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2 Winemack Street
Oak Bluffs MA 02557 US

$1,195,000

Active Listing ID 22603994
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3 bed
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2,173 square feet
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2.00 Bath (2 Full)
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Lot: 0.11 Acres
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Single Family Residence

$1,195,000

Active Listing ID 22603994
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2 Winemack Street 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.

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Property Features

  • Facts
  • Lot Size: 0.11 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 2
  • Exterior Finish: Outdoor Shower
  • Floor Covering: Laminate, Tile
  • Roof Type: Asphalt
  • Heating Fuels: Propane (Heating)
  • Additional Features
  • Basement
  • Patio

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1195000
  • unparsedaddress: 2 Winemack Street
  • postalcity: Oak Bluffs
  • stateorprovince: MA
  • country: US
  • postalcode: 02557
  • bathroomsfull: 2
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.11
  • lotsizeunits: Acres
  • lotsizearea: 0.11
  • livingarea: 2173
  • livingareaunits: Square Feet
  • latitude: 41.462709
  • longitude: -70.576208
  • listagentfullname: Rene A Ben David
  • listagentemail: renebendavid@oceanparkmv.com
  • listagentkey: 3yd-CCIAORMA-U5363
  • listagentmlsid: U5363
  • listagentpreferredphone: 5088474864
  • listagentofficephone: 5088474864
  • listofficekey: 3yd-CCIAORMA-CPRK
  • listofficemlsid: CPRK
  • disclaimer: Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CCIAORMA
  • yearbuilt: 1988
  • listingcontractdate: 2026-08-12
  • listagentfax: 5086932612
  • countyorparish: Dukes
  • parcelnumber: OAKB M:0004 B:0126 L:000
  • elementaryschooldistrict: Martha's Vineyard
  • middleorjuniorschooldistrict: Martha's Vineyard
  • highschooldistrict: Martha's Vineyard
  • appliances: Tankless Water Heater, Range Hood, Gas Range, Dishwasher, Microwave, Refrigerator, Washer
  • constructionmaterials: Shingle Siding
  • flooring: Laminate, Tile
  • heating: Propane (Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 3
  • parkingfeatures: Driveway, Paved or Surfaced
  • roof: Asphalt
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Attic Storage
  • exteriorfeatures: Outdoor Shower
  • rooms: Bathroom 1, Bathroom 2, Basement, Bedroom 3, Bedroom 1, Bedroom 2
  • otherstructures: Storage
  • patioandporchfeatures: Deck
  • speciallistingconditions: Standard
  • basement: Finished, Walk-Out Access
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -70.57621, 41.462708
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CCIAORMA-22603994", "OpenHouseEndTime": "2026-08-16 12:00:00", "OpenHouseId": "8152567", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-08-16 10:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-CCIAORMA-22603994", "OpenHouseEndTime": "2026-08-15 12:00:00", "OpenHouseId": "8152569", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-08-15 10:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-CCIAORMA-22603994", "OpenHouseEndTime": "2026-08-18 11:00:00", "OpenHouseId": "8152571", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-08-18 10:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":null, "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"renebendavid@oceanparkmv.com", "ListBrokerageCity":null, "ListBrokerageCountry":null, "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":null, "ListBrokeragePhone":null, "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":null, "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"69 Circuit Ave. ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"CPRK", "ListOfficeCity":"Oak Bluffs", "ListOfficeCountry":"US", "ListOfficeEmail":null, "ListOfficePostalCode":"02557", "ListOfficeStateOrProvince":"MA", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Oak Bluffs, MA", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/2-Winemack-St_Oak-Bluffs_MA_02557_M42156-77935?f=listhub&s=CCIAORMA&m=22603994&c=rexren", "MLSModificationTimestamp":"2026-08-15 12:40:36", "Neighborhoods":[{"Description":null, "Name":"Oak Bluffs"}], "PostalCode":null, "RoomCount":4, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":4092, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 8/15/2026 1:33:39 PM GMT
Source Updated Date: 8/16/2026 12:55:56 AM GMT

Courtesy of: Rene A Ben David, Ocean Park Realty, Inc., renebendavid@oceanparkmv.com

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.