Active
53 Days on market
139 Chappaquiddick Road Edgartown — Photo 1 of 42

139 Chappaquiddick Road Edgartown — Photo 1 of 42

$12,250,000

139 Chappaquiddick Road, Edgartown, MA 02539

Edgartown, MA 02539 — Chappaquiddick

Beds

7

Baths

4

SqFt

4,855

Style

Single Family

Built

1938

You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village yet set along one of the most spectacular stretches of beach, with a 190' private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road, with the availability of an additional conforming lot further elevating this offering — providing the opportunity to create a one-of-a-kind family compound and enduring legacy estate. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

Key facts

It was listed on August 13, 2026. The annual property taxes are $19,582 (2026 tax year). It sits on a 5.03-acre (219,106 sq ft) lot.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$2523/sqft
Local Avg (Edgartown)$1425/sqft
77% AboveMarket Average

* Analysis is based on 15 actively listed and recently sold comparable properties strictly within Edgartown, MA.

Property Details

Financials

Original Price$12,250,000
Annual Taxes$19,582

Parking

Garage1
Off-Street7

Interior Specifications

Total Rooms17
Fireplaces2
Flooring--
BasementPartial, Crawl Space, Interior Entry

Climate & Utilities

HeatingForced Air
CoolingCentral Air
WaterPrivate
SewerPrivate Sewer

Building & Exterior

Construction--
Roof--
FoundationOther
ZoningR120

Property & Lot

Acres5.03
SqFt Lot219,106
Lot FeaturesCleared, Gentle Sloping, Level

Geography

Questions about this home

When was 139 Chappaquiddick Road, Edgartown listed?

139 Chappaquiddick Road, Edgartown was listed on August 13, 2026.

Has the price of 139 Chappaquiddick Road, Edgartown changed?

The price hasn't changed since it was listed at $12,250,000.

What are the property taxes for 139 Chappaquiddick Road, Edgartown?

The annual property taxes for 139 Chappaquiddick Road, Edgartown are $19,582 (2026 tax year).

How big is the lot at 139 Chappaquiddick Road, Edgartown?

139 Chappaquiddick Road, Edgartown sits on a 5.03-acre (219,106 sq ft) lot.

What is the status of 139 Chappaquiddick Road, Edgartown?

139 Chappaquiddick Road, Edgartown is actively listed for sale.

Population

5,278

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$125K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

13.0%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Dukes County

170 housing units permitted in the last 12 months (+110% vs the prior 12 months) — 35 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,855 sq ft principal dwelling). Lot size: 219,106 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Katie Donahue & Rachel Serwa Group

Listing Office: Sandpiper Realty, Inc.

MLS® Number: 73563263