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Not exactly white bread design but sober and prudent; more like the beach cabana than the main house; mischief and prank-Palladian windows; authentic and charming Carpenter Gothic

Reach for the Sky

The corollary of flat land is a big sky. And a special, ever changing kind of light. All are abundant in the Hamptons. They were among the important reasons artists—starting in the nineteenth century and up to the present time—came to this area. Just look at the colors in Jackson Pollock paintings before and after his move from New York City to the Springs. Artists may interpret nature in myriad ways, but the land, the sky and the light are blessings here for all of us all the time.

Architecture: Elements such as Dutch gables, dormers, columned porches, and shingle cladding are heedful of local tradition. The interiors, especially a dramatic, gee whiz staircase, are zippier, but not over-the-top.

Site: Bridgehampton, on 5 ½ acres, with pool, pond, lots of grassy lawn, all under that big sky wherever you look on this property.

The inside word: It’s not exactly white bread design but it is sober and prudent. Such caution and control usually pay off in the long run. When houses with more artifice and with more architectural idiosyncrasies start to look dated, the durable, sedate, reliable qualities of this house will still be appreciated. Offered at $6.995 million.

Pied a Mer

Each of us—at least everyone we come across in the Hamptons—likes to be pampered. That’s why we spend so much money renting those perfect little vacation bungalows on islands and beaches. When we recently came across this hotel suite-sized cottage just off the beach in East Hampton, we were reminded of all those $1,000 a night villas that in the end were actually worth the money.

Architecture: It’s the simplest of structures, a stalwart grey shingle cottage with white trim that would be at home in Nantucket or Block Island but in this case is an authentic expression of East Hampton as it used to be.

Site: One of six cottages on 2 ½ acres just 400 feet from Main Beach. Once part of the fabled Sea Spray hotel, the property is a co-op with a full-time caretaker.

The inside word: Don’t compare this to the swell mansions in the neighborhood. The DNA is totally different. Think of it as a totally carefree getaway, more like a beach cabana than the main house. Monthly maintenance covers lots of services. Offered at $995,000.

Sand Castle

Beach houses are subject to different standards than their inland cousins, at least in our rulebook. The extravagances, the architectural frippery and furbelows that we’d find disdainful in most locations can take on a playful quality when a house is built on sand, and even the tinsel can become beguiling.

Architecture: There is a nice iconoclastic twist here. Someone was up to some mischief, toying with scale and shape and tradition, especially in the large gables with the gothic themed, prank-Palladian windows.

Site: Amagansett oceanfront, just a half acre and no pool, but they managed to fit in a cute house with terrific views.

The inside word: We like the vernacular sensibility, the idea that the location and views created an offbeat and engaging composition. It is a house with a storybook quality, more than the sum its architecture or materials. So if you are feeling individualistic, disobedient and bit a rebellious, and have $6.15 million to spend, get moving.

Coming Up Roses

Houses, like people, change and grow and get made over. At least the lucky ones. Others just run down, and that’s sad to see. When it’s a good house to begin with, the best policy is to improve and enhance but not to radically alter. A house ought to take on some aspects of the owners, reflecting their tastes, but not transitory trends. Owners must also respect the integrity of the structure. After all, houses should endure for generations.

Architecture: Authentic and charming Carpenter Gothic. The front façade, with its first floor bay, second floor splayed roof overhanging the windows, third floor pointed arched windows, and gingerbread trim on the eaves, is pure gothic heaven.

Site: A nicely landscaped two acres with pool on the Montauk Highway in Bridgehampton.

The inside word: It’s the kind of house that stays in your mind. We’ve admired it over the years for the architecture, the colors, and the name “Rose Hall.” The soft rose color of the siding with cool grey-green trim is the successor (if we recall correctly) to stronger shades of pink and red. It’s a fascinating architectural pedigree. Offered at $2.5 million.

Delicacy and fluidity in a farmhouse, nice to see; ravishing: dramatic night lighting, jazzy music, expensive baubles; colonnaded first floor porches; avoiding a hodgepodge of clichés

A petit something in search of a chateau; subdued and understated but also cogent and charismatic; bringing a centuries old beauty up to date; it’s just a house, not a status symbol