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I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

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  1. Home
  2. Listings
  3. 139 Chappaquiddick Road, Edgartown, MA 02539
Active
12 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. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$2523/sqft
Local Avg (Edgartown)$1625/sqft
55% AboveMarket Average

* Analysis is based on 14 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

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

164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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.

Full Edgartown, MA market report ZIP 02539 market data
Listing Provided By

Listing Agent: Katie Donahue & Rachel Serwa Group

Listing Office: Sandpiper Realty, Inc.

MLS® Number: 73563263

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