This property sits right on a bus route, so you can step outside and take the free VTA bus straight into Vineyard Haven, Oak Bluffs, or Edgartown with ease. Newly built, the complex unfolds as a four-bedroom home nestled into a building with an above-garage apartment, plus a separate two-bedroom guest house—designed for togetherness with space to spread out. Fresh paint, fresh linens, and brand-new kitchen appliances set the tone for a…
(To book this property, please scroll down to the calendar. Available weeks are clearly listed. This home has a Friday-Friday turnover from July 31st to August 7th & a Sunday-Sunday turnover August 30th to September 6th, so online bookings must begin and end on its turnover day. A minimum stay of 7 nights is required. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com)
This property sits right on a bus route, so you can step outside and take the free VTA bus straight into Vineyard Haven, Oak Bluffs, or Edgartown with ease. Newly built, the complex unfolds as a four-bedroom home nestled into a building with an above-garage apartment, plus a separate two-bedroom guest house—designed for togetherness with space to spread out. Fresh paint, fresh linens, and brand-new kitchen appliances set the tone for a…
Welcome to Seaview Condominium #203 at 2 Pennacook Avenue, a beautifully appointed coastal retreat offering elevated views and relaxed comfort in the heart of Oak Bluffs. This thoughtfully furnished two-bedroom, two-bath residence blends contemporary style with easy Vineyard living. The open-concept living and dining area is filled with natural light and designed to highlight the surrounding water views, creating a bright and inviting space for gathering, relaxing, and unwinding after a day…
(To book this property, Available weeks are clearly listed. A minimum stay of 7 nights is required. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com) Private Guest House with Its Own Driveway – Brand New & Fully Detached This private two-bedroom apartment offers a comfortable, fully independent stay with complete privacy. The space features two bedrooms, a full bathroom with a shower/tub combination, and in-unit washer and dryer for added convenience. The…
Perched on the top floor of the Seaview Condominiums, Unit #304 at 2 Pennacook Avenue delivers one of Oak Bluffs’ most captivating vantage points. With sweeping ocean views from nearly every room, dramatic vaulted ceilings, and a private balcony overlooking the water, this beautifully furnished two-bedroom, two-bath residence offers a refined and memorable Martha’s Vineyard vacation experience. The interior is contemporary and thoughtfully styled, blending comfort with clean, modern design. The open…
Effortless Vineyard living begins the moment you arrive. Perfectly positioned along the free VTA bus line, this newly built compound makes exploring the island simple! Step outside and ride straight into Vineyard Haven, Oak Bluffs, or Edgartown without ever moving your car.
Updated for bookings in 2026!! SO CLOSE TO TOWN! If you are searching for a place that accommodates your group while staying close to Oak Bluffs town center, then search no further. Your guests will have a choice of two first floor bedrooms, and 3 upstairs bedrooms including a master suite that has its own private seating area. This property offers 3 full bathrooms and one outdoor shower. The kitchen offers high…
Available weeks are listed for your convenience. Turnover days may adjust depending on the calendar, and minimum night stays may apply during high-demand weeks. I’m happy to answer any questions or help with booking — please reach out to Ashley Killian at Ashley@portfoliopropertiesmv.com. Wake up to serene views and easy island living at this bright and welcoming Oak Bluffs retreat. Nestled near local beaches, charming town spots, and scenic bike paths, this…
Step into this breathtaking Hutker-designed post-and-beam masterpiece overlooking the shimmering waters of Sengekontacket Pond. Nestled on Brush Island Lane in Oak Bluffs, this custom-built residence offers a rare combination of architectural sophistication, coastal tranquility, and private shoreline access — complete with a small, sandy beach for launching kayaks or simply soaking in the island sun. With approximately 3,600 square feet of inspired living space, this home balances soaring exposed-beam ceilings, walls of…
Discover one of the most magical waterfront experiences on Martha’s Vineyard at "The Westlake House", a unique three-level Vineyard-style cottage perched atop a 25-foot bluff overlooking the shimmering waters of Lagoon Pond and Nantucket Sound. With panoramic views, direct beach access, and postcard-perfect sunsets, this home captures everything you dream of in an island vacation. Follow the private wooded path down to over 110 feet of your own sandy shoreline—calm, clean, and…
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