Carroll & Vincent Real Estate
508-627-0286 · carrollandvincent.com

25 Oak Avenue, Oak Bluffs New Listing

$1,950,000

Thought to have been moved from the Campgrounds to the Highlands in the early 1900’s, the Mary E. Gilkes house has been transformed into a sophisticated and easy-living Island abode. The thoughtful, intentional design and execution of this renovation/addition pays homage to its Victorian roots while adding every modern amenity for year-round or summer use. Every detail has been carefully considered from the mahogany front porch with Vineyard-blue ceilings that typifies the Oak Bluffs cottage history, to the “bonus” room/loft, to infrastructure which meets HERS requirements for energy efficiency. There isn’t an inch of wasted space in this little powerhouse and the property offers a wealth of possibilities for expansion. The location is quiet and bucolic, and just up the hill from Circuit Ave., with easy access to East Chop and Eastville Beach. Roll right off the ferry and bring your Vineyard vision to life in this enchanting home where history, style and modern comfort come together!

The front porch offers two entry points, thru the front door and into the living room or enter a sweet mudroom with built-in cabinets and lots of storage space. The kitchen features gorgeous custom cabinetry by Crown Point with English oak pulls. The high-end appliances are paneled for a sleek and finished look and the veined quartz countertops, induction stove and white tile backsplash will delight today's cooks. The dining room and living area have cathedral ceilings and tasteful, modern lighting fixtures. A bright corner bedroom looks out over the private, fully fenced back yard and the attached large ensuite bath can also be accessed from the hall to serve as the powder room when company arrives. Open the back door to a mahogany deck which leads to a large mahogany outdoor shower.
An open stairwell with cable railings is a beautiful feature of the living area and ascends to a landing that features a large linen closet with built-ins and steps into a "bonus" loft that can literally be anything -- an office, a reading room, a quiet corner. A second primary bedroom with a tiled, ensuite bath has cathedral ceilings and double closets.  Both bathrooms have heated tile floors with beautiful modern chrome fixtures and teak and marble vanities.
Full basement with high ceilings can be partially finished for additional living space.
Parking for two cars on a textured concrete pad. There is also additional off-street parking.
There is a concrete pad that was part of a pre-existing, non-conforming structure. There is a possibility that it could be used as the foundation for a garage or an ADU but would have to be confirmed by the OB Building Dept. Additionally, there is room on the lot to build a conforming structure as an outbuilding or ADU. The septic system was built to accommodate another bedroom with the addition of another tank. The concrete pad currently serves as a two-car parking area for the house.

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Data last updated: 10/24/2026. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update. Listed by Sandpiper Realty© 2026 LINK, All Rights Reserved. LINK does not warrant the accuracy, reliability or completeness of this information.