For sale

$2,995,000

Est. $17,552/mo —

•

1,731

sq ft

27 Beach Rd, Oak Bluffs, MA 02557

About this home

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.

Single-familyProperty Type

1920Year Built

8,712 sq ftLot Size

$1,730Price/Sq.Ft.

4 spacesParking

Listed by Bonnie Pierce • Wallace & Co. Sotheby's International Realty

Listed by Mark Jenkins • Wallace & Co. Sotheby's International Realty

Listing updated: Sep 2, 2026 at 06:17pm

Redfin checked: a minute ago

•Source:CCIMLS #22604007

Payment calculator

$16,604 per month

Principal and interest$15,740

Property taxes

$864

HOA dues

Home insurance

Utilities

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Open houses

No upcoming open houses.

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Around this home

Schools

K - 12
Preschool & daycare

Oak Bluffs Elementary School

Public PreK-8 • Assigned • 1.2mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.1mi

6/10

Provided by GreatSchools

About

Eastville

Eastville, located between Oak Bluffs Harbor and Lagoon Pond, is a waterfront and residential Oak Bluffs neighborhood with working-boat scenery and salt-air walking routes. The neighborhood’s character concentrates around the Eastville Avenue stretch by the Oak Bluffs Harbor shoreline, where marinas, low-key eateries, and dockside foot traffic set the tempo. The Martha’s Vineyard Museum and the Strand Theatre act as cultural anchors close by, while Nancy’s Restaurant keeps the harborfront tradition in motion. Architecture leans coastal and practical—shingled cottages, compact capes, and porch-lined homes—framed by beach grass and boat masts. Side streets feel quiet, while the shoreline stays active with ferries, fishing gear, and sunset watchers.

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
HU cable TV
Porch

Bathrooms
1 full bath
1 half bath

Kitchen
Microwave
Electric range
Refrigerator

Laundry & utility
Washer
Electric dryer
Electric dryer hookup
Washer hookup
Water heater

Flooring
Hardwood

Heating & cooling
No heating
No cooling
1 fireplace

Sale and tax history for 27 Beach Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$9,189 (+15.0%)

$1,368,600 + $371,800

$1,740,400

2022

$7,991 (−13.6%)

$859,000 + $317,900

$1,176,900

2021

$9,244 (−3.5%)

$976,700 + $277,600

$1,254,300

2020

$9,580 (+0.6%)

$1,026,300 + $261,300

$1,287,600

2019

$9,520 (−1.1%)

$981,100 + $256,900

$1,238,000

2018

$9,623 (+4.9%)

$972,100 + $256,900

$1,229,000

2017

$9,175 (+0.3%)

$892,400 + $233,400

$1,125,800

2016

$9,151 (+2.9%)

$920,000 + $208,400

$1,128,400

2015

$8,897

$920,000 + $197,700

$1,117,700

Public record

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

8,712 Sq. Ft.

Year renovated

1988

Finished Sq. Ft.

1,731

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,731

Year built

1920

Style

Single Family Residential

County

Dukes County

APN

3874913

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 88° expected this year, 17 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Oak Bluffs, MA • 02557

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

92/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 24% for direct sun exposure in Oak Bluffs. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9 hrs

5.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 27 Beach Rd

$2,897,074

$98K under list price of $3.00M

Nearby comparable homes

The Redfin Estimate uses 2 recent nearby sales, priced between $1.9M to $2.2M.

SOLD AUG 19, 2026
$2,195,000 Last sold price
4 beds2.5 baths2,890 sq ft
30 Daggett Ave, Vineyard Haven, MA 02568
$970/sq ft
smaller lot
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SOLD DEC 4, 2025
$1,865,000 Last sold price
4 beds4 baths2,820 sq ft
71 Netock Ave, Oak Bluffs, MA 02557
$1069/sq ft
larger lot
62 years newer