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Windmill architecture, too adventurous now? good taste juiced up; barn interior, modern exterior

Tilting at Windmills

Houses are narratives of the lives of previous owners and past societies, and in most cases the older the house the richer and more evocative the story. History counts in real estate, not just in terms of human interest, but in real value. Ancestry gets the cash register ringing, and smart buyers will pay for that perfect pedigree.

Architecture: “Windmill architecture” is a minor category of late 19th century design, but something so wildly imaginative and romantic and offbeat that none of the solid burghers building in the 21st century would be this adventurous. How conventional we’ve become.

Site: In the historic district of East Hampton, on a private road off Main Street, a splendidly landscaped 3.5 acres with main house, pool, tennis, garage, potting shed and guest house—and that windmill incorporated into it.

The inside word: When Sidney Lumet filmed the movie “Deathtrap” here in 1981, the place was dark and scary, the right setting for a murder. These days it is bright and beckoning, and the setting celebrates life, or more exactly the good life. The last restoration was sensitively done and the taste and quality are impressive. The place is courtly, with lots of glamour and not a bit of glitz. Offered at $16.5 million.

Old Money Talks

We all like old money. It’s gotten so expensive however that it usually takes lots of new money to buy it, at least to buy that old money look in real estate. Is it worth it? It’s hard to match the prestige of owning a true Summer Colony “cottage” in the East Hampton or Southampton estate areas. This newly listed house is the real thing. Built in 1899, it is among the early generation of homes built specifically as vacation houses.

Architecture: The expansive Dutch gambrel frame, thin columns and recessed porch are early shingle-style features. A well planned restoration with the addition of some modern comforts has only improved this house.

Site: A manicured acre with pool, flower gardens and terraces on a quietly posh lane near the ocean. With today’s lifestyles a larger lot would be welcome, but generations of landscaping balance this out.

The inside word: This is conservative good taste juiced up as far as it can go, old money, as edgy, sharp and undaunted as it can get. It’s refined and mature with a dollop of opulence. If you crave tradition and Summer Colony correctness without the fusty old plumbing, move right in. Offered at $7.750 million.

Red Hot and Rural

Old barns converted to residences speak of the romantic, unusual and spacious. Unfortunately, many of them turn out to be awkward, dark, and difficult to divide into discrete spaces. It makes you realize that they may be better suited to housing animals and farm supplies than families and furniture.

Architecture: The clean-lined contemporary exterior contains an 18th century chestnut wood barn. It’s a fine piece of architecture, handsome, tempered and finely balanced, designed by Harry Bates in 1982.

Site: Wooded 1.1 acres in north Water Mill with pool, decks and inviting landscaping.

The inside word: The idea of living in a barn is so attractive—it’s the reality that gets in the way. When does a sagging wall cease to be charming? The combination of barn interior and modern exterior seems to have solved all those problems and resulted in a comfortable and livable space. More than one city dweller with dreams of living in a country barn will be bidding on this property. Offered at $1.750 million.

A house with a well-upholstered soul; Bluff Road, expensive and sought after; luscious, frilly, showy and over the top; a legacy of the whaling trade on Captain’s Row

Christy Brinkley at home in Tower Hill