Despite the numerous insurgencies mounted by Gramercy keyholder O. Aldon James, the bow-tied, pink-bespectacled eccentric president of the National Arts Club (most famously a civil-rights lawsuit set in motion when a park trustee called the police on 40 mostly minority students from neighboring Washington Irving High School, who Mr. James had brought in for a field trip), the forbidden Eden is unlikely to be democratized anytime soon, remaining, like many beautiful things in Manhattan, rich and mostly empty.

VIEW SLIDESHOW > THE STREET WHERE YOU LIVE

Take the former Bell Labs factory, converted in the 1960s into the world's largest subsidized housing complex for artists. Westbeth's artists pay a fraction of the rents of their increasingly well-moneyed neighbors. But as with any paradise, few want to leave: The community has considered hiring a social worker to address the needs of its aging population. And for artists not yet Social Security eligible, by the time they get in, they may be: The waiting list for admission is up to 10 years long.

Across the street, meanwhile, another vanquished factory made way for an entirely different brand of utopia. The Superior Ink luxury condos and flawlessly manicured Stepford townhouses, selling for millions, come equipped with Hudson River views and valet service for your bike.

SEE THE SLIDESHOW HERE.

If the project of Manhattan is a chaotic scramble upward, Battery Park City is a slightly incongruous footnote lingering at the margins, a pristine planned development plopped on a 92-acre landfill. A developer's dream-no malting brownstones, no cumbersome rent regulations-the 1960s extension of the city's boundaries was helped in part by the ground dug up to build the World Trade Center.

Decades later, in the wake of Sept. 11, state-issued Liberty Bonds financed a wealth of gleaming, eco-chic development, securing Battery Park City's position as the No. 1 neighborhood for environmentally conscious yacht owners.

MOVE ALONG RIVER TERRACE > VIEW THE SLIDESHOW

When the Whitney, chronically in want of space and funds, finally makes its leap downtown, like any longtime Upper East Sider in less lofty altitudes, the museum will have some things to get used to, not least the insouciant High Line sunbathers and gritty-chic meatpacking clubsters for neighbors. But Whitney Number One-finally unyoked from oft-thwarted dreams of an uptown expansion and now in the process of selling its surrounding brownstones-may also be coming into some new neighbors.

Residents of East 75th Street have long paid fortunes for views that include the inverted gray ziggurat, and the Whitney's soon-to-be-former property will undoubtedly shake up the block's high-stakes real estate roulette, where the likes of Barbara Walters and Mike Nichols have cast their hand.

VIEW SLIDESHOW> THE STREET WHERE YOU LIVE: BUH-BYE, WHITNEY!

Like the distilled, airy boutiques (Belhaus, United Nude) popping up on Bond, developers became curators of design for the sumptuously rich. The Herzog & de Meuron-designed 40 Bond Street is a dazzler of green glass and cast-aluminum graffiti rising up and tangling like wisteria vines. Two doors down is Deborah Berke's pared-down vision of modern revival.

In the future, we'll visit Bond and recall, for better or worse, this decade's delirious architecture, its equally delirious prices and, above all, its genre of choice, the luxury condominium.

VIEW SLIDESHOW > THE STREET WHERE YOU LIVE: BLING ON BOND

Chelsea hides. At least, it used to. Edgy new galleries secreted in anonymous factory brick, industrial-kitsch nightclubs skulking in basements-that was the old Chelsea.

What you catch glimpses of now is a Chelsea that surfaces like a mirage of glass, a shimmery, see-though world more suggestive than transparent, before dissolving back into brick. It's true of the whole city, this turning, building by building, into glass, but nowhere does the old-an industrial seaport-clash so visibly with the new. On West 16th Street, artisan bread loaves rise in old factory buildings and vitreous apartments turn lives into nonstop installations.

Above it all stretches the High Line, one long horizon of a stage, catwalk, and high-rise bleacher from which the city's exhibitionist compulsions-the unambiguously sheer Standard Hotel, for instance-are enacted.

Forget the galleries, the real exhibits are everywhere, and just as costly.

VIEW SLIDESHOW > CHELSEA, LATELY

The disreputable ghosts of Boweries past-the gangsters, vagabonds and punk rockers who saw the street shape—shift over the past century and a half—likely have more in common with each other than with the citizens of the Bowery lately. The last few years' barrage of the new (new luxury condos, new cuisine, the boxy metal lines of the New Museum) is revealed in the worlds traversed from block to block: One cross street up and you've gone from overcrowded industrial kitchen suppliers to minimalist boutiques displaying Rodarte and Brian Reyes.

But whether it's a designer boutique's glass-enshrined relics of CBGB or a trendy new club's flophouse aesthetic, the old Bowery hasn't been forgotten altogether—it's reassembled into industrial-chic window-dressing for the new.

VIEW SLIDESHOW > TOUR THE BOWERY

Maybe because it's been dragged through the verses of so many folk songs, MacDougal Street has an immediate, familiar force to it—a preformed memory, a kind of Greenwich Village reenactment. The scene may be self-romanticizing, the costumes slightly campy, but when you round the corner and it whirs to life, a perpetual carnival just for you, you can't help but go a little weak-kneed. It's here, deep in the Village's cramped arteries, that Eugene O'Neill saw his early dramas spark to life, Dylan Thomas took his last drink (or 13) and Basquiat's spray-paint proclamations invented SAMO, then declared him dead. It's the combustible quarter where the city once pushed its artists, anarchists and alcoholics, its dispossessed and discontented, a place where even the streets play renegade to the imperious grid, Fourth Street overrunning 10th.

In the early 1960s, a property owner around MacDougal could nail up a sign that said "Folk Music" and be in the thriving coffeehouse business. Though today's residents are more likely to have starred in the glossy biopic version of the Village's freewheeling days, the street is still noisy with ghosts, their stillborn plays and lost guttural ballads. — Emily Geminder

SLIDESHOW > TOUR MACDOUGAL STREET, PAST AND PRESENT

For the real believers, tales of a subterranean New York have either at least a germ of truth (mole people, alligators in the sewers) or have yet to be proven (Masonic tunnels, government chambers beneath the Empire State Building). But to those of its denizens who have an enduring preoccupation with all things underground, the city offers up at least one incontrovertible concession: the Doyers Street tunnel.

Chinatown's Doyers Street, that narrow little hyphen between Pell and the Bowery, witnessed most of the ambushing, stabbing, shooting and general racketeering of the Tong Wars, fought by rival Chinese gangs a century ago. Dense with saloons, opium dens and fan-tan parlors, the Bloody Angle—the moniker given to the 90-degree street in the press—was rumored to conceal trapdoors and secret panels leading down to a network of tunnels. At least one of those tunnels remains: Beneath the old Chinese Opera House, a flight of stairs twists down to a sunken underpass. It snakes indifferently beneath buildings before finally spitting out its cargo at Chatham Square.

Though today its benign shops and linoleum floors—all awash in fluorescent lighting—blot out most of the tunnel's darker associations, it's oddly comforting to know that a onetime nefarious escape route veers unseen beneath the street. — Emily Geminder

SLIDESHOW > TOUR CHINATOWN'S DOYERS STREET