# 2 Winemack Street, Oak Bluffs, MA 02557 > **TL;DR:** 3bd/2ba single family, $1,095,000 ($504/sqft), built 1988, 2,173 sqft. Est. $5,856/mo. Listed 37 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,095,000 | | Price/sqft | $504 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 2,173 | | Year Built | 1988 | | Lot Size | 4,792 sqft (0.11 acres) | | Stories | 2 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 37 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,537 | | Estimated Insurance | $319 | | **Total** | **$5,856** | ## Property Highlights - Built in 1988 - 0.11 acre lot - 2 stories - 3 parking spaces ## Description ### Agent 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. ## Location - **Address:** 2 Winemack Street, Oak Bluffs, MA 02557 - **County:** Dukes - **Coordinates:** 41.462709, -70.576208 - **Google Maps:** https://www.google.com/maps?q=41.462709,-70.576208 ## Listing Agent - **Name:** Rene A Ben David - **Brokerage:** Ocean Park Realty, Inc. - **Phone:** 5088474864 - **Broker Phone:** 5086934210 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/2-Winemack-St_Oak-Bluffs_MA_02557_M42156-77935?f=listhub&s=CCIAORMA&m=22603994&c=propsimple) ## Photos ![2 Winemack Street - Photo 1](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2480678981r.jpg) ![2 Winemack Street - Photo 2](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f472859573r.jpg) ![2 Winemack Street - Photo 3](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2791702580r.jpg) ![2 Winemack Street - Photo 4](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f972503263r.jpg) ![2 Winemack Street - Photo 5](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f1731801419r.jpg) ![2 Winemack Street - Photo 6](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2626442926r.jpg) ![2 Winemack Street - Photo 7](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f335654628r.jpg) ![2 Winemack Street - Photo 8](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2765561675r.jpg) ![2 Winemack Street - Photo 9](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2518832926r.jpg) ![2 Winemack Street - Photo 10](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2073129045r.jpg) ![2 Winemack Street - Photo 11](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f558701710r.jpg) ![2 Winemack Street - Photo 12](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f3813079535r.jpg) ![2 Winemack Street - Photo 13](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2797330158r.jpg) ![2 Winemack Street - Photo 14](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f1295025054r.jpg) ![2 Winemack Street - Photo 15](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2310309435r.jpg) ![2 Winemack Street - Photo 16](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f1126951028r.jpg) ![2 Winemack Street - Photo 17](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2279247603r.jpg) ![2 Winemack Street - Photo 18](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f408632409r.jpg) ![2 Winemack Street - Photo 19](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f3833041797r.jpg) ![2 Winemack Street - Photo 20](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f2939166042r.jpg) ![2 Winemack Street - Photo 21](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f3108864488r.jpg) ![2 Winemack Street - Photo 22](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f4249304713r.jpg) ![2 Winemack Street - Photo 23](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f352568654r.jpg) ![2 Winemack Street - Photo 24](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f201692077r.jpg) ![2 Winemack Street - Photo 25](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f1819054723r.jpg) ![2 Winemack Street - Photo 26](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f1507423595r.jpg) ![2 Winemack Street - Photo 27](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f3443196658r.jpg) ![2 Winemack Street - Photo 28](http://lh.rdcpix.com/cbdc8daafe192934543229bb508fdd3dl-f963151369r.jpg) --- **MLS#:** 22603994 | **Updated:** 2026-08-22 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/2-winemack-street-oak-bluffs-ma-02557-22603994) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/2-winemack-street-oak-bluffs-ma-02557-22603994#listing", "url": "https://www.propertysimple.ai/listing/2-winemack-street-oak-bluffs-ma-02557-22603994", "name": "2 Winemack Street, Oak Bluffs, MA 02557", "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. 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