Pending
Price CutPrice Drop: $100K (10/06)
Sale Pending at 2 Winemack St, Oak Bluffs, MA 02557 | MLS# 22603994 | Listing updated on 2026-10-06
Photo 1 of Sale Pending at 2 Winemack St, Oak Bluffs, MA 02557 | MLS# 22603994 | Listing updated on 2026-10-06
Photo 2 of Sale Pending at 2 Winemack St, Oak Bluffs, MA 02557 | MLS# 22603994 | Listing updated on 2026-10-06
Photo 3 of Sale Pending at 2 Winemack St, Oak Bluffs, MA 02557 | MLS# 22603994 | Listing updated on 2026-10-06
Photo 4 of Sale Pending at 2 Winemack St, Oak Bluffs, MA 02557 | MLS# 22603994 | Listing updated on 2026-10-06
24+
Beds Icon

Street View

$1,095,000

Monthly Est:$5,450

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,173sqft

2 Winemack St, Oak Bluffs, MA 02557

$5,450/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1988

  • $-- HOA

  • 0.11 acre lot

  • $504/sq.ft

Description

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.

  • Houzeo last checked: 4 minutes ago
  • Listing updated: October 6, 2026 at 2:04 pm
  • Listing Provided by: Rene A Ben David (508) 847-4864 | Ocean Park Realty, Inc. (508) 693-4210
  • Source: Cape Cod And Islands MLS-MA | MLS#: 22603994 Cape Cod And Islands MLS-MA

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Dukes County

  • City

    Oak Bluffs

  • Neighborhood

    --

  • Year Built

    1988

  • HOA Fees

    -

  • Finished Area

    2,173 sqft

  • Lot Size

    0.11 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Cape Cod And Islands MLS

  • MLS Number

    22603994

  • MLS Status

    Pending

  • Days on Market

    56

  • Cumulative Days on Market

    47

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Interior Features

    Attic Storage

  • Heating

    Propane

  • Appliances

    Tankless Water Heater, Range Hood, Gas Range, Dishwasher, Microwave, Refrigerator, Washer

  • Exterior Features

    Outdoor Shower

  • Sewer

    Septic Tank

  • Cooling

    None

  • Flooring

    Other, Laminate, Tile

Construction

  • Year Built

    Year Built: 1988

  • Home type

    Single Family Residence

  • Construction Materials

    Shingle Siding

  • Foundation Details

    Poured

  • Architectural Style

    Cape Cod, Shingle

  • Roof

    Asphalt, Pitched

Utilities & Energy

  • Parking Features

    Unpaved, Driveway

  • Water Source

    Public

  • Basement

    Walk Out Access, Bulkhead Access, Interior Access, Finished

  • Laundry Features

    Electric Dryer

Other Features

  • Patio And Porch Features

    Deck

Price History

DateEventPrice

10/06/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603994

Pending

$1,095,000 -8.37%

$504/sqft

08/15/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603994

Listed for Sale

$1,195,000

$550/sqft

Nearby Homes

Based on information from the Cape Cod and Islands Multiple Listing Service, Inc. through Oct 10, 2026, 10:45PM. Information is provided exclusively for consumers’ personal, non-commercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and the data is deemed reliable but is not guaranteed accurate by the MLS. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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