Completely Reimagined * 4 Bedrooms * 3.5 Bathrooms * 2 Acres * Luxury Primary Suite * Finished Lower Level Welcome to 275 W Main Street, where classic New England charm meets a stunning, comprehensive renovation. Set on 2 beautiful acres directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll notice the attention to detail. Beautifully refinished hardwood floors flow throughout the home, complementing bright, open living spaces designed for both everyday comfort and entertaining. Multiple fireplaces preserve the warmth and character of the original home while the extensive upgrades bring it firmly into the modern era. At the heart of the home is a show-stopping new kitchen, beautifully appointed with quartz countertops and premium THOR Gordon Ramsay Collection appliances. Whether you're hosting family and friends or enjoying a quiet evening at home, this kitchen was designed to impress. Retreat upstairs to the luxurious primary suite, complete with a 6-foot walk-in closet and custom closet system. The spa-inspired primary bathroom creates your own private escape, featuring a custom rain shower and freestanding soaking tub-the perfect place to unwind. And the living space doesn't stop upstairs. The approximately 800-square-foot permitted finished lower level has been transformed. Incredible extension of the home, featuring luxury vinyl plank flooring, a half bathroom, and its own dedicated heating and cooling zone. Create the ultimate entertainment room, home theater, game room, gym, office, or combination of them all. The renovation goes far beyond what you can see. Major improvements include a new septic system, new plumbing, complete electrical rewire with 200-amp service, hardwired security system, new windows, new siding, new gutters, and a new 3-zone central heating and air-conditioning system serving the first floor, second floor, and finished lower level. Step outside onto the new 12' 12' wood deck and enjoy the professionally landscaped grounds and peaceful surroundings of your private 2-acre property. Nearly every detail has been thoughtfully addressed. With extensive permitted renovations, luxury finishes, major new mechanical systems, generous indoor and outdoor living space, and an incredible Chester setting, 275 W Main Street isn't simply renovated-it's ready to be enjoyed. Come experience this one-of-a-kind Chester property and make it home.

Listing courtesy of Shirley Tapper of Great Estates, CT Office Phone: (203) 200-7030 Broker Contact: (475) 202-2586



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Last checked: 2026-10-03 11:37 PM UTC.