27 Beach Road Oak Bluffs, MA $ 2,995,000
27 Beach Road
$ 2,995,000
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27 Beach Road

Oak Bluffs, MA, 02557
$ 2,995,000
Bedrooms5 Baths1.1 Sq 1,731

Monthly Estimate*

$ 20,686

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Single Family Home for sale in Oak Bluffs, MA

for $2,995,000 with 5 bedrooms and 1 full bath, 1 half bath. This 1,731 square foot home was built in 1920 on a lot size of 0.2.

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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Single Family Active

Price

$ 2,995,000

Bedrooms

5

Full Bath

1

Half Bath

1

Property Type

Single Family

Taxes

$ 10,365

Style

Cottage

Lot Size

0.2

Year Built

1920

Town/City

Oak Bluffs

County/Region

Dukes

MLS | Web ID

22604007

Features
General
Sewer Public Sewer
Heating None
Cooling None
Roof Asphalt
Appliances Microwave Electric Range Refrigerator Washer Water Heater
Patio/Porch Features Porch
Architectural Style Cottage
Construction Materials Shingle Siding
Year Built 1920
Stories Count 2
Property Subtype Single Family Residence
Tax Year 2026
Waterfront Features Waterview Waterfront Other
County Dukes
Property Type Residential
HOA false
Attached Garage false
Garage Y/N false
Total Rooms 8
Full Baths 1
Status Active
City Oak Bluffs
Body of Water Other Salt
MLS Area Oak Bluffs
Lot Size Units Acres
Lot Size Square Feet 8712
Tax Annual Amount 10365
Showing Instructions Please call listing agent
Home Warranty Y/N false
Building Area Units Square Feet
Standard Status Active
Tax Assessed Value 608300
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Interior
Interior Amenities HU Cable TV
Flooring Hardwood
Total Fireplaces 1
Air Conditioning Y/N false
Heating Y/N false
Half Baths 1
Laundry Features Electric Dryer Electric Dryer Hookup Washer Hookup
Total Bedrooms 5
Total Baths 2
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Exterior
Exterior Amenities Outdoor Shower
Fencing Partial
Parking Features Driveway Off Street
Lot Features Fenced/Enclosed Cleared Views
Water Source Public
Total Parking 4
Lot Size Area 0.2
Building Area Total 1731
Lot Size Acres 0.2
Waterfront Y/N true
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* Excluded Features
List By
Bonnie J Pierce

Listing Agent

Wallace & Co. Sotheby's International Realty

Broker

bonnie@wallacemv.com

Email

Affordability Calculator

$21,549
Per Month
96%
4%
0%
Monthly Principal & Interest
$20,686
Monthly Property Taxes
$864
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
9/2/2026$2,995,000 Listed Price

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27 Beach Road, Oak Bluffs, MA, 02557 is a Single Family Home for sale at $2,995,000 with 1,731 sqft and a lot size of 0.2. 27 Beach Road has 5 bedrooms, 1.1 baths, and was built in 1920. The property's zip code is 02557 which is in Oak Bluffs, MA