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For sale
    • Price cut: $50K (4/20)
    $739,900

    269 Academy Road, Cheshire, CT 06410

    4beds
    3,020sqft
    : 
    Single Family Residence
    Built in 1968
    0.96 Acres Lot
    $-- Zestimate®
    $245/sqft
    $-- HOA

    What's special

    Welcome to this beautifully expanded Cape perched gracefully above the street on a private, nearly one acre setting - just minutes from the heart of Cheshire. Inside, you'll find 2,755 sq ft of open living space with hardwood floors throughout. The sun-filled living room anchored by a wood-burning fireplace flows into a stylish gourmet kitchen featuring stainless steel appliances, granite countertops and a center island. The dining area continues 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 265 sq ft of living space, a 2nd wood-burning fireplace, and plenty of space to relax and entertain. The upper level offers two oversized bedrooms, each with en-suite baths and walk-in closets creating calming retreats. The tranquil backyard features a two-level deck ideal for dining & unwinding, a fire pit and fully fenced yard for added privacy & safety. Abundant storage throughout including a 2-car attached garage, 1,317 sq ft of basement space, and generous closets. Among the many noteworthy upgrades are a new driveway (2023), a 30-year architectural roof (2021), paver front walkway (2022), a five-zone boiler and dual central air systems (2018) and generator-ready since 2024. Schedule your private tour today!
    14 days
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    2,951
    |
    101
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    Zillow last checked:

    Listing updated:

    Listed by:

    Frank Santino (203)314-3986,

    MidState Realty, LLC 203-314-3986

    Source: Smart MLS,MLS#: 24164730MLS Logo

    Tour with a local agent

      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: 270 Square Feet
      • Dimensions: 15 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: 3,020
      • Total interior livable area: 3,020 sqft
      • Finished area above ground: 2,755
      • Finished area below ground: 265

      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: $245/sqft
      • Tax assessed value: $355,600
      • Annual tax amount: $10,576
      • Date on market: 4/7/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/20/2026Price change$739,900-6.3%$245/sqft
        Source: Smart MLS #24164730 Report a problem
        4/10/2026Listed for sale$789,900+95.5%$262/sqft
        Source: Smart MLS #24164730 Report a problem
        10/31/2018Sold$404,000+1%$134/sqft
        Source: Smart MLS #170084490 Report a problem
        8/12/2018Price change$399,999-3.6%$132/sqft
        Source: Lasko Real Estate, LLC #170084490 Report a problem
        7/24/2018Price change$414,999-3.5%$137/sqft
        Source: Lasko Real Estate, LLC #170084490 Report a problem
        6/7/2018Price change$429,999-4.4%$142/sqft
        Source: Lasko Real Estate, LLC #170084490 Report a problem
        5/16/2018Listed for sale$449,999+136.8%$149/sqft
        Source: Lasko Real Estate, LLC #170084490 Report a problem
        12/8/2017Sold$190,000-9.5%$63/sqft
        Source: Smart MLS #170002118 Report a problem
        11/6/2017Price change$209,900-6.7%$70/sqft
        Source: Calcagni Real Estate #170002118 Report a problem
        10/5/2017Price change$224,900-6.3%$74/sqft
        Source: Calcagni Real Estate #170002118 Report a problem
        9/7/2017Price change$239,900-5.9%$79/sqft
        Source: Calcagni Real Estate #170002118 Report a problem
        8/3/2017Listed for sale$254,900+10.9%$84/sqft
        Source: Homepath Report a problem
        3/31/2017Listing removed$229,900$76/sqft
        Source: Calcagni Real Estate #N10121220 Report a problem
        12/2/2016Pending sale$229,900$76/sqft
        Source: Calcagni Real Estate #N10121220 Report a problem
        9/1/2016Price change$229,900-8%$76/sqft
        Source: Calcagni Real Estate #N10121220 Report a problem
        4/20/2016Price change$249,900-3.5%$83/sqft
        Source: Calcagni Real Estate #N10121220 Report a problem
        4/1/2016Listed for sale$259,000-13.6%$86/sqft
        Source: Calcagni Real Estate #N10121220 Report a problem
        3/29/2014Listing removed$299,900$99/sqft
        Source: Calcagni Real Estate #N339895 Report a problem
        11/18/2013Price change$299,900-2.9%$99/sqft
        Source: Calcagni Associates #N339895 Report a problem
        11/12/2013Price change$309,000-3.1%$102/sqft
        Source: Calcagni Associates #N339895 Report a problem
        7/27/2013Listed for sale$319,000+35.7%$106/sqft
        Source: Calcagni Real Estate #N339895 Report a problem
        9/15/2000Sold$235,000+59.3%$78/sqft
        Source: Smart MLS #N171353 Report a problem
        8/19/1994Sold$147,500$49/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax 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

        Monthly payment

        Est. payment
        $4,908/mo
        Principal & interest
        $3595
        Property taxes
        $1313
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          Climate risks

          Neighborhood: Chesire Village

          Getting around

          35 / 100
          Car-Dependent
          20 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          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.

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