Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - minutes from the heart of Cheshire. Offering 2,755 sq ft, this home boasts hardwood floors throughout and a flexible open floor plan for one-level living while providing three finished levels to suit your lifestyle. The sun-filled living room with 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 315 sq ft of living space, a 2nd wood-burning fireplace and plenty of room to relax or entertain. Upstairs, you'll find two expansive bedrooms, both featuring their own full bath and walk-in closet. 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 tour today!
Est. $3,939 per month, based on comparable rentals
Sale and tax history for 269 Academy Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24164730
Jul 21, 2026
Sold
$722,906
$235/sq ft
May 20, 2026
Pending
—
May 18, 2026
Price Changed
$699,500
$228/sq ft
Apr 29, 2026
Relisted
—
Apr 28, 2026
Pending
—
Apr 20, 2026
Price Changed
$739,900
$241/sq ft
Apr 10, 2026
Listed
$789,900
$257/sq ft
Apr 6, 2026
Coming Soon
$789,900
$257/sq ft
Smart MLS #170084490
Oct 31, 2018
Sold
$404,000
$132/sq ft
Sep 16, 2018
Listing Removed
—
Aug 12, 2018
Price Changed
$399,999
$130/sq ft
Jul 24, 2018
Price Changed
$414,999
$135/sq ft
Jun 7, 2018
Price Changed
$429,999
$140/sq ft
May 16, 2018
Listed
$449,999
$147/sq ft
Look no further. Just a short drive from the heart of Cheshire, this immaculate 4 bedroom cape sits on a .96 acre lot. Upon entering you will notice fully refinished hard wood floors throughout. The open floor plan encompasses four spacious bedrooms with plenty of room for study, sleep and storage, and a sleek and stylish gourmet kitchen with all new stainless Samsung appliances that flows through to the living area. The expansive living room sports a stone fireplace and leads you through the library, to the spacious rear deck (great for entertaining), with views of the grassy backyard. Just a short trip down the stairs to the basement, you will notice a finished bonus room with a second fireplace along with a new boiler and central air cooling system. This turn key property wont last! UPDATE - new septic
Smart MLS #170002118
Dec 11, 2017
Listing Removed
—
Dec 8, 2017
Sold
$190,000
$62/sq ft
Aug 4, 2017
Listed
$209,900
$68/sq ft
Located on a nice private acre lot is this 4 bedroom Cape with 1st floor master bedroom & 1st floor family room. This house has a ton of space with over 2,700 sq ft.