1827. This Georgian triangular structure is the only building in New York, or perhaps anywhere, with one side on two streets (Grove and Christopher) and two sides on one street (Waverly Place). Edgar Allen Poe was once treated here.

Van Campen Taylor, 1887. Teak-encrusted townhouse built by a teak manufacturer. On one of the most picturesque residential blocks in Greenwich Village. Next door to home of Village writer Dawn Powell. In 1900 a writer for House Beautiful called it the “most beautiful Indian House in America."

Jardine, Kent, and Jardine, 1903. New York's last surviving horse and carriage auction mart building, used as an assembly line training facility for women during WWII, and later used as a studio by artist Frank Stella for several decades. Saved from destruction by the Greenwich Village Society for Historic Preservation in 2006.

Frederick A. Peterson, 1859. The muscular neo-Romanesque shell of Cooper Union is the oldest standing steel framed building in America. Peter Cooper envisioned the elevator as the interior transportation of the future and installed a cylindrical shaft in Cooper Union (before the elevator was actually invented!). But for more than 100 years a box-shaped cab ran in Cooper's shaft, a square peg in a round hole.

McKim, Mead, and White, 1892. Baptist Pastor Edward Judson began a campaign in the late 19th century to build "the most beautiful churches among the homes of the poor, so that it would be only a step from the squalor of the tenement houses." John D. Rockefeller Sr. donated the money for the church to be built and Judson named it after his father, a Protestant missionary. Architectural firm Stanford, Mead, and White described their design as, "Romanesque, strongly influenced by early basilica." John La Farge designed stained glass windows which are still in the church.

1873. Both writer Edna St. Vincent Millay and anthropologist Margaret Mead lived here. It's less than 10 feet wide on the exterior.

Louis Sullivan, 1898. The only New York building by Louis Sullivan, father of the skyscraper. Vertical! Steel! Organic bas relief on the facade!

1891. This stunner of a church was built in the Gothic Revival style by architect J.C. Cady (the same guy who designed the American Museum of Natural History’s south addition). The facade is made from Kentucky limestone, and it has beautifully carved stained glass windows.

1903. A Soho classic, the Little Singer Building was restored to its original grandeur in 2008. Architect Ernest Flagg created the whimsical, delicate design with lace-like cast and wrought iron ornamentation, red brick and terracotta detailing, and large expanses of windows. The facade is topped with an elaborate iron arch and ornate cornice supported by scrolled iron brackets. Flagg was inspired by Parisian architecture, and the exposed iron and steel look was very avant-garde for the time. [Photo via Curbed Flickr pool]

1857. The Haughwout Building is a great example of Soho's many cast iron buildings. Architect John P. Gaynor created the design using cast-iron from Daniel D. Badger's Architectural Iron Works. Although the design was typical of the time, the dual street fronts made the building a challenge—the weight of the two facades could bring down the building. According to Wikipedia, "To avoid this, rather than hanging the facades off the brickwork, as was usually done, Gaynor and Badger convinced Haughwout to allow them to use the strength of the cast-iron itself to support the building. This use of a structural metal frame was a precursor to the steel-framed skyscrapers that would start to be built in the early 20th century; in fact, some consider it to the first skyscraper and 'the most important cast-iron structure ever built.'"

1849. This Gothic Revival synagogue is no longer used as a religious institution, but its beautiful architecture makes it a popular place for weddings. The building was original constructed by Alexander Saeltzer for the Reform Congregation Ansche Chesed. At the time, it was the largest synagogue built in the United States, and it is still one of the few designed in the Gothic Revival style. It was purchased by artist Angel Orensanz in the '80s and lovingly restored.

1905-1909. A Curbed favorite, the grand Police Building was designed and built by the firm of Hoppin & Koen to replace the older police headquarters on Mulberry Street. The majestic Beaux Arts masterpiece was designed to "to impress both the officer and the prisoner with the majesty of the law." The dome and facade are filled with intricate carved details, like the graceful female figures that hold placards with the name of each borough. In the '80s, the building was converted to condos, and many, like the Gwathmey-designed gymnasium home, are some of the most unique spaces in the city.

1912. Like many other buildings on this map, the old Jewish Forward Building is now residential. Architect George Boehm created the building as offices for the Forward newspaper, embellishing the facade with marble columns, stained glass windows, and carved base reliefs depicting prominent Socialist figures, including Karl Marx. [Photo by Joel Raskin/Curbed Flickr pool]

1912. This 12-story Beaux Arts beauty has been in the news lately because the owner recently won Landmarks approval to restore the historic structure and convert it into a hotel. The renovation will gussy up the limestone and terracotta facade created by architects Rouse & Goldstone, but unfortunately, it will not bring back the building's original cupola. [Photo via the LoDown]

1896. Curbed recently dove into the history of the William B. Tubby-design American Thread Building, as it encapsulates Tribeca's role as a manufacturing center in the early 20th century. Author Lisa Santoro wrote: "Completed in 1896, the eleven-story Renaissance revival building conformed to the street, creating a stately façade that curved nearly 175 feet from Beach Street along the building's south façade onto West Broadway. The building's three-story base, comprised of an alternating limestone and Roman brick pattern, was to house the Wool Exchange. [...] The building features various decorative elements that distinguish it from the factories and warehouses prevalent in the area; such features include round arched windows, scrolled iron cartouche spandrel panels, keystones, medallions and Roman Ionic columns around the entranceway." Today, the building holds condos (one of which is an impressive domed penthouse).

1891. Built for a confectioner but best know as the former home of the Mohawk Electric Company, the Romanesque Revival building at 161 Duane Street underwent an extensive restoration in 2007 as part of its conversion into condos. The sandstone and brick facade is dominated by broad arches that frame the windows. It's topped with a carved balustrade and cornice with a small turret at the corner, and the bottom is punctuated by a rusticated design of protruding bands.

This landmark is being transformed into 285 hotel rooms and 85 residential units. The landmark status means that, thankfully, the building's lovely Victorian atrium will be preserved in the conversion.

1764. The older, smaller sister to the famed Trinity Church, St. Paul's Chapel is one of the oldest structures in New York City. Constructed by Thomas McBean, the Georgian-style chapel is made of Manhattan mica-schist with brownstone quoins and the classic boxy portico.

1891. Designed by James Brown Lord, this brick building is more famous for the restaurant, the iconic Delmonico's steakhouse, it holds than its architecture. The building is a classic Romanesque Revival structure that was praised by the Times for being "admirable in its simplicity and elegance." It was landmarked in 1995, and the commission described it as such: "Faced in orange iron-spot brick, brownstone, andterracotta, the facade features giant arcades and a rounded corner bay which is distinguished by two tiers of giant columns and a semicircular entrance porch. The sensitive handling of materials, rich colors, and elaborate decorative programincorporating Renaissance motifs makes this one of the finest surviving late-nineteenth-century buildings in Manhattan's financial district."

1719. The Fraunces Tavern is famous for its prominent role in the Revolutionary War (George Washington dined here), but it's also architecturally important because it's one of the oldest buildings in the city. It was originally built by Etienne Delancey as a family residence.