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Street View
$1,095,000
Monthly Est:$5,450
3 Beds
- 2 Baths
2 full baths
2,173sqft
2 Winemack St, Oak Bluffs, MA 02557
$1,095,000
$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

Property Details
Status
Pending
Type
Single Family Residence
No. of Stories
2
County
City
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
| Date | Event | Price |
|---|---|---|
10/06/2026 Source: | Pending | $1,095,000 -8.37% $504/sqft |
08/15/2026 Source: | Listed for Sale | $1,195,000 $550/sqft |
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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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