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$2,995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 3,462 Sq. Ft.
  • 0.2 Acres
  • Updated 3 days ago
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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.

Full Property Details for 27 Beach Rd

General

  • Price: $2,995,000
  • Taxes: $10,365 (2026)
  • Status: Active
  • Type: Single Family
  • Source: CCI
  • MLS ID: 22604007
  • Updated: 8/17/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Hookup for Cable TV
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Dryer, Washer, Refrigerator, Electric Range, Microwave, Electric Water Heater
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Exterior

  • Exterior Features: Outdoor Shower
  • Deck/Patio: Porch

Parking

  • Total Spaces: 4

Location

  • County: Dukes

Heating & Cooling

  • Cooling Type: None
  • Heating Type: None

Utilities

  • Sewer: Public Sewer

Structural Information

  • Architectural Style: Cottage
  • Construction: Shingle Siding
  • Exterior Const.: Shingle Siding
  • Basement Desc.: Crawl Space
  • Roof: Asphalt
  • Stories/Levels: 2
  • Square Feet: 3,462
  • Year Built: 1920
  • Property Condition: Actual

Lot Features

  • Lot Size (Acres): 0.2
  • Lot Size (Sq. Ft.): 8,712
  • Lot Size Source: Assessor
  • Frontage: Public
  • Street/Road Desc.: Paved
  • Zoning: R1
  • Fencing (Description): Fenced, Partial

Water Features

  • Water Front: Yes
  • Water View: Yes

Financial Considerations

  • Price Per Sq. Ft.: $865
  • Assessment Amount: $608,300
  • Land Assmt: $179,100
  • Tax Amount: $10,365
  • Tax Year: 2026

Disclosures and Reports

  • Special Conditions: None
  • Property ID: OAKB M:0006 B:0036 L:000

Listed by Wallace & Co. Sotheby's International Realty, Bonnie J Pierce and Wallace & Co. Sotheby's International Realty, Mark D Jenkins

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Listing agents

— 27 Beach Rd —

  • Bonnie J Pierce

    Wallace & Co. Sotheby's International Realty

  • Mark D Jenkins

    Wallace & Co. Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 27 Beach Rd

School Districts:Oak Bluffs School District, Martha's Vineyard School District
NameGradesDistance
Oak Bluffs Elementary School
50 Tradewinds Road, Oak Bluffs, MA 02557
PK-81.6 mi
Marthas Vineyard Regional High School
100 Edgartown-Vineyard Haven R, Oak Bluffs, MA 02557
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Beach Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/17/2026
Listed
$2,995,000
299499900%
MLS
9/09/2009
Sold
$1
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 27 Beach Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,864
5%
$2,151,300
9%
2024
$10,365
13%
$1,981,900
14%
2023
$9,189
15%
$1,740,400
48%
2022
$7,991
-14%
$1,176,900
-6%
2021
$9,244
-4%
$1,254,300
-3%
2020
$9,580
1%
$1,287,600
4%
2019
$9,520
-1%
$1,238,000
1%
2018
$9,623
5%
$1,229,000
9%
2017
$9,175
—
$1,125,800
—
2016
$9,151
3%
$1,128,400
1%
2015
$8,897
4%
$1,117,700
2%
2014
$8,546
—
$1,094,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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with our affiliated lender
NMLS#: 1598647

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Listed by Wallace & Co. Sotheby's International Realty, Bonnie J Pierce and Wallace & Co. Sotheby's International Realty, Mark D Jenkins

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27 Beach Road, Oak Bluffs, MA 02557 (MLS# 22604007) is a Single Family property with 4 bedrooms, 1 full bathroom and 1 partial bathroom. 27 Beach Road is currently listed for $2,995,000 and was received on August 17, 2026. Want to learn more about 27 Beach Road? Do you have questions about finding other Single Family real estate for sale in Oak Bluffs? You can browse all Oak Bluffs real estate or contact a Coldwell Banker agent to request more information.

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