2 Winemack Street
Oak Bluffs, MA, 02557 $ 1,195,000
Bedrooms3 Baths2.0 Sq 2,173 Monthly Estimate*
$ 7,545
for $1,195,000 with 3 bedrooms and 2 full baths. This 2,173 square foot home was built in 1988 on a lot size of 0.11.
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.
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FeaturesGeneralSewer Septic Tank Septic Tank
Heating Hot Water
Cooling None
Roof Asphalt Pitched
Appliances Dishwasher Washer Range Hood Refrigerator Gas Range Microwave Electric Dryer
Zoning R1
Patio/Porch Features Deck
Architectural Style Cape Cod Shingle
Construction Materials Shingle Siding
Year Built 1988
Stories Count 2
Township Oak Bluffs
Property Subtype Single Family Residence
Tax Year 2026
County Dukes
New Construction false
Property Type Residential
HOA false
Garage Y/N false
Total Rooms 4
Full Baths 2
Status Active
Directions Off New York Ave Winemack Street turn at the yellow stucco house see Ocean Park sign
City Oak Bluffs
High School District Martha's Vineyard
Lot Size Units Acres
Lot Size Square Feet 5000
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 4092.34
Showing Instructions Owner resides in residence with 2 tenants 24 hr notice preferred
Home Warranty Y/N false
Property Condition Updated/Remodeled Actual
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Martha's Vineyard
Elementary School District Martha's Vineyard
Tax Assessed Value 998700
Tax Lot 126
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InteriorBasement Bulkhead Access Interior Entry Finished
Flooring Other Tile Laminate
Air Conditioning Y/N false
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Total Bedrooms 3
Main Level Bathrooms 1
Below Grade Finished Area Unit Type Square Feet
Total Baths 2
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ExteriorExterior Amenities Outdoor Shower
Lot Features Marina Medical Facility Shopping
Total Parking 3
Lot Size Area 0.11
Foundation Details Poured
Building Area Total 2173
Lot Size Acres 0.11
Road Surface Type Paved
Lot Size Source Assessor
Waterfront Y/N false
Road Frontage Type Public
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* Excluded FeaturesList ByRene A Ben DavidListing Agent
Ocean Park Realty, Inc.Broker
renebendavid@oceanparkmv.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $7,545
- Monthly Property Taxes
- $341
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Oak Bluffs, MA
Average List Price $2,298,765
Percent of Sale Price 92%
About Oak Bluffs, MA 4,795 Population
29% Since 2002
$ 64,471 Median Income
46.88 Median Age
19% Households with Children
Trends Information provided by ATTOM Data Solutions.
2088120 Elementary School
2088116 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 8/15/2026 | $1,195,000 | | Listed Price |