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A traditional but testosterone loaded residence; 70s modern where that architecture is in the closet; retro country club look that we like; straightforward and not for the Prada crowd

Trophy Collecting

Certain houses, like expensive cars and gentlemen’s toys, are evident in their intentions. They want to exhilarate and dazzle. The casual visitor may admire the owner’s good taste and good fortune—or wonder what in the world he might be compensating for.

Architecture: James Bond gone traditional in a testosterone-loaded residence. The original 1840 house, vaguely Greek revival, seems to have detonated in all directions in a brash, eclectic and teasing way. It’s oddly seductive.

Site: Lumber Lane in Bridgehampton, a lovely if busy street of fine old homes. Once again we see an estate quality home edging into a formerly unpretentious but respectable neighborhood.

The inside word: We like the boldness of this house. Yes, it’s over the top in size (6,300 square feet), price ($4,300,000) and amenities (just name it, it’s there). We see a perfect match in some strong-willed, trophy-collecting buyer.

Outside the Box

Can the seventies have come full circle? Already? We’re used to barely retro looks on fashion runways with revivals lasting ten minutes—but architecture is a more serious business. This 1973 house proves how exciting it can be thinking outside of the shingled box.

Architecture: At thirty years old this house is the antithesis of current fashions in homebuilding in the Hamptons—and all the more remarkable for demonstrating how unimaginative and formulaic much of our new construction has become. It’s a dynamic and innovative composition that remains spirited. Interesting architecture, we see, is not subject to fads.

Site: Further Lane, the top tier in East Hampton real estate, where contemporary architecture is still slightly in the closet.

The inside word: Brokers shouldn’t even waste their time showing this to buyers with their hearts set on rambling traditionals. They will most likely perceive the structure as a malformed doughnut. It’s takes a more adventurous taste to appreciate this large, vital and effervescent residence. It also takes $5,200,000.

Country Club Calm

When does a house go from being generously proportioned to being, well, tubby and out of shape? What is the right amount of space and detailing and what is overload? These are relevant question in a place and time of excess.

Architecture: Going against the tide, this sprawling six thousand square foot house is surprisingly understated—at least on the exterior. Federal details and the New England added-on look suggest roots in a laid back part of Fairfield County rather than a more aggressive Hamptons statement.

Site: Ideally we’d like to see this on several acres, but the richly landscaped acre and a half in the heart of the Water Mill estate area works well enough.

The inside word: Quite possibly this spread-out, highly decorated residence will remind you of your parents’ country club—but that might not be such a bad association. Tasteful in a mature, non-trendy way. Luxe calme et volupté. And if only you had that all that quiet service again. There’s another big difference: you signed and they paid for it all. This time you sign and you pay $3,900,000.

Safe Harbor

Billy Joel has been rumored to be interested in every substantial bayfront property on the East End, and we’ve been following his moves. We know he tried to buy a certain waterfront estate on Three Mile Harbor. The wealthy owner, who has had the property for many years, was not interested in selling the entire parcel, but he has now decided to offer the guesthouse with four acres for $5,000,000.

Architecture: A New England style Cape, shingled, weathered and straightforward. The kind of architecture than once defined the area. It’s not going to impress the crowd that shops at Prada. But let’s remember that a house like this in its contextually right location does not come with an expiration date.

Site: Four acres with knockout views looking west across Three Mile Harbor in The Springs.

The inside word: If Three Mile Harbor were in the South of France, or even south of the highway, people would assault it with their checkbooks as weapons. We detect some changes of late, a growing appreciation for this particular part of the Hamptons. Our advice to a potential buyer: forget the psychological baggage and pack your slicker for carefree days of sailing.

An overview of real estate at midseason: the priciest deals, the headliners involved, the prattle, chatter and buzz, the big agency secrets no one blabs about and you won’t see anywhere else but here

House OK, location deciding factor; dressed up and strutting its stuff; a neo-Victorian capable of serious retinal damage; and the furthest in on Further Lane