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Mapping the Moves of New York City's Past Property Barons

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The houses that rich people build nowadays might seem ridiculous and ostentatious—and they often are—but imagine how bad it would be if the city was full of open, undeveloped land and populated by dozens of steel magnates, oil barons, and other such captains of industry, all competing against each other to see who could build the biggest, most opulent, most over-the-top-extravagant home. Actually, you don't have to imagine, because that was pretty much exactly how things were a century ago. These historical whales were unencumbered by zoning restrictions, wealthy beyond anyone's wildest dreams, and they played dirty. Take William Waldorf Astor, who built an entire hotel to block his aunt's views, or Andrew Carnegie, who spent today's equivalent of $30 million on an empty parcel of land near his mansion because he didn't trust a random buyer to share his exceptional architectural taste. What a bunch of (Moby) Dicks these guys were.

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1. Archibald Gracie (1755-1829)

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88 East End Avenue
New York, NY 10028

Gracie, a shipping magnate, lived downtown and had the Gracie Mansion, which became the official residence of the mayor in 1896, built as his family's country home. In 1804, after his friend Alexander Hamilton was killed in a duel, Gracie bought Hamilton's house and sold it back to his widow, Elizabeth, at half price.

2. Isaac Vail Brokaw (1835-1913)

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1 East 79th Street
New York, NY 10075

In 1887, clothing merchant Isaac Vail Brokaw commissioned architects Rose & Stone to build him a French castle on East 79th Street. He also had three French Gothic mansions built next door for each of his three children. Brokaw's house stood until 1965, when it was torn down by developers, leading to the Landmark Law of 1965.

3. Andrew Carnegie (1835-1919)

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2 East 91st Street
New York, NY 10128

Steel magnate Andrew Carnegie owned not only the enormous mansion at East 91st and Fifth Avenue (now the Cooper-Hewitt Museum), but most of the surrounding area. He sold land discriminatingly only to people whose architectural tastes he knew he could trust, and once, in 1917, paid $1.7 (over $30 million adjusted for inflation) for a parcel of land at Fifth and 90th so that no one could build anything blocking his southern light.

4. William A. Clark (1839-1925)

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5th Avenue & East 77th Street
New York, NY 10075

Huguette Clark's father Senator William A. Clark spent $7 million in 1907 to build a 121-room, 32-bathroom, Beaux-Arts palace, with a private underground rail line to bring in the coal. For unapparent reasons, he went with a team of unknown architects and the house was subsequently referred to as "an appropriate residence for the late P. T. Barnum" by The Architectural Record and "Clark's Folly" by the Pittsburgh Post-Gazette. The latter was after Clark's death, when the mansion was sold for only $3 million to a developer, who tore the building down.

5. John D. Rockefeller (1839-1937)

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4 West 54th Street
New York, NY 10019

The world's first billionaire, Rockefeller was actually fairly reserved in terms of New York City real estate holdings. He bought the northeast corner of 72nd Street and Fifth Avenue sometime around 1880, but instead of building a huge mansion like all his friends, he moved into a four-story brownstone on West 54th and began to buy up all the adjacent properties in order to ensure that the area around his home would remain strictly residential. Many of those properties would later be developed by his son, John D. Rockefeller, Jr, who also developed Rockefeller Center.

6. Cornelius Vanderbilt II (1843-1899)

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1 West 57th Street
New York, NY

The first son of the first son of the original Cornelius Vanderbilt, Cornelius Vanderbilt II built the world's largest private residence in 1883. Designed by George Post and Richard Morris Hunt, the brick and limestone mansion contained, among other things, a two story smoking room, and required 37 servants to run. It was demolished in 1927.

7. Joseph De Lamar (1843-1918)

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233 Madison Avenue
New York, NY 10016

Businessman Jospeh De Lamar commissioned architect C.P.H. Gilbert to build him an enormous, opulent Parisian mansion in Murray Hill in 1905. The Beaux-Arts palace was the headquarters for the National Democratic Club in the 1920s. In 1973, the Polish government acquired the house for $900,000 to serve as its consulate.

8. William Waldorf Astor (1848-1919)

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2207 Broadway
New York, NY 10024

The most industrious Astor in terms of commissioning enormous, ornate buildings was, without a doubt, William Waldorf Astor, who, in 1890, within three months of inheriting $100 million in real estate, embarked on a mission to spite his hated aunt by building a 12-story hotel next to her house (with a blank wall facing her, for good measure.) This became the original Hotel Waldorf, and Astor followed it with the Hotel Netherland in 1893 (now the Sherry-Netherland), the Exchange Court office building in 1898 (since destroyed), Harlem's Graham Court apartment building in 1899, the Hotel Astor in 1902, and the Apthorp in 1908. Astor himself probably didn't spend much time in the buildings, though—he moved to England in 1891 to escape the mocking American press.

9. Henry Clay Frick (1849-1919)

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1 East 70th Street
New York, NY 10021

Henry Clay Frick and Andrew Carnegie were rivals both in business and in real estate, and Frick had his Thomas Hastings-designed limestone mansion built in 1912 to rival Carnegie's mansion 20 blocks to the north. Legend has it that Frick's stated intention was to "make Carnegie's place look like a miner's shack." Frick died in 1919, five years after the house's completion and four months after Carnegie. The mansion is now the Frick Museum and houses his private art collection.

10. Charles M. Schwab (1862-1939)

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Riverside Drive & West 73rd Street
New York, NY 10023

Carnegie protege Charles M. Schwab spent $865,000 in 1901 on a parcel of land on Riverside Drive between 73rd and 74th Streets. It took six years for his Maurice Hebert-designed 75-room mansion—including a four-car garage, a service tunnel beneath the garden, an indoor swimming pool, a bowling alley, a belfry with chimes, a roof garden, and a private chapel—to be completed. Schwab unsuccessfully lobbied the city to buy the house as a mayoral residence in 1936, but the house was doomed both by its over-the-top size (taking up an entire city block) and by being on the wrong side of the park. It was demolished in 1948 and replaced by an apartment building.

11. William Zeckendorf, Sr. (1905-1976)

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405 Lexington Avenue
New York, NY 10017

The original Zeckendorf, "Big Bill," as he was known, owned the Chrysler Building, the Hotel Astor, and a parcel of land along the East River which later became the site of the United Nations Headquarters. Zeckendorf introduced the architecture of I.M. Pei to the city, and his grandsons, Arthur and William Lie, would go on to develop 15 Central Park West.

12. Harry Helmsley (1909-1997)

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230 Park Avenue
New York, NY 10017

One of the city's greatest all time real estate investors, Helmsley amassed a $5 billion real estate empire over the course of his career, including the Empire State Building, the Ritz-Carlton, the Helmsley Building, various hotels, and many others. He summed up his success saying, "I only invested in real estate, not stock, and I really never sold. I worked very hard, and I bought the best properties that could be found. After all, I've been in business since 1925, so you accumulate a lot of property over 50 years.''

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1. Archibald Gracie (1755-1829)

88 East End Avenue, New York, NY 10028

Gracie, a shipping magnate, lived downtown and had the Gracie Mansion, which became the official residence of the mayor in 1896, built as his family's country home. In 1804, after his friend Alexander Hamilton was killed in a duel, Gracie bought Hamilton's house and sold it back to his widow, Elizabeth, at half price.

88 East End Avenue
New York, NY 10028

2. Isaac Vail Brokaw (1835-1913)

1 East 79th Street, New York, NY 10075

In 1887, clothing merchant Isaac Vail Brokaw commissioned architects Rose & Stone to build him a French castle on East 79th Street. He also had three French Gothic mansions built next door for each of his three children. Brokaw's house stood until 1965, when it was torn down by developers, leading to the Landmark Law of 1965.

1 East 79th Street
New York, NY 10075

3. Andrew Carnegie (1835-1919)

2 East 91st Street, New York, NY 10128

Steel magnate Andrew Carnegie owned not only the enormous mansion at East 91st and Fifth Avenue (now the Cooper-Hewitt Museum), but most of the surrounding area. He sold land discriminatingly only to people whose architectural tastes he knew he could trust, and once, in 1917, paid $1.7 (over $30 million adjusted for inflation) for a parcel of land at Fifth and 90th so that no one could build anything blocking his southern light.

2 East 91st Street
New York, NY 10128

4. William A. Clark (1839-1925)

5th Avenue & East 77th Street, New York, NY 10075

Huguette Clark's father Senator William A. Clark spent $7 million in 1907 to build a 121-room, 32-bathroom, Beaux-Arts palace, with a private underground rail line to bring in the coal. For unapparent reasons, he went with a team of unknown architects and the house was subsequently referred to as "an appropriate residence for the late P. T. Barnum" by The Architectural Record and "Clark's Folly" by the Pittsburgh Post-Gazette. The latter was after Clark's death, when the mansion was sold for only $3 million to a developer, who tore the building down.

5th Avenue & East 77th Street
New York, NY 10075

5. John D. Rockefeller (1839-1937)

4 West 54th Street, New York, NY 10019

The world's first billionaire, Rockefeller was actually fairly reserved in terms of New York City real estate holdings. He bought the northeast corner of 72nd Street and Fifth Avenue sometime around 1880, but instead of building a huge mansion like all his friends, he moved into a four-story brownstone on West 54th and began to buy up all the adjacent properties in order to ensure that the area around his home would remain strictly residential. Many of those properties would later be developed by his son, John D. Rockefeller, Jr, who also developed Rockefeller Center.

4 West 54th Street
New York, NY 10019

6. Cornelius Vanderbilt II (1843-1899)

1 West 57th Street, New York, NY

The first son of the first son of the original Cornelius Vanderbilt, Cornelius Vanderbilt II built the world's largest private residence in 1883. Designed by George Post and Richard Morris Hunt, the brick and limestone mansion contained, among other things, a two story smoking room, and required 37 servants to run. It was demolished in 1927.

1 West 57th Street
New York, NY

7. Joseph De Lamar (1843-1918)

233 Madison Avenue, New York, NY 10016

Businessman Jospeh De Lamar commissioned architect C.P.H. Gilbert to build him an enormous, opulent Parisian mansion in Murray Hill in 1905. The Beaux-Arts palace was the headquarters for the National Democratic Club in the 1920s. In 1973, the Polish government acquired the house for $900,000 to serve as its consulate.

233 Madison Avenue
New York, NY 10016

8. William Waldorf Astor (1848-1919)

2207 Broadway, New York, NY 10024

The most industrious Astor in terms of commissioning enormous, ornate buildings was, without a doubt, William Waldorf Astor, who, in 1890, within three months of inheriting $100 million in real estate, embarked on a mission to spite his hated aunt by building a 12-story hotel next to her house (with a blank wall facing her, for good measure.) This became the original Hotel Waldorf, and Astor followed it with the Hotel Netherland in 1893 (now the Sherry-Netherland), the Exchange Court office building in 1898 (since destroyed), Harlem's Graham Court apartment building in 1899, the Hotel Astor in 1902, and the Apthorp in 1908. Astor himself probably didn't spend much time in the buildings, though—he moved to England in 1891 to escape the mocking American press.

2207 Broadway
New York, NY 10024

9. Henry Clay Frick (1849-1919)

1 East 70th Street, New York, NY 10021

Henry Clay Frick and Andrew Carnegie were rivals both in business and in real estate, and Frick had his Thomas Hastings-designed limestone mansion built in 1912 to rival Carnegie's mansion 20 blocks to the north. Legend has it that Frick's stated intention was to "make Carnegie's place look like a miner's shack." Frick died in 1919, five years after the house's completion and four months after Carnegie. The mansion is now the Frick Museum and houses his private art collection.

1 East 70th Street
New York, NY 10021

10. Charles M. Schwab (1862-1939)

Riverside Drive & West 73rd Street, New York, NY 10023

Carnegie protege Charles M. Schwab spent $865,000 in 1901 on a parcel of land on Riverside Drive between 73rd and 74th Streets. It took six years for his Maurice Hebert-designed 75-room mansion—including a four-car garage, a service tunnel beneath the garden, an indoor swimming pool, a bowling alley, a belfry with chimes, a roof garden, and a private chapel—to be completed. Schwab unsuccessfully lobbied the city to buy the house as a mayoral residence in 1936, but the house was doomed both by its over-the-top size (taking up an entire city block) and by being on the wrong side of the park. It was demolished in 1948 and replaced by an apartment building.

Riverside Drive & West 73rd Street
New York, NY 10023

11. William Zeckendorf, Sr. (1905-1976)

405 Lexington Avenue, New York, NY 10017

The original Zeckendorf, "Big Bill," as he was known, owned the Chrysler Building, the Hotel Astor, and a parcel of land along the East River which later became the site of the United Nations Headquarters. Zeckendorf introduced the architecture of I.M. Pei to the city, and his grandsons, Arthur and William Lie, would go on to develop 15 Central Park West.

405 Lexington Avenue
New York, NY 10017

12. Harry Helmsley (1909-1997)

230 Park Avenue, New York, NY 10017

One of the city's greatest all time real estate investors, Helmsley amassed a $5 billion real estate empire over the course of his career, including the Empire State Building, the Ritz-Carlton, the Helmsley Building, various hotels, and many others. He summed up his success saying, "I only invested in real estate, not stock, and I really never sold. I worked very hard, and I bought the best properties that could be found. After all, I've been in business since 1925, so you accumulate a lot of property over 50 years.''

230 Park Avenue
New York, NY 10017