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!
Under contract
Price cut: $40.4K (5/18)
$699,500
269 Academy Road, Cheshire, CT 06410
4beds
3,070sqft
Single Family Residence
Built in 1968
0.96 Acres Lot
$-- Zestimate®
$228/sqft
$-- HOA
What's special
- 60 days |
- 1,082 |
- 26 |
Zillow last checked:
Listing updated:
Listed by:
Frank Santino (203)314-3986,
MidState Realty, LLC 203-314-3986
Source: Smart MLS,MLS#: 24164730
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 231 Square Feet
- Dimensions: 11 x 21
Bedroom
- Features: Hardwood Floor
- Level: Main
- Area: 196 Square Feet
- Dimensions: 14 x 14
Bedroom
- Features: Hardwood Floor
- Level: Main
- Area: 132 Square Feet
- Dimensions: 12 x 11
Bedroom
- Features: Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 300 Square Feet
- Dimensions: 20 x 15
Family room
- Features: Vaulted Ceiling(s), Beamed Ceilings, Dry Bar
- Level: Main
- Area: 294 Square Feet
- Dimensions: 14 x 21
Kitchen
- Features: Granite Counters, Dining Area, Kitchen Island, Hardwood Floor
- Level: Main
- Area: 288 Square Feet
- Dimensions: 12 x 24
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 285 Square Feet
- Dimensions: 15 x 19
Office
- Features: Bookcases, French Doors, Hardwood Floor
- Level: Main
- Area: 90 Square Feet
- Dimensions: 9 x 10
Rec play room
- Features: Fireplace
- Level: Lower
- Area: 315 Square Feet
- Dimensions: 17.5 x 18
Heating
- Hot Water, Oil
Cooling
- Central Air
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water Heater
- Laundry: Main Level, Mud Room
Features
- Basement: Full,Heated,Storage Space,Cooled,Partially Finished
- Attic: Access Via Hatch
- Number of fireplaces: 2
Interior area
- Total structure area: 3,070
- Total interior livable area: 3,070 sqft
- Finished area above ground: 2,755
- Finished area below ground: 315
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Deck
Lot
- Size: 0.96 Acres
Details
- Parcel number: 1084285
- Zoning: R-40
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1968
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Green energy
- Energy efficient items: Thermostat
Community & HOA
Community
- Features: Library, Medical Facilities, Park, Playground, Near Public Transport, Shopping/Mall
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Cheshire
Financial & listing details
- Price per square foot: $228/sqft
- Tax assessed value: $355,600
- Annual tax amount: $10,576
- Date on market: 4/7/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/20/2026 | Pending sale | $699,500$228/sqft |
Source:  Smart MLS #24164730 Report a problem | ||
| 5/18/2026 | Price change | $699,500-5.5%$228/sqft |
Source: Smart MLS #24164730 Report a problem | ||
| 4/29/2026 | Listed for sale | $739,900$241/sqft |
Source: Smart MLS #24164730 Report a problem | ||
| 4/28/2026 | Pending sale | $739,900$241/sqft |
Source: Smart MLS #24164730 Report a problem | ||
| 4/20/2026 | Price change | $739,900-6.3%$241/sqft |
Source: Smart MLS #24164730 Report a problem | ||
| 4/10/2026 | Listed for sale | $789,900+95.5%$257/sqft |
Source: Smart MLS #24164730 Report a problem | ||
| 10/31/2018 | Sold | $404,000+1%$132/sqft |
Source: Smart MLS #170084490 Report a problem | ||
| 8/12/2018 | Price change | $399,999-3.6%$130/sqft |
Source: Lasko Real Estate, LLC #170084490 Report a problem | ||
| 7/24/2018 | Price change | $414,999-3.5%$135/sqft |
Source: Lasko Real Estate, LLC #170084490 Report a problem | ||
| 6/7/2018 | Price change | $429,999-4.4%$140/sqft |
Source: Lasko Real Estate, LLC #170084490 Report a problem | ||
| 5/16/2018 | Listed for sale | $449,999+136.8%$147/sqft |
Source: Lasko Real Estate, LLC #170084490 Report a problem | ||
| 12/8/2017 | Sold | $190,000-9.5%$62/sqft |
Source: Smart MLS #170002118 Report a problem | ||
| 11/6/2017 | Price change | $209,900-6.7%$68/sqft |
Source: Calcagni Real Estate #170002118 Report a problem | ||
| 10/5/2017 | Price change | $224,900-6.3%$73/sqft |
Source: Calcagni Real Estate #170002118 Report a problem | ||
| 9/7/2017 | Price change | $239,900-5.9%$78/sqft |
Source: Calcagni Real Estate #170002118 Report a problem | ||
| 8/3/2017 | Listed for sale | $254,900+10.9%$83/sqft |
Source: Homepath Report a problem | ||
| 3/31/2017 | Listing removed | $229,900$75/sqft |
Source: Calcagni Real Estate #N10121220 Report a problem | ||
| 12/2/2016 | Pending sale | $229,900$75/sqft |
Source: Calcagni Real Estate #N10121220 Report a problem | ||
| 9/1/2016 | Price change | $229,900-8%$75/sqft |
Source: Calcagni Real Estate #N10121220 Report a problem | ||
| 4/20/2016 | Price change | $249,900-3.5%$81/sqft |
Source: Calcagni Real Estate #N10121220 Report a problem | ||
| 4/1/2016 | Listed for sale | $259,000-13.6%$84/sqft |
Source: Calcagni Real Estate #N10121220 Report a problem | ||
| 3/29/2014 | Listing removed | $299,900$98/sqft |
Source: Calcagni Real Estate #N339895 Report a problem | ||
| 11/18/2013 | Price change | $299,900-2.9%$98/sqft |
Source: Calcagni Associates #N339895 Report a problem | ||
| 11/12/2013 | Price change | $309,000-3.1%$101/sqft |
Source: Calcagni Associates #N339895 Report a problem | ||
| 7/27/2013 | Listed for sale | $319,000+35.7%$104/sqft |
Source: Calcagni Real Estate #N339895 Report a problem | ||
| 9/15/2000 | Sold | $235,000+59.3%$77/sqft |
Source: Smart MLS #N171353 Report a problem | ||
| 8/19/1994 | Sold | $147,500$48/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,576 +8.3% | $355,600 |
| 2024 | $9,765 +4.5% | $355,600 +33.5% |
| 2023 | $9,343 +2.2% | $266,270 |
| 2022 | $9,138 +1.8% | $266,270 |
| 2021 | $8,979 +0% | $266,270 |
| 2020 | $8,979 +1.5% | $266,270 |
| 2019 | $8,845 +11.5% | $266,270 +9.5% |
| 2018 | $7,931 +2.1% | $243,140 |
| 2017 | $7,766 +2.4% | $243,140 |
| 2016 | $7,584 +1.6% | $243,140 |
| 2015 | $7,462 +1.5% | $243,140 |
| 2014 | $7,355 -0.5% | $243,140 -9.2% |
| 2013 | $7,391 +1.4% | $267,800 |
| 2012 | $7,292 +1.4% | $267,800 |
| 2011 | $7,190 +1.3% | $267,800 |
| 2010 | $7,097 +1.7% | $267,800 |
| 2009 | $6,976 -3% | $267,800 +4.5% |
| 2008 | $7,191 +1.6% | $256,360 |
| 2007 | $7,076 +1.7% | $256,360 |
| 2006 | $6,960 +1.9% | $256,360 |
| 2005 | $6,832 +23.3% | $256,360 +49.2% |
| 2002 | $5,542 +48.2% | $171,840 +27.7% |
| 1997 | $3,740 | $134,530 |
Find assessor info on the county website
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: Chesire Village
Nearby schools
GreatSchools rating
- 9/10Highland SchoolGrades: K-6Distance: 0.8 mi
- 8/10Dodd Middle SchoolGrades: 7-8Distance: 1 mi
- 9/10Cheshire High SchoolGrades: 9-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: Highland
- Middle: Dodd
- High: Cheshire
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- New Haven County
- Cheshire
- 06410
- Chesire Village
- 269 Academy Road
Nearby cities
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Nearby zip codes
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