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Getaways on Martha's Vineyard, Land of Subdued Summering

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The Massachusetts island of Martha's Vineyard has maintained a low-key atmosphere, despite a long roster of celebrity summer visitors—from President Obama to actor Bill Murray to director Spike Lee—and astronomical property prices. If anything, the preppy social pressures on the island have lead to a preference for tastefully worn-in interiors, even in the most expensive listings. Take the waterfront compound known as Chapeda Hill (above). In the same family since its construction in the late 1920s, the estate sits in a coveted position on Edgartown Harbor, enjoying close proximity to town, a private beach, and a deep-water dock. The interiors look to have been outfitted a couple of generations ago, with questionable wallpaper, wood-paneled everything, and a 1950s kitchen. Nevertheless, the value real estate on Martha's Vineyard is, as most everywhere else, dictated by location, and this 1.7-acre estate is certainly well located judging by the $14.25M asking price.

? The listing for this charming waterfront home and accompanying 12.2-acre property in sparsely populated Chilmark is lacking any interior photography. Chances are that's because the insides are a little behind the times. Thankfully, the undulating dunes and spectacular ocean views are timeless—at least until mother nature reclaims the dunes. This gorgeous peninsula property is asking $12.75M.

? Set between a lightly trafficked side street and Vineyard Haven's outer harbor, this historic shingle-style compound offers Martha's Vineyard waterfront for $3.55M. Granted, there's no beach to speak of, and the dock looks to have been ravaged by a storm of the last century, but the 1920s house is a MV classic, with uninsulated walls, a motley collection of furnishings, and a waterfront hammock. The listing is right to emphasize the views, which include glorious sunrises over Vineyard Sound.

? This 2001 construction, though obviously bereft of the midcentury kitchens and deferred maintenance of its older neighbors, still adheres to a simple design, letting the natural beauty of its surroundings—on the dunes of the far western hamlet of Aquinnah—shine through. The 1,800-square-foot beach house contains two bedrooms, two bathrooms, and an airy, all-white living space, complete with fireplace. The stylish cottage is currently listed for $2.9M.

? Vineyard house hunters looking for a sizable waterfront parcel, a large house, and updated interiors should be prepared to pay through the nose. The impressive Herring Creek Farm, including 25 acres, a 5,600-square-foot main house, and ample Great Pond waterfront, is listed for $19.5M. Currently owned by a California-based LLC, the sprawling estate has some of the island's most modern interiors, but is still done in an understated style, befitting its modest-yet-expensive neighbors.

· 31 Tower Hill Road [Sotheby's International Realty]
· 78 Squibnocket Farm Road [Landvest]
· 47 Harbor View Lane [Landvest]
· Oxcart Way [Tea Lane Associates]
· 61 Butlers Cove Road [Sotheby's International Realty]