Late-night funnyman David Letterman has increased the size of his spread in North Salem, N.Y., paying $5 million, according to the New York Post, to purchase a 19.96-acre property that is adjacent to his 88.23-acre estate in the Westchester County town.

The Post's Braden Keil last week reported that Dave has bought the adjacent acreage from graphic artist and illustrator Ivan Chermayeff. Indeed, public records show that Chermayeff and Jane Clark have been longtime owners of the property, at 155 June Road in North Salem. That land is adjacent to Letterman's longtime estate at 193 Baxter Road in North Salem, which he purchased in 1994, also for $5 million. Although Letterman bought the 88.23-acre estate on North Baxter Road in North Salem in 1994, the comic didn't move to the estate until the late 1990s. Longtime Letterman fans will recall that he previously had been a longtime resident of New Canaan, Conn., where he had owned an oblong, eight-room house at 893 North Wilton Road since buying it for $400,000 in 1983. He very quietly sold that 3,925-square-foot house in 2002 for $1.1 million (my column on it at the time in the Chicago Tribune was essentially the first national press coverage of the sale; I've pasted that column below this item, for your perusal).

Letterman owns or rents plenty of other properties around North America, including a ranch near Choteau, Mont.; a place on Martha's Vineyard on Katama Bay View Road in Edgartown, Mass.; and a place in St. Bart's in the Caribbean, according to news accounts and public records.

Back in North Salem, Letterman now has a spread of just over 108 acres. His recent purchase has not yet cleared the public records databases to which we have access. When it does, we'll provide you with any additional color on Letterman's purchase.

And now, the 2002 article on Letterman selling his house in New Canaan:

Chicago Tribune

May 5, 2002 Sunday
CHICAGOLAND FINAL EDITION

Letterman sells longtime home in Connecticut

BYLINE: By Bob Goldsborough. Special to the Tribune

SECTION: REAL ESTATE; ZONE: C; UPPER BRACKET.; Pg. 3

David Letterman has quietly sold his New Canaan, Conn., home of 19 years for $1.1 million.

The late-night funnyman listed his 202-year-old converted barn last year, according to information from New Canaan's Board of Realtors, and though the Realtors would not disclose a listing price, research of the multiple listing service turned up a figure of $1.3 million. Letterman bought the 3,925-square-foot, three-bedroom house, which sits on 2.4 acres, in January 1983 for $400,000, according to public records and Board of Realtors information.

The oblong, eight-room home has a four-car garage, heated pool, spa, tennis court, and a great room with beams, random-width floor boards and a stone fireplace, according to Board of Realtors information.

The home also has a security gate, which Letterman no doubt found necessary to protect himself against the public as well as from several stalkers he encountered in the 1980s and 1990s, including repeated stalker Margaret Ray, who committed suicide in 1998 after seven arrests and multiple imprisonments and institutionalizations for incidents involving the talk-show host's property. From 1988 to 1993, Ray broke into his home several times, visited his property on several other occasions, was once discovered sleeping near his tennis courts, and was once arrested while driving his $80,000 Porsche, according to news accounts.

The sale has drawn virtually no national press coverage. And the extremely private entertainer's representatives were tight-lipped on the sale.

"We don't talk about the listings of our clients, and specifically about [Letterman's] house," said co-listing agent Lydee Conway of Country Living Associates in New Canaan. Tom Keaney of Letterman's Worldwide Pants production company also declined any comment on the sale.

However, two real estate sources in New Canaan confirmed that Letterman had indeed sold the house, which was available for immediate occupancy and therefore presumably long-vacated, because he had officially moved to a six-bedroom, six-fireplace, 8,300-square-foot, two-story house on nearly 89 acres in North Salem, N.Y., which is in the far northeast corner of Westchester County.

The property, which Letterman bought in 1994 for $5 million, according to the New York Times, was originally purchased for "investment purposes," Letterman's spokeswoman told wire services at the time. The estate, which is in the same town as a 20-acre farm owned by New York City Mayor Michael Bloomberg, the home of actor Stanley Tucci and a $3.8 million home that Hillary Clinton considered buying in 1999, also is a short distance away from Letterman's bandleader Paul Shaffer's 4-acre Bedford, N.Y., estate, according to public records.