$1,049,000 $151K PRICE DROP
- Land
- 0.25 Acre
- $4,196,000 per Acre
- 0 Temahigan Ave
- Unit 160
- Oak Bluffs, MA
2 Winemack St Oak Bluffs, MA 02557
Oak Bluffs NeighborhoodEstimated payment $6,570/month
Total Views
17,931
3
Beds
2
Baths
1,456
Sq Ft
$752
Price per Sq Ft
About This Home
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.
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $4,092
Year Built
- Built in 1988 | Remodeled in 2025
Lot Details
- 5,000 Sq Ft Lot
- Property is zoned R1
Interior Spaces
- 1,456 Sq Ft Home
- Furnished
- Washer
- Basement
Bedrooms and Bathrooms
- 3 Bedrooms
- 2 Full Bathrooms
Outdoor Features
- Deck
Utilities
- Septic Tank
- Cable TV Available
Listing and Financial Details
- Tax Lot 126
- $527,300 per year additional tax assessments
Map
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Home Values in the Area
Average Home Value in this Area
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/22/2026 08/22/26 | Price Changed | $1,095,000 | -8.4% | $752 / Sq Ft |
| 08/12/2026 08/12/26 | For Sale | $1,195,000 | -- | $821 / Sq Ft |
Source: LINK (Vineyard)
About the Listing Agent
Rene’ Ben David, REALTOR ®, at Ocean Park Realty, Oak Bluffs, Ma. Rene’ is a native of Martha’s Vineyard , born and raised in Oak Bluffs. The Ben David family goes back many generations on the Vineyard. Growing up Rene worked on the Oak Bluffs Harbor for years pumping gas at church’s pier marina as well as helping out at Ben David Motors where his dad Arthur and Uncle Donald owned a Dodge /Chrysler dealership. Rene still lives in Oak Bluffs with his wife Mel and two children.
He
Rene's Other Listings
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$1,049,000 $151K PRICE DROP
- Land
- 0.25 Acre
- $4,196,000 per Acre
- 0 Temahigan Ave & Dover St
- Unit 22602202
- Oak Bluffs, MA
Source: LINK (Vineyard)
MLS Number: 44805
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