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7 Beds
4 Baths
4,855 sqft

$12,250,000

139 Chappaquiddick Road, Edgartown MA, 02539

Price per sqft$2,523.17
Built in1938
Property size4,855 sqft
Property typeResidential

Overview

Active

Listed Aug 13, 2026

Updated 8h ago

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.

$81,500/mo

Est. mortgage payment based on a $12,250,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73563263

Interior Features

Bedrooms
7
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
5.03 Acres

Other Property Details

Taxes
$19,582
Tax Frequency
Annually
Garage
Yes
View
Yes
Waterfront
Yes
55+/Senior Community
No

This listing is provided by Katie Donahue & Rachel Serwa Group with Sandpiper Realty, Inc.

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Data last updated 4:12 AM UTC, 10/9/2026

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