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 cover 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.
Property Details
Price:
$1,095,000
MLS #:
22603994
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
oakbluffs
Listed Date:
Aug 12, 2026
Finished Sq Ft:
2,173
Total Sq Ft:
2,173
Lot Size:
5,000 sqft / 0.11 acres (approx)
Year Built:
1988
See this Listing
Schools
Interior
Appliances
Dishwasher, Microwave, Gas Range, Refrigerator, Range Hood, Washer, Propane Gas, Tankless Water Heater
Bathrooms
2 Full Bathrooms
Cooling
None
Flooring
Other, Laminate, Tile
Heating
Propane
Interior Features
Attic Storage
Laundry Features
Electric Dryer
Exterior
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower
Parking Features
Driveway, Unpaved
Parking Spots
3
Parking Total
3
Patio And Porch Features
Deck
Roof
Asphalt, Pitched
Stories
2
Financial
Tax Year
2026
Taxes
$4,092
Map
Community
- Address2 Winemack Street Oak Bluffs MA
- CityOak Bluffs
- CountyDukes
- Zip Code02557
Market Summary
Current real estate data for Single Family in Oak Bluffs as of Aug 25, 2026
15
Single Family Listed
72
Avg DOM
1,193
Avg $ / SqFt
$1,772,067
Avg List Price
Property Summary
- 2 Winemack Street Oak Bluffs MA is a Single Family for sale in Oak Bluffs, MA, 02557. It is listed for $1,095,000 and features 3 beds, 2 baths, and has approximately 2,173 square feet of living space, and was originally constructed in 1988. The current price per square foot is $504. The average price per square foot for Single Family listings in Oak Bluffs is $1,193. The average listing price for Single Family in Oak Bluffs is $1,772,067. To schedule a showing of MLS#22603994 at 2 Winemack Street in Oak Bluffs, MA, contact your Gibson Sotheby’s Int’l Realty agent at 5084327856.
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