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2 Winemack Street

Oak Bluffs, MA 02557
  • $1,095,000
  • STATUS: Pending
  • ON SITE: 59 Days
  • MLS #: 22603994
Pending
UPDATED: 32 min ago
$1,095,000
  • 3
    BEDS
  • 0.11
    ACRES
  • 2
    BATHS
  • 0
    1/2 BATHS
  • 2,173
    SQFT
  • $504
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1988
County:
Area:

School Ratings & Info

School District:

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.

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Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Cape Cod Real Estate Group. Data last updated: 2026-10-14T11:25:28.327.
www.capecodrealestategroup.com/homes/180184127
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2 Winemack Street Oak Bluffs, MA 02557

  • Price: $1,095,000
  • Status: Pending
  • On Site: 59 Days
  • Updated: 32 min ago
  • MLS #: 22603994
3
Beds
2
Baths
0
½ Baths
0.11
Acres
2,173
SQFT
$504
$/SQFT
1988
Built
Neighborhood:
Oak Bluffs
County:
Dukes
Area:
Oak Bluffs
School District:
Martha's Vineyard
Property 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.
Exterior Features

Architectural Style Cape CodShingle Attached Garage YN No Construction Materials Shingle Siding Exterior Features Outdoor Shower Foundation Details Poured Garage YN No Parking Features DrivewayUnpaved Parking Total 3 Patio And Porch Features Deck Private Pool No Roof AsphaltPitched Separate Living Quarters No

Interior Features

Appliances DishwasherMicrowaveGas RangeRefrigeratorRange HoodWasherPropane GasTankless Water Heater Basement Finished Basement Description Bulkhead AccessFinishedWalk-Out AccessInterior Access Cooling None Cooling YN No Flooring OtherLaminateTile Heat Hot WaterHeat Pump Heating Propane Heating YN Yes Interior Features Attic Storage Laundry Features Electric Dryer Rooms Total 4

Property Features

Association YN No Convenient To MarinaShoppingMedical Facility FEMAFlood Zone X Golf Course Front No Golf Course View No Home Warranty YN No Miles To Beach .1 - .3 Property Sub Type Single Family Residence Region Dukes County Renovated Yes Special Listing Conditions Standard Tax Annual Amount 4092.34 Tax Assessed Value 998700 Tax Year 2026 Water Source Public Waterfront YN No Year Round Yes

Cape Cod & Islands MLS logo Listing information © 2026 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of Rene A Ben David of Ocean Park Realty, Inc.:


Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Cape Cod Real Estate Group. Data last updated: 2026-10-14T11:25:28.327.
 
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