269 Academy Road Cheshire, CT $ 789,900
269 Academy Road
$ 789,900
Recently Listed
Open House 4/12 2pm - 4pm
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269 Academy Road

Cheshire, CT, 06410
$ 789,900
Bedrooms4 Baths3.0 Sq 2,755

Monthly Estimate*

$ 4,864

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Single Family Home for sale in Cheshire, CT

for $789,900 with 4 bedrooms and 3 full baths. This 2,755 square foot home was built in 1968 on a lot size of 0.96.

Welcome to this exquisite 4-bedroom, 3-bath cape nestled on just under an acre and a short drive from the heart of Cheshire. Inside, you will find hardwood floors throughout and 2,755 sq ft of open living space. The light filled living room offers a wood burning fireplace that flows into a stylish gourmet kitchen featuring stainless steel appliances, granite counter tops and a center island. The kitchen flows into a dining area and a stunning family room with a vaulted ceiling and wood beams that create a warm and inviting space for everyday living and entertaining. The main level features a library/home office and a laundry/mudroom for added convenience. Main level also includes two bedrooms and one full bathroom. A gorgeous sliding door leads you to the lower level featuring an additional 265 sq ft of living space with a 2nd wood burning fireplace and plenty of room to relax or entertain. The upper level boasts two primary suites offering en-suite baths and walk in closets creating calming retreats. The tranquil yard features a two-level deck for dining and unwinding and a few steps down lead to the green grass with a fire pit and enclosed yard to keep children and pets safe. Storage space galore with a two-car attached garage, 1,317 sq ft in basement and closets and more closets. A few of the many noteworthy upgrades include a new driveway in 2023, new roof in 2021 and new paver front walkway in 2022. Schedule your private tour today to view this like new home!

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Open House

4/12/2026 2:00 PM - 4:00 PM
269 Academy Road Cheshire, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 789,900

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 10,576

Style

Lot Size

0.96

Year Built

1968

Town/City

Cheshire

MLS | Web ID

24164730

Features
General
Zoning R-40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.96
Directions Academy Road
High School Cheshire
City Cheshire
Elementary School Highland
Sq Ft Total 2755
DOM 0
Year Built 1968
Style Cape Cod
Year Built Source Public Records
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Interior
Cooling System Central Air
Total Rooms 10
Basement Description Full
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Exterior
Water Source Private Well
Lot Description N/A
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* Excluded Features
List By
Frank Santino

Listing Agent

Midstate Realty, Llc

Broker

franksantino@att.net

Email

Affordability Calculator

$5,745
Per Month
85%
15%
0%
Monthly Principal & Interest
$4,864
Monthly Property Taxes
$881
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
895992 Elementary School
1232875 Middle School
Cheshire High School High School
Pricing History
DatePricePrice ChangeDescription
4/7/2026$789,900 Listed Price

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269 Academy Road, Cheshire, CT, 06410 is a Single Family Home for sale at $789,900 with 2,755 sqft and a lot size of 0.96. 269 Academy Road has 4 bedrooms, 3.0 baths, and was built in 1968. The property's zip code is 06410 which is in Cheshire, CT