For sale

$12,250,000

Est. $67,644/mo —

•

4,855

sq ft

139 Chappaquiddick Rd, Edgartown, MA 02539

About this home

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.

Single-familyProperty Type

1938Year Built

5.03 acresLot Size

$2,523Price/Sq.Ft.

1 garage spacesParking

Listed by Katie Donahue & Rachel Serwa Group • Sandpiper Realty, Inc.

Listing updated: Aug 17, 2026 at 03:05am

Redfin checked: a minute ago

•Source:MLS PIN #73563263

Payment calculator

$67,644 per month

Principal and interest$63,563

Property taxes

$1,632

HOA dues

Home insurance

$2,450

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (2)

Around this home

Schools

K - 12
Preschool & daycare

Edgartown Elementary School

Public PreK-8 • Assigned • 1.9mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 6.1mi

6/10

Provided by GreatSchools

About

Chappaquiddick

Chappaquiddick, located between Edgartown Harbor and Cape Poge Bay, is a coastal and rural Edgartown neighborhood with barrier beaches and salt marshes. The Chappy Ferry landing on Chappaquiddick Road concentrates the island’s daily rhythm, with bikes lining up, beach gear in tow, and the water crossing setting the pace. The Mytoi Japanese Garden, Cape Poge Wildlife Refuge, and the Chappaquiddick Community Center act as cultural anchors beyond the shoreline. Architecture leans to shingled cottages and low-profile homes tucked behind scrub oak. Dirt lanes, dunes, and quiet ponds shape a outdoors-first routine. Sunrises over Cape Poge and sunsets back toward Edgartown define the geography.

Provided by Walk Score and Local Logic

Offer insights

139 Chappaquiddick Rd · $12,250,000

Strong offer

$12.3M and above

75% chance or better to win

Why $12.3M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 63 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
17 total rooms
Partial basement with crawl space and interior entry
2 fireplaces

Bedrooms
Bedrooms not specified

Bathrooms
4 full bathrooms

Kitchen
Kitchen details not specified

Laundry & utility
Laundry/utility details not specified

Flooring
Flooring details not specified

Heating & cooling
Forced air heating
Central air conditioning

Sale and tax history for 139 Chappaquiddick Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$17,121 (−13.4%)

$4,274,500 + $2,519,600

$6,794,100

2022

$19,778 (−11.8%)

$4,881,427 + $1,646,000

$6,527,427

2020

$22,432 (−11.1%)

$4,881,427 + $1,814,700

$6,696,127

2019

$25,232 (−0.3%)

$4,881,400 + $1,638,600

$6,520,000

2018

$25,299 (+3.0%)

$4,881,400 + $1,655,700

$6,537,100

2017

$24,561 (+4.6%)

$5,423,800 + $1,494,800

$6,918,600

2016

$23,474 (+5.3%)

$4,989,900 + $1,494,700

$6,484,600

2015

$22,294

$4,989,900 + $1,434,900

$6,424,800

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6.8 Acres

Year renovated

—

Finished Sq. Ft.

4,855

Unfinished Sq. Ft.

—

Total Sq. Ft.

4,855

Year built

1938

Style

Single Family Residential

County

Dukes County

APN

3770247

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 88° expected this year, 20 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Edgartown, MA • 02539

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

99/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.6 hrs

5.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 139 Chappaquiddick Rd

$11,961,608

$288K under list price of $12.3M

Nearby comparable homes

The Redfin Estimate uses 5 recent nearby sales, priced between $1.6M to $4.7M.

SOLD JUN 26, 2026
$4,700,000 Last sold price
4 beds3.5 baths4,168 sq ft
27 Knoll Dr, Edgartown, MA 02539
$1395/sq ft
smaller lot
67 years newer
SOLD JUL 23, 2026
$1,600,000 Last sold price
3 beds2.5 baths1,962 sq ft
109 Litchfield Rd, Edgartown, MA 02539
$1708/sq ft
49 years newer
SOLD AUG 11, 2026
$1,695,000 Last sold price
3 beds3 baths2,296 sq ft
177 West Tisbury Rd, Edgartown, MA 02539
$1785/sq ft
smaller lot
46 years newer
SOLD JUN 26, 2026
$2,600,000 Last sold price
4 beds2.5 baths2,428 sq ft
2 Cosmos Way, Edgartown, MA 02539
$1452/sq ft
smaller lot
55 years newer
SOLD JUL 29, 2026
$1,885,000 Last sold price
5 beds3.5 baths2,527 sq ft
18 Puritan Dr, Oak Bluffs, MA 02557
$1777/sq ft
smaller lot
58 years newer

Rental earnings

Est. $4,523 per month, based on comparable rentals

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Nearby similar homes

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3 beds2 baths1,962 sq ft

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$4,725,000

3 beds4 baths2,969 sq ft

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VIDEO TOUR

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3 beds3.5 baths3,056 sq ft

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3 beds2 baths1,588 sq ft

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New listings for sale in 02539

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3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

$2,395,000

4 beds3 baths1,968 sq ft

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6 beds1 bath1,957 sq ft

49 The Blvd, Edgartown, MA 02539

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$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

$12,250,000

7 beds4 baths4,855 sq ft

139 Chappaquiddick Rd, Edgartown, MA 02539

Details provided by MLS PIN and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Mortgage resources

See this home in person

Nearby open houses (2)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 139 Chappaquiddick Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 139 Chappaquiddick Rd

Early Access listings

Nearby similar homes

New listings for sale in 02539

More real estate resources