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For sale
    • $2,395,000

    249 Chestnut Hill Road, Wilton, CT 06897

    5beds
    8,685sqft
    : 
    $16,318/mo
    Get pre-qualified
    Single Family Residence
    Built in 2008
    1 Acres Lot
    $-- Zestimate®
    $276/sqft
    $-- HOA

    What's special

    Exceptional privacyGorgeous custom detailsExtensive high-end upgradesViking six-burner gas cooktopPremium appliancesSpa-inspired primary bathNantucket shingle-style residence
    Sophisticated South Wilton Colonial: This Nantucket shingle-style residence blends timeless architectural elegance with seamless modern luxury, ideally positioned for effortless commuting to town, the train, and the Merritt Parkway. Thoughtfully designed for both grand entertaining and everyday comfort, the home features gorgeous custom details, extensive high-end upgrades, and an integrated three-zone surround sound system. The chef's kitchen is outfitted with premium appliances including a Viking six-burner gas cooktop, double ovens with a warming drawer, a built-in refrigerator, and a Miele dishwasher, opening directly into an inviting family room with custom built-ins and fireplace. On the main level, a sophisticated room provides versatile living space, seamlessly accommodating a formal dining room or private work space. Upstairs, the master bedroom serves as a luxurious private sanctuary with a cozy fireplace, a dedicated sitting area, expansive walk-in closets, and a spa-inspired primary bath. There are four additional bedrooms on this floor, two with ensuite bathrooms and two with a connected full-bath. The upper third level boasts a sixth bedroom suite and a large multi-generational living space with extensive built-ins, including cozy window-seating. The finished lower level provides an ideal versatile space featuring a spacious dedicated play/ game room, home gym, and a comfortable TV-watching area designed to grow right along with your kids... French doors off the kitchen and living room open seamlessly to an expansive bluestone patio with a large built-in Lynx grill with slate countertops and overlooking a flat, manicured lawn with exceptional privacy and space for a pool. This home is perfectly oriented on a ridge to capture both golden and pink sunrises and sunsets. Across the street is a favorite town-farm. The home has a high end reverse-osmosis water system and Generac 20-watt generator. Experience the perfect balance of refined craftsmanship and prime convenience in this exceptional South Wilton home.
    1 day
    651
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    Zillow last checked:

    Listing updated:

    Listed by:

    The Gatt Team at William Raveis Real Estate,

    Meghan Gatt (203)904-8064,

    William Raveis Real Estate 203-854-5116,

    Co-Listing Agent: Carla Kupiec 917-685-9100,

    William Raveis Real Estate

    Source: Smart MLS,MLS#: 24206451MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 7
      • Full bathrooms: 5
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Gym, Laundry, Sitting Room, Workshop
      Primary bedroom
      • Features: Vaulted Ceiling(s), Built-in Features, Dressing Room, Fireplace, Full Bath, Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Features: High Ceilings, Full Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: High Ceilings, Built-in Features, Full Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: High Ceilings, Built-in Features, Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: High Ceilings, Built-in Features, Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Dining room
      • Features: High Ceilings, Hardwood Floor
      • Level: Main
      Family room
      • Features: High Ceilings, Bookcases, Built-in Features, Fireplace, Hardwood Floor
      • Level: Main
      Great room
      • Features: Bookcases, Built-in Features, Wall/Wall Carpet, Hardwood Floor
      • Level: Third,Upper
      Kitchen
      • Features: High Ceilings, Built-in Features, Granite Counters, Dining Area, Kitchen Island, Hardwood Floor
      • Level: Main
      Library
      • Features: High Ceilings, Built-in Features, Hardwood Floor
      • Level: Main
      Living room
      • Features: High Ceilings, Fireplace, Hardwood Floor
      • Level: Main
      Other
      • Features: Full Bath
      • Level: Upper
      Rec play room
      • Features: Built-in Features
      • Level: Lower
      Heating
      • Forced Air, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Upper Level, Mud Room
      Features
      • Entrance Foyer
      • Doors: French Doors
      • Basement: Full
      • Attic: None
      • Number of fireplaces: 3
      Interior area
      • Total structure area: 8,685
      • Total interior livable area: 8,685 sqft
      • Finished area above ground: 6,380
      • Finished area below ground: 2,305
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached
      • Attached garage spaces: 3
      Features
      • Patio & porch: Patio
      • Fencing: Stone
      Lot
      • Size: 1 Acres
      • Features: Level
      Details
      • Parcel number: 1923626
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Shake Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 2008

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Subdivision: South Wilton
      HOA
      • Has HOA: No
      Location
      • Region: Wilton

      Financial & listing details

      • Price per square foot: $276/sqft
      • Tax assessed value: $1,227,030
      • Annual tax amount: $30,752
      • Date on market: 9/14/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        9/14/2026Listed for sale$2,395,000+19.8%$276/sqft
        Source: Smart MLS #24206451 Report a problem
        10/20/2025Listing removed--
        Source: Owner Report a problem
        10/20/2025Pending sale$2,000,000$230/sqft
        Source: Owner Report a problem
        10/14/2025Listed for sale$2,000,000+25%$230/sqft
        Source: Owner Report a problem
        6/18/2013Sold$1,600,000-3%$184/sqft
        Source: Smart MLS #99002272 Report a problem
        2/18/2013Price change$1,649,999-2.9%$190/sqft
        Source: Coldwell Banker Residential Brokerage - Darien Office #99002272 Report a problem
        10/16/2012Price change$1,699,999-5%$196/sqft
        Source: Coldwell Banker Residential Brokerage - Darien Office #99002272 Report a problem
        9/9/2012Price change$1,789,000+0.5%$206/sqft
        Source: Coldwell Banker Residential Brokerage - Darien Office #99002272 Report a problem
        9/7/2012Listed for sale$1,780,000+15.6%$205/sqft
        Source: Coldwell Banker Residential Brokerage - Darien Office #99002272 Report a problem
        7/11/2011Sold$1,540,000$177/sqft
        Source: Smart MLS #98492535 Report a problem
        3/17/2011Price change$1,540,000+2.7%$177/sqft
        Source: William Pitt Sotheby's International Realty #98492535 Report a problem
        3/12/2011Price change$1,499,000-9.2%$173/sqft
        Source: William Pitt Sotheby's International Realty #98492535 Report a problem
        2/24/2011Price change$1,650,000+6.5%$190/sqft
        Source: Higgins Group Report a problem
        11/4/2010Price change$1,550,000-6.1%$178/sqft
        Source: Higgins Group #98478755 Report a problem
        10/23/2010Price change$1,650,000-8.1%$190/sqft
        Source: Higgins Group #98478755 Report a problem
        10/18/2010Price change$1,795,000-10%$207/sqft
        Source: Higgins Group #98478755 Report a problem
        10/2/2010Listed for sale$1,995,000-12.5%$230/sqft
        Source: Higgins Group #98478755 Report a problem
        8/15/2008Listing removed$2,279,000$262/sqft
        Source: Homes & Land Report a problem
        2/14/2008Listed for sale$2,279,000+652.1%$262/sqft
        Source: Homes & Land Report a problem
        2/28/1995Sold$303,000$35/sqft
        Source: Smart MLS #95075436 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$29,952 +2%$1,227,030
        2024$29,375 +3.2%$1,227,030 +26.1%
        2023$28,474 +3.6%$973,140
        2022$27,472 +1.3%$973,140
        2021$27,121 +1.5%$973,140
        2020$26,722 -3.8%$973,140
        2019$27,773 -13.3%$973,140 -14.4%
        2018$32,035 +1.5%$1,136,380
        2017$31,557 +1.6%$1,136,380
        2016$31,069 +2.9%$1,136,380 +1%
        2015$30,183 +3.6%$1,124,970 +2.3%
        2014$29,142 +2%$1,099,280
        2013$28,570 -2.2%$1,099,280 -20.8%
        2012$29,212 +1%$1,387,750
        2011$28,935 +3.4%$1,387,750
        2010$27,977 +3%$1,387,750
        2009$27,172 +13.6%$1,387,750 +12%
        2008$23,924 +59%$1,238,930 +99.5%
        2007$15,048 +76.9%$621,040 +70.7%
        2006$8,507 +3.7%$363,720
        2005$8,202 +5%$363,720
        2004$7,813 +6.9%$363,720
        2003$7,311 +13.5%$363,720 +58.8%
        2001$6,440 +8.5%$229,100 0%
        2000$5,936 +7.6%$229,110
        1999$5,517 $229,110
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 06897

        Getting around

        7 / 100
        Car-Dependent
        23 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Miller-Driscoll
        • High: Wilton

        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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