The Hart Haven house tour

A peek-a-boo benefit for Featherstone Center for the Arts.

Hart Haven tour house No. 1 — the White House, on Farm Pond Road, owned by Nina Moore Hall. — Sam Moore

We are all agreed, I think, that we may dub an event “annual” when it comes round a second time. Last year a few feisty ladies on the board of our beloved Featherstone Center for the Arts organized a fundraising tour of select houses in East Chop. The affair was a success, a number of guests got glimpses of ocean views, lovingly tended gardens, beach-friendly furniture, and inviting interiors. Last week the second “annual” tour was developed around that fabled enclave of swimsuits, cocktails on the veranda at 5, and the joy of summer living, Yankee-style, known as Hart Haven.

The Hart family arrived on the Vineyard in 1870. The paterfamilias of the clan, and founder of the steel company Stanley Works, started buying up Oak Bluffs lots from Farm Pond east to Sengekontacket and all along the shore. William and Martha Hart built a white manor house — the Downton Abbey of Hart Haven — that so many of us have admired as we drive east in the direction of Lola’s, our eyes scanning southward down a long drive ending in what Hart Havenists call “the White House.”

Mr. Hart was eager to supply building sites for his ample family and their ample descendants. Nowadays, folks with surnames other than Hart own many of the 40 properties, but a surprising number of them are related to the original William, and everyone embraces the casual elegance of these many acres along the shore.

The clever Featherstone staff, fortified by lots of friendly volunteers, made it easy for sightseers: Park at Lola’s, look for artistic director Ann Smith at a table under an umbrella, and receive a brochure with a guide to the houses. Touring was made easy with a fleet of vans hired for the occasion, and there always seemed to be one rolling into a driveway just when you needed it.

House No. 1 on the tour was none other than the White House itself, now owned by Nina Moore Hall, great-great-great-granddaughter of William Hart. She writes in the brochure, “My husband, three children, and I moved from Philadelphia nine years ago, and have been restoring the house, keeping the same footprint and same character of the original house.”

A good-size living room accommodates a brick fireplace and Mission-style furniture. The home’s design shows a positive libido for capturing the outdoors, from the huge screened-in dining porch on the west flank to a glassed-in porch on the far side with white floors and walls, white wicker furniture, an open deck beyond, and all of it fronting on the long and wide allée to Nantucket Sound.

No. 2 on the tour — not that we weren’t free to mix and match as we flagged down vans or strolled from door to door — was 370 Seaview Avenue, an old school grand “cottage” rising above the sea. It’s now owned by Lynne and Michael Comb, who have three sons and a grandson. The new owners purchased the property in 2012 from the family of artist Douglas Prizer. They’ve updated and repaired, but only insofar as nothing disturbs the original character of the house. Ms. Comb too is a painter, and her scenic watercolors decorate the den, sitting room, and living room of the downstairs. Six upstairs bedrooms carry through the classic blue-and-white motif of linens and textiles against dark wood-paneled walls. Views of the ocean lie straight ahead. To the east are stunning vistas of the coves and saltwater inlets of Cow Bay.

No. 3 on the tour, at 23 Martha’s Park Road, provides contemporary contrast, designed by iconic Island architects, and husband and wife, Stephanie Mashek and Ken MacLean. The very first sight of it, with a central house and appending guest houses to form a U-shape around a central garden, is magical in the extreme: black-stained woodwork supports longitudinal wooden strips of utmost violet. The interior of the main house compartmentalizes the couple’s domestic priorities. A central cathedral ceiling houses a long dining room table accompanied by a well-stocked kitchen of equal length. To the right a small but sumptuously comfy set of overstuffed chairs, sofas, and a hearth says in no uncertain terms, “Let’s gather and talk about everything from gossip to the Hegelian dialectic.” Through a lintel is the TV room. A straight ladder leads to an overhead loft bedroom. The far side of the house has other bedrooms and offices for both architects, all in manageable sizes.

No. 4 is owned by the Hart-descended Woollacott family, at 16 Martha’s Park Road. The spacious house with a layout of light and bright rooms once enjoyed an overlook of the Sound, still visible in the winter when shrubs and trees cast off their leaves. The gorgeous white kitchen and butler’s pantry have been “freshened” without destroying the original charm and essence.

House No. 5 is a contemporary blend of bleached-wood floors, high and angled white walls, all rooms with striking double water views of an inlet of Sengekontacket at the end of the lawn and, beyond that, the ever-present (to Hart Haven) Sound. This, the final house, owned by Eric Hager of Washington, D.C., and daughter and son-in-law Elizabeth and Chris Finley, yielded one of Featherstone’s signature gala feasts, this one desserts only (sorry, Mom, couldn’t eat my veggies first). Organizers Patsy McCormack and Judy Cunniffe directed this reporter to the last of the heavenly lemon cookies, but my next and final objective was an obscenely layered, frosted, and marshmallow-ed brownie which I wrapped in a napkin to enjoy on the van ride back to Lola’s parking lot, this covert action designed to avoid conversing with teeth, lips, and lower face covered in chocolate.

Watch for Featherstone’s third “annual” house tour next year, fairy-tale destination to be revealed.