Cheshire Real Estate

Homes for Sale in Cheshire, CT Over $1,500,000

Welcome to your dedicated resource for Homes for Sale Over $1,500,000 in Cheshire, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Cheshire, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available over $1,500,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Cheshire, CT Homes for Sale Over $1,500,000

$1,748,600
6 Beds ⋅ 7 Baths ⋅ 24190202 MLS
Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and pool for effortless indoor/outdoor entertaining - enjoy quiet mornings by the water and evenings out back to socialize. The main level also features the primary suite, complete with a private sitting room and fireplace - a true retreat at the end of the day - along with a sunroom and a wood-paneled study. The finished lower level adds a home gym and an indoor basketball court, convertible to a squash or racquetball court, so game nights and workouts happen without ever leaving home. Adding rare flexibility, a semi-private au pair apartment (approx. 40' x 22') includes its own kitchen, full bath, living room, and bedroom - ideal for extended family, live-in help, or guests who want their own space to come and go as they please. This isn't just a home - it's a lifestyle built around space, privacy, and the freedom to live exactly how you want.

25 Whispering Hollow Ct, Cheshire
$1,711,500
4 Beds ⋅ 5 Baths ⋅ 24190982 MLS
Lovely contemporary Colonial set on 2.26 acres offers over 6,000 square feet of above-grade living space w/ a versatile multi-level layout. Step into the dramatic two-story brick foyer featuring floor-to-ceiling windows, & radiant floor heating throughout the 1st floor. This level offers outstanding add'l living space w/ a comfortable family room, 43' x 15' rec room, private office, full BA, & walkout access to the covered lower deck. Whether you're looking for a home gym, guest retreat, or simply extra space to spread out, you have endless possibilities! The main living level features a large kitchen w/granite countertops, center island, quality appliances, & sunny breakfast nook with lots of windows overlooking the peaceful landscape. Dining room, living room, & vaulted Great Room w/ pellet stove provide inviting spaces for everyday living & entertaining. Upper deck is conveniently accessible from the breakfast nook or great room. The primary suite features radiant floor heating, en-suite BA, double closets, & walk-in closet. 1/2 BA w/ laundry completes this level. Upstairs you'll find 3 generously sized BRs, including one w/ its own private BA, plus an additional full BA. Backing directly to Cheshire Land Trust, this property offers exceptional privacy, a putting green, pickleball court, & peaceful views from nearly every room. Whether enjoying your morning coffee on the deck or relaxing indoors, the natural setting has a sense of tranquility that's hard to find.

644 S Brooksvale Rd, Cheshire
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