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$789,900 Just Listed
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Property Description
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!
Full Property Details
Full Property Details for 269 Academy Rd
General
- Price: $789,900
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24164730
- Updated: 4/10/2026
- Added to Site: 4 day(s) ago
Interior
- Number of Rooms: 10
- Interior Features: Security System
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Walk-In Closet, Hardwood Floor, 19 x 15, Upper
- Bedroom 1: Bedroom - Hardwood Floor, 16 x 17, Main
- Bedroom 2: Bedroom, 18 x 15, Main
- Bedroom 3: Bedroom - Hardwood Floor, 11 x 14, Upper
Other Rooms
- Living Room: Living Room, Main
- Dining Room: Dining Room, Main
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Parking: Attached Garage
Location
- County: New Haven
- Driving Directions: Academy Road
School Information
- Elementary School: Highland
- Middle School: Dodd
- High School: Cheshire
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Water, Oil
- Heating Fuel: Oil
- Water Heater: Other
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Cape Cod
- Construction Status: No/Resale
- Exterior Const.: Vinyl Siding
- Basement Desc.: Full
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,755
- Above Ground: 2,755 Sq. Ft.
- Year Built: 1968
Lot Features
- Lot Size (Acres): 0.96
- Zoning: R-40
- Lot Description: N/A
Financial Considerations
- Assessment Amount: $355,600
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 1084285
Listed by MidState Realty, LLC, Frank Santino
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Schools
Schools serving 269 Academy Rd
School District:Cheshire School District
| Name | Grades | Distance |
|---|---|---|
Highland School, Cheshire, CT 490 Highland Avenue, Cheshire, CT 06410 | 1-6 | 0.8 mi |
Dodd Middle School 100 Park Place, Cheshire, CT 06410 | 7-8 | 1 mi |
Cheshire High School 525 South Main Street, Cheshire, CT 06410 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 269 Academy Rd
Date
Details
Price
Change
Source
4/10/2026
Listed
$789,900
95.52%
MLS
10/30/2018
Sold
$404,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 269 Academy Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,576
8%
$355,600
—
2023
$9,765
5%
$355,600
34%
2023
$9,343
2%
$266,270
—
2022
$9,138
2%
$266,270
—
2021
$8,979
2%
$266,270
—
2020
$8,845
—
$266,270
—
2019
$8,845
12%
$266,270
10%
2018
$7,931
2%
$243,140
—
2017
$7,766
2%
$243,140
—
2016
$7,584
2%
$243,140
—
2015
$7,462
1%
$243,140
—
2014
$7,355
—
$243,140
-9%
2011
$7,391
—
$267,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 269 Academy Rd
269 Academy Road, Cheshire, CT 06410 (MLS# 24164730) is a Single Family property with 4 bedrooms and 3 full bathrooms. 269 Academy Road is currently listed for $789,900 and was received on April 06, 2026. Want to learn more about 269 Academy Road? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

