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.
For sale
Price cut: $100K (8/22)
$1,095,000
2 Winemack Street, Oak Bluffs, MA 02557
3beds
2,173sqft
Single Family Residence
Built in 1988
4,791 Square Feet Lot
$1,060,600 Zestimate®
$504/sqft
$-- HOA
What's special
Small manageable yardOff-street parking
- 15 days
- 1,217
- 38
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Rene A Ben David 508-847-4864,
Ocean Park Realty, Inc.
Source: CCIMLS,MLS#: 22603994
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 1
Heating
- Hot Water
Cooling
- None
Appliances
- Included: Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer
Features
- Flooring: Other, Tile, Laminate
- Basement: Bulkhead Access,Interior Entry,Finished
- Has fireplace: No
Interior area
- Total structure area: 2,173
- Total interior livable area: 2,173 sqft
Property
Parking
- Total spaces: 3
- Parking features: Open
- Has uncovered spaces: Yes
Features
- Stories: 2
- Patio & porch: Deck
- Exterior features: Outdoor Shower
Lot
- Size: 4,791 Square Feet
- Features: Marina, Medical Facility, Shopping
Details
- Parcel number: OAKB M:0004 B:0126 L:000
- Zoning: R1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod, Shingle
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Poured
- Roof: Asphalt, Pitched
Condition
- Updated/Remodeled, Actual
- New construction: No
- Year built: 1988
- Major remodel year: 2026
Utilities & green energy
- Sewer: Septic Tank, Septic Tank
Community & HOA
HOA
- Has HOA: No
Location
- Region: Oak Bluffs
Financial & listing details
- Price per square foot: $504/sqft
- Tax assessed value: $998,700
- Annual tax amount: $4,092
- Date on market: 8/15/2026
- Cumulative days on market: 19 days
- Road surface type: Paved
Estimated market value
$1,060,600
$1.01M - $1.11M
$6,805/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/22/2026 | Price change | $1,095,000-8.4%$504/sqft |
Source: LINK #44805 Report a problem | ||
| 8/12/2026 | Listed for sale | $1,195,000$550/sqft |
Source: LINK #44805 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,877 +1.2% | $965,700 +4.8% |
| 2024 | $4,818 -4.7% | $921,200 -3.8% |
| 2023 | $5,056 +1.5% | $957,500 +30.5% |
| 2022 | $4,983 +15.5% | $733,900 +25.3% |
| 2021 | $4,316 +5.4% | $585,600 +6.4% |
| 2020 | $4,095 +1.7% | $550,400 +5.1% |
| 2019 | $4,026 +9.2% | $523,500 +11.2% |
| 2018 | $3,687 +6.1% | $470,900 +10.4% |
| 2017 | $3,475 +7.8% | $426,400 +7.2% |
| 2016 | $3,225 +6.3% | $397,600 +4.3% |
| 2015 | $3,035 +6.5% | $381,300 +4.5% |
| 2014 | $2,849 -3.7% | $364,800 -4.9% |
| 2013 | $2,958 +4.3% | $383,600 |
| 2012 | $2,835 +7.3% | $383,600 +2.1% |
| 2011 | $2,641 -6.1% | $375,700 -15.9% |
| 2010 | $2,814 -0.6% | $446,700 -4.7% |
| 2009 | $2,831 +7.3% | $468,700 |
| 2008 | $2,639 +1.8% | $468,700 +1% |
| 2007 | $2,593 +7.6% | $463,900 +10.7% |
| 2006 | $2,409 +12.2% | $418,900 +18.4% |
| 2005 | $2,148 +5.1% | $353,800 +121.5% |
| 2001 | $2,044 | $159,700 |
Find assessor info on the county website
Monthly payment
Est. payment





