Realty Digest

The Upper West Side was settled by Dutch immigrants in the early and mid-seventeenth century, though not without resistance from the Munsee Indians living on the north end of the island of Manhattan. Warfare with and raids by the Munsees temporarily ended the northward expansion of the Dutch settlers in the 1650s, leaving them with a stretch of land north of the city known as Bloemendal.

Mainly farms and rolling countryside, Bloomingdale was a large producer of tobacco at the beginning of the eighteenth century (but not a department store). In 1703, Bloomingdale Road - later to become the Boulevard, and even later to become Broadway - was built to handle the traffic required by the increasing commerce. The road originated at what is now 23rd Street and stretched to 114th Street. By the late eighteenth century, many wealthy merchants had country estates in the relative isolation and wilderness of Bloomingdale, and fine homes and farms dotted the area.

The West End of the early nineteenth century was composed of small, distinct villages, which existed independently of each other. The wealthy (though rapidly becoming less "country") estates continued to multiply, elegant mansions competing with the rocky landscape. Despite the gridding and numbering of the streets in 1811, landholdings and natural obstructions kept this innovation largely theoretical until the end of the century. The 1853 creation and construction of Central Park displaced residents of the site, changing the economic face of the West End. As squatters and lower-income tenants were forced to abandon the park, many simply moved west, building small shacks and lean-tos. Every year the growing population brought the suburb closer to the big city, and by the end of the Civil War, the area once named Bloemendal, or "valley of flowers," was assimilated into New York City.

Despite its increasingly metropolitan feel, the West End remained largely underdeveloped throughout the nineteenth century. The projects that were undertaken - the improvement and widening of Bloomingdale Road and its rebirth as the Boulevard, the laying of new sewage systems, and the extension of the elevated railroad up the West Side by way of Ninth Avenue - appealed to forward-looking land buyers and developers, who nonetheless remained cautious.

Apartment buildings were, in many ways, the key to the successful development or "gentrification" of the area. Throughout the late nineteenth century, high rises shot up on the West End, as real estate developers invested in such grand projects as the Dakota and the San Remo. The avenues began to acquire their distinct characters: Columbus offered commerce; Amsterdam sported low rent housing and small shops; Riverside Drive (opened in 1880), an alternately elegant and seedy residential park-fronted way; and West End, a quiet residential street.

The Boulevard hosted an odd collection of hotels and vacant lots; many of these belonged to developers who continued to await an economic boom that would raise the value of their property and merit construction on a grand scale. Apartment housing pushed out the home-owner oriented row housing, which had dominated the building trends of the West End for half a century, and began to form the landscape of the Upper West Side that exists today.

Another addition to the modern New York cityscape was the subway system - the first in the country - which opened in 1904. It revolutionized public transportation and shoved the rickety "el" into obscurity; the elevated tracks were nonetheless left standing until 1940. Improved access enhanced the appeal of the Upper West Side, and as the nineteenth century came to a close apartment buildings proliferated, citifying the once rural West End.

In the 1890s Columbia University relocated from the East Side to Morningside Heights, taking over the grounds of the Bloomingdale Lunatic Asylum. Part of a rising intellectual/artistic trend on the Upper West Side, Columbia contributed to the already active cultural life. The artists and academics shared the neighborhood with the equally lively mob, which played and fought its flashy way through the early decades of the twentieth century. The roaring 20s found Riverside and West End Avenue still wealthy, but Broadway and areas east were seedier, with lower middle class families living in neglected old buildings. Development and construction ceased from the early thirties through the early eighties, and the Upper West Side's popularity and social attractiveness waned, making it an undesirable address.

Partially because of its racial, ethnic and economic diversity, the Upper West Side has retained a liberal constituency and a bohemian attitude. Major urban renewal, starting in the mid-'50s under Robert Moses, was the first step in the revival of the Upper West Side; in particular, furious debate centered on the slum clearance undertaken to make way for Lincoln Center in 1959. Despite its unpopularity throughout the'70s, the Upper West Side maintained a sense of community, attracting artists, writers and young families with its relatively low rents and neighborhood feel. The wealth of the '80s renewed the area, raising rents and drawing yuppies and their accompanying incomes; this influx prompted renovation of the grand old buildings of the earlier era.

Still seen as more intellectual and less wealthy than the East Side, the Upper West Side is, however, once again experiencing an inundation of young affluent 30-somethings, as the available apartments in New York began to disappear faster than they appeared on the market. Gentrification has wiped out many of the small businesses that once made the Upper West Side distinctive, but holdouts remain, and you can still find everything from good bagel shops to great bookstores and competent shoemakers.

Here is a small sampling of Upper West Side properties currently on the market: