$1,195,000
OPEN TUE 10AM - 11AM

2 Winemack St Oak Bluffs, MA 02557

Estimated payment $6,922/month

3 Beds
2 Baths
1,456 Sq Ft
$821 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.
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.

Listing Agent

Rene Ben David

Ocean Park Realty Inc Listed on: 08/12/2026

Open House Schedule

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

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

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Frontage: None
  • Lot Features: yes
  • LotSizeAcres: 0.1147
  • View: None
  • Co List Office Mls Id: 787
  • Building Area Total: 1456
  • Has Fireplace?: No
  • Effective Year Built: 2025
  • Year Built: 1988
  • reviewed: Yes
  • Special Features: OpenHouse
  • Year Built: 1988
  • Year Renovated: 2025

Interior Features

  • Appliances: Stove: yes , gas, Washer: yes
  • Has Basement: Full Basement recently renovated to add more living space
  • Full Bathrooms: 2
  • Total Bedrooms: 3
  • Fireplace Features: no
  • Flooring: 2
  • Interior Amenities: Ins,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

Exterior Features

  • Pool Private: No
  • Exterior Features: PubBch, Deck
  • Foundation Details: Pour cement, Partially finished with interior and exterior access

Garage/Parking

  • Parking Features: yes offstreet parking 2-3 cars

Utilities

  • Heating: GFHW
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town

Lot Info

  • Lot Size Sq Ft: 5000
  • Zoning: R1

Multi Family

  • Number Of Units Furnished: Furnished

Tax Info

  • Tax Annual Amount: 4092.34
  • Tax Lot: 126
  • Tax Map Number: 4
  • Tax Other Annual Assessment Amount: 527300
  • Tax Year: 2026

Map

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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
08/12/2026 08/12/26 For Sale $1,195,000 -- $821 / Sq Ft
Source: LINK (Vineyard)

About the Listing Agent

Rene Ben David
Rene Ben David

Ocean Park Realty Inc

(508) 501-5195

Section Image

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

View Rene's Profile

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Source: LINK (Vineyard)

MLS Number: 44805

Massachusetts Dukes County Oak Bluffs

2 Winemack St, Oak Bluffs, MA

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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Rene Ben David
Rene Ben David
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Ocean Park Realty Inc
(508) 501-5195
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