27 Beach Road, Oak Bluffs, MA 02557 (MLS# 22604007)

27 Beach Road, Oak Bluffs, MA 02557

$2,995,000

Property Type: Residential Bedrooms: 5 Baths: 2 Square Footage: 1,731 Lot Size (sq. ft.): 8,712 Status: Active

Current Price: $2,995,000 List Date: 8/17/2026 Last Modified: 9/02/2026

Overview

Description

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 possibilit ... (Read more)

Listing Details MLS# 22604007

Contract Info

Original List Price: 2995000
List Price/SqFt: 1730.21

Legal and Taxes

Street #: 27
Street Name: Beach
Street Suffix: Road
County: Dukes
Town: Oak Bluffs
Village: Oak Bluffs
State: MA
Zip Code: 02557
Tax ID: OAKB M:0006 B:0036 L:000
Estimated Annual Taxes: 10365
Tax Year: 2026
Building Assessments: 429200
Total Assessment: 608300
Underground Fuel Tank: No
Lead Base Paint: Unknown
Flood Ins Required: Yes: verify w/insurance agent
Mass Use Code: 101 - Residential, single family

General Property Info

Comp Sale YN: No
Region: Dukes County
School District: Martha's Vineyard
Zoning: R1
Property Sub-Type: Single Family Residence
Year Built: 1920
Renovated: No
Total Finished Space: 1731
Field Card SqFt: 1731
Additional SqFt Source: Public Records
Basement: No
Total Rooms: 8
Stories: 2
Private Pool: No
Private Dock: Yes
Leased Land: No
Lot Size SqFt: 8712
Lot Size Source: Assessor
Acres: 0.2
Association: No
Garage: No
# of Parking Spaces: 4
Year Round: No
Bedrooms - Total: 5
Baths - Full: Yes
Baths - Half: Yes
Baths - Total: 2
Golf Course Front: No
Golf Course View: No
Waterfront: Yes
Water Body: Other
Waterfront Type: Other
Water Body Type: Salt
Water Access Type: Private
Waterview: Yes
Water Body View: Other
Waterview Type: Other
Miles to Beach: 0 - .1
Fireplace: Yes
# Fireplaces: Yes
Warranty Available: No
Property Includes Recording Devices: Yes
Device Records: Video

Baths Per Level

Baths - Level 1: Yes
Baths - Level 2: Yes

DPR Eligibility

DPR Eligible: No

Room Types

Bathroom 2 Level: First
Bathroom 3 Level: Second
Bathroom 4 Level: Second
Bathroom 5 Level: First
Bedroom 2 Level: Second
Bedroom 3 Level: Second
Bedroom 4 Level: Second
Bedroom 5 Level: Second
Kitchen Level: First
Living/Dining Combo Level: First
Primary Bathroom Level: First
Primary Bedroom Level: First

More Information

Property Features

Street Description: Paved; Public Special Listing Cond: None Architectural Style: Cottage Year Built Desc: Actual Foundation Details: Crawl Space Lot Features: Cleared; Fenced/Enclosed Parking Features: Driveway; Off Street Convenient To: Bike Path; Marina; Medical Facility; Shopping Waterview Direction: All Appliances: Electric Dryer; Electric Range; Microwave; Refrigerator; Washer Floors: Hardwood Interior Features: Electric Dryer Hookup; HU Cable TV; Washer Hookup Patio And Porch Features: Porch Private Dock Description: Ch. 91 License; Deep Water Exterior Features: Outdoor Shower; Private Yard Fencing: Fenced; Partial Roof Description: Asphalt Siding Description: Shingle Sewer: Public Sewer Heating: None Cooling: None Fuel Type: None Water: Public Hot Water: Water Heater Hot Water Source: Electric Room Types: Bathroom 2; Bathroom 3; Bathroom 4; Bathroom 5; Bedroom 2; Bedroom 3; Bedroom 4; Bedroom 5; Kitchen; Living/Dining Combo; Primary Bathroom; Primary Bedroom

Room Information

Room Name	Level
Living/Dining Combo	First
Kitchen	First
Bathroom 2	First
Primary Bedroom	First
Bedroom 2	Second
Bedroom 3	Second
Bedroom 4	Second
Bedroom 5	Second

Documents

Home Inspection Disclosure ›

Lead Paint Disclosure ›

Listing Office: Wallace & Co. Sotheby's International Realty

Listing Agent: Bonnie J Pierce

Last Updated: September - 02 - 2026

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