27 Beach Road, Oak Bluffs, MA 02557
Property image
Property image
FOR SALE

$2,995,000

  • 5 Beds
  • 1.5 Baths
  • 1,731 sqft

27 Beach Road, Oak Bluffs, MA 02557

Est. Mortgage $16,515/mo*
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We estimate this home will sell faster than 93% nearby.

Home Highlights

Single-Family Home
Built in 1920
$1,730/sqft
Open Parking

Local Information

  • Map ViewExplore the area around 27 Beach Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 11 hours ago
Listing courtesy of Bonnie J Pierce, (508) 367-2303
Wallace & Co. Sotheby's International Realty
Mark D Jenkins, (508) 627-3313
Wallace & Co. Sotheby's International Realty
Source: CCIMLS, MLS#22604007
Also Listed on CCIMLS, LINK, LINK.
We estimate this home will sell faster than 93% nearby.

Home Details for 27 Beach Road

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Appliances & Utilities
Appliances: Microwave, Electric Range, Refrigerator, Washer, Water HeaterLaundry: Electric Dryer,Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: NoneNo CoolingAir Conditioning: NoneNo Heating
Fireplace & Spa
Number of Fireplaces: 1
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PorchFencing: PartialExterior: Outdoor Shower
Parking & Garage
No GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Driveway,Off Street
Frontage
WaterfrontWaterfront: Waterview, Waterfront, OtherOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Other, Salt

Days on Market

Cumulative Days on Market: 16Days on Market: 23

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle SidingDoes Not Include Home Warranty
Property Information
Parcel Number: OAKB M:0006 B:0036 L:000

Price & Status

Price
List Price: $2,995,000Price Per Sqft: $1,730

Active Status

MLS Status: Active

Location

Direction & Address
City: Oak Bluffs

Agent Information

Listing Agent
Listing ID: 22604007

Building

Building Area
Building Area: 1731 Square Feet

HOA

No HOA

Lot Information

Lot Area: 8712 sqft

Listing Info

Special Conditions: None

Miscellaneous

Mls Number: 22604007Showing Requirements: Appointment Required, Call Listing Agent

Around this home

What Locals Say about Oak Bluffs

At least 18 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 86 % Say kids play outside

  • 83 % Say yards are well-kept

  • 79 % Say it's walkable to restaurants

  • 79 % Say car is needed

  • 78 % Say people would walk alone at night

  • 78 % Say it's walkable to grocery stores

  • 73 % Say there's wildlife

  • 73 % Say they plan to stay for at least 5 years

  • 70 % Say there's holiday spirit

  • 67 % Say it's quiet

  • 62 % Say parking is easy

  • 59 % Say neighbors are friendly

  • 47 % Say there are community events

  • 44 % Say there are sidewalks

  • 36 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Easy to walk dogs"
    0
    Flag
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
    0
    Flag
  • Adrianalleyne
    "Oak Bluffs has a vibrant history and continues to be a bastion of African American culture. It’s worth checking out some of the many cultural sites in Oak Bluffs and throughout the island "
    0
    Flag
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
    0
    Flag
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
    0
    Flag
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
    0
    Flag
  • Andrea H.
    "This is fantasy island. It is not like the real world it's not fast paced. we say we're on island time. there's hardly any crime it's safe for kids. and it's a good community."
    0
    Flag
  • tkurian
    "I own a property in Oak Bluffs"
    0
    Flag
  • Kristin Z.
    "We live here year round in what most people think is a vacation paradise for the rich and famous. But in actuality it is one of the best communities to live in terms of caring wonderful neighbors and exciting intellectual stimulation throughout the winter in the form of performances, music groups, communities by interests. "
    0
    Flag
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."
    1
    Flag

Market trends in Oak Bluffs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM

Home Value

Trulia Estimate
$2.8M
Since last month
Increased$421K (+17.6%)
Since last year
Increased$542K (+24%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +122% in the last 10 years
MonthEstimated value
2026
September 2026$2.8M
August 2026$2.84M
July 2026$2.38M
June 2026$2.36M
May 2026$2.3M
April 2026$2.22M
March 2026$2.27M
February 2026$2.19M
January 2026$2.22M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Beach Rd, Oak Bluffs, MA
0.03
Single-Family Home
$975,000
09/30/25
3
2
836
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.42
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Ave, Vineyard Haven, MA
0.42
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
9 Bay View Ave, Oak Bluffs, MA
0.64
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
311 E Chop Dr, Oak Bluffs, MA
0.70
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
71 Netock Ave, Oak Bluffs, MA
0.48
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
5 Johns Way, Oak Bluffs, MA
0.65
Single-Family Home
$880,000
10/17/25
3
2
1,365
78 Winemack St, Oak Bluffs, MA
0.66
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
67 New York Ave, Oak Bluffs, MA
0.78
Single-Family Home
$1,400,000
01/30/26
3
2
1,629

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
32 Beach Rd, Oak Bluffs, MA 02557
0.03
$998,800
3
2
836
Off Market
11 Beach Road, Oak Bluffs, MA 02557
0.08
$1,745,000
2
1
561
For Sale
45 Windemere Rd, Oak Bluffs, MA 02557
0.11
$1,768,000
2
1.5
676
Off Market
34 Windemere Rd, Oak Bluffs, MA 02557
0.11
$2,579,000
4
2
1,399
For Sale
111 Eastville Ave, Oak Bluffs, MA 02557
0.16
$2,600,000
6
4
2,400
For Sale
68 Eastville Ave, Oak Bluffs, MA 02557
0.24
$1,240,000
3
2
1,411
Off Market
76 Eastville Ave, Oak Bluffs, MA 02557
0.25
$1,020,300
2
1.5
1,032
Off Market
35 E Side Rd, Oak Bluffs, MA 02557
0.34
$1,346,200
3
2
1,964
Off Market
35 Temahigan Ave, Oak Bluffs, MA 02557
0.33
$2,304,400
5
3
2,069
Off Market
35 Temahigan Ave #5, Oak Bluffs, MA 02557
0.33
-
-
-
-
Off Market
35 Temahigan Ave #6, Oak Bluffs, MA 02557
0.33
-
-
-
-
Off Market

Price and Tax history

DateEventPrice
Aug 7, 2026
Source: LINK #44793
Listed For Sale
$2,995,000

LGBTQ Local Legal Protections

Bonnie J Pierce, Wallace & Co. Sotheby's International Realty
Agent Phone: (508) 367-2303
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-09 00:13:26 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Frequently asked questions about 27 Beach Road

  • What is the estimated monthly payment for 27 Beach Road?
    Based on a $2,995,000 list price with 20% down at today's rates, the estimated monthly payment for 27 Beach Road in Oak Bluffs, MA is approximately $17,207 (about $15,884 principal & interest, $1,248 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See homes for sale in Oak Bluffs, MA.
  • What are the closest schools to 27 Beach Road?
    The closest schools to 27 Beach Road in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
  • What is 27 Beach Road estimated to be worth?
    Trulia's estimated value for 27 Beach Road in Oak Bluffs, MA is $2,804,200.
  • Does 27 Beach Road have laundry facilities?
    Yes, 27 Beach Road in Oak Bluffs, MA has laundry facilities.
  • How big is the lot at 27 Beach Road?
    The lot at 27 Beach Road in Oak Bluffs, MA is about 0.20 acres (8,712 sq ft).
27 Beach Road, Oak Bluffs, MA 02557 is a 5 bedroom, 2 bathroom, 1,731 sqft single-family home built in 1920. This property is currently available for sale and was listed by CCIMLS on Aug 17, 2026. The MLS # for this home is MLS# 22604007.