For Sale
Price CutPrice Drop: $1.5M (10/09)
Single family home for sale at 139 Chappaquiddick Rd, Edgartown, MA 02539 | MLS# 73563263 | Listing updated on 2026-10-13
Photo 1 of Single family home for sale at 139 Chappaquiddick Rd, Edgartown, MA 02539 | MLS# 73563263 | Listing updated on 2026-10-13
Photo 2 of Single family home for sale at 139 Chappaquiddick Rd, Edgartown, MA 02539 | MLS# 73563263 | Listing updated on 2026-10-13
Photo 3 of Single family home for sale at 139 Chappaquiddick Rd, Edgartown, MA 02539 | MLS# 73563263 | Listing updated on 2026-10-13
Photo 4 of Single family home for sale at 139 Chappaquiddick Rd, Edgartown, MA 02539 | MLS# 73563263 | Listing updated on 2026-10-13
33+
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Street View

$10,750,000

Monthly Est:$53,507

  • Beds Icon7 Beds
  • Beds Icon
    4 Baths
  • Beds Icon4,855sqft

139 Chappaquiddick Rd, Edgartown, MA 02539

$53,507/moEst:

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  • Single Family Residence

  • Built in 1938

  • $-- HOA

  • 5.03 acres lot

  • $2,214/sq.ft

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.

  • Houzeo last checked: 4 minutes ago
  • Listing updated: October 13, 2026 at 7:05 am
  • Listing Provided by: |
  • Source: MLS Property Information Network-MA | MLS#: 73563263 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Dukes County

  • City

    Edgartown

  • Neighborhood

    --

  • Year Built

    1938

  • HOA Fees

    -

  • Finished Area

    4,855 sqft

  • Lot Size

    5.03 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73563263

  • MLS Status

    Active

  • Days on Market

    83

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 7

    Bathrooms: 4

Interior

  • Heating

    Forced Air

  • Cooling

    Central Air

  • Sewer

    Private Sewer

Construction

  • Year Built

    Year Built: 1938

  • Home type

    Single Family Residence

  • Foundation Details

    Other

  • Architectural Style

    Other (see Remarks)

Utilities & Energy

  • Parking Features

    Detached

  • Water Source

    Private

  • Basement

    Partial, Crawl Space, Interior Entry

Other Features

  • Lot Features

    Cleared, Gentle Sloping, Level

  • Subdivision Name

    Chappaquiddick

Price History

DateEventPrice

10/09/2026

Source: mls_logoMLS Property Information Network-MA #73563263

Price Decreased

$10,750,000 -12.24%

$2,214/sqft

08/13/2026

Source: mls_logoMLS Property Information Network-MA #73563263

Listed for Sale

$12,250,000

$2,523/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Nov 04, 2026, 11:45PM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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