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.
For sale
$2,995,000
27 Beach Road, Oak Bluffs, MA 02557
4beds
3,462sqft
Single Family Residence
Built in 1920
8,712 Square Feet Lot
$2,879,600 Zestimate®
$865/sqft
$-- HOA
What's special
Waterfront cottagePrivate sandy beachDeep-water dockOriginal architectural detailsNew roofNew cedar shinglesBeautiful mahogany porches
- 12 days
- 1,280
- 71
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
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
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Heating
- None
Cooling
- None
Appliances
- Included: Electric Dryer, Washer, Refrigerator, Electric Range, Microwave, Electric Water Heater
Features
- HU Cable TV
- Flooring: Hardwood
- Basement: Crawl Space
- Number of fireplaces: 1
Interior area
- Total structure area: 3,462
- Total interior livable area: 3,462 sqft
Property
Parking
- Total spaces: 4
- Parking features: Open
- Has uncovered spaces: Yes
Features
- Stories: 2
- Patio & porch: Porch
- Exterior features: Outdoor Shower
- Fencing: Fenced, Partial
- Has view: Yes
- Has water view: Yes
- Water view: Other
- On waterfront: Yes
- Body of water: Other
Lot
- Size: 8,712 Square Feet
- Features: Bike Path, Medical Facility, Shopping, Marina, Cleared
Details
- Parcel number: OAKB M:0006 B:0036 L:000
- Zoning: R1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cottage
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Roof: Asphalt
Condition
- Actual
- New construction: No
- Year built: 1920
Utilities & green energy
- Sewer: Public Sewer
Community & HOA
HOA
- Has HOA: No
Location
- Region: Oak Bluffs
Financial & listing details
- Price per square foot: $865/sqft
- Tax assessed value: $608,300
- Annual tax amount: $10,365
- Date on market: 8/17/2026
- Road surface type: Paved
Estimated market value
$2,879,600
$2.74M - $3.02M
$7,045/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/7/2026 | Listed for sale | $2,995,000$865/sqft |
Source: LINK #44793 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,864 +4.8% | $2,151,300 +8.5% |
| 2024 | $10,365 +12.8% | $1,981,900 +13.9% |
| 2023 | $9,189 +15% | $1,740,400 +47.9% |
| 2022 | $7,991 -13.6% | $1,176,900 -6.2% |
| 2021 | $9,244 -3.5% | $1,254,300 -2.6% |
| 2020 | $9,580 +0.6% | $1,287,600 +4% |
| 2019 | $9,520 -1.1% | $1,238,000 +0.7% |
| 2018 | $9,623 +4.9% | $1,229,000 +9.2% |
| 2017 | $9,175 +0.3% | $1,125,800 -0.2% |
| 2016 | $9,151 +2.9% | $1,128,400 +1% |
| 2015 | $8,897 +4.1% | $1,117,700 +2.1% |
| 2014 | $8,546 +10% | $1,094,300 +8.6% |
| 2013 | $7,766 +4.3% | $1,007,300 |
| 2012 | $7,444 +16.3% | $1,007,300 +10.7% |
| 2011 | $6,399 +1.1% | $910,200 -9.4% |
| 2010 | $6,329 -11.6% | $1,004,600 -15.3% |
| 2009 | $7,160 +7.3% | $1,185,500 |
| 2008 | $6,674 +7.7% | $1,185,500 +7% |
| 2007 | $6,195 +3% | $1,108,200 +5.9% |
| 2006 | $6,015 -7.4% | $1,046,000 -2.3% |
| 2005 | $6,496 | $1,070,200 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 02557
Nearby schools
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