27 Beach Road
Oak Bluffs, MA · $2,995,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

27 Beach Road

Oak Bluffs, MA 02557
$2,995,000
0 days on market · Listed Aug 17, 2026
Data refreshed Aug 17, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
4
Baths
1.5
Sq Ft
3,462
Acres
0.2
Year Built
1920
$ / Sq Ft
$865
Days on Market
0

Investment Snapshot

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Location & Nearby

Map of 27 Beach Road, Oak Bluffs MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Dede lanches
    0.03 mi
  • B
    🌲 Doug's Cove Preserve
    0.42 mi
  • C
    🏖️ Eastville Beach
    0.49 mi
  • D
    🍽️ Mo's Lunch
    0.75 mi
  • E
    🍽️ Honorary Tavern
    0.82 mi
  • F
    🛝 Oak Bluffs School Playground
    1.08 mi
  • G
    Tisbury Wharf Company
    1.08 mi
  • H
    🚴 Oak Bluffs-Edgartown Bike Path
    1.09 mi

About this property

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.

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📋 Oak Bluffs Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Oak Bluffs
Listed by Bonnie J Pierce, Wallace & Co. Sotheby's International Realty