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Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

More Info

Basic Information

  • Bedrooms7
  • Mls StatusActive
  • Bathroom4
  • Lot Features Cleared, Gentle Sloping, Level
  • Parcel Number 3770247

Tax Information

  • Tax Assessed Value $7,895,941
  • Tax Year 2026
  • Taxes$19,582

Parking

  • Parking Spaces7
  • Covered Spaces 1
  • Garage YN Yes
  • Parking Features Detached

Rooms

  • Bathrooms Total Decimal 4
  • Full Bath4

Basic Information

  • List Price$10,750,000
  • MLS Number73563263
  • Modification Date10/13/2026
  • Property SubTypeSingle Family Residence

Location

  • NeighborhoodChappaquiddick
  • SubdivisionChappaquiddick
  • Address139 Chappaquiddick Road
  • Building Number139
  • CountyDukes
  • StateMA
  • StreetChappaquiddick Road
  • TownEdgartown
  • Zip02539

Building

  • BasementPartial, Crawl Space, Interior Entry
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 2
  • FoundationOther
  • Garage Spaces1
  • Property StyleOther (See Remarks)
  • Rooms17
  • Year Built1938
  • Year Built Details Actual, Renovated Since
  • Year Built Source Public Records

Property

  • Acreage5.03

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Forced Air
  • Sewer Private Sewer
  • Water Source Private

Property Information

  • Square Feet4,855
  • Building Area Source Public Records
  • Living Area 4,855
  • Lot Size Square Feet 219,106
  • Lot Size Units Acres
  • View YN Yes

Water Body

  • Miles to Beach0.1
  • WaterfrontYes
  • Waterfront Features Waterfront, Ocean, Harbor, Dock/Mooring, Private, Harbor, Ocean, Direct Access,0 to 1/10 Mile To Beach, Beach Ownership(Private, Public)

Other

  • Date Listed08/13/2026
  • Farm Land Area Units Square Feet
  • View Count12

Map Location

Driving Directions

Listed by Katie Donahue & Rachel Serwa Group of Sandpiper Realty,Inc.

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