The House: The Not So Boring History of Housing in the Hamptons

On the day the settlers arrived on the East End in the 1600s, they were told how to build homes for themselves by the friendly Shinnecock and Montauk Indians who met them.

You dig a deep circular hole, and around the circle you arrange small supple trees that can be bent to create a dome with an open hole at the top, so when you build a fire inside during the hard, cold winter, the smoke will go straight up and out. Large animal skins can be roped onto the outside of the trees to keep the wind and rain out. The fire will keep you warm.

The settlers were grateful for the idea, and they got through the winter that way, with the dome up above. But the next spring, they chopped down trees into logs and, using wood pegs for nails, made houses like the ones they’d lived occupied in Lynn, Massachusetts, where they had sailed from. Rectangular, with a wood plank floor and a peaked slanted roof with two rooms just below, they called them saltboxes. The Halsey House has survived until today in Southampton, the “Home Sweet Home” in East Hampton.

For the next 200 years, the Indians lived in the woods their way, and the settlers built farmhouses, churches, meeting houses and assembled their saltboxes in neat little rows on what they called “Main Street.” They fished, farmed, sold dry goods, went to church, milked their cows. They were taught by the Shinnecocks how to harpoon whales close to shore, then how to haul them onto the beach.

The houses the settlers lived in were for the most part variations on the saltbox, with an occasional rich man—from farming or whaling—building a larger house, often as not, with columns out front in the Greek Revival style. They might have eight rooms—parlor, living room, dining room, kitchen, four bedrooms above. Outhouse. Seaweed was used as insulation. That was a rich man’s house back then.

At the end of those 200 years, the railroad pushed through to the East End, which meant by hook or by crook they would find ways to get rights-of-way through the Indian land, and while they were at it, confine the Indians further into the woods. Into this situation, by train from New York, came the first groups of superrich and their families—tycoons, they were called—who also built large eight-room mansions, some even larger, to found what we today call the “Summer Colony.” Oddly, their summer mansions, assembled largely in Quogue, Southampton and East Hampton, were largely unheated, uninsulated, uncomfortable and barely electrified. Some didn’t even have hot running water.

For many of the rich of New York, going out to the Hamptons was like going camping. Enjoy the bracing healthy air for the summer. So much better than New York. Get under quilts for those summer nights, if you like. The men would come out on the trains for the weekend, the wives and children the whole summer. It was roughing it. But there was the beach.

Also coming out here on the new railroad were middle-class people buying small parcels of land near or at the ocean and building on them tiny beach shacks. These were for the growing group of working men and women who now lived in the Bronx, Queens or Brooklyn. Many were avid fishermen. The land was cheap, the shacks or cabins were often constructed by the men themselves, and like a miniature copy of the filthy rich, the women and children would live out here by the ocean all summer and their menfolk would come out weekends to join them for early morning fishing and afternoon barbecue.

Notably, these modest beach houses went up on Dune Road in Westhampton Beach and the Quogues, in Hampton Bays and Noyac and the end of North Sea. The children and grandchildren of these people remember these places fondly. Sand in your toes, starfish and crabs at your feet, fish caught in the ocean or bay for dinner over a fire.

The well-to-do local people continued to live in their large, insulated homes but none of them were welcome into the “Summer Colony” society. Those in society were organized in the community’s annual Blue Book, which gave the name, address and education of those at the listed addressees. The book got updated every year. Locals not welcome.

Meanwhile, the merchants, professional people, lawyers and judges began to build mid-sized houses, while the working class—the local Bonackers (fishermen and clammers)—lived in still smaller houses. Tourists came but did not build houses. They rented space in rooming houses, then went home after a day or two.

This was the situation I came into when I arrived as a teenager to live out here in 1955. There was an odd tension between the Summer Society and the well-to-do locals. The locals, claiming “I came over on the Mayflower” status, wanted invitations to the Summer Society. But the Summer Society did not jump at the opportunity. Meanwhile, the working people—my dad was a pharmacist who bought a drug store in Montauk—would be denied entry into either society. But my dad did build us a nice house.

But something else was happening in housing about the time I arrived. After World War II ended, in 1945, artists, intellectuals, poets, movie stars and writers began to move out into the Hamptons, often taking residence in shacks on the beach or in quiet secluded areas, or, if more successful, something entirely new—small new homes designed by modern architects. These homes, often with flat roofs, curving walls and sliders leading out to a deck, were something new here. The homes, still relatively small, were “statements,” pieces of art themselves, often reviewed in The New York Times Sunday magazine section. In any case, the intelligentsia claimed their little patches.

It might seem odd today, but back in the 1950s and 1960s, the fear was that all this would be overrun by suburbia. The developers had chewed up farms and built out suburbia as far as Bay Shore and Port Jefferson. There seemed no stopping them. They’d buy up our homes and build new Massapequas. Ruin this beautiful place. Nobody imagined we would someday be a world-class resort.

Beginning around 1980, massive wood-shingled summer homes began to appear. They’d be 10 bedrooms and 12 baths, with obligatory swimming pools and tennis courts. Some came about by taking over some of the homes in the Summer Colony…and then enlarging them. Many were built by celebrities or those in the financial world. And they had all the conveniences imaginable. Farms were purchased and the land broken up into five-acre parcels for these new homes. The sites for them soon ran out, however, and as a result, the prices for such homes, now called McMansions, went through the roof.

Now McMansions became “investments” that you could grandly live in and then, down the road, sell for more than you paid. When the prices for such properties tipped into the millions and tens of millions, it soon became clear that there would have to be teardowns, and everything was on the table, even the summer mansions.

Today, McMansions are the dominant feature in much of the Hamptons, almost all wood-shingle and pitched-roof reminders of the old saltbox or Summer Colony homes, and almost all boxed in by hedgerows. Have they really not been there forever? Fortunately, as the Hamptons became “The Hamptons,” a retreat for the superrich, a very large part of its history, views over farm field and classic New England downtowns, has been saved—due to a wonderful 2% transfer tax on most real estate transactions in all our communities. The money, totaling more than a billion during its first 10 years, has been used to buy open spaces at current prices to become trails, farms, parks, preserves and wild overgrown public lands. Some are even on the beach.

Meanwhile, a majority of the smaller homes remain. There seems to be room for everybody. And that’s the story of the homes in the Hamptons, from the tree saplings to the McMansions to the world record Rennert residential property—which is a home for Ira Rennert, his wife, Ingeborg, and their three children, built on a former 63-acre oceanfront potato field in Sagaponack and measuring out at 110,000 square feet of private residence. Among the many buildings features, Forbes and others have reported, are 29 bedrooms, 39 bathrooms, a dozen chimneys, a formal dining room the size of a basketball court, a bowling alley, two squash courts, two tennis courts, a play house for children, a theater, guardhouse and a $150,000 hot tub. It took eight years to build.

Almost unparalleled for a private home in America, the former farm field it sits on has now been beautifully re-forested with thousands of trees, and so the general public gets only a few glimpses of any of it. Or, of course, you can get invited. If you are, you will be met at the front gate on Daniels Lane by a gatekeeper.