Oak Bluffs, MA 02557 2 Winemack Street

2 Winemack Street Oak Bluffs, MA - Image 12 Winemack Street Oak Bluffs, MA - Image 22 Winemack Street Oak Bluffs, MA - Image 3
23 more
2 Winemack Street Oak Bluffs, MA - Image 42 Winemack Street Oak Bluffs, MA - Image 52 Winemack Street Oak Bluffs, MA - Image 62 Winemack Street Oak Bluffs, MA - Image 72 Winemack Street Oak Bluffs, MA - Image 82 Winemack Street Oak Bluffs, MA - Image 92 Winemack Street Oak Bluffs, MA - Image 102 Winemack Street Oak Bluffs, MA - Image 112 Winemack Street Oak Bluffs, MA - Image 122 Winemack Street Oak Bluffs, MA - Image 132 Winemack Street Oak Bluffs, MA - Image 142 Winemack Street Oak Bluffs, MA - Image 152 Winemack Street Oak Bluffs, MA - Image 162 Winemack Street Oak Bluffs, MA - Image 172 Winemack Street Oak Bluffs, MA - Image 182 Winemack Street Oak Bluffs, MA - Image 192 Winemack Street Oak Bluffs, MA - Image 202 Winemack Street Oak Bluffs, MA - Image 212 Winemack Street Oak Bluffs, MA - Image 222 Winemack Street Oak Bluffs, MA - Image 232 Winemack Street Oak Bluffs, MA - Image 242 Winemack Street Oak Bluffs, MA - Image 252 Winemack Street Oak Bluffs, MA - Image 262 Winemack Street Oak Bluffs, MA - Image 27
Presented By: Rene Ben David with Ocean Park Realty Inc -
  • MLS# 44805
  • 08/12/2026
  • Request Tour
  • Request Info
  • Beds • 3
  • Baths • 2
  • SQFT • 1,456

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

Bedrooms

Main Level Bedrooms1
Total Bedrooms3

Bathrooms

Half Baths

Other Interior Features

BasementFull Basement recently renovated to add more living space
Fireplace Featuresno
Fireplace Y/NNo
Flooring2
Furnished Y/NFurnished
Interior AmenitiesIns, OSh, Floor 1: Open concept, living room, dining room , kitchen, a full bath, and bedroom., Floor 2: 2 more bedrooms with a shared full bathroom

General for 2 Winemack Street

AppliancesStove: yes , gas, Washer: yes
Building Area UnitsSquare Feet
CityOak Bluffs
Full Baths2
HeatingGFHW
Lot Size Square Feet5000
MLS Area3
Property SubtypeSingle Family Residence
Property Type1 Family
SewerSeptic Tank
Standard StatusActive
StatusA
Tax Annual Amount4092.34
Tax Assessed Value471400
Tax Lot126
Tax Year2026
TaxOtherAnnualAssessmentAmount527300
Total Rooms4
UtilitiesCbl
ViewNone
Year Built1988
Year Built Effective2025
ZoningR1

Exterior for 2 Winemack Street

Building Area Total1456
Exterior AmenitiesPubBch, Deck
Foundation DetailsPour cement, Partially finished with interior and exterior access
Frontage TypeNone
Lot Featuresyes
Lot Size Acres0.1147
Lot Size Area0.1147
Parking Featuresyes offstreet parking 2-3 cars
Water SourceTown

Additional Details

Price History

David Adams

Managing Partner
Price $1,095,000
MLS#44805
List Date 08/12/2026
Property Type Single Family
Phone
Request Tour
Request Info
Visit My Website

Similar Properties to 2 Winemack Street