269 Academy Rd

Cheshire, CT 06410

$739,900
Price
4
Beds
3,070 Sq. Ft.
$241 / Sq. Ft.
3,070
Sq. Ft.
$241
per Sq. Ft.
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Description

Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - just minutes from the heart of Cheshire. Step inside to 2,755 sq ft of an open-concept floor plan offering effortless one-level living while providing three finished levels for expanded living. 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...Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - just minutes from the heart of Cheshire. Step inside to 2,755 sq ft of an open-concept floor plan offering effortless one-level living while providing three finished levels for expanded living. 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 private tour today!

Property Details for 269 Academy Road

Basement Description
Full, Heated, Storage, Cooled, Partially Finished, Full With Hatchway
Direct Waterfront
No
Expected Active Date
04-10-2026
Garages Number
2
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING UPDATED: 05/04/2026 04:12 PM

Property Details for 269 Academy Road

StatusActive
MLS #24164730
Days on Market23
Taxes$10,576 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1968
Lot Size0.96 AC / 41,817 SF
CountyNew Haven County
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Location

Listing Courtesy of MidState Realty, LLC, Frank Santino
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Building Information for 269 Academy Road

Stories-Year Built1968Building Size-Lot Size0.96 AC / 41,817 SF

Payment Calculator

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$4,607 per month

30 year fixed, 6.46% Interest

Principal and Interest

$3,726

Property Taxes

$881

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 269 Academy Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Highland Ave to Academy Road
  • Elementary School: Highland
  • Flood Zone: No
  • High School: Cheshire
  • Latitude: 41.499889
  • Longitude: -72.891415
  • Middle Jr High School: Dodd
  • Neighborhood Amenities: Library, Medical Facilities, Park, Playground/Tot Lot, Public Transportation, Shopping/Mall, Walk to Bus Lines
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,576
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer
  • Attic Description: Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: Main level, Mud Room
  • Rooms Additional: Mud Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.0
Room 2
  • Room Entry Order: 2
  • Room Features: Granite Counters,Dining Area,Island,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 12.0
Room 3
  • Room Entry Order: 3
  • Room Features: Book Shelves,French Doors,Hardwood Floor
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 9.0
Room 4
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Beams,Dry Bar
  • Room Length: 21.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.0
Room 5
  • Listing Key: 4EBBF66EC9BA4A90E063E201100A4859
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 14.0
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 7
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 11.0
Room 8
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 20.0
Room 9
  • Listing Key: 4EBBF66EC9BA4A90E063E201100A4859
  • Room Entry Order: 9
  • Room Features: Fireplace
  • Room Length: 18.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 17.5
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1968
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Est Heated Below Grade: 315
  • Living Area SQFT Per Public Records: 2755
Lot Information
  • Lot Description: N/A
  • Parcel Number: 1084285
  • Sq Ft Est Heated Above Grade: 2755.0
  • Sq Ft Total: 3070.0
  • Zoning: R-40
Utilities
  • Energy Features: Generator Ready, Programmable Thermostat
  • Heat Fuel Type: Oil
  • Hot Water Description: Other
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 269 Academy Road

DateEvent & SourcePriceAppreciation
Oct 30, 2018

Closed (Public Record)

Public Record #634318200

$404,000

+132.2% / yr

Dec 7, 2017

Closed (Public Record)

Public Record #611926899

$190,000

-1.2% / yr

Sep 18, 2000

Closed (Public Record)

Public Record #92163789

$235,000

+8.0% / yr

DateEvent & SourcePrice
10/30/2018

Closed (Public Record)

Public Record #634318200

$404,000

+132.2% / yr

12/07/2017

Closed (Public Record)

Public Record #611926899

$190,000

-1.2% / yr

09/18/2000

Closed (Public Record)

Public Record #92163789

$235,000

+8.0% / yr

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 269 Academy Road

Taxable ValueLand$79,800Additions$275,800Total$355,600
Tax Record2024$10,576 ($881 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,755 SqFtAbove Grade Finished SqFt2,755 SqFtUnfinished Basement SqFt1,267 SqFtStories2Lot Size41,818 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1998ZoningR-40CountyNEW HAVENAPNCSHR M:58 B:29 L:Fireplace TypeHas Fireplace

Schools near 269 Academy Road

This home is within Cheshire School District.
Rating
School
Type
Grades
Distance
Highland School
Public - K to 6
Dodd Middle School
Public - 7 to 8
Cheshire High School
Public - 9 to 12
The Cheshire Academy
Private - 9 to 12
Rating
School
Distance
Highland School
PublicK to 6

Dodd Middle School
Public7 to 8

Cheshire High School
Public9 to 12

The Cheshire Academy
Private9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 269 Academy Road, Cheshire, CT 06410

269 Academy Road is a single family home for sale in Cheshire, CT 06410. This property was listed for sale on April 6, 2026 by MidState Realty, LLC, it's currently listed at $739,900. It has been on the market for a total of 23 days and was last sold on October 30, 2018. This listing's school district is Cheshire School District. Nearby schools include Highland School, Dodd Middle School and Cheshire High School. 269 Academy Road is a 4-bed, 3-bath, 3,070 sqft single family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of MidState Realty, LLC, Frank Santino

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.