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For sale
  • $12,250,000

    139 Chappaquiddick Rd #75, Edgartown, MA 02539

    7beds
    4,855sqft
    : 
    $70,677/mo
    Get pre-qualified
    Single Family Residence
    Built in 1938
    5.03 Acres Lot
    $-- Zestimate®
    $2,523/sqft
    $-- HOA

    What's special

    Grounds are equally captivatingEver-changing scenery
    You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.
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    Zillow last checked:

    Listing updated:

    Listed by:

    Katie Donahue and Rachel Serwa,

    Sandpiper Realty

    Source: LINK,MLS#: 44777

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 4
      • Full bathrooms: 4
      • Main level bedrooms: 6
      Heating
      • GFHA
      Appliances
      • Included: Stove: Viking, Washer: LG
      Features
      • A, AC, Ins, Irr, OSh, Floor 1: Upon entry, you are welcomed into a fully equipped kitchen that flows into the main living areas of the home, including a formal living and dining space. A built-in bar area, with an ice machine and refrigerator, sits just outside the enclosed porch, which offers ample space for both dining and relaxation, overlooking a large back deck and Edgartown Harbor. Two bedroom wings, each with three bedrooms and a full bath. A full bath with exterior access to the tennis court and outdoor shower., Floor 2: Private staircase to the primary suite, which boasts water views, an ensuite bathroom, and a large walk-in closet. A separate spiral staircase brings you to the "cupola, " perfect as an office or sitting room with expansive water views. Two large attics with built-in storage.
      • Flooring: Wood, Tile
      • Basement: Partial basement under kitchen with built-in storage and work bench.
      • Fireplace features: 2 - wood burning
      Interior area
      • Total structure area: 4,855
      • Total interior livable area: 4,855 sqft

      Property

      Parking
      • Parking features: Plenty
      Features
      • Exterior features: Tennis, PvtBch, PubBch, WViews, Porch, H/Tub, Garden, Deck
      • Has view: Yes
      • View description: Harbor, Ocean
      • Has water view: Yes
      • Water view: Harbor,Ocean
      • Waterfront features: Bay/Harbor
      • Frontage type: Bay/Harbor
      Lot
      • Size: 5.03 Acres
      • Features: Lush and well manicured
      Details
      • Additional structures: Detached single car garage.
      • Zoning: R120

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Partial basement and crawl space.
      Condition
      • Year built: 1938
      • Major remodel year: 1990

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cbl

      Community & HOA

      Location
      • Region: Edgartown

      Financial & listing details

      • Price per square foot: $2,523/sqft
      • Tax assessed value: $7,895,941
      • Annual tax amount: $19,582
      • Date on market: 8/12/2026
      • Listing agreement: E

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/12/2026Listed for sale$12,250,000$2,523/sqft
        Source: LINK #44777 Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Est. payment

        Payment breakdown

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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.
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        Climate risks

        Neighborhood: 02539

        Getting around

        4 / 100
        Car-Dependent
        40 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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