2 Winemack Street Oak Bluffs, MA $ 1,095,000
2 Winemack Street
$ 1,095,000
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2 Winemack Street

Oak Bluffs, MA, 02557
$ 1,095,000
Bedrooms3 Baths2.0 Sq 2,173

Monthly Estimate*

$ 7,563

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Single Family Home for sale in Oak Bluffs, MA

for $1,095,000 with 3 bedrooms and 2 full baths. This 2,173 square foot home was built in 1988 on a lot size of 0.11.

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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Single Family Pending

Price

$ 1,095,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 4,092

Style

Cape Cod, Shingle

Lot Size

0.11

Year Built

1988

Town/City

Oak Bluffs

County/Region

Dukes

MLS | Web ID

22603994

Features
General
Heating Propane
Cooling None
Roof Asphalt Pitched
Appliances Dishwasher Microwave Gas Range Refrigerator Range Hood Washer Propane Gas Tankless Water Heater
Patio/Porch Features Deck
Architectural Style Cape Cod Shingle
Construction Materials Shingle Siding
Year Built 1988
Stories Count 2
Property Subtype Single Family Residence
Tax Year 2026
County Dukes
Property Type Residential
HOA false
Attached Garage false
Garage Y/N false
Total Rooms 4
Full Baths 2
Status Pending
Directions Off New York Ave Winemack Street turn at the yellow stucco house see Ocean Park sign
City Oak Bluffs
MLS Area Oak Bluffs
Lot Size Units Acres
Lot Size Square Feet 5000
Tax Annual Amount 4092.34
Showing Instructions Owner resides in residence with 2 tenants 24 hr notice preferred
Home Warranty Y/N false
Building Area Units Square Feet
Standard Status Pending
Tax Assessed Value 998700
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Interior
Interior Amenities Attic Storage
Basement Finished
Flooring Other Laminate Tile
Air Conditioning Y/N false
Heating Y/N true
Half Baths 0
Laundry Features Electric Dryer
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Outdoor Shower
Parking Features Driveway Unpaved
Water Source Public
Total Parking 3
Lot Size Area 0.11
Building Area Total 2173
Lot Size Acres 0.11
Waterfront Y/N false
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* Excluded Features
List By
Rene A Ben David

Listing Agent

Ocean Park Realty, Inc.

Broker

renebendavid@oceanparkmv.com

Email

Affordability Calculator

$7,904
Per Month
96%
4%
0%
Monthly Principal & Interest
$7,563
Monthly Property Taxes
$341
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
9/3/2026$1,095,000 Listed Price

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2 Winemack Street, Oak Bluffs, MA, 02557 is a Single Family Home for sale at $1,095,000 with 2,173 sqft and a lot size of 0.11. 2 Winemack Street has 3 bedrooms, 2.0 baths, and was built in 1988. The property's zip code is 02557 which is in Oak Bluffs, MA