Residence photography unavailable
01 / 12
For Sale

139 Chappaquiddick Road, Edgartown MA 02539

Edgartown, MA 02539

$10.75M
7 BD · 4 BA · 4,855 sf · 5.03 ac · Built 1938
The residence

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.

At a glance
Property type
Single Family Residence
Status
Active
Year built
1938
Lot size
5.03 acres
Living area
4,855 sf
MLS#
2b3067fccaa04c012f25fc9c7b47f65b
Beds · Baths
7 · 4
Location

Edgartown, MA.

Edgartown is Martha's Vineyard at its most formal: white Greek Revival captains' houses, a working harbour, and Chappaquiddick a short ferry ride across.

Estimated Monthly Payment+
$52K/mo
Approximate · principal & interest only
Display Currency
$10.75M

Indicative conversion — settlement always in USD.

Private Showing

Arrange a viewing.

A senior advisor will reply personally to coordinate access at a time that suits you. All inquiries are held in confidence.

Submitted in confidence to the listing advisor. By submitting, you consent to be contacted by SZ INC. Realty at the number and email provided, including by call and text; message and data rates may apply, and consent is not a condition of any purchase or lease. See our Privacy Policy.

Listing courtesy of Sandpiper Realty, Inc. · MLSPIN

MLS Property Information Network.The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

Listings updated Oct 13, 2026

Fair Housing