139 Chappaquiddick Road, Edgartown, MA 02539
139 Chappaquiddick Road, Edgartown, MA 02539
139 Chappaquiddick Road, Edgartown, MA 02539
37
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$10,750,000
Est. payment /mo
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7 Beds
4 Baths
4,855 SqFt
Price Dropped by $1.5M

139 Chappaquiddick Road Edgartown, MA 02539

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Michael Peppino

Michael Peppino

+1(617) 875-4352

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,855 sqft

Price per Sqft $2,214

Subdivision Chappaquiddick

MLS Listing ID 73563263

Style Other (See Remarks)

Bedrooms 7

Full Baths 4

HOA Y/N false

Year Built 1938

Annual Tax Amount $19,582

Tax Year 2026

Lot Size 5.030 Acres

Acres 5.03

Property Sub-Type Single Family Residence

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.

Location

State MA

County Dukes

Area Chappaquiddick

Zoning R120

Direction From Chappy Ferry, take Chappaquiddick Road for roughly a mile, #139 is on the left.

Rooms

Basement Partial, Crawl Space, Interior Entry

Interior

Heating Forced Air

Cooling Central Air

Fireplaces Number 2

Exterior

Garage Spaces 1.0

Waterfront Description Waterfront,Ocean,Harbor,Dock/Mooring,Private,Harbor,Ocean,Direct Access,0 to 1/10 Mile To Beach,Beach Ownership(Private,Public)

View Y/N Yes

View Scenic View(s)

Total Parking Spaces 8

Garage Yes

Building

Lot Description Cleared, Gentle Sloping, Level

Foundation Other

Sewer Private Sewer

Water Private

Architectural Style Other (See Remarks)

Others

Senior Community false

Listed by Sandpiper Realty, Inc.
Michael Peppino
Michael Peppino

Broker MA Broker Lic 9584945

+1(617) 875-4352 | michaelpeppino@gmail.com

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139 Chappaquiddick Road