INQUIRE ABOUT THIS LISTING

INQUIRE ABOUT THIS LISTING

This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail

2 Winemack Street, Oak Bluffs

$1,195,000

Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha’s Vineyard so special. Martha’s Vineyard Hospital is also just a short two-minute drive away.
Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home’s usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities.
A newly completed “doghouse”-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own.
Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living.
Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs.
Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

HIGHLIGHTS

Link ID 44805
Bedrooms 3
Baths 2
Rooms 4
Living Space 1456
Acreage 0.11

FEATURES AND AMENITIES

Link ID
44805
Price
$1,195,000
Baths
2
Rooms
4
Living Space
1456
Acreage
0.11
Zoning
R1
Water
Town
Sewer
Septic Tank
Heat
GFHW
2026 Tax Assessment
$998,700
Building Assessment
$471,400
Land Assessment
$527,300
Estimated Taxes
$4,092
Outdoor Spaces
Beach Access - Public
Deck
Year Built
1988
Fireplaces
None
Flooring
2
Listing Broker
Ocean Park Realty Inc

2 Winemack Street, Oak Bluffs

Copyright 2026 LINK MV. All rights reserved. Information deemed reliable but is not guaranteed.
Buyer note, 2% Land Bank fee.
X