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Sold for $722,906
    • $722,906

    269 Academy Road, Cheshire, CT 06410

    4beds
    3,070sqft
    Single Family Residence
    Built in 1968
    0.96 Acres Lot
    $690,800 Zestimate®
    $235/sqft
    $4,468 Estimated rent

    Home value

    $690,800

    $656,000 - $725,000

    $4,468/mo

    Zestimate® history
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    What's special

    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!

    Zillow last checked:

    Listing updated:

    Listed by:

    Frank Santino (203)314-3986,

    MidState Realty, LLC 203-314-3986

    Bought with:

    Joe Waters, REB.0795622

    JW Realty Group LLC

    Source: Smart MLS,MLS#: 24164730MLS Logo

    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: $235/sqft
    • Tax assessed value: $355,600
    • Annual tax amount: $10,576
    • Date on market: 4/7/2026

    Price history

    DateEventPrice
    7/21/2026Sold$722,906+3.3%$235/sqft
    Source: Smart MLS #24164730 Report a problem
    5/20/2026Pending sale$699,500$228/sqft
    Source: Smart MLS #24164730 Report a problem
    5/18/2026Price change$699,500-5.5%$228/sqft
    Source: Smart MLS #24164730 Report a problem
    4/29/2026Listed for sale$739,900$241/sqft
    Source: Smart MLS #24164730 Report a problem
    4/28/2026Pending sale$739,900$241/sqft
    Source: Smart MLS #24164730 Report a problem
    4/20/2026Price change$739,900-6.3%$241/sqft
    Source: Smart MLS #24164730 Report a problem
    4/10/2026Listed for sale$789,900+95.5%$257/sqft
    Source: Smart MLS #24164730 Report a problem
    10/31/2018Sold$404,000+1%$132/sqft
    Source: Smart MLS #170084490 Report a problem
    8/12/2018Price change$399,999-3.6%$130/sqft
    Source: Lasko Real Estate, LLC #170084490 Report a problem
    7/24/2018Price change$414,999-3.5%$135/sqft
    Source: Lasko Real Estate, LLC #170084490 Report a problem
    6/7/2018Price change$429,999-4.4%$140/sqft
    Source: Lasko Real Estate, LLC #170084490 Report a problem
    5/16/2018Listed for sale$449,999+136.8%$147/sqft
    Source: Lasko Real Estate, LLC #170084490 Report a problem
    12/8/2017Sold$190,000-9.5%$62/sqft
    Source: Smart MLS #170002118 Report a problem
    11/6/2017Price change$209,900-6.7%$68/sqft
    Source: Calcagni Real Estate #170002118 Report a problem
    10/5/2017Price change$224,900-6.3%$73/sqft
    Source: Calcagni Real Estate #170002118 Report a problem
    9/7/2017Price change$239,900-5.9%$78/sqft
    Source: Calcagni Real Estate #170002118 Report a problem
    8/3/2017Listed for sale$254,900+10.9%$83/sqft
    Source: Homepath Report a problem
    3/31/2017Listing removed$229,900$75/sqft
    Source: Calcagni Real Estate #N10121220 Report a problem
    12/2/2016Pending sale$229,900$75/sqft
    Source: Calcagni Real Estate #N10121220 Report a problem
    9/1/2016Price change$229,900-8%$75/sqft
    Source: Calcagni Real Estate #N10121220 Report a problem
    4/20/2016Price change$249,900-3.5%$81/sqft
    Source: Calcagni Real Estate #N10121220 Report a problem
    4/1/2016Listed for sale$259,000-13.6%$84/sqft
    Source: Calcagni Real Estate #N10121220 Report a problem
    3/29/2014Listing removed$299,900$98/sqft
    Source: Calcagni Real Estate #N339895 Report a problem
    11/18/2013Price change$299,900-2.9%$98/sqft
    Source: Calcagni Associates #N339895 Report a problem
    11/12/2013Price change$309,000-3.1%$101/sqft
    Source: Calcagni Associates #N339895 Report a problem
    7/27/2013Listed for sale$319,000+35.7%$104/sqft
    Source: Calcagni Real Estate #N339895 Report a problem
    9/18/2000Sold$235,000+59.3%$77/sqft
    Source: Public Record Report a problem
    8/19/1994Sold$147,500$48/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

    Neighborhood: Chesire Village

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    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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