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27 Beach Road, 
Oak Bluffs, MA 02557

$2,995,000


4

Beds


2

Baths


3,462

Sq Ft


Single Family

Active

Listed by

Bonnie J Pierce

Mark D Jenkins

Wallace & Co. Sotheby'S International Realty

Last updated:

August 29, 2026, 03:04 PM

MLS#

22604007

Source:

CAPECOD

About This Home

27 Beach Road

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

Home Facts

Single Family

2 Baths

4 Bedrooms

Built in 1920

Price Summary

2,995,000

$865 per Sq. Ft.

MLS #:

22604007

Last Updated:

August 29, 2026, 03:04 PM

Added:

13 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

2


Structure

Structure

Building Area:

3,462 Sq. Ft.

Year Built:

1920


Lot

Lot Size (Sq. Ft):

8,712


Finances & Disclosures

Finances

Price:

$2,995,000

Price per Sq. Ft:

$865 per Sq. Ft.

MLS Logo
Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor Coldwell Banker Murray Real Estate shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.