A region composed of squatters' shacks, leveled forests, and graveyards might seem an unlikely birthplace for the Dakota, one of the Upper West Side's most luxurious addresses, but to a maverick businessman like Edward S. Clark, the head of Singer Sewing Machine Co., such a desolate locale was fertile breeding ground for the birth of a legend.

In the late 19th Century, the area destined to become the Upper West Side bore the sarcastic moniker Dakota because of its distance from the bustling urban center farther downtown. Locals said it was so far north, it might as well be part of the Dakota Territory, in which General George Armstrong Custer and his troops had recently met their demise. Clark's colleagues anticipated a financial massacre when the wealthy lawyer - known for pursuing unconventional business directions - tried to lure tenants into a building situated in such a largely undeveloped area.

In addition to that was the stigma associated with apartment life, which increased the likelihood of Clark's failure. "In the 1870s, when the Dakota project got started, "˜nice' people - respectable, upper-middle-class folk - had houses," says Peter Salwen, author and president-elect of the Society for New York City History (SNYCH) in Manhattan. "Nonetheless, Clark remained optimistic."

The entrepreneur's challenge, Salwen elaborates, was to offer tenants "the amenities, the style, and the sense of seclusion they expected. You had to somehow compensate for the fact that the public areas - the parlors and the dining rooms - were on the same floor as the bedrooms, which was rather risqué." He says such buildings were referred to as "French Flats," which lent them a disreputable air often associated with apartments. Salwen adds that a tenement - which, under the law, the Dakota qualified as - was associated with the lower orders of society.

In order to "get his feet wet" and explore the area's real estate potential, Salwen explains, Clark first built a row of brownstones from the north side of West 73rd Street in Central Park to Columbus Avenue, which successfully attracted lower class rental tenants. After that, he developed the block-long, 200-by-200-foot Dakota with a young, still-unknown architect named Henry Hardenbergh, whose later credits included the separate Waldorf and Astoria hotels, the Plaza Hotel and the Art Students League building on West 57th Street.

The buff-colored, fortress-like building, with its brewery-brick Victorian, neo-Gothic eclectic façade, towers ten stories high over West 72nd Street with a mansard roof and bay and octagonal windows complete with niches, balconies and balustrades. Elaborate terra-cotta spandrels, panels and heavy cornices adorn three sides of the building; the fourth side is made of red brick. The apartments - which currently total 103 from an original 65 suites and 623 rooms in all - can measure up to 41 feet in length with 14-foot ceilings. The floors were originally made of oak and cherry. The apartment house was built around a courtyard that leads to separate lobbies and passenger elevators. "It's so rich in detail," says Patricia Burnham, president of P.S. Burnham Inc., a Manhattan-based real estate firm specializing in luxury high-end property. "I've never seen anything like it. It has great presence, even when you pull up."

"[Hardenbergh] gave the building a tremendous presence and style, a European look with a three-story-high roof," Salwen says. Clark also gave his building a name that was an ironic reference to his colleagues' verbal jabs. He actually did more than just adopt the name - he decorated the building accordingly. Clark put a terra-cotta portrait of a Native American chief in the medallion over the high, arched entrance of the building on 72nd Street, and decorated the main dining room with sheaves of maize and other native-inspired decorations.

Salwen points out that although "the building was a rather majestic enterprise overlooking Central Park "¦ it was on the West Side." Thus the location, already alienated from Manhattan's urban hub, became an even larger hurdle to overcome. "In those days, people of fashion really did not live on the West Side," Salwen notes. Clark saw that as an untapped opportunity rather than a liability, however. "There was a lot of talk about [migration into the area] maybe starting to happen sometime soon," explains Salwen.

At the time, the area occupied by the Dakota comprised little more than the traces of a small village and large estates left over from earlier times that had been converted to roadhouses. Noxious, property-cheapening enterprises like ashworks and cemeteries were among the only businesses that could be found in the remote hinterlands of Manhattan. The opening of Central Park forced large groups of poor people and immigrants to relocate, creating squatter villages and shantytowns, which in turn further devalued the region. But, according to Salwen, Clark realized that Central Park had been created to draw people to the West Side, which "everybody had been saying for years was going to be a great place to dwell, a great place to build a nice, large house with plenty of land around it."

In 1879 - the year Clark and Hardenbergh began to work on the Dakota - the advent of the Third Avenue elevated railroad (the second major development in the area following the opening of the first wing of the Museum of Natural History) seemed to poise the area for quick development. Although Clark's sudden death prevented him from seeing the Dakota's completion four years later, his vision came to fruition on opening day, by which time every apartment was rented.

The Dakota, like its surrounding neighborhood, attracted a certain kind of person. "The Dakota has very unique apartments, and it attracts a very, very specific buyer," Burnham confirms. "Certainly not someone who's going to go to a modern, sleek, glass high rise. It's so unique and one of a kind that if that's what someone's looking for, they will go specifically there because that's what they want to buy. You wouldn't be going to Trump Tower and Dakota all in the same breath. So that's not for the person who's looking for a two-bedroom condominium. That's a totally different market." Apartment prices vary, she says. "It depends on the size. If it's a large one facing the park it [goes for a different price] than a small one without a view."

Many of the Dakota's original tenants had aspirations to move to the East Side. Those that did not developed a defensive attitude about their address that persists today. Yet whether they were social climbers or not, the clientele was upscale and artistic from the start. "It attracts people from the arts," says Burnham. "Always has. More people in that industry prefer [a building like the Dakota] than the modern high rise. That's why there are so many famous people there."

Among the building's first occupants were piano manufacturer Theodor Steinway and his friend, music publisher Gustave Schirmer, whose guests included Mark Twain, William Dean Howells, Herman Melville and Peter Tchaikovsky. Movie stars began moving in during the 1930s, the first of whom was Boris Karloff. Later celebrity tenants included Judy Garland, Lauren Bacall, and Leonard Bernstein. Former Beatle John Lennon and his wife, Yoko Ono, also claimed residence there until Lennon was shot outside the building in December 1980. The apartment house even served as the setting of the film Rosemary's Baby in 1968.

The end of Clark's life marked the beginning of a new era of architectural and real estate development in Manhattan. The visionary's contemporaries and descendents who continued to build in the burgeoning area around the Dakota included Clark's daughter-in-law, who developed some of the last roadhouses - some of which still can be found on West 74th Street. According to Salwen, "Once [Clark and his partners] had shown it could be done, a whole crowd of enthusiastic developers came into the area."

Development around the Dakota was soon moving at a breakneck pace - a pace that continues to this very day, with residential buildings, retail shops, and restaurants springing up like mushrooms.

Nobody touches the Dakota, however. "It's been a well-known address for years," says Burnham. "Almost everybody has retained the original detail. Very few [apartments] have been modernized. They're all pretty much just restored."

The same can be said for the Dakota's nearest neighbors, many of which remain largely unchanged from their heyday. During the 1970s, developers discovered other buildings - mostly nearby brownstones that had been cut up to create smaller apartments - that remained largely untouched beneath the minor renovations made decades ago. "People flocked into the West Side to restore the old architecture," says Salwen, adding that "by and large, the best and the most cherished buildings were built between the time of the Dakota and the '20s: The Majestic, The San Remo, the El Dorado."

While the Dakota itself has remained relatively unchanged since its debut, the grand building's environs have undergone successive waves of development and evolution. Full-bore gentrification over the years has eradicated any hint of the Upper West Side's once-remoteness, but for all the development and burgeoning cost of living, the Dakota's turf still has a rangier, more intellectual cachet than its old-moneyed, blue-blooded counterpart across the park. According to Salwen, the East Side "always remained a little more cachet than the West Side." He describes the social divide between the two as being so vast at one point as to necessitate two separate society columns in the local papers.

The era of warring social registers is long over now, and, says Salwen, "The Dakota has held its value extremely well." The numbers commanded by apartments for sale around the building attest to its enduring appeal. While specific asking prices for apartments in the Dakota itself are divulged upon request by serious buyers, last year prices for studio apartments in the low 70's on Central Park ran between $170,000 and $400,000. Two-bedrooms could cost between $700,000 and $1.5 million, and "classic sixes" with views of the park were let go for between $2 million and $5 million. Townhouses were on the market for upwards of $7 million. Clearly, the West Side residents lucky enough to live within shouting distance of the grand old Dakota understand the beauty - and value - of Edward Clark's century-old dream.