Windham County, CT Real Estate | Windham County, CT 4 Bathroom 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

$400,000

3 Beds ⋅ 4 Baths ⋅ 24192221 MLS

LEGAL IN-LAW! Multi-generational living? Single Family with In-Law! Location great for MA, CT, or RI. Need a home office? Guest suite? This one has options! Room count doesn't tell the whole story. Fully remodeled home featuring a legal in-law apartment with both interior access and a private entrance. A connecting bedroom between the main home and in-law. THREE FULL & ONE HALF BATH! New kitchen: Stainless appliances, Butcher block Counters, Soft Close Cabinets, Ceramic Tile, 9' Long counter area with more storage, & Pantry Cabinet. New windows, New 100-amp electrical panel, PEX water lines, LED lighting, interconnected wireless smoke/CO detectors, New shed on concrete pad, and New sidewalks. Roof, boiler, & oil tank, all under 4 years old. Boiler tuned up 2/26'. Hardwood floors, ceramic tile, covered front porch with composite decking. Rear patio 34' long! Rear Fenced in yard. Radon mitigation system in place (fan dated 11/24). The finished walk-out lower level is heated along with a full bath. Finished attic space provides more usable area. TWO Laundry hookups: In-law and basement. Attached garage, also insulated. All work has been permitted. Town card is updated: Estimated HEATED Sq.Ft. above grade is 1,913 and HEATED below grade is 978; total 2,891. (MLS assessed value is 51k short of town card, taxes may be adjusted)

48 Edmond St, Putnam

$624,000

4 Beds ⋅ 4 Baths ⋅ 73543854 MLS

Beautifully maintained and built to last, this spacious 4 bedroom, 3.5 bath home offers comfort, quality, and exceptional living space in a prime location near prestigious Thompson Hill. Situated on a manicured corner lot, the home features newer vinyl siding with a lifetime warranty, and 50-year shingles for peace of mind. Designed for easy living and entertaining, enjoy the oversized composite deck with electric awning, expansive paver patio, and a recently remodeled family room with custom built-ins and abundant natural light. The oversized two-car garage is wired for heat and connects to a convenient mudroom and laundry room. Inside, you'll find generous room sizes, oversized closets, and flexible living space throughout, including a partially finished lower level with fireplace, wet bar, and half bath. The oversized primary suite features a newly remodeled spa-like bath with soaking tub, walk-in shower, double sinks, and quartz counters.Some photos may be virtually staged.

1 Maple Lane, Thompson

$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

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 24185273 MLS

This extraordinary waterfront estate on Chamberlain Lake offers a lifestyle rarely found in Connecticut. With 200ft of private lake frontage, this custom post-and-beam Cape was thoughtfully crafted using timber milled directly from trees harvested on the property, creating a residence that is as authentic as it is remarkable. A dramatic center chimney anchors the home, while wide-board pine floors, exposed beams, and walls of windows showcase breathtaking views. The primary suite features a private balcony overlooking the lake, two walk-in closets, and a spa-like bath. Generously sized rooms and oversized step-in closets throughout the home provide exceptional comfort and storage. A private entrance way will lead you to the lake to enjoy fishing, kayaking, canoeing, swimming and peaceful lake living await. Gather around the fire pits, enjoy the outdoor shower after a day on the water, or simply relax on the covered deck among professionally landscaped grounds. This exceptional property combines privacy, craftsmanship, recreation, and timeless New England beauty in one truly unforgettable offering.

95 Pole Bridge Rd, Woodstock

$1,350,000

3 Beds ⋅ 4 Baths ⋅ 24185378 MLS

158 ACRES W/EXPANSIVE HALLS POND FRONTAGE - 3 PARCELS, FULLY RENOVATED 2-FAMILY DWELLING, & ENDLESS POSSIBILITIES! Encompassing a remarkable combination of income-producing real estate, significant waterfront acreage, 3 contiguous parcels, & extraordinary natural beauty, this is one of the most compelling land offerings to become available in Northeast CT in recent memory. Sale inclusive of .5 acre parcel (w/2-family house), 102.59 acre waterfront parcel w/substantial frontage along Halls Pond, highlighted by a stunning peninsula extending into the water, & an additional 56 acre parcel that expands the property's remarkable scale, privacy, & potential. The 2,700sf 2-family residence, completely renovated in 2017, welcomes w/front porch leading to common entry hall & access to the full basement, offering laundry facilities & abundant storage. Both residences feature open-concept floor plans, hardwood & LVP flooring, spacious kitchens w/center islands, & generously sized living spaces. The main level unit offers 2 bedrooms, & 2 full baths, while the upper-level residence features 1 bedroom, a connected den/office, & 2 baths, creating flexibility for multigenerational living, rental income, guest accommodations, or owner occupancy. Rolling woodlands, scenic water views, abundant wildlife, & extensive shoreline combine to create an unparalleled setting for recreation, conservation, estate living, or future development opportunities. ***CONTINUED***

25 Kennerson Reservoir Rd, Eastford

$400,000

3 Beds ⋅ 4 Baths ⋅ 24183962 MLS

LEGAL IN-LAW! Multi-generational living? Location great for MA, CT, or RI. Need a home office? Guest suite? This one has options! Room count doesn't tell the whole story. Fully remodeled home featuring a legal in-law apartment with both interior access and a private entrance. A connecting bedroom between the main home and in-law. THREE FULL & ONE HALF BATH! New kitchen: Stainless appliances, Butcher block Counters, Soft Close Cabinets, Ceramic Tile, 9' Long counter area with more storage, & Pantry Cabinet. New windows, New 100-amp electrical panel, PEX water lines, LED lighting, interconnected wireless smoke/CO detectors, New shed on concrete pad, and New sidewalks. Roof, boiler, & oil tank, all under 4 years old. Boiler tuned up 2/26'. Hardwood floors, ceramic tile, covered front porch with composite decking. Rear patio 34' long! Rear Fenced in yard. Radon mitigation system in place (fan dated 11/24). The finished walk-out lower level is heated along with a full bath. Finished attic space provides more usable area. TWO Laundry hookups: In-law and basement. Attached garage, also insulated. All work has been permitted. Town card is updated: Estimated HEATED Sq.Ft. above grade is 1,913 and HEATED below grade is 978; total 2,891. (MLS assessed value is 51k short of town card, taxes may be adjusted)

48 Edmond St, Putnam

$599,000

3 Beds ⋅ 4 Baths ⋅ 24182721 MLS

Discover the possibilities at 165 Huntington Road in scenic Scotland, Connecticut. Set on over 21 acres of picturesque countryside and surrounded by the natural beauty of northeastern Connecticut, this unique property offers open space and endless opportunities to roam, recreate, or simply enjoy the peaceful setting. Inside you'll find three bedrooms to include a generously sized Master Bedroom. Enjoy the jacuzzi tub in the attached private bathroom. At the other end of the residence is an enormous Great Room that can serve as an entertainment space for years to come. A wrap around deck adds a little extra to take in the scenic view. Relax in the sunroom year-round while enjoying peace of the surrounding landscape. Needing a bit of a facelift in some areas, this residence offers the canvas for imagination and personal touch. Solar panels offer an alternative for energy while the generator can be ready to go during emergencies. Ample parking is offered between three garage bays and an expansive driveway system. Enjoy the charm of small-town living while remaining within convenient reach of local amenities, schools, and major commuter routes. Subject to Probate Court approval. Subject to Lienholder approval. Contingent upon Cell Tower lease being assumed. Contingent upon Solar lease being assumed.

165 Huntington Rd, Scotland

$625,000

4 Baths ⋅ 24181986 MLS

Discover the potential of this exceptional commercial property in Thompson, CT! Set on 1.4 acres with ample parking, this expansive building offers over 6,000 square feet of versatile hall space with soaring 25-foot ceilings-ideal for a variety of business ventures. The main level includes a spacious hall with a service bar, prep kitchen space, bathrooms, and generous storage. The lower level features a full bar, a private sectioned room, a commercial kitchen, walk-in cooler, and dedicated office space. ADA compliant and thoughtfully designed, the flexible layout is perfect for a gym, restaurant, event venue, bar, or multi-use facility. With the ability to divide the space as needed, the opportunities are endless. Conveniently located just 30 minutes from Worcester and about an hour from Providence, Hartford, and Boston, this property offers excellent access and visibility-an outstanding investment for your next business endeavor.

1017 Riverside Dr, Thompson

$2,495,000

4 Beds ⋅ 4 Baths ⋅ 24180508 MLS

Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square feet, 4 bedrooms, and 4 bathrooms, the home was rebuilt from the ground up with next level quality and craftsmanship. Designed for both elegant entertaining and everyday enjoyment, the layout includes a formal dining room, spacious family room, custom mudroom, and a beautiful living room with propane fireplace overlooking Quasset Lake. The showpiece kitchen is truly one-of-a-kind, featuring handcrafted cabinetry by a New York artisan cabinet maker, thick quartzite countertops, premium built-in appliances, and a dramatic tray ceiling with custom white oak detailing. Luxury finishes continue throughout with veneer plaster walls, custom white oak vanities, a professionally designed primary closet, handmade laundry room cabinetry, and architectural flangeless LED lighting seamlessly integrated into the wood ceilings. Built with 2x6 construction, engineered floor systems, 2x12 roof rafters, red cedar siding and trim, central air, all-new heating and cooling systems, underground 400-amp service, and an automatic whole-house generator. Step outside and embrace the ultimate lake lifestyle.

158 W Quasset Rd, Woodstock

$699,000

4 Beds ⋅ 4 Baths ⋅ 24121525 MLS

Welcome to this timeless 4 bedroom Contemporary Colonial estate offering over 3000 square feet of refined living space, nestled in the heart of scenic Pomfret. This stately home blends classic New England charm and privacy in the cul-de-sac neighborhood.Step inside this grand entryway to find rich wood flooring throughout lending warmth and sophistication to every room. The main level boasts a sunlit living room with a fireplace and french doors leading out to a deck that overlooks 5 acres of privacy.The spacious and thoughtfully designed layout features 2 LUXURIOUS primary suites ideal for multi generational living or accommodating guests.

81 Anderson Rd, Pomfret

$790,000

3 Beds ⋅ 4 Baths ⋅ 24173131 MLS

Welcome to this exceptional, custom built brick home, set on a stunning piece of property where quality, craftsmanship, and timeless design come together beautifully. From the moment you step inside, you will appreciate the vaulted ceilings, open layout, and impressive mix of hardwood, marble and tile flooring. The heart of the home features a beautifully designed kitchen with quartz countertops, custom built cupboards, 2 ovens, trash compactor and more! The dining room features a wood-burning fireplace that's never been used! With enough room for the largest table. Off the kitchen, enjoy a heated sunroom that offers peaceful views overlooking the inground pool and hot tub, create a perfect space to relax year-round. The main level offers a spacious primary suite with a separate sitting room, custom walk in closet. The en suite features a soaking tub and walk in shower with a heated lamp, double sink vanity and marble countertops. An office on the main floor provides flexibility for working from home or additional living space. Convenient first floor laundry with a half bath adds every day practicality. Upstairs you'll find two additional bedrooms and a full bathroom. The heated basement has an additional half bathroom and offers endless possibilities for recreation, wood shop, storage, gym, or finished space. Additional features include a four car garage, central air, Buderus, furnace, water softener, 200 amp, electrical service, and security system. This is a rare opportuni

524 Wauregan Rd, Brooklyn

$624,000

4 Beds ⋅ 4 Baths ⋅ 24164619 MLS

Beautifully maintained and built to last, this spacious 4 bedroom, 3.5 bath home offers comfort, quality, and exceptional living space in a prime location near prestigious Thompson Hill. Situated on a manicured corner lot, the home features newer vinyl siding with a lifetime warranty, and 50-year shingles for peace of mind. Designed for easy living and entertaining, enjoy the oversized composite deck with electric awning, expansive paver patio, and a recently remodeled family room with custom built-ins and abundant natural light. The oversized two-car garage is wired for heat and connects to a convenient mudroom and laundry room. Inside, you'll find generous room sizes, oversized closets, and flexible living space throughout, including a partially finished lower level with fireplace, wet bar, and half bath. The oversized primary suite features a newly remodeled spa-like bath with soaking tub, walk-in shower, double sinks, and quartz counters. Additional highlights include five heating zones, two central air zones, and a whole-house propane generator for year-round comfort and reliability. Spacious, solidly built, and meticulously cared for - this is a home designed to stand the test of time.

1 Maple Ln, Thompson

$825,000

4 Baths ⋅ 24145561 MLS

Prime Commercial Property Off I-395 in Moosup, CT Property Overview: Size: Over 8,000 sq ft Location: Strategically positioned just off Interstate 395 in Moosup, Connecticut, ensuring excellent visibility and accessibility Current Tenant is the Music Lady Cafe: A well-established bar and restaurant with a loyal customer base, occupying one side of the building. The other side of the property offers a spacious open layout, suitable for various business ventures, office space and many possibilities. Immediate access to I-395 facilitates easy commutes and attracts a steady flow of potential customers. The area has recently welcomed major companies like Amazon and Uline, signaling a robust economic environment and increased business opportunities Plainfield and the surrounding regions are experiencing notable commercial development, with significant investments from prominent corporations. This trend enhances the appeal of the area for businesses and investors alike. This property presents a unique opportunity to acquire a substantial commercial space in a thriving locale. Its strategic location, combined with the flexibility of the available space and the stability of an existing tenant, makes it an attractive investment for discerning buyers.

4-6 Green Hollow Rd, Plainfield

$699,900

4 Beds ⋅ 4 Baths ⋅ 24150988 MLS ⋅ Grandview Estates BLDG.

Development Opportunity! Fully approved condominium project on a private lot with views, offering a turnkey development package including land, two existing townhouses with garages, and approvals for eight additional units to be built, with fully engineered plans available by request. Town approvals are in place, underground utilities are on site, and initial infrastructure has been completed. Public water and sewer available, condominium documents recorded, and unit building plans are available. Existing units provide immediate value while allowing future expansion of the remaining approved units - ideal for developers seeking income with significant upside. This is an opportunity to own or develop a planned community in the northeast corner of Connecticut, with convenient proximity to both Rhode Island and Massachusetts.

115 Groveland Ave Unit 7 & 8, Putnam

$399,999

4 Baths ⋅ 24137267 MLS

This property is a show piece of the downtown area with its historic character and corner location. Tastefully landscaped with wrought iron fencing and shrubbery, the entrance is inviting for your future businesses. Generous space in both units with updated flooring and well maintained amenities. Separate entrances to both units. Elevator accessibility. Both units have kitchenettes and two baths. First floor has large desk/reception in place. Central air. 2 Buderus boilers 5 years new; one for each unit. Ramp for entry and easy parking. Many possibilities for this building!

181 Main St, Killingly

Windham County, CT 4 Bathroom Homes for Sale

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