If you’ve never heard of Waccabuc—a sleepy, sylvan Westchester hamlet just off the Connecticut border, near more-manicured and better-known New York towns like Bedford and Pound Ridge—you’re not alone.

“People ask my wife and me where we are going this summer, and we just smile and say, ‘Nowhere,’ ” retired publisher Warren Schloat says. “To us, this is kind of like we died and went to heaven, 50 miles from New York City.”

Unknown, and exclusive, is just how many of Waccabuc’s residents like it.

The discreet little burg is home to a collection of privacy-loving C.E.O.’s and bright stars in other firmaments. Residents include chef-restaurateur Jean-Georges Vongerichten; William Lauder, president and C.E.O. of the cosmetic giant started by his grandmother Estée; and Stan O’Neal, chairman of Merrill Lynch. Former S.E.C. chairman Bill Donaldson and his family are also one of roughly 300 clans that call Waccabuc home for at least part of the week, as is former Fed chairman Bill McDonough. Alfred DelBello, onetime lieutenant governor of New York, and his wife, Dee, C.E.O. and publisher of the Westchester County Business Journal, tend a herd of alpaca on a Waccabuc farm when they aren’t out raising money for Democratic causes.

And though Martha Stewart doesn’t live in Waccabuc, she knows it well and wants to capitalize on its clubby yet relaxed character. In recent months, after meeting with heated resistance when she tried to trademark the name of nearby Katonah for a discount-lawn-furniture line, Stewart turned to Waccabuc as an alternative.

Fran and Barry Weissler, independent Broadway producers with six Tony Awards to their credit, had never heard of Waccabuc before they bought their 22-acre property seven years ago. Now they spend every weekend there; she arrives on Friday and he on Saturday.

“The sheer beauty of it and the peace of it are very calming,” says Fran, whose company, National Artists Management, has produced Chicago, Grease, and Annie Get Your Gun.

Waccabuc has attracted the very wealthy since the 18th century. Back then, it was a one-family town, populated mostly by the Meads, who made their fortune in real estate and railroad development, says Maureen Koehl, historian of the town of Lewisboro. They remained the dominant clan until about the 1960s, when family members began selling off the farms and cottages that lined Mead Street. Wealthy refugees from New York and elsewhere were only too happy to buy into the genteel lifestyle that had thrived quietly in Waccabuc for centuries.

Today, Waccabuc has Democrats and more than a few Republicans, but the town is not so much conservative as fiercely conservation minded. Zoning regulations are strict and bend only in the direction of becoming more strict. “Special character zones,” the local equivalent of landmarking, restrict the type and scope of renovations that can be made to properties. In most areas, lots must be a minimum of two acres; on Mead Street, the postcard-pretty main drag, the minimum size for a lot is four acres, and the prices are accordingly high. Four years ago, residents banded with the state, city, and county to buy 100 acres of Waccabuc land to be kept as a conservation area, says Susan Mead Henry, a sixth-generation Waccabuc resident whose family settled the town and who is active in local land trusts.

Some of Waccabuc’s roads remain unpaved—not, of course, because the town can’t afford the asphalt. Some residents are happy to endure rough drives if it means discouraging outsiders from cruising through town. And Lake Waccabuc, with adjoining lakes Oscaleta and Rippowam, is a haven for boating, fishing, and swimming in summer—for the lucky few who have permission to use it. Thirty-five acres of waterfront are part of a conservation area, but there is no public beach. Access can come via direct ownership of lakefront property, through inclusion in a neighborhood association, or with membership in the Waccabuc Country Club, whose main house, a crisp white clapboard structure on Mead Street, serves as canteen, local bar, guesthouse, clubhouse, day camp, and casual retreat.

Set along Mead Street or off in the woods, Waccabuc’s houses run from massive contemporary structures with pools in the middle of sprawling compounds to 1950s suburban-style homes. Also in the mix are some 18th- and 19th-century clapboard farmhouses and early 20th-century cottages that hark back to a more genteel era. In Waccabuc, there is little turnover. According to real estate broker Ken Sobel, only 12 houses in Waccabuc have sold during the past year. “They ranged in price from $600,000 for a teardown to $4.7 million for a beautiful colonial on Mead Street, with six bedrooms and seven baths,” he says.

On the market currently is a five-bedroom, 4½-bath contemporary selling for $2.14 million. It has a pool, a three-car garage with an office, a garden, and woodlands, and it is listed by Sobel. The priciest property for sale at the moment is Treetops Lodge, a two-level, 3,800-square-foot wooden contemporary with a pool and tennis courts on 17 acres, owned by a Manhattan attorney. It is priced at $4.25 million, according to Susan Stillman, exclusive broker with Houlihan Lawrence Real Estate. For smaller budgets, $1 million will buy you a home in Hunt Farms, a late-1980s cluster-zoned development where each house sits on half an acre of landscaped property.

Lakefront houses rarely come up for sale, and when they do, there’s a line of people wanting to buy. According to a broker, actress Blythe Danner sold her custom-built waterfront stone cottage on 29 acres for $6 million two years ago. Last summer, a three-bedroom, two-bath contemporary sold for $1.3 million, Stillman says. There is not one waterfront property among the 16 active listings in Waccabuc.

Then again, 16 is a higher than usual inventory for Waccabuc, and houses are lingering on the market for up to 200 days instead of between 150 and 160 days, which had been the norm. According to Sobel, a drop in prices might be in the cards. “Prices rose so steeply over a short period of time that even the most optimistic buyers had trouble stepping over the threshold,” he says.