Windham County, CT Real Estate Search

Windham County, CT Homes for Sale

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Windham County, CT Homes for Sale

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Newest Windham County, CT Homes for Sale

$350,000
3 Beds 2 Baths 24160862 MLS
Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places. Maybe it's the quiet and peace that magically flows through a home like this. Built in 1837 as the town parsonage, this home has been part of this community's story for nearly 200 years. Now it's looking for someone ready to write the next chapter. 11 rooms await for the exciting next chapter. The big work is already done. New roof. New electrical panel. Foundation fully repointed with fresh mortar, inside and out. Chimney repointed and stuccoed, New stainless steel liner, crown, and cap installed. What's left to do is the part that lets the new owner make it their own: cosmetic updates, with flooring quotes already in hand for new carpet and refinished hardwood. Set on nearly an acre of flat, open land, this is the kind of property that rewards patience and vision. For the history lover who's been waiting for a home with a past worth preserving, the hands-on owner who sees potential where others see projects, or the investor eyeing the space and the location near UConn and ECSU, this one is worth it all. Come and see what was once part of the past and how it can be a part of your future

60 Chaplin St, Chaplin

$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

$525,000
3 Beds 2 Baths 24178930 MLS
Custom passive solar Contemporary set on 5+ private acres surrounded by natural beauty and peaceful scenery. A 5-year-young sunroom with tile flooring offers flexible space for relaxing, gardening, or enjoying year-round views of the landscape. Step outside to the spacious deck, ideal for outdoor dining or quiet mornings overlooking the tranquil setting. The inviting living room features a newer pellet stove and tile flooring designed for comfort and easy maintenance. Country dining room with wide plank floors, exposed reclaimed wood beams, and newer Andersen slider leading to the deck. Bright kitchen includes 3 skylights, porcelain farmhouse sink, solid wood cabinetry, stainless steel appliances, tile floor, and walk-in pantry. Convenient laundry/mudroom connects the kitchen to the attached 2-car garage. First Floor Primary Bed with new carpet, ceiling fan, slider to the deck to listen to the cute garden pond with water fountain. The second floor offers 2 additional bedrooms with exposed wood beams, a partially finished recreation room, and full bath with shower stall. The upper level sunroom includes a propane stove for supplemental heat. Energy-efficient design with strong insulation and berm construction helps maintain comfortable temperatures year-round. Additional updates include newer roof, water heater, washer and dryer, and new well water line. Convenient location close to shopping, dining, and commuter routes. Approx. 25 minutes to UCONN and 40 minutes to Hartford.

30 Grant Hill Rd, Brooklyn

$2,950,000
4 Beds 5 Baths 24115278 MLS
A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175 acres of open space, this home sits high with long eastern views into RI! A 1,000 ft paved driveway leads past over 500 ft of hand-laid stone walls to the stunning residence, framed by 10" cedar columns and solid mahogany double doors. The interior exudes craftsmanship with 8' solid wood doors, mahogany floors, 12" triple crown molding, and Marvin windows throughout. The grand great room boasts 20' ceilings and a massive fieldstone fireplace, while the private office stuns with a redwood ceiling, fireplace, and custom cherry built-ins. The chef's kitchen features Viking and Meile appliances, granite counters, cherry details, and opens to a sunny morning room and expansive veranda. The primary suite is a retreat with vaulted ceilings, a luxurious spa bath, radiant heated travertine floors, custom vanities, arched alcoves, and dual walk-ins. Additional highlights include a 3-car garage with Spanish cedar doors, Sonos sound system, generator, 139-head irrigation system, and walk-up basement ready to finish. This is a one-of-a-kind legacy property -stately, expansive, and exquisitely built.

282 & 260 Searles Rd, Pomfret

$1,450,000
4 Beds 6 Baths 24177811 MLS
Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence offers over 6,000SF above grade plus an extensively finished lower level designed for entertaining and everyday comfort. The kitchen features granite countertops, a large center island, and abundant cabinetry. The first-floor primary suite includes tray ceilings, a spa-like bath with double sinks, a 2-person jetted tub, and separate shower. The finished lower level offers a completely unique atmosphere with a custom speakeasy-style bar, theater room, full bath, dog washing station, laundry area, and private office suite with 2 rooms and an additional full bath. An attached in-law apartment has its own bedroom, full bath, kitchen & loft/office area, and newly added white oak flooring. 4 oversized garage bays, 2 of which offer unfinished loft space above. Outside, enjoy the fenced inground pool area with beautifully updated landscaping & a pool house complete with plumbing, granite counters, half bath, & outdoor shower. Fiber internet with mesh nodes provides seamless connectivity throughout the house. A rare Woodstock Valley retreat where privacy, nature, and luxury come together.

1374 Rte 171, Woodstock

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