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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

Correct English

In recent years in the Hamptons a kind of architectural Darwinism has favored the enormous single mansion to the virtual exclusion of other sizes, forms and styles. Whether by natural selection or survival of the fittest, the mammoth single house is the evolutionary leader. But it was not always like this. In the late nineteenth and early twentieth centuries, architects experimented with a number of styles and produced some memorable estates.

Architecture: A definite English sensibility is at work here. A sturdy brick structure with a minimum of fuss and frills connotes a patrician confidence and durability. Age—the house is 108 years old—only enhances this sense.

Site: A house like this requires appropriate surroundings, and the 3.3 acres of lawn and mature specimen trees are exactly right. A walled garden in the English style by noted landscape designer Deborah Nevins, a pool with a pavilion, and additional gardens complete a very pretty outdoor picture on a prestigious Southampton street.

The inside word: A property that was enchanting to begin with has been made absolutely captivating. The controlled and restrained landscape and outdoor amenities perfectly match the restored stateliness of the home. Compared with much of what is around, it’s subdued, harmonious and fastidious. Only the price of $14 million reminds us that in the Hamptons restraint goes only so far.

Playland

You can get guarantees on the appliances, the furnace and the central air anyplace you go. But in the Hamptons and a few other indulgent places properties come with an unwritten but openly understood guarantee that you’ll never be bored. Or at least that only the most doltish and regressive of buyers could fail to be constantly stimulated by the luxuries and material pleasures that come with the deed.

Architecture: A virtual handbook of current shingle style features, forming nice asymmetrical elevations on the exterior and generous and varied spaces on the inside. A 20-foot tall paneled entrance hall is just the start of lots of dramatic rooms.

Site: In the hills on the north side of Water Mill, a gated entry to the five-acre property keeps friends from wandering in and observing any clownish lobs on the tennis court, golf hole or basketball court. Pool, spa and pool house are waiting when you’ve perfected your swing.

The inside word: There is no need to ever slow down. The finished basement has a media room with fireplace, game room, wine cellar and sauna. This is a home with instant gratification hardwired into it along with a 21-zone sound system. It’s a playground where big shots, big wheels, big deals, big cats, bigwigs and big guns can be little boys and girls again. Offered at $5.5 million.

Social Security

There are many social indicators in the Hamptons—the crowd you run around with, the restaurants, parties and places you go, the clothes you wear. But nothing rocks the needle on our social compass as much as the right address. While there are many more right addresses now than there were just a few years ago, the established estate areas continue to be the most elite.

Architecture: Designed by I.H. Green, the architect of the original Maidstone Club, this three-story house is a consummate example of early twentieth century shingle-style. Dormers, porches, irregular rambling shapes without ornament all blend into a masterful composition with a shingle skin covering providing the unity.

Site: Off Georgica Road in the heart of the East Hampton estate section. On 1.3 acres with pool, pool house and apartment above the garage.

The inside word: This house is sublime and statuesque. It expresses a totally American look created a century ago in the seaside resorts of New England and Long Island. The inspiration for much new architecture, an original house like this is equivalent to owning a major piece of art. Offered at $10.8 million.

Tudor Dynasty

In the years from the early 1900s up to World War II, American architects were influenced by the work of the great English architect, Sir Edwin Lutyens. Lutyens designed some of the most distinguished English country houses of the early twentieth century, with a playful respect for classical forms.

Architecture: With gables of varied sizes and proportions and Tudor suggestions, this house is reminiscent of an English house by Lutyens, and given its age—it was built in the 1920s—it is likely the designers had him in mind. Overall it manages to make a very pleasing and cohesive statement.

Site: A very posh two acres in Southampton estate area, with pool, poolhouse, tennis court, three-car garage and luscious grounds.

The inside word: Lots of rooms (eight bedrooms, eleven baths) and lots of comfort make this an extremely appealing house for anyone with $12.5 million to spend. Sure, it’s a lot of money, but this is the top-drawer of Hamptons real estate.

Lasata, the Bouvier family home where Jackie, Lee and Little Edie spent their summers is on the market

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