Home Homes for Sale Cheshire, CT 269 Academy Road

269 Academy Road, Cheshire, CT 06410

Single Family For Sale

$739,900
$241/sqft
269 Academy Road, Cheshire, CT
Active
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4
Bedrooms
3
Bathrooms
3,070
Sq Ft
0.96
Acres
1968
Year Built

About This Home

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!

Listed by Frank Santino (203) 314-3986 with MidState Realty, LLC (203) 314-3986

Listing Snapshot

Price $739,900 Days on Our Site 36 days
Property Tax $10,576/yr Style Cape Cod
Year Built 1968 Total Sq Ft 3,070
Lot Size 0.96 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 3
Total Rooms 10 Half Baths 0

Key Features

Interior
  • Security System
Appliances
  • Oven/Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Disposal
  • Washer
  • Dryer
Outdoor
  • Deck
Nearby
  • Library
  • Medical Facilities
  • Park
  • Playground/Tot Lot
  • Public Transportation
  • Shopping/Mall
  • Walk to Bus Lines

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Attached Garage
Below Grade 315 sq ft

Systems & Utilities

Heat Hot Water
Fuel Oil
Cooling Central Air
Hot Water Other
Water Private Well
Sewer Septic

Schools

Elem Highland
Middle Dodd
High Cheshire

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $881/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Apr 28, 2026 Under Contract
Apr 20, 2026 Price Reduced $739,900
Apr 6, 2026 Listed $789,900

Frequently Asked Questions

How much does 269 Academy Road in Cheshire, CT cost?
This property is listed at $739,900, which works out to $241 per square foot.
How many bedrooms does 269 Academy Road have?
This home has 4 bedrooms and 3 bathrooms.
What is the square footage of 269 Academy Road?
The home is 3,070 square feet, situated on 0.96 acres.
When was 269 Academy Road in Cheshire built?
This property was built in 1968.
Is 269 Academy Road, Cheshire, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 269 Academy Road, Cheshire in?
This home is served by the Cheshire public school system, with Highland as the elementary school and Cheshire as the high school.
How do I schedule a tour of 269 Academy Road, Cheshire, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Frank Santino · (203) 314-3986

MidState Realty, LLC · (203) 314-3986

MLS# 24164730 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated May 11, 2026 12:19 PM UTC