269 Academy Road

Cheshire, CT 06410

Discover this beautifully expanded, like-new 3-level Cape, perched high above the street on a private, nearly one-acre lot - just minutes from the heart of Cheshire. Inside, you'll find 2,755 sq ft of open living space with hardwood floors throughout. The sun-filled living room anchored by a wood-burning fireplace flows into a stylish gourmet kitchen featuring stainless steel appliances, granite countertops and a center island. The kitchen opens into a stunning family room with a vaulted ceiling and wood beams, creating a warm, inviting space for hosting and everyday living. The main level also offers a library/home office, a convenient laundry/mudroom, two bedrooms and a full bathroom. A gorgeous sliding door opens to the lower level featuring an additional 265 sq ft of living space, a 2nd wood-burning fireplace, and plenty of room to relax or entertain. Two spacious upper-level suites with en-suite baths and walk-in closets offer versatile living for guests, multigenerational needs, or everyday ease. The tranquil backyard features a two-level deck ideal for unwinding, a fire pit and a fully fenced yard for added privacy & security. Abundant storage throughout including a 2-car attached garage, 1,317 sq ft of basement space, and generous closets. Among the many upgrades are a new driveway (2023), 30-yr architectural roof (2021), paver front walkway (2022), 5-zone boiler and dual central air systems (2018) & generator-ready since 2024. Schedule your private tour today!

Listing courtesy of Frank Santino of MidState Realty, LLC Office Phone: (203) 314-3986 Broker Contact: (203) 314-3986



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Last checked: 2026-05-01 01:13 AM UTC.