
What happens when you have more money than you know what to do with during the Gilded Age? Why not build a massive mansion, fill it with antiques and never live in it. This is what happened with Gertrude Rhinelander Waldo and her house on 72nd and Madison. Completed in 1898, it would remain mostly empty until the 1920s, and wouldn’t be fully restored until the 1980s when it became the flagship store for Ralph Lauren. If you want to get an idea of what it would have been like to live in a big old mansion, it might be time to do some shopping. #gildedagemansions
Every so often, I like to remind myself of what the Flatiron building looked like before it was covered with scaffolding. To do that, though, I had to pull out this photo from August of 2019. The Flatiron has to be one of the most iconic buildings to those of us who live in New York, bu there are a few misconceptions surrounding it. The first is that the building didn’t get its name from its shape, but rather the plot of land it was built on was known as the flatiron long before construction began. The second misconception is that it was the first skyscraper in New York, when in fact, multiple buildings had used the modern construction method in the 1880s and 90s, including the Park Row Tower, which was 392 feet tall. Despite all of that, the Flatiron remains one of the most notable and beautiful buildings in New York, described by contemporaries as a ship’s prow sailing up Broadway. Today, it is undergoing a very complicated condo conversion. I can’t wait to see it in all of its unobstructed glory again. The Flatiron was landmarked on September 20th, 1966.
One of the most common questions I get from readers is why are certain buildings landmarked. There are a couple different answers to that. It could be because the building itself has some historical significance, or it gives us a glimpse of what the area used to be like. The latter applies in this case, these buildings were designed by renowned New York architect Henry Hardenburg, the creator of the Dakota apartments. Dozens of Hardenburg flats were built across the Upper East Side, these are six of the few that remain. All of these were built in 1889 on the corner of 89th and Lexington by the Rhinelander real estate empire as mid level housing compared to the mansions to its west and tenements to its east. The buildings originally had stoops and the corner building used to have one on the side that you can see the entrance to. The Hardenberg/Rhinelander Historic District was created on May 5th, 1998.
In my opinion, one of the coolest and most enjoyable landmarks I’ve tracked down so far is Pomander Walk on the Upper West Side. It was built in 1921 by Thomas Healy, who wanted to design a group of apartments to mimic Tudor England. It’s wedged between 94th and 95th Street between Broadway and West End Avenue. The complex has 25 houses between two and three stories high. The main street has two rows of townhouses facing each other with little yards and hedges in front of each of them with a gate at either end. Unfortunately, it’s not open to the public, but you can get a glimpse through the entrance. Healy was very involved in the theater and named the street after a comedy by Lewis Park called “Pomander Walk”. It was landmarked on September 14th, 1982.
Boerum Hill has a decent amount of buildings from the 1850s, most of which are brick, but luckily for us, a few wooden ones still remain. This house at 360 Pacific Street was built in 1851 for Thomas and Elizabeth Westervelt on land that was formerly an estate. The main developers at the time who were selling off plots were Charles Hoyt and Russell Nevins; Brooklynites will be familiar with the streets that bear their names. This home served as a church rectory before turning back into a private residence. It was landmarked as a part of the Boerum Hill Historic District on November 20th, 1973.
View from Grand Army Plaza.
I’ve always loved these apartments on Prospect Park West. Their brownstone facades are in contrast to the lighter stone and brickwork of the neighboring blocks. Couple that with their height, and it is an imposing group of buildings. What’s even more impressive is that when they were built in 1899 by developer Charles Hart, they were designed as individual townhouses. These must have been some of the largest single-family homes south of 3rd Street in Park Slope. At the time they were built, the neighborhood was beginning its transformation in earnest from distant farmland to a tony commuter suburb of Manhattan. They were converted into apartments later on in their life, and all but one has its original L-shape stoop removed. The remaining one is at No. 102. The 5 buildings were all landmarked as a part of the Park Slope Historic District on July 17th, 1973.
This group of row houses on Hancock Street in Bed-Stuy was built for developer George H. Stone. Stone owned and developed many buildings in this area in the 1870s and 1880s; these were built in 1884. For reference, most of the buildings in this part of Bed-Stuy were built in this twenty-year period. Prior to this, the land that makes up the neighborhood was four family farms that were subdivided into lots for development. It was one of the fastest neighborhoods to develop from farmland to residential and had some of New York’s most prolific architects designing homes such as Heinz and Lafarge and Montrose Morris. These were designed by Gilbert A. Schellenger. 198-202 Hancock Street were landmarked as a part of the Bedford Historic District on December 8th, 2015.

Most of us dream of being able to afford a starter home, with just enough space for our growing family. Well, if you were Oliver Gould Jennings in 1899, you would build this house at 7 East 72nd Street for your family of 3, soon to be 4. The home was designed by Flagg and Chambers and mimicked the neighboring Sloan Mansion. Oliver Jennings’ father, Oliver Burr Jennings, tried to strike it rich in the California Gold Rush but realized he was not good at actually finding gold. He, however, realized how profitable outfitting those looking for their fortunes was and patterned himself with Benjamin Brewster in a dry goods business. Brewster’s sister married William Rockefeller, who convinced Benjamin and Oliver to invest in their new Standard Oil Company, which made both men incredibly rich. Oliver Gould Jennings lived a life of luxury and philanthropy from his father’s fortune and had two other estates, one in Fairfield, CT, and Newport. Tune in for part 2 where we look at those houses. #nychistory #gildedage #gildedagemansions
If you’ve somehow never been to Clinton Hill, stop reading this post and go visit. I’ll wait. OK, now that you’re back, can we talk about the incredible freestanding mansions that line its avenues? Clinton Hill began as a suburban retreat from the city of Brooklyn and began to see high-scale development at the end of the 19th century spurred by the building of the Pratt Mansion. This house at 447 Clinton Avenue is one of the oldest remaining houses in the area, dating to roughly 1850. This predates much of the development in the neighborhood and makes Clinton Avenue one of the most historically diverse streets in terms of architecture. According to the Landmarks Preservation Commission, the first owner of this home was an auctioneer named Daniel Burdette. He sold it to Charles Zugalla, who was a furrier, followed by an ink manufacturer named William Wade, whose family would own the home from 1866 to 1920. In the 1980s, the building was home to the Galilee Baptist Church. Today, it is shockingly rental apartments. It was landmarked as part of the Clinton Hill Historic District on November 10th, 1981.
This building at 226 West Broadway represented a huge leap in firefighting technology in New York City. Built in 1912 and designed by August Shepard Jr. for the City of New York, this was the former workshop of the high-pressure fire service system. Now, what is a high-pressure fire service system, you ask? As buildings continued to get taller in New York, increased water pressure was required to help firefighters hit the higher floors as well as pump water through those taller buildings. The high-pressure fire service system was modeled after a similar one in Philadelphia, which allowed for hydrants in the area, aided by electric pump stations to provide much higher water pressure than before. This system required a lot of maintenance, which led to this building. You can even see hydrant and pipe motifs scattered about its terracotta facade. Because it was a city-owned building throughout the 20th century, it remained pretty unscathed and is pretty much original on the outside. It was converted into a single-family home and last sold in 2011 for $6.5 million. It was landmarked as a part of the Tribeca West Historic District on May 7th, 1991. The graffiti on the door has since been removed since this photo was taken.
88 and 90 Grove Street in the Village are two dramatically different takes on what to do with townhouses from 1827. Both of these homes would have started as two-story Federal buildings with dormer windows for their attics. No. 88 on the right was built by mason Henry Halsey and had a full third story added in the 1850s. The third floor is a 2nd French Empire style, which basically means it looks vaguely Parisian. No. 90 on the left has a dramatically different look. Built by a different mason, William Banks, this house underwent modifications in 1893 when it was bought by artist Frederick Blum. He hired an architectural team of Carrère & Hastings, who designed the main branch of the New York Public Library, to modify the top two floors into a large studio space. Frankly, I assumed that this was a modification from the 1960s rather than the end of the 19th Century, but there you go. Both of these buildings were landmarked as a part of the Greenwich Village Historic District on April 29th, 1969.

When I give my tours of the Upper East Side, my guests tend to be pleasantly surprised that so many buildings from the Gilded Age, including mansions, still exist. This almost always leads to the question of why did these survive, so we talk about the different categories of reuse that the mansions fall under. I figured I would give you a little virtual tour and encourage you to go explore yourself. Self plug, you can also join me for an in person tour.
Gracie Mansion is one of the oldest remaining wooden buildings in Manhattan. It was constructed in 1799 for Archibald Gracie, a Scottish-born merchant, as a country home. At the end of the 18th century, this area of Yorkville on the Upper East Side would have been 5 miles north of the city, taking nearly over half a day to get to. Prior to Gracie Mansion, the plot was home to the Belview Mansion, which was used by both British and American forces during the Revolution. The home was destroyed by cannon fire from the East River. One of the canon balls can be seen above the mantle in the yellow room. Gracie split his time between New York and Virginia, making money in the tobacco trade. While being a member of the New York Manumission Society, he still enslaved two Black men. He manumitted them in 1801. Copies of that document can be seen at the home.
The Gracies would stay here until the 1820s when they were forced to sell due to bankruptcy. By the 1890s, the City had purchased the home, where it was temporarily used for restrooms and concessions for East River Park (later Carl Schurz Park). In the 1920s, it was the first home of the Museum of the City of New York, who found that storing valuable collections in a wooden building was a little daunting. After they moved out, everyone’s favorite urban planner (sarcasm) Robert Moses decided it should be used for the home of the Moses. Moses had a real issue with then-Mayor LaGuardia living in a tenement in East Harlem and dragged him kicking and screaming in 1942. He used the excuse that the mayor needed the ability to be quickly evacuated and that it would save the city money in security costs. Caption continues in the comments.
Happy first day of school! Brooklyn has a long history of public education dating back to its founding in the 17th Century. As a result it is dotted with beautiful school buildings. This is PS 39 also known as the Henry Bristow school. It was built in 1877 by Samuel Leonard to alleviate the crowding of PS 2 in Gowanus. While the school was being constructed, Henry Bristow, a member of the Brooklyn Board of Education and future congressman, used his home as an overflow space for students at PS 2. PS 39 was later named after him in 1916. PS 39 has served the park slope community for almost 150 years. It was landmarked on March 8th, 1977. This photo was taken on 120mm Kodak Ektar 100.
In the steel canyons of lower Manhattan it can be odd to see an eight story office building but in the late 1800s, these would have been a normal site. This particular building at 127 Fulton Street was home to the Keuffel and Esser company who specializes in drafting and architectural tools. It was built in 1893 by the firm of De Lemos and Cordes. The land on John Street was leased from the Dutch Reform Protestant Church who acquired the property in 1791. They church only sold it in 2004, a fairly impressive span of ownership. The building was landmarked on April 26th, 2005.
This double-wide townhouse in the West Village dates from before the Civil War. It was constructed in 1857 for a carpenter, Albert Bogart. At the time, the area this home sits in would have been full of dock workers loading and unloading ships along the Hudson. The most distinctive part about this building has to be the stars on the facade. Those aren’t just there for show; they are actually disguising the ends of tension rods that prevent the face of the building from falling over. In more recent years, the entire building sold for $12 million in 2006 and is currently apartments. It was landmarked as a part of the Greenwich Village Historic District on April 29th, 1969.
I don’t know which stood out to me more about this building, the color or the size. I’ve found that the shorter the building in lower Manhattan, the older it tends to be, and 34 White Street is dwarfed by its neighbors. Located in Tribeca, this building was constructed in 1805 as a house for Abraham Moore. The house would have looked a little different than it does today; it was only two stories with a peaked roof. As Tribeca became more industrial, so would this home. It was converted into a grocery store and would remain as one for the majority of the 19th Century with various owners and operators. In 1877, the full third floor was added on. In more recent years, it was home to the Baby Doll Lounge, and in the late 90s, the upper floors were converted into apartments. It was landmarked as a part of the Tribeca East Historic District on December 8th, 1992.
The area known today as NoHo was owned by some of New York’s wealthiest families. As with much of the city’s history, these farms gave way to residential development. By the mid-1800s, the neighborhood was changing yet again, with small single-family homes being torn down in place of factories and apartments. This building, at the corner of Bowery and Bleecker Street, was built in 1868 for Robert Irwin. It was originally supposed to be a store and “Dwelling” in its initial building application but ultimately was used as a store and warehouse. It was converted into a hotel around the turn of the century before going back to an industrial space used alternately as a hardware store and hat manufacturer. As the area de-industrialized, it was converted yet again, this time as a theater and lofts. Today, it is mixed use with apartments and retail. I took this photo back in 2021 when it had this Blondie Mural; it is updated fairly regularly. If you’ve been by recently, let me know what it is now. 2 Bleecker Street was landmarked as a part of the NoHo East Historic District on June 24th, 2003.
Brooklyn Heights has some of my favorite architecture in the city. This particular building on the corner of Hicks and Cranberry Street always catches my eye. Officially, it was built in 1822, but some estimates peg its construction a few years earlier in 1816, making it one of the oldest buildings in the neighborhood. It was built for a cooper named John Rogers, who used it as his home until he fell on tough times and had to move out. One of its claims to fame was that it served as the offices of John, Washington, and Emily Roebling, the designers of the Brooklyn Bridge. In the 1950s, it was converted into a veterinarian’s office and is still home to an animal hospital. It was landmarked as a part of the Brooklyn Heights Historic District on November 23rd, 1965.