Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$699,500

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,070 Sq. Ft.
  • 2 Car Garage
  • Updated 6 days ago
See This Home
Save This Home
See This Home
Save 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!

Full Property Details for 269 Academy Rd

General

  • Price: $699,500
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24164730
  • Updated: 5/20/2026
  • Added to Site: 50 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Mud Room
  • Interior Features: Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Walk-In Closet, Hardwood Floor, 21 x 11, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 11 x 12, Main
  • Bedroom 2: Bedroom - Hardwood Floor, 14 x 14, Main
  • Bedroom 3: Bedroom - Full Bath, Walk-In Closet, Hardwood Floor, 15 x 20, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 19 x 15, Main
  • Family Room: Family Room - Vaulted Ceiling, Beams, Dry Bar, 21 x 14, Main
  • Kitchen: Kitchen - Granite Counters, Dining Area, Island, Hardwood Floor, 24 x 12, Main
  • Office: Office - Book Shelves, French Doors, Hardwood Floor, 10 x 9, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Fireplace, 18 x 17.5, Lower
  • Rec Room: Fireplace, 18 x 17.5, Lower
  • Laundry: Main Level

Exterior

  • Exterior Features: Deck
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Driving Directions: Highland Ave to 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, Heated, Storage, Cooled, Partially Finished, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,070
  • Above Ground: 2,755 Sq. Ft.
  • Below Ground: 315 Sq. Ft.
  • Year Built: 1968

Lot Features

  • Lot Size (Acres): 0.96
  • Zoning: R-40
  • Lot Description: N/A

Green Features

  • Energy Features: Generator Ready, Programmable Thermostat

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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 269 Academy Rd —

  • Frank Santino

    MidState Realty, LLC

Agent Contact: (203) 314-3986 Office Contact: (203) 314-3986

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 269 Academy Rd

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-60.8 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-81 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.1 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/18/2026
Price Reduced
$699,500
-5.46%
MLS
4/20/2026
Price Reduced
$739,900
-6.33%
MLS
4/10/2026
Listed
$789,900
95.52%
MLS
10/30/2018
Sold
$404,000
—
Public Record
Get Price Alerts and Save Property
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 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
—
View All
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 for 269 Academy Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by MidState Realty, LLC, Frank Santino

Similar Properties near 269 Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

59 Williams Rd, Cheshire, CT 06410 - Photo 1 Just Listed
$659,900

59 Williams Rd  Cheshire, CT 06410

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,124
    Sq. Ft.
Listed by Lamacchia Realty
735 Cook Hill Rd, Cheshire, CT 06410 - Photo 1
$729,900

735 Cook Hill Rd  Cheshire, CT 06410

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 2,748
    Sq. Ft.
Listed by LAER Realty Partners
42 Chimney Sweep Rd, Wallingford, CT 06492 - Photo 1
$669,900

42 Chimney Sweep Rd  Wallingford, CT 06492

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,408
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
1050 Jarvis St, Cheshire, CT 06410 - Photo 1
$685,000

1050 Jarvis St  Cheshire, CT 06410

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 2,506
    Sq. Ft.
Listed by Ventura Group Realty LLC

Just Listed near 269 Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

11 Cheshire Rd, Prospect, CT 06712 - Photo 1 Just Listed
$399,900
Open House

11 Cheshire Rd  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,551
    Sq. Ft.
Listed by Ascend Realty LLC
7 Holley Ln, Prospect, CT 06712 - Photo 1 Just Listed
$169,900

7 Holley Ln  Prospect, CT 06712

  • Land Residential
  • Active
  • Updated 5 days ago
  • 2.44
    Acres
Listed by Pavlik Real Estate LLC
44 Summit Rd, Prospect, CT 06712 - Photo 1 Just Listed
$439,900

44 Summit Rd  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,982
    Sq. Ft.
Listed by Pavlik Real Estate LLC
21 Sigwin Dr, Wallingford, CT 06492 - Photo 1 Just Listed
$159,999

21 Sigwin Dr  #21  Wallingford, CT 06492

  • Condo
  • Active
  • Updated 1 day ago
  • 1
    Bed
  • 1
    Total Bath
  • 672
    Sq. Ft.
Listed by Samantha Celentano (203) 871-8254

Price Reduced near 269 Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

882 N Colony Rd, Meriden, CT 06450 - Photo 1 Price Reduced
-$20,000 (-8%)
$229,900

882 N Colony Rd  #31  Meriden, CT 06450

  • Townhouse
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,022
    Sq. Ft.
Listed by Advantage Realty Group, Inc.
128 Hobart St, Meriden, CT 06450 - Photo 1 Price Reduced
-$20,000 (-6.27%)
$299,000

128 Hobart St  Meriden, CT 06450

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,813
    Sq. Ft.
Listed by Best Real Estate Brokerage LLC
171 Oregon Rd, Meriden, CT 06451 - Photo 1 Price Reduced
-$99,100 (-9.02%)
$999,900

171 Oregon Rd  Meriden, CT 06451

  • Single Family
  • Active
  • Updated 5 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,650
    Sq. Ft.
Listed by Luxe Realty LLC
50 Smithfield Ave, Meriden, CT 06451 - Photo 1 Price Reduced
-$10,900 (-3.3%)
$319,000

50 Smithfield Ave  Meriden, CT 06451

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,469
    Sq. Ft.
Listed by Advantage Realty Group, Inc.

Recent Sales near 269 Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

106 Far Horizon Dr, Cheshire, CT 06410 - Photo 1 Sold
$659,900

106 Far Horizon Dr  Cheshire, CT 06410

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,872
    Sq. Ft.
Listed by Calcagni Real Estate
Sold by Dow Della Valle
462 Castle Glenn, Cheshire, CT 06410 - Photo 1 Sold
$683,000

462 Castle Glenn  Cheshire, CT 06410

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,290
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
Sold by Berkshire Hathaway NE Prop.
4 Brookfield Ct, Cheshire, CT 06410 - Photo 1 Sold
$670,000

4 Brookfield Ct  Cheshire, CT 06410

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,300
    Sq. Ft.
Listed by Calcagni Real Estate
Sold by BHGRE Gaetano Marra Homes
106 Woodland Dr, Cheshire, CT 06410 - Photo 1 Sold
$605,000

106 Woodland Dr  Cheshire, CT 06410

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,247
    Sq. Ft.
Listed by Felipe Segura and Odalys Bekanich
Sold by Right Move Team

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 $699,500 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.

Tour this property