England charm meets modern convenience. Set on nearly 4 private acres, this one-of-a-kind estate offers endless possibilities for multi-generational living, rental income, a hobby farm, or the perfect retreat. The beautifully maintained main residence showcases the character and craftsmanship of the 18th century while benefiting from numerous thoughtful renovations and updates throughout. An attached apartment provides excellent flexibility for extended family, guests, or additional income potential. Adding even more value, a separate building on the property offers additional living or occupancy opportunities, making this an exceptional property for those seeking space and versatility. Outside, you'll find an impressive collection of amenities including your own private dock, multiple garage spaces, several outbuildings, and charming sheds that are ideal for entertaining, gatherings, workshops, or creative spaces. The expansive grounds offer room to relax, garden, explore, and enjoy the peaceful surroundings. Whether you're searching for a unique historic home, an investment opportunity, or a private country estate with endless possibilities, this extraordinary property is truly unlike anything else on the market.

1530 Hartford Pike, Killingly

$599,000

5 Beds ⋅ 4 Baths ⋅ 24194145 MLS

Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen, updated bathrooms, and new windows throughout the home. Warm wood finishes, abundant natural light, and a propane stove create a welcoming atmosphere, while a fuel oil boiler provides efficient baseboard and radiant heat throughout much of the home. Perfect for multi-generational living or extended guests, the property also includes a fully equipped in-law suite complete with its own kitchen, full-bathroom, and two bedrooms. Includes separate utilities. Recent improvements include:* 2 beautifully updated kitchens* 4 renovated full bathrooms* New windows throughout the entire home (2025)* 2 new water heaters* Refinished decks (2026)* Partially finished basement* Nearly 4 private acres* Peaceful country setting on a quiet dead-end lane. Local Schools Chaplin Elementary: ~7 mins Parish Hill Middle/High: ~6 mins Mansfield Elementary: ~5 mins University of Connecticut (UConn), Storrs: ~12minEastern Connecticut State University (ECSU): ~13minAirports and Travel Bradley Intl Airport (BDL): ~50 mins Rhode Island T.F. Green Intl Airport (PVD): ~1hr. See also MLS # 24187395

21 Linkkila Ln, Chaplin

$399,900

5 Beds ⋅ 4 Baths ⋅ 24192242 MLS

Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-bath antique Colonial, where historic character and spacious living come together on a picturesque setting. Rich in original details, this one-of-a-kind home showcases wide-plank hardwood floors, stunning decorative fireplaces with ornate mantels, oversized windows, and classic architectural craftsmanship throughout. The spacious country kitchen offers ample room for gathering and opens to multiple living and entertaining spaces, including a formal dining room, inviting family room, and generously sized bedrooms filled with natural light. A flexible floor plan provides endless possibilities for today's lifestyle, whether you're looking for space for a home office, guest quarters, or multi-generational living. Outside, the property continues to impress with a welcoming covered front porch, expansive yard, and an oversized detached 2-car garage/barn offering exceptional storage, workshop space, or hobby potential. Surrounded by mature trees and timeless New England scenery, this remarkable property delivers the perfect balance of privacy, history, and functionality. Whether you're drawn to the craftsmanship of a bygone era or looking for a home with room to grow, this exceptional antique Colonial is ready for its next chapter. Schedule your private showing today and experience the character and possibilities this unique property has to offer.

394 Jerusalem Rd, Windham

$699,000

5 Beds ⋅ 3 Baths ⋅ 24191051 MLS

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

$470,000

5 Beds ⋅ 3 Baths ⋅ 24190726 MLS

Built in 1825 in the Quaint town of Oneco this Adorable 3 Family on Oneco Pond is a great Waterfront Property!!! In the Summertime enjoy Kayaking, Canoeing, Swimming, Fishing or just sit and enjoy the Beautiful Views of the Pond from the deck or back yard. 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. Oil Heat for two units with two separate furnaces which are only about 6 years old and the upstairs unit has electric heat. Shared drilled well and newer shared septic. Many recent updates to the property include 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!

Plainfield Pike, Sterling

$269,000

5 Beds ⋅ 2 Baths ⋅ 24190067 MLS

Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but the elbow grease will make you TONS of equity. Come look and make an offer!!!

1008 Windham Rd, Windham

$349,900

5 Beds ⋅ 2 Baths ⋅ 24189093 MLS

Investment opportunity!! This up and down duplex is in Downtown Putnam, a destination town, where so many eat, work, and play. The 2 units were renovated before these amazing tenants moved in. The walk up attic is just waiting to be finished off to unlock even more income potential. The sooner you buy this one the sooner you will will be building equity. Make your appointment ASAP. Tenants need 24 hours notice. ALL INTERIOR PHOTOS WERE TAKEN BEFORE TENANTS MOVED IN.

27 Railroad St, Putnam

$599,000

5 Beds ⋅ 4 Baths ⋅ 24187395 MLS

Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen, updated bathrooms, and new windows throughout the home. Warm wood finishes, abundant natural light, and a propane stove create a welcoming atmosphere, while a fuel oil boiler provides efficient baseboard and radiant heat throughout much of the home. Perfect for multi-generational living or extended guests, the property also includes a fully equipped in-law suite complete with its own kitchen, full-bathroom, and two bedrooms. Includes separate utilities. Recent improvements include:* 2 beautifully updated kitchens* 4 renovated full bathrooms* New windows throughout the entire home (2025)* 2 new water heaters* Refinished decks (2026)* Partially finished basement* Nearly 4 private acres* Peaceful country setting on a quiet dead-end lane. Local Schools Chaplin Elementary: ~7 mins Parish Hill Middle/High: ~6 mins Mansfield Elementary: ~5 mins University of Connecticut (UConn), Storrs: ~12minEastern Connecticut State University (ECSU): ~13minAirports and Travel Bradley Intl Airport (BDL): ~50 mins Rhode Island T.F. Green Intl Airport (PVD): ~1hr. See MLS #24194145

21 Linkkila Ln, Chaplin

$575,000

5 Beds ⋅ 5 Baths ⋅ 73532742 MLS

Oversized Colonial offering exceptional space, flexibility, and income potential. This well-appointed home features a spacious layout with generous living areas, ideal for both everyday living and entertaining. A separate in-law apartment provides the perfect setup for extended family, guests, or additional rental income, offering privacy and versatility. The main residence showcases classic Colonial charm with expansive rooms, abundant natural light, and a functional floor plan. A two-car garage adds convenience and storage, while the property's layout accommodates a variety of lifestyle needs. Equipped with a Generac generator, this home ensures peace of mind and uninterrupted comfort year-round. Whether you're seeking multi-generational living or an opportunity to offset your mortgage with supplemental income, this property delivers both value and flexibility in one impressive package.

41 Margaret Henry Road, Killingly

$429,900

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

$350,000

5 Beds ⋅ 2 Baths ⋅ 73521896 MLS

Opportunity shines in this spacious 2,285 sq. ft. ranch set on a beautiful 1.3-acre park-like lot in the desirable Pomfret area. The spacious main level offers 4 comfortable sized beds, 2 baths, hardwood floors, and a flexible layout ready for your vision. The lower-level walk-out basement features a legal in-law suite with 1 bed, 1 updated bath, and new tile floors, adding exceptional versatility. Recent major updates include a new roof and new oil tank. Outside, enjoy a separate 2-car garage plus a separate wired workshop, ideal for hobbies, storage, or projects. The main floor bath has been gutted to the studs and the kitchen partially removed, creating a prime chance to customize, build equity, or pursue a flip opportunity. Much of the building materials needed to finish the kitchen and bath are included in the sale. **House WILL NOT pass FHA/VA/USDA without renovation component**

796 Hampton Rd, Pomfret

$350,000

5 Beds ⋅ 2 Baths ⋅ 24177164 MLS

Opportunity shines in this spacious 2,285 sq. ft. ranch set on a beautiful 1.3-acre park-like lot in the desirable Pomfret area. The spacious main level offers 4 comfortable sized beds, 2 baths, hardwood floors, and a flexible layout ready for your vision. The lower-level walk-out basement features a legal in-law suite with 1 bed, 1 updated bath, and new tile floors, adding exceptional versatility. Recent major updates include a new roof and new oil tank. Outside, enjoy a separate 2-car garage plus a separate wired workshop, ideal for hobbies, storage, or projects. The main floor bath has been gutted to the studs and the kitchen partially removed, creating a prime chance to customize, build equity, or pursue a flip opportunity. Much of the building materials needed to finish the kitchen and bath are included in the sale. **House WILL NOT pass FHA/VA/USDA without renovation component**

796 Hampton Rd, Pomfret

$399,000

5 Beds ⋅ 2 Baths ⋅ 24173306 MLS

Step into living history at 21 Brunswick Ave, a lovingly preserved 1890 Victorian in the heart of Moosup. Built when craftsmanship and artistry defined construction, this home announces itself from the moment you cross the threshold. Original hardwood floors anchor every room with warmth and authenticity. A stunning hammered tin ceiling in the bathroom catches the light and the eye, a detail so singular it becomes a conversation piece. The primary bedroom opens into a gracious sitting room, an architectural intimacy that modern floor plans rarely achieve. Ornate trim, unexpected proportions, and eccentric Victorian beauty reveal themselves around every corner. This is not a neglected relic. For more than two decades, its current owner has cared for it with deep pride, preserving its soul while leaving meaningful room for the next steward to add their own mark. The bones are exceptional and the flowering plants and fruit trees are just about to make their debut. The character is irreplaceable. Whether you are a devoted admirer of historic architecture, a lover of Victorian design, or simply someone who believes a home should have a personality, this property will speak to you. Homes like this surface rarely and do not stay available long. Schedule your private showing today.

21 Brunswick Ave, Plainfield

$424,900

5 Beds ⋅ 2 Baths ⋅ 24170264 MLS

Step back in time with this beautifully preserved circa 1815 antique home, known as the Old Danielson house, set on an expansive 6.1acre lot. Rich in history and timeless character, this 2,760sqft residence seamlessly blends classic New England charm with thoughtful modern updates for today's lifestyle. Inside you'll find 5 bedrooms, 1.5 baths, and 10 total rooms, offering a versatile layout with warm, inviting spaces. The home features a living room with a wood stove, a spacious family room, and a kitchen with a cozy breakfast nook that is perfect for everyday living and entertaining. Updated elements throughout enhance comfort while preserving original character, creating a home that feels both historic and functional. Set on over 6 acres of land, the property provides privacy and endless opportunity whether you envision outdoor entertaining, gardening, hobby farming, or simply enjoying peaceful surroundings. Pond located just a short walk from the main house adds to the natural beauty and charm. The current owners have completed a wetlands assessment, offering insight into the land's potential, and suggesting the possibility for additional dwellings or expansion. Buyers is responsible for verifying all information regarding future use and development. Ample parking and a convenient location close to local amenities. A rare opportunity to own a piece of local history with the updates you want and character you can't recreate.

760 Upper Maple, Killingly

$310,000

5 Beds ⋅ 3 Baths ⋅ 24158358 MLS

Investors take notice! This home is a money maker. Whether you decide to owner-occupy this spacious home while rental income helps with the mortgage, or rent out both units, you can't go wrong. The living areas provide warm spaces perfect for relaxing or gathering with friends and family. The kitchens offer ample cabinet and counter space, making everyday cooking convenient and enjoyable. The large yard space can be enjoyed year round. The lot may also have the potential to be subdivided to add another home. All information should be verified with the town. Don't miss this opportunity!

125 Mountain St, Windham

$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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