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355 Boylston St / (617) 233-5800

139 Chappaquiddick Road

Chappaquiddick - Edgartown, MA ID #73563263

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139 Chappaquiddick Road

Chappaquiddick - Edgartown, MA ID #73563263

Property Description

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.

Additional Details

  • Status: Active
  • Type: Single Family, Single Family Residence
  • Area: Chappaquiddick
  • Zip Code: 02539
  • Taxes: 19,582
  • Acres: 5.03

Parking

  • Garage: 1
  • Garage Capacity: 1
  • Parking: Detached
  • Parking Spaces: 7

Rooms/Dimensions

  • Total Rooms: 17
  • Has Basement: Yes

Location

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Content © 2026 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Katie Donahue & Rachel Serwa Group of Sandpiper Realty, Inc.. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.