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2 Winemack Street

$1,195,000

East Chop, Oak Bluffs, MA 02557

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Single Family Residence in East Chop, Oak Bluffs

3 bedrooms

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2 bathrooms

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1456 SqFt

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0.1147 acres

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MLS #44805

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.

Property highlights

Washer

Furnished

Public Beach

Deck

Septic Tank

Cable

Town Water

Property Details

Association Fee:
Association Fee Includes:
Basement:
Full Basement recently renovated to add more living space
Fireplace Features:
no
Flooring:
2
Foundation Types:
Pour cementPartially finished with interior and exterior access
Frontage Type:
None
Heating:
GFHW
Interior Features:
Ins,OShFloor 1: Open concept, living room, dining room , kitchen, a full bath, and bedroom.Floor 2: 2 more bedrooms with a shared full bathroom
Link MLS Comments:
Off New York Ave,
Lot Features:
yes
Parking Features:
yes offstreet parking 2-3 cars
Possible Use:
Assessed Building Value:
471400.00
Assessed Land Value:
527300.00

Price History

August 12, 2026
$1,195,000

Tax Information

This property was most recently assessed in 2026. It has been assessed at a value of $998,700. The annual tax responsibility for this property is $4,092.

Contact an Agent
Phone number
(508) 696-7777

Property Location

©2022 LINK, All Rights Reserved. Not responsible for misinformation or typographical errors. Prices are subject to change without notice. Listed by Ocean Park Realty Inc.