269 Academy Rd

Cheshire, CT 06410

$789,900
Price
4
Beds
2,755 Sq. Ft.
$287 / Sq. Ft.
2,755
Sq. Ft.
$287
per Sq. Ft.
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Coming Soon
Coming Soon

Description

Welcome to this exquisite 4-bedroom, 3-bath cape nestled just a short drive from the heart of Cheshire. Inside, you will find a spacious open layout featuring a light and bright living room with a wood burning fireplace that flows into a functional and stylish gourmet kitchen with stainless steel appliances, granite counter tops and a center island. The kitchen flows into a dining area and a stunning family room with vaulted ceilings and wood beams that create a warm and inviting space for everyday...Welcome to this exquisite 4-bedroom, 3-bath cape nestled just a short drive from the heart of Cheshire. Inside, you will find a spacious open layout featuring a light and bright living room with a wood burning fireplace that flows into a functional and stylish gourmet kitchen with stainless steel appliances, granite counter tops and a center island. The kitchen flows into a dining area and a stunning family room with vaulted ceilings and wood beams that create a warm and inviting space for everyday living and for entertaining friends and family. The main level features a library/home office and a thoughtfully designed laundry/mudroom for added convenience. Main level also includes two bedrooms and one full bathroom. A gorgeous sliding door leads you to the partially finished lower level with a wood burning fireplace and plenty of open space to relax or entertain. The upper level boasts two primary suites offering en-suite baths and walk in closets creating relaxing retreats. The tranquil yard features a two-level deck for dining and relaxing with a few steps down into 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, basement storage and closets and more closets. Just a few, of the many, noteworthy improvements to mention 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 breathtaking home for yourself!
  1. Listed by Frank Santino • MidState Realty, LLC
    P: (203)-314-3986 C: (203)-314-3986 franksantino@att.net

Property Details for 269 Academy Road

Basement Description
Full
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: 04/07/2026 11:05 PM

Property Details for 269 Academy Road

StatusComing Soon
MLS #24164730
Days on Market-
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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$4,859 per month

30 year fixed, 6.46% Interest

Principal and Interest

$3,978

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: Academy Road
  • Elementary School: Highland
  • High School: Cheshire
  • Latitude: 41.499889
  • Longitude: -72.891415
  • Middle Jr High School: Dodd
  • 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
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, 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
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 15.0
Room 4
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 5
  • Listing Key: 4EBBF66EC9BA4A90E063E201100A4859
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 17.0
Room 6
  • Room Entry Order: 6
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 15.0
Property
Property and Assessments
  • 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
  • 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: 2755.0
  • Zoning: R-40
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Other
  • 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

Aug 19, 1994

Closed (Public Record)

Public Record #92149666

$147,500—
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

08/19/1994

Closed (Public Record)

Public Record #92149666

$147,500

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 Coming Soon in Cheshire, CT 06410. This property is currently priced at $789,900. 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, 2,755 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.