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



The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-04-30 05:10 PM UTC.