INQUIRE ABOUT THIS LISTING

INQUIRE ABOUT THIS LISTING

This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail

27 Beach Road, Oak Bluffs

$2,995,000

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.

HIGHLIGHTS

Link ID 44793
Bedrooms 5
Baths 1
Half Baths 1
Rooms 8
Living Space 1713
Acreage 0.20
Water Frontage Oceanfront
Waterview
Yes
Private|Assoc Beach
Yes

FEATURES AND AMENITIES

Link ID
44793
Price
$2,995,000
Bedrooms
5
Baths
1
Half Baths
1
Rooms
8
Living Space
1713
Acreage
0.20
Zoning
R1
Water Frontage
Oceanfront
Water
Town
Sewer
Town
Heat
None
2026 Tax Assessment
$2,220,200
Building Assessment
$429,200
Land Assessment
$1,791,000
Estimated Taxes
$11,010
Outdoor Spaces
Water Views
Deck
Porch
Beach Access - Private
Year Built
1920
Fireplaces
Yes
Flooring
hardwood
Listing Broker
Wallace & Co. Sotheby's

27 Beach Road, Oak Bluffs

Copyright 2026 LINK MV. All rights reserved. Information deemed reliable but is not guaranteed.
Buyer note, 2% Land Bank fee.
X