Oak Bluffs, MA 025572 Winemack Street

$1,095,000

2 Winemack Street Oak Bluffs, MA - Image 12 Winemack Street Oak Bluffs, MA - Image 22 Winemack Street Oak Bluffs, MA - Image 32 Winemack Street Oak Bluffs, MA - Image 4
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Presented By: Rene Ben David with Ocean Park Realty Inc
  • MLS# 44805
  • 08/12/2026
  • Pending
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  • Beds • 3
  • Full/Half Baths • 2 / 0
  • Acres • 0.1147

Home Details

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. Title 5 System failed, Seller is offering a credit at closing to help with costs(to be determined). 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.
Presented By: Rene Ben David with Ocean Park Realty Inc

Interior Features for 2 Winemack Street

Total Bedrooms3
Full Baths2
Half Baths0
BasementFull Basement recently renovated to add more living space
Flooring2
HeatingGFHW
AppliancesStove: yes , gas, Washer: yes

General for 2 Winemack Street

Property Type1 Family
Property SubtypeSingle Family Residence
StatusPending
Year Built1988
Total Rooms4
SewerSeptic Tank
MLS Area3
Tax Annual Amount4092.34
Tax Assessed Value471400
Tax Year2026

Exterior for 2 Winemack Street

Lot Size Acres0.1147
Lot Size Square Feet5000
Exterior FeaturesPubBch, Deck
Parking Featuresyes offstreet parking 2-3 cars
Water SourceTown
ViewNone

Additional Details

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Listing information is provided by LINK MLS and is deemed reliable but not guaranteed. Listing courtesy of Ocean Park Realty Inc.