Cheshire Real Estate

Recently Sold Listings in Cheshire, CT

Welcome to your dedicated resource for viewing Sold listings in Cheshire, CT. As local Cheshire, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Cheshire, CT below, or if you are looking to sell a home in Cheshire, CT contact a local agent to discuss the possibilities.

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All Recently Sold in Cheshire, CT

$1,100,000
4 Beds 4 Baths 24174186 MLS
Impeccably maintained and impossible to overlook, this Cheshire home stands in a class of its own. Set on nearly an acre of land in a desirable cul-de-sac neighborhood and bordering protected land, this original-owner gem is a rare find! From the moment you arrive, the charming front porch invites you to stay awhile. Enter a spacious two-story foyer that sets the tone for the exceptional craftsmanship and details found throughout. Rich hardwood floors flow seamlessly through the formal living and dining rooms, home office, stunning eat-in kitchen with center island and impressive family room anchored by a gas fireplace and custom built-ins beneath soaring ceilings. A guest bath, mudroom, and laundry room complete the main level. Ascend to the primary suite w tray ceiling, walk-in closet, and spa-inspired en-suite with heated floors, soaking tub, and water closet. 3-4 additional bedrooms plus a 2nd full bath nicely complete the upstairs amenities. The finished walk-out basement w half bath and home gym provides exceptional versatility. A low-maintenance Trex deck w motorized awning and direct gas line for grilling creates an effortless flow to the bluestone patio. Additional features include speakers in/out, in-ground sprinklers, Invisible fence, underground utilities, public water/sewer, and (2024) water heater. Conveniently located just minutes from The Shops at Stone Bridge and 691/84. If your next chapter is 60 Kensington Court...your happily ever after is sure to follow!

60 Kensington Ct, Cheshire

$1,100,000
5 Beds 5 Baths 24174911 MLS
Exceptionally updated and detailed, this classic, custom 5-bedroom, 5-bath (3 full, 2 half) Colonial sits on a level, professionally landscaped 2-acre lot with a fenced, heated gunite pool. The grand two-story foyer welcomes you with elegant open railings and gleaming hardwood floors that flow throughout the entire first floor. A chef's dream, the new kitchen (2014) features a butler's pantry, granite counters, beveled granite island, Sub-Zero refrigerator, 6-burner Wolf range, built-in wall oven, and a microwave. This space opens to a bright, sun-drenched breakfast room with a vaulted ceiling. Relax in the living room by the propane fireplace, or enjoy the family room where atrium doors lead to a large patio overlooking the beautiful yard and pool. Off Fine architectural details include extensive crown molding and raised-panel wainscoting. Practicality meets style with a bluestone entrance leading to a side porch, a tiled mudroom, laundry, and a half bath. A private first-floor office and guest half-bath complete the main level. Upstairs, the primary suite features hardwood floors, two custom walk-in closets, and a newer bath (2014) with a gorgeous windowed shower and soaking tub. Two additional large bedrooms share a full bath with double granite vanity (2014). The charming third floor hosts two more bedrooms with cozy window seats and a full bath. Downstairs, a partially finished basement provides the perfect flexible space for a playroom and home gym (over 800sf).

701 Andrea Ct, Cheshire

$1,075,000
3 Beds 5 Baths 24067776 MLS
Nestled on 6.5 serene acres next to the Fresh Meadows open space in Cheshire, CT, this worldclass property offers privacy, peace and elegance. The home boasts 4,896 sq ft of living space, complemented by an additional 4,400 sq ft dedicated to studios, a gym, garages, a woodshop, and ample storage - perfect for working from home or pursuing hobbies. Designed by Tom Pritchard and Edward Tufte, the property features a thoughtful kitchen, spacious dining area, visitor suite, beautifully landscaped grounds, and a network of walking trails. The entire property exudes a park-like charm with practical features like a swimming pool, natural windbreaks of trees, stone walls and high ground reducing risk of flooding. The location is enhanced by Cheshire's highly-rated schools. This home was the residence of Yale Professor Edward Tufte for over 40 years. Renowned as the "Galileo of Graphics" (Bloomberg) and the "da Vinci of Data" (NY Times), Tufte used this space as a creative haven, writing and designing six acclaimed books, crafting sculptures, and planning his 234-acre art park at Hogpen Hill Farms in Litchfield County. The property is 15 miles from Yale University and Yale New Haven Hospital, 5 miles from Quinnipiac University, and within easy reach of Wesleyan University and major airports. New York City and Boston are both accessible in under two hours by car or train, making this an ideal location for those seeking a balance of rural tranquility and urban accessibility.

1161 Sperry Rd, Cheshire

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