Single Family Residence at 139 Chappaquiddick Road, Edgartown MA 02539
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$10,750,000

139 Chappaquiddick Road, Edgartown MA 02539
Edgartown, MA 02539
Listed by Katie Donahue & Rachel Serwa Group
Bedrooms
7
Bathrooms
4
Living area
4,855 sqft
Year built
1938

About this home

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.

Highlights

WaterfrontViewFireplace

Property details

MLS
MLS Property Information Network
MLS #
73563263
Property type
Single Family Residence
Subdivision
Chappaquiddick
Status
Active
Days on market
69
On market date
August 13, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
1
Parking spaces
7
Lot size
5.03 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Edgartown Elementary
1.89 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
397
Student:teacher ratio
9.0:1
District
Edgartown
Middle
None found nearby
High
Martha's Vineyard Regional High
6.17 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
706
Student:teacher ratio
9.3:1
District
Martha's Vineyard

Walkability

Blended score for Edgartown's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

26
Car-dependent
out of 100
EPA National Walkability Index
6.2 / 20 -- Below average walkable
Google Places amenity density
18 / 100
Restaurants & cafes1
Grocery stores0
Parks3
Schools0
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in Edgartown, from live MLS data.

On the market 69 days -- 355 fewer days than Edgartown's current average of 424 days.
For reference, the median list price across 99 active listings in Edgartown right now is $2,700,000.

Mortgage calculator

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Est. monthly payment
$64,888/mo
$2,150,000 down
$8,600,000 loan
Principal & interest$55,779
Property tax (est.)$8,958
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 9 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.