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OAK BLUFFS
Single Family Residence

27 Beach Road, Oak Bluffs, MA 02557

$2,995,000.00
Listed 7th August, 2026 for $2,995,000
LINK ID: 44793
STATUS: AVAILABLE
Bedrooms: 5
Baths: 1
Half Baths: 1
Rooms: 8
Living Space: 1713
Acreage: 0.2000
Water Frontage: Oceanfront
1st Floor Bedrooms 1

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Outdoor Spaces: Water Views, Deck, Porch, Beach Access - Private
Features: Outdoor Shower
Year Built: 1920
Year Renovated: 2023
Second Dwelling: None
Zoning: R1
Water: Town
Sewer: Twn
Lead Paint: Unknown
Heat: None
Fireplaces: Yes
Yard Type: Lovely side yard
Flooring: hardwood
Stove: Yes - electric
Washer: Yes
TV: Cable

DESCRIPTION

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.

FIRST FLOOR DESCRIPTION
Open living/dining area, kitchen, primary bedroom, half bathroom and laundry

SECOND FLOOR DESCRIPTION
4 bedrooms and 1 full bathroom

SECOND DWELLING
None

PARKING
ample parking
Martha's Vineyard - Island Wide Listings - Updated September 20, 2026
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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals
PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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