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For sale
  • $4,995,000

    39 Chippechaug Trl, Mystic, CT 06355

    4beds
    4,293sqft
    : 
    $34,926/mo
    Get pre-qualified
    Residential, Single Family Residence
    Built in 1968
    2.05 Acres Lot
    $-- Zestimate®
    $1,164/sqft
    $-- HOA

    What's special

    Own dockGeothermal heatingThree-car garagePrivate sandy beachSpectacular waterfront residenceExpansive lawnsExpansive windows
    A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings. Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape. Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline. A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions. There is an ease to life here that is difficult to replicate a home where mornings begin on the water, afternoons unfold along the shoreline and evenings are framed by the beauty of the surrounding landscape. Equally suited as a year-round residence or an exceptional coastal retreat, 39 Chippechaug Trail is a rare opportunity to experience Mason's Island living at its finest.
    156 days
    444
    15

    Zillow last checked:

    Listing updated:

    Listed by:

    Danielle Malloy 203-921-9987,

    Serhant Connecticut LLC,

    Jessica Lane 203-489-7779,

    Serhant Connecticut LLC

    Source: Greenwich MLS, Inc.,MLS#: 124927MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 3
      • 1/2 bathrooms: 2
      Heating
      • Forced Air, Geothermal
      Cooling
      • Central Air
      Features
      • Eat-in Kitchen, Bookcases, Built-in Features, Entrance Foyer, Pantry
      • Basement: Full,Unfinished
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,293
      • Total interior livable area: 4,293 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Garage
      • Garage spaces: 3
      Features
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Deep Water, LI Sound, Waterfront
      Lot
      • Size: 2.05 Acres
      • Features: Garden, Level
      Details
      • Parcel number: 00449800
      • Zoning: OT - Out of Town

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Post Modern
      • Property subtype: Residential, Single Family Residence
      Materials
      • See Remarks
      • Roof: Other
      Condition
      • Year built: 1968

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public

      Community & HOA

      Community
      • Security: Security System
      Location
      • Region: Mystic

      Financial & listing details

      • Price per square foot: $1,164/sqft
      • Tax assessed value: $1,657,500
      • Annual tax amount: $35,769
      • Date on market: 5/7/2026
      • Inclusions: Washer/Dryer, All Kitchen Applncs

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/7/2026Price change$4,995,000-16.7%$1,164/sqft
        Source: Greenwich MLS, Inc. #124927 Report a problem
        5/7/2026Listed for sale$5,995,000$1,396/sqft
        Source: Greenwich MLS, Inc. #124927 Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Est. payment

        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: 06355

        Getting around

        1 / 100
        Car-Dependent
        38 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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