One of the more expensive neighborhoods to live and to eat in, Gramercy Park feels like a small village in the heart of a city. Centered around a small private park (you need to have a key to get in) it is home to many well-to-do individuals who often work in the area as well. Apart from elaborate brownstones and quaint narrow streets, the neighborhood offers a very diverse and vibrant nightlife. From a number of city-renowned restaurants, many of which include live music, to the recent openings of local late night and after-hours bars and clubs, Gramercy is no longer strictly a residential district.

The area’s architecture and neighborhood ambiance is what really draws people to visit and to live in this small and unique part of the city. Big and elaborate brownstones, whose Victorian style architecture can easily compete with the originals from London or Paris surround the park and the outgoing streets. Inside these fancy structures tenants can often find over sized apartments that offer more living space than an average city building and come with much more character and utility. Of course all is served at an according price, and Gramercy sure is not cheap.

One additional plus of the neighborhood is its central location. Gramercy is within walking distance to the offices of midtown, shopping galleries of NoHo, Soho and Chinatown as well as the nightclubs of East and West Village. And for those further excursions there are at least 5 different subway lines with a 5 minute walk of the park. Soaring office rents in Midtown in the early 1980’s led many tenants to search for less expense accommodations and, led by the advertising, publishing and related industries, many settled in Midtown South in older office structures on Park Avenue South and Fifth Avenue.

Before long, many new restaurants, some quite extravagant, opened, and a major wave of rehabilitation and upgrading of older properties was underway and the "Midtown South" area became very "hot" and chic and the Flatiron District, Fifth Avenue to Park Avenue in the high teens and low 20’s, in particular, became one of the most exciting areas in the city, not just for commercial uses, but also for residential and retail, as people rediscovered its wonderful architectural heritage.

The Flatiron District is named after the 1902 triangular building at the intersection of Fifth Avenue and Broadway at 23rd Street that was originally the Fuller Building and designed by D. H. Burnham & Co., in a highly ornamental style with curved corner windows.

The Flatiron Building is but one of many several great landmarks surrounding Madison Square Park at the foot of Madison Avenue. The Metropolitan Life Insurance Company Tower at 1 Madison Avenue once was the world’s tallest office building. Designed by Napoleon Le Brun and completed in 1909, much of its fine detailed was lost in a 1964 remodeling, but its great clocks remain, although its observatory has been closed for decades. The insurance company commissioned a much taller annex building, designed by Harvey Wiley Corbett and E. Everett Waid, immediately to its north at 11 Madison Avenue, but the Depression halted construction when it was only about a third of its planned height. With its four great corners, arched entrances and scalloped, limestone facades, this palatial behemoth is a great building, despite its stunted size. Presumably, in better times, it will be completed. In the late 1990’s, it was renovated and leased out quickly to major office tenants including Credit Suisse First Boston.

To the north of it is one of the city’s jewels, the small but exquisite Appellate Division Courthouse of the New York State Supreme Court, designed by James Stewart Lord with great statues by Daniel Chester French, Karl Bitter and others around its facade and completed in 1900. The building’s interiors are as glorious as its exteriors.

This great row of distinguished architecture was broken, unfortunately, by the Rudin Organization, which erected a bronze-glass, 41-story office building on the southeast corner of Madison Avenue and 26th Street, a building that would have been all right on Third Avenue, but is a glaring interloper here, especially since it is across 26th Street from the spectacular and great New York Life Insurance Building, designed by Cass Gilbert with its huge, gilded pyramid roof. This full-block insurance company building, completed in 1928 as a worthy rival to the Metropolitan Life tower, replaced the magnificent Madison Square Garden complex and tower designed by Stanford White, the famous architect who was shot and killed in 1906 in its roof garden by Eugene Thaw, who was angry at White for stealing the affections of his wife, the famous actress Evelyn Nesbit, in one of the century’s most celebrated crimes. The site was formerly occupied by the Union Depot of the New York and Harlem Railroad and in 1871, when the railroads moved their major station to 42nd Street, the depot was converted to Gilmore’s Garden and then P. T. Barnum’s Hippodrome and then refinanced and renamed Madison Square Garden.

White’s new building for the garden opened in 1892 and its tower was modeled on the Giralda in Seville, Spain, and was topped with a gilded statue of Diana by Augustus St. Gaudens, one of the world’s greatest skyline ornaments.

The garden then moved to a new facility, far less glamorous on Eighth Avenue at 50th Street and subsequently moved from that location to an unglamorous new circular structure on the western half of the site of the demolished and greatly lamented Pennsylvania Station, the greatest project ever completed by Stanford White’s famous firm, McKim, Mead & White.

In one of the city’s better ironies, William Zeckendorf Jr. redeveloped the Eighth Avenue site of the garden with a very fine Post-Modern skyscraper, World Wide Plaza, designed by Skidmore, Owings & Merrill whose model was the New York Life building on Madison Avenue. Perhaps inspired by Zeckendorf, the Rudins finally built a superb office building near WorldWide Plaza at 1675 Broadway at 52nd Street. Madison Square Park, of course is but one of several in this area and the most famous is Gramercy Park, perhaps the nicest residential enclave in the city because of its small size and eclectic architectural surroundings.

Samuel B. Ruggles created the park in 1831. The townhouses that were created around the park before the Civil War were among the best in the city and not long after the war apartment buildings began to sprout. The Stuyvesant on East 18th Street was designed by Richard Morris Hunt in 1869 and is widely thought to have been the first major apartment house. It has been demolished but another at 129 East 17th Street still stands from 1879 and is believed to be the oldest surviving apartment house. One of the earliest cooperative apartment buildings is the Queen Anne-style 34 Gramercy Park East, designed by George da Cunha, which was erected in 1883.

The handsomest apartment house on the park is the 12-story One Lexington Avenue, which was built in 1911 and designed by Herbert Lucas. It was a fence from the building that had originally been erected for Cyrus Field, who planned the Atlantic cable, and which was altered by a later owner, Henry Poor by architect Stanford White. Other attractive apartment buildings on the park include 60 Gramercy Park North, designed by Emery Roth & Sons, 44 Gramercy Park North, designed by Schwartz & Gross, 45 Gramercy Park North, designed by G. A. & H. Boehm, and the neo-Gothic structure at 36 Gramercy Park East, designed by James Reilly Gordon and completed in 1910. Residents of buildings facing the park have keys to the park, which is private.

Particularly interesting are the clubhouses on the south side of the park of the National Arts Club and the Players Club. The former was originally the Samuel Tilden House, designed in Victorian Gothic style with busts of literary figures by Vaux & Radford and completed in 1884. Tilden resigned as governor of New York to run for the Presidency in 1876, but lost to Rutherford B. Hayes. The building was acquired in 1906 by the club, which holds many exhibitions and his roster has included many prominent American artists. The Players Club was built as a single-family Gothic Revival-style brownstone in 1848 and remodeled by Stanford White of McKim, Mead & White in 1888 when it was acquired by the Players Club. The building’s stoop was removed and White, who was commissioned by Edwin Booth, the famous actor whose brother assassinated President Lincoln, created a two-tiered porch in Italian Renaissance-style with elaborate ironwork and stained glass windows.

The site of Gramercy Park was originally a swamp, but ever since it was developed by Ruggles it has been regarded as the city’s nicest small park, rivaling those of London. Other attractive buildings in the vicinity include 81 Irving Place, an apartment building designed by George Pelham and completed in 1930, the former Russell Sage Foundation Building, now apartments, at 122-130 East 22nd Street, designed by Grosvenor Atterbury and built in 1915, and the 1914 Con Edison tower, whose clocktower is illuminated at night, at 4 Irving Place, designed by Henry Hardenbergh with additions by Warren & Wetmore and Thomas E. Murray Inc. The Friends Meeting House (now the Brotherhood Synagogue), which was designed by King & Kellum and completed in 1859, is an individually designated landmark.

The large red-brick townhouse at 19 Gramercy Park South was originally the Stuyvesant Fish House and for a while was lived in by legendary actor John Barrymore before it was acquired by legendary publicist Benjamin Sonnenberg. It is known Evyan House. It is imposing because of its size, but not as beautiful as 3 and 4 Gramercy Park West, two townhouses with notable ironwork designed by Alexander Jackson Davis and completed in 1846.

The block between Irving Place and Third Avenue has long been known as "The Block Beautiful" because of the handsome houses that were renovated in 1909 by architect Frederick H. Sterner.

Adjacent to the Flatiron District, the Gramercy Park area has many popular and impressive restaurants, one of the oldest of which is Pete’s Tavern at Irving Place and 17th Street.

This area has two other important small parks, Stuyvesant and Union Square. Stuyvesant Park, which is an historic district like Gramercy Park, is very similar to Gramercy Park, except that it is public and is divided by Second Avenue. Laid out in 1846 on land donated to the city by Peter Gerard Stuyvesant, each of its two blocks between 15th and 17th Street, are surrounded by cast-iron fences. Major individually designated landmarks here include St. George’s Episcopal Church on Rutherford Place, the western street fronting on the park, at 16th Street, which was designed by Blesh & Eidlitz and completed in 1856, and the Friends Meeting House and Seminary at 15 Rutherford Place and 226 East 16th Street, which was completed in 1861. The eastern street fronting on the park is known as Nathan Perlman Place, part of which is occupied by the New York Infirmary/Beekman Downtown Hospital. The very ornate and interesting structure at 305 Second Avenue between 17th and 18th Streets was originally the Lying-In Hospital, designed by R. H. Robertson, before it was converted to apartments in 1985. Union Square, the furthest south of this area’s four squares and parks, was originally known as Union Place and also was referred to as "The Forks" because it interrupted the flow of Broadway and the Bowery, which switched to Fourth Avenue at 14th Street (before being renamed to Park Avenue South). Following the northward flow of residential Manhattan, the square was quite fashionable before the Civil War and it became an important theatrical district as well with the 1854 opening of the Academy of Music on the present site of the Con Edison Building. (One of the city’s largest theaters, the Academy of Music, was built directly across 14th Street from the Con Edison Building and in the 1940’s and 1950’s it showed double features and a vaudeville show, and later was converted spectacularly into the disco, Palladium, designed by Arata Isozaki, but in the late 1990’s New York University acquired it for student housing.)

In the 1920’s, Union Square, which extends from 14th to 17th Streets and was laid out in 1830, was the scene of May Day parades as many radical publications of the political left were centered in the area, and it was a popular Speaker’s Corner, especially during the Depression. The park was raised on a platform to accommodate the vast and complex subway stations beneath it. In the 1960’s, the park became a drug haven and the area began to deteriorate badly until William Zeckendorf Jr., the developer, decided to build a four-tower, mixed-used complex on the block bounded by Park Avenue South and Irving Place and 14th and 15th Streets, which was the site of S. Klein’s-on-the-square, a popular discount department store.

Zeckendorf Towers, as the project was known, was designed by Davis, Brody & Associates and completed in 1987, a year after a major redesign of Union Square Park, designed by Bronson Binger, was completed and a popular farmer’s market opened at the north end of the square. The project included office space in a base and four residential towers, each topped with an open, illuminated pyramid.

Although the renaissance of Midtown South and the Flatiron District was already well underway, the completion of Zeckendorf Towers was very important in dramatically changing the ambiance of the area and removing much of its blight. Subsequently, the vast subway stations began to be renovated and a very handsome Barnes & Noble bookstore opened on the north side of the square.

To the east of the four squares and parks are several important residential complexes and, along First Avenue, several major hospital complexes. The most spectacular of the residential complexes is Waterside, a 1,600-unit enclave of very tall, partially chamfered, red-brick towers erected on a platform between 25th and 30th Streets along the East River. They were completed in 1974 and designed by Davis, Brody & Associates, which also designed a similar complex along the Harlem River and a related project known as Ruppert Houses on the Upper East Side. Just to the north of Waterside is the very attractive Water Club restaurant that opened on a barge in 1982.

The most attractive of the residential complexes is Kips Bay Plaza, two exposed concrete, 21-story slabs designed by I. M. Pei & Associates and S. J. Kessler and completed between 1960 and 1965 on the blocks bounded by Second and First Avenues and 30th and 33rd Streets.

Other handsome complexes are East Midtown Plaza between Second and First Avenues between 23rd and 25th Streets, designed by Davis, Brody & Associates and completed in 1974, and Phipps Plaza along the east side of Second Avenue between 26th and 29th Streets, designed by Frost Associates and completed in 1976. Peter Cooper Village, east of First Avenue between 20th and 23rd Streets, and the 8,755-unit Stuyvesant Town, between 14th and 20th Streets, east of First Avenue, were enormous red-brick apartment complexes developed shortly after World War II by the Metropolitan Life Insurance Company. The former had a bit more space and was more expensive and both were designed by Irving Clavan and Gilmore Clarke and had extensive landscaping and long waiting lists even though most of the units did not have air-conditioning.

The Roman Catholic Church of the Epiphany at 373 Second Avenue at 22nd Street is one of the most modern in the city and was designed by Belfatto & Pavarini and completed in 1967.

The western part of this district has superb architecture, great retail, and fine transportation while the eastern part is quieter but still convenient.