Fifth Avenue skyline

View of Fifth Avenue from roof of Metropolitan Museum

By Carter B. Horsley

The Upper East Side has been New York City's most prestigious residential district for almost all of the 20th Century, but that reputation is misleading.

Pratesi boutique on Madison Avenue

Boutiques line Madison Avenue including the stainless-steel curved entrance at Pratesi

While it has many impressive residential buildings, architecturally it is not as impressive as the Upper West Side generally. Much of its fame really rests on the ever-changing chic boutique scene on Madison Avenue that dominated the city's "luxury" market after World War II for several decades and still is very vibrant although "trendy" stores began to proliferate in abundance in other areas downtown towards the end of the 20th Century. Perhaps in reaction to the multiplicity of "good" retail locations, retail on Madison Avenue began to change in the late 1990s and the start of the "Millennium" as Armani and DKNY, shown below, started a trend towards bigger, multi-level boutiques.

DKNY boutique on Madison Avenue

New Donna Karan store opened just in time for the Millennium on Madison Avenue, part of a trend towards larger, multi-level retail spaces on the famous boutique boulevard

Despite competition from the Flatiron and SoHo Districts, Madison Avenue is not likely to lose its cachet for finery because of the presence of so many cultural institutions and the proximity of Central Park.

View up Fifth Avenue from 58th Street

The commercial conversion of midtown drove "millionaires" north, up Fifth Avenue along Central Park where they erected a impressive stretch of mansions that become known at the start of the 20th Century as "Millionaire's Row." The boom, which began in the 1890s and lasted through the 1920s, not only filled the lots on Fifth Avenue with sumptuous and sometimes palatial residences but also led less fortunate rich people to built impressive townhouses on the sidestreets as far west generally as Lexington Avenue. The Third Avenue "El," which was not torn down until the 1950s discouraged further "luxury" residential development to the east with the exception of the area around Carl Schurz Park.

Former Smithers Center on East 93rd Street

In 1999, the Spence School bought this major townhouse on 93rd Street between Madison and Park Avenues that was formerly the Smithers Center and before that was once owned by showman Billy Rose

The diversity of townhouse design on the Upper East Side is full of surprises.

One of the grandest mansions is the former Pulitzer home at 11 East 73rd Street, shown below, that has been subdivided, with sensitivity, into apartments.

Former Pulitzer Mansion at 11 East 73rd Street

Former Pulitzer mansion at 11 East 73rd Street was subdivided into apartments

There are few "perfect" blocks on the Upper East Side. There are, however, sections of a few streets that are impressive such as the middle of the south side of 80th Street between Park and Lexington Avenue that has several major townhouses including one, the light-colored facade, that was converted by the Junior League of New York.

Junior League of New York

Some are mini-chateaus with arched windows and tall chimneys like the Fabbri mansion on 62nd Street between Fifth and Madison Avenue, shown below.

Fabbri mansion

One of the largest townhouses is the former Fabbri Mansion on 62nd Street near Fifth Avenue, and two doors away from a modern synagogue to the left

Some are provincial like the white stucco house with garden wall built by Paul Mellon on 70th Street between Park and Lexington Avenues, shown below.

70th Street Between Park and Lexington Avenues

Paul Mellon, the art collector, built the Provincial-style townhouse with garden wall on the north side of 70th Street between Park and Lexington Avenue, a block widely considered one of the finest in the city

Some are modern like the ornate grill facade example, shown below, that was designed by Edward Durell Stone on 64th Street between Park and Lexington Avenues.

Edward Durell Stone-designed townhouse

Edward Durell Stone designed the townhouse with the ornate grill facade at the left on 64th Street between Park and Lexington Avenues several houses to the east of another "modern" townhouse with a black-glass facade

Some of the Upper East Side's most charming houses, however, are not the marble and limestone townhouses, but plain old wooden houses such as the one, shown below, on 93d Street between Lexington and Park Avenues, which has a tall wooden tower at its rear that is visible from 92nd Street.

Wood house on 93rd Street

This wood house on 93rd Street has a tall wood tower at its rear

There are not many of these left. Another pair is one block south on 92nd Street, shown below.

Wood houses on 92nd Street

Two charming wood houses on 92nd Street

Many townhouses were acquired by diplomatic missions and philanthropies and many more were subdivided into apartments.

Many townhouses have been taken over by diplomatic missions or divided into apartments like this row on the south side of 65th Street between Fifth and Madison Avenues

The "El," of course, was a great spur to the residential development of the area with non-luxury housing, a mix of tenements and utilitarian apartment houses that filled most of the rest of the Upper East Side, which is bounded by Fifth Avenue and the East River and 59th and 96th Streets. There were some commercial properties such as the Ruppert Brewery along Third Avenue at 90th Street and some institution properties such as the New York Hospital complex in the 60's along the East River that would be later abutted by Rockefeller University to the south.

The burying in a vast tunnel of the exposed train tracks leading into and out of Grand Central Terminal on Park Avenue soon after the start of the 20th Century led to the rapid development of luxury apartment buildings on that boulevard that has a landscaped median that lead to its name.

While Fifth and Park Avenue were quickly filled with high-quality apartment buildings that were usually about 15 stories tall in compliance with the city's zoning that was enacted in 1916, Madison and Lexington Avenues did not have great park vistas or the formality of Park Avenue and were left unofficially to serve as retail locations to cater to the denizens of the formidable Fifth and Park Avenue addresses.

Former Andrew Carnegie mansion on Fifth Avenue at 91st Street

Andrew Carnegie's home on 91st Street was converted into the National Museum of Design

Although the Metropolitan Museum of Art was founded in 1870, it did not become the sprawling presence it is today overnight. The museum, of course, is the city's foremost cultural asset, but it did not spawn the "Museum Mile" right away.

Metropolitan Museum

The Metropolitan Museum

Henry Clay Frick and Andrew Carnegie, steel barons from Pittsburgh, would erect blockfront mansions with gardens at 70th and 90th Streets, respectively, that would ultimately become major cultural institutions: The Frick Collection and the National Museum of Design of the Smithsonian Institution, respectively. Carnegie's mansion, shown above, in fact lead to the creation of the "Carnegie Hill" neighborhood, that is now among the most desirable in the city because it has many schools and many pre-war buildings with large apartments for families.

The Frick Collection on Fifth Avenue

Henry Clay Frick built this mansion on Fifth Avenue in 1917 and it was converted into a public museum known as The Frick Collection in 1935

The Frick Collection, perhaps the finest museum in terms of the quality of its works of art, in the country despite its relatively small size, shown above, opened to the public in 1935, but the real cultural institution invasion would not come for several more decades. The Depression and World War II changed many things, and many of the great mansions were torn down and redeveloped as apartment buildings, or converted into diplomatic properties, or clubs, and some become cultural institutions such as the National Academy of Design between 89th and 90th Streets.

The Solomon R. Guggenheim Museum on Fifth Avenue at 89th Street

The Solomon R. Guggenheim Museum, designed by Frank Lloyd Wright, on Fifth Avenue is one of the city's, and the world's, most spectacular buildings

In 1959, the Solomon R. Guggenheim Museum designed by Frank Lloyd Wright opened on Fifth Avenue between 88th and 89th Streets and the next decade the Whitney Museum of American Art moved uptown into a major new building designed by Marcel Breuer on Madison Avenue at 75th Street, shown below.

The Whitney Museum on Madison Avenue at 75th Street

The Whitney Museum of American Art, designed by Marcel Breuer, at 75th Street, looking south

Wright's great rotunda and Breuer's powerful cantilevered building with trapezoidal windows are two of the great modern buildings in the city, but despite their architectural brilliance they did not lead to a design revolution in their neighborhoods for the pre-war days of construction excellence and elegance were over and replaced by the utilitarian/cheap era of minimum quality typified by the "white-brick monstrosities" that seemed to sprout everywhere once the "El" was torn down.

The Spence School on 91st Street

Red building in center is the Spence School on 91st Street off Fifth Avenue. The entrance to the former Andrew Carnegie mansion is on the right and the former Otto Kahn mansion is on the left

The white-brick "monstrosities" began with Manhattan House, the huge apartment house developed by the Metropolitan Life Insurance Company that occupied the full block between Third and Second Avenues and 65th and 66th Streets. Designed by Skidmore, Owings & Merrill, the architects also of Lever House, Manhattan House was distinguished by its extensive gardens on the south and its own mini-street and driveways on the north and its huge lobbies with large windows. The building has many balconies and they were white and the mass of the building was modulated with setbacks. The building was too successful and imitators copied its basic formula and look, albeit on smaller scale and often with a gray rather than white brick facade.

Manhattan House on Third Avenue at 66th Street

Manhattan House on 66th Street and Third Avenue looking towards Second Avenue

Manhattan House, shown above, itself was never considered a "monstrosity." Indeed, it heralded the some of the best planning intentions of the modern movement that includes the Bauhaus and the International Style: towers-in-a-park, clean lines, and modern conveniences. Just as Lever House, and soon thereafter the Seagram Building, shook up the corporate world and launched an elegant new architecture style that dominated the world for more than a generation until the reactionary Post-Modernism style took root in the late 1970's and early 1980s, Manhattan House and the "white bricks" were regarded initially as a fresh breath of air in comparison with stodgy old, pre-war buildings whose apartments were designed for staffs of servants and would eventually see many of their large units divided into smaller ones.

The other white-bricks, which dominated the burst of new construction on Third, Second and First Avenues and also invaded many sidestreets, unfortunately were not in landscaped parks and usually were slapdash affairs with no panache. They were bland, banal and bad.

The Upper East Side has many religious institutions, including Temple Emanu-el and the Episocopal Churchof the Heavenly Rest on Fifth Avenue, St. James Episcopal Church on Madison Avenue, the Brick Presbyterian Church on Park Avenue, shown below.

The Brick Presbyterian Church on Park Avenue

The Brick Presbyterian Church on Park Avenue

The Upper East Side has the city's greatest concentration of private schools.

The Marymount School on Fifth Avenue at 84th Street

The Marymount School combined three great mansions on Fifth Avenue at 84th Street across from the Metropolitan Museum of Art at the right

Marymount combined three impressive townhouses on Fifth Avenue at 84th Street, shown above, and the Lycée Français took over several different mansions in different areas including the one shown below on 72nd Street near Fifth Avenue.

Former Lycée Français on 72nd Street

Former Lycée Français on 72nd Street between Fifth and Madison Avenues

Not all the schools on the Upper East Side are quite so grand. Hunter College has a large International Style building on Park Avenue at 68th Street and it also has a school, shown below, on 94th Street and Park Avenue that takes its castellated style from the former Squadron A Armory that occupied the full block but was demolished for the school and its midblock playground with only its impressive Madison Avenue facade left standing.

The Hunter School on Park Avenue at 94th Street

The Hunter School on Park Avenue at 94th Street takes its castellated style from the armory that used to occupy the full block and now only has its Madison Avenue facade still standing

The Upper East Side also has the city's highest concentration of private clubs including the Metropolitan, the Knickerbocker, the Union, the Colony, the Cosmopolitan and the Lotos, shown below.

The Lotus Club

The Lotus Club

The Upper East Side, however, is not without its oddities, such as the pink pavilion on Park Avenue of Lenox Hill Hospital, shown below, or a pale blue apartment building on Madison Avenue.

Lenox Hill Hospital on Park Avenue

Former pink facade of a pavilion of Lenox Hill Hospital was utlimately reclad

The Upper East Side still has a great many tenement buildings whose handsome facades are generally marred by fire escapes. Some of the older apartment buildings, like the one below on 91st Street between Lexington and Thid Avenues, did occasionally have unusual features such as the undulating cornice curves.

91st Street fire escapes east of Lexington Avenue

There are plenty of fire escapes still left on the Upper East Side such as those on this building on 91st Street between Lexington and Third Avenues. The giant towers of Ruppert Houses loom in the background on Third Avenue.

A modern city, of course, needs garages and The Upper East Side has several that are rather unusual such as the one shown below.

East Side garage

One of several attractive garage buildings on the Upper East Side

The skyline of the Upper East Side has sprouted significantly in recent decades as towers have replaced many tenements. Many art galleries had been attracted to Madison Avenue because the Parke-Bernet auction house was located in an impressive low-rise building, shown below on Madison Avenue across from the Carlyle Hotel, one of the Upper East Side's major landmarks. Sotheby's took over the auction house and soon moved it to a former warehouse on York Avenue and 72nd Street, and within a few years several major new "luxury" towers sprouted around it.

Former Parke-Bernet building on Madison Avenue at 76th Street

Low-rise building on Madison Avenue between 76th and 77th Streets for years was occupied by Parke-Bernet, the auction house that was eventually taken over by Sotheby's and relocated to York Avenue and 72nd Street. Aby Rosen commissioned Sir Norman Foster to design a curved residential glass tower above the building but the design was not accepted by the city's Landmarks Preservation Commission

For many decades, nightlife in city was clustered in Greenwich Village and midtown and on the Upper East Side, first along 86th Street in Yorkville where there were many dance halls, then on First Avenue in the 60's and then on Third Avenue in the 70's where restaurants such as Jim McMullen's where among the most popular and glamorous in the city. Starting in the 1980's, the Upper West Side and Columbus Avenue in particular, enjoyed a trendy renaissance, however, and an explosion of new, large and fashionable restaurants and clubs opened up downtown in SoHo, TriBeCa and the Flatiron districts took away much of the nightlife activity from the Upper East Side, whose staid and establishment "image" seemed conservative to many of the new "trendsetters."

Despite such competition, however, the elegance of much of Fifth, Madison and Park Avenues and the awesome array of important cultural institutions that also include the 92nd Street Y on Lexington Avenue and the Jewish Museum, the Museum of the City of New York and the Asia Society, guarantee that the Upper East Side is not about to be abandoned. Indeed, Second Avenue in the 70's and Third and Madison Avenues in the 90's are teeming with attractive and popular restaurants and real estate prices and rents soared at the start of the Millennium to record levels, although they receeded a bit after the terrorist attacks of September 11, 2001.

The Congressional seat that represents the Upper East Side had long been known as the "Silk Stocking District," a phrase that become popular after World War II. Silk stockings may not be as much in vogue in the new Millennium, but the Upper East Side still is. Much of the eastern half of it is architecturally disappointing, but a new crop of buildings has already transformed Third Avenue into an attractive boulevard and quality is once again a concern - a good concern - in much of the new development, even if much of it is not inspired design.

An article in the December 24-31, 2007 edition of New York magazine observed that "It's not fashionable to love the Upper East Side these days." "Anyone who considers themselves at all groovy and/or comes into a juicy, multi-zeroed bonus/three-picture deal/inheritance heads south, for square footage in Soho and Tribeca, or West Village quaintness. There's good reason for this. It's stodgy uptown." The article's headline noted that "the Upper East Side has no interest in being the next cool neighborhood."

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