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The exterior of a triangular five-story building. Boston Globe via Getty Images

Boston’s 10 most underrated buildings, mapped

Spare a thought for this set, which includes East Boston’s library, Boston City Hall, and a Roslindale substation

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No question that Boston has plenty of incredible buildings with beautiful interiors and done in all sorts of architectural styles, from federal to modern. (And it’s got quite a few aesthetic clunkers.)

Then there are those buildings that don’t quite get their proper due. Routinely overlooked or habitually dismissed, these are the city’s 10 most underrated buildings.

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East Boston branch of the Boston Public Library

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The nearly seven-year-old building that William Rawn Associates designed pops inside and outside.

The glass facade and the column-free interior mean the entire building is like one big room—with plenty of open air and sunlight. Eastie’s is probably the most beautiful of the Boston Public Library’s branches.

A tall, glassy building shaped like a rising wave. AIA

Boston City Hall

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Routinely derided as one of the ugliest buildings the human mind hath ever conceived, Boston’s brutalist municipal hub deserves endless second chances. Why? Precisely because of that in-your-face look first unveiled in 1969.

Other city halls tend to go for baroque in their designs—think Philly or San Fran—but when it came to building a new city hall in the 1960s, Boston went with the brutalist conception from Kallmann, McKinnell & Knowles.

It turned out to be not only a bold statement architecturally, but psychologically as well—and at a pivotal time for the city, too: Boston was willing to try new things and think outside the civic box.

More than 50 years on now, and people are still discussing Boston’s City Hall.

The exterior of the Boston City Hall. The building has a flat roof and many windows. Shutterstock

The Ritz-Carlton, Boston

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This building that Handel Architects designed is worth a reappraisal not so much for its look but for its significance in recent Boston real estate history.

The Ritz-Carlton’s 2000 opening upended the Boston housing market for all coming time (it looks like). It was the city’s first condo to offer luxury-hotel services and the first to regularly claim $1,000 a square foot for its homes. (The original Boston Ritz Carlton is now the Newbury Boston.)

It opened, too, on the edge of what until recently had been nicknamed the Combat Zone, an especially seedy and combustible slice of downtown Boston.

That area was out, and developments such as the Ritz-Carlton were in.

The entrance of a hotel on a city sidewalk, with two doormen at the doors. Ritz-Carlton Boston

Federal Reserve Bank Building

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At 32 stories and 614 feet, the 41-year-old Fed tower is one of the five tallest buildings in Boston, but fellow neck-craners such as the Pru and 200 Clarendon often overshadow it (literally and figuratively).

Hugh Stubbins Jr. designed the Fed tower. He is perhaps best-known for Ronald Reagan’s presidential library and the Citigroup Center in Manhattan.

The 140-foot gap at the bottom is there to allow sea breezes to blow through—and it makes the tower distinct among Boston’s downtown skyscrapers.

A skyscraper stretching toward the clouds, and the building looks like smoothed stone from the side. Shutterstock

One Financial Center

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The 46-story tower that is 590 feet to its roof is one of the 10 tallest buildings in Boston, but, like with the Fed tower, its fellow skyscrapers can swallow its modern glory.

For that is what One Financial is: A solid example of modern architecture in a city best known for older styles.

Appropriately enough, Pietro Belluschi, a pioneer of modern architecture in the United States, designed it.

A kind of layer-cake-looking skyscraper as shown from just beyond some trees. Shutterstock

South Station

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So many people pass through New England’s busiest train and bus station daily that it’s easy to see the main building itself as nothing more than utilitarian—a garden shed with tracks.

But South Station—which dates from 1899 and which Shepley, Rutan, and Coolidge (now Shepley Bulfinch) designed—is an excellent example of Classical revival architecture.

Better yet, that architecture sheaths a vibrant and evolving complex—design and functionality helping to get you to points north, west, and south with (relative) ease.

A giant brown building. There is a street intersection in the foreground with people. Abdullah Al-Eisa/Getty Images

Cyclorama

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William T. Sears and Charles A. Cummings designed this building in the early 1880s to host views of cyclorama paintings. It’s currently an arts hub (the picture herein is from 1974).

Its salient feature—a steel-trussed dome 127 feet in diameter—makes the Cyclorama worth a second look on its own.

But the Classical revival building is also an excellent reminder of how Boston buildings can evolve.

It hosted everything from boxing tournaments to roller skating after the cyclorama craze died down; and then became the site of auto-body shops and spark-plug concerns before ending up for decades as the hub of the city’s flower trade.

A two-story, monolithic-like building extending for most of a city block. Boston Globe via Getty Images

Bruce C. Bolling Municipal Building

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Architecture firms Sasaki and Mecanoo designed this redevelopment of the old Ferdinand Building in Dudley Square. The City of Boston was the developer.

The building opened in 2015, and houses the headquarters of Boston Public Schools. Capacious and light-filled, it’s a slam-dunk design-wise.

As Globe architecture critic Robert Campbell so memorably put it: “Compared with the clueless architecture often produced by the private real estate market, the Bolling is a Taj Mahal. It is a good place to work, and it is equally good as a piece of the city.”

A capacious lobby with tall floor-to-ceiling windows and a big staircase in the middle. Boston Globe via Getty Images

Hibernian Hall

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Edward T.P. Graham and Joseph M. Dolan designed this four-story building 106 years ago as a hall for an Irish-Catholic fraternal organization.

Its fortunes have ebbed and flowed over the ensuing century-plus, and Hibernian Hall is now used as an arts hub. The building stands as a reminder of the changes in Boston itself during that time.

Roslindale substation

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This cavernous building dating from 1911—its ceiling stretches to 46 feet—was originally built to convert converted AC to DC for localized distribution of electricity to power street cars. Hence the dimensions.

It fell into disrepair for decades beginning in the 1970s, but has taken on new life since 2017 as a location for popup and permanent retailers.

So the Classical revival building is an excellent example of the re-purposing of bits of Boston beyond downtown. But its sheer bulk and Robert S. Peabody design make it worth a second look.

A sort of monolithic-looking brick building with large arched windows in the front and on the side. Photo courtesy of Roslindale.net

East Boston branch of the Boston Public Library

A tall, glassy building shaped like a rising wave. AIA

The nearly seven-year-old building that William Rawn Associates designed pops inside and outside.

The glass facade and the column-free interior mean the entire building is like one big room—with plenty of open air and sunlight. Eastie’s is probably the most beautiful of the Boston Public Library’s branches.

A tall, glassy building shaped like a rising wave. AIA

Boston City Hall

The exterior of the Boston City Hall. The building has a flat roof and many windows. Shutterstock

Routinely derided as one of the ugliest buildings the human mind hath ever conceived, Boston’s brutalist municipal hub deserves endless second chances. Why? Precisely because of that in-your-face look first unveiled in 1969.

Other city halls tend to go for baroque in their designs—think Philly or San Fran—but when it came to building a new city hall in the 1960s, Boston went with the brutalist conception from Kallmann, McKinnell & Knowles.

It turned out to be not only a bold statement architecturally, but psychologically as well—and at a pivotal time for the city, too: Boston was willing to try new things and think outside the civic box.

More than 50 years on now, and people are still discussing Boston’s City Hall.

The exterior of the Boston City Hall. The building has a flat roof and many windows. Shutterstock

The Ritz-Carlton, Boston

The entrance of a hotel on a city sidewalk, with two doormen at the doors. Ritz-Carlton Boston

This building that Handel Architects designed is worth a reappraisal not so much for its look but for its significance in recent Boston real estate history.

The Ritz-Carlton’s 2000 opening upended the Boston housing market for all coming time (it looks like). It was the city’s first condo to offer luxury-hotel services and the first to regularly claim $1,000 a square foot for its homes. (The original Boston Ritz Carlton is now the Newbury Boston.)

It opened, too, on the edge of what until recently had been nicknamed the Combat Zone, an especially seedy and combustible slice of downtown Boston.

That area was out, and developments such as the Ritz-Carlton were in.

The entrance of a hotel on a city sidewalk, with two doormen at the doors. Ritz-Carlton Boston

Federal Reserve Bank Building

A skyscraper stretching toward the clouds, and the building looks like smoothed stone from the side. Shutterstock

At 32 stories and 614 feet, the 41-year-old Fed tower is one of the five tallest buildings in Boston, but fellow neck-craners such as the Pru and 200 Clarendon often overshadow it (literally and figuratively).

Hugh Stubbins Jr. designed the Fed tower. He is perhaps best-known for Ronald Reagan’s presidential library and the Citigroup Center in Manhattan.

The 140-foot gap at the bottom is there to allow sea breezes to blow through—and it makes the tower distinct among Boston’s downtown skyscrapers.

A skyscraper stretching toward the clouds, and the building looks like smoothed stone from the side. Shutterstock

One Financial Center

A kind of layer-cake-looking skyscraper as shown from just beyond some trees. Shutterstock

The 46-story tower that is 590 feet to its roof is one of the 10 tallest buildings in Boston, but, like with the Fed tower, its fellow skyscrapers can swallow its modern glory.

For that is what One Financial is: A solid example of modern architecture in a city best known for older styles.

Appropriately enough, Pietro Belluschi, a pioneer of modern architecture in the United States, designed it.

A kind of layer-cake-looking skyscraper as shown from just beyond some trees. Shutterstock

South Station

A giant brown building. There is a street intersection in the foreground with people. Abdullah Al-Eisa/Getty Images

So many people pass through New England’s busiest train and bus station daily that it’s easy to see the main building itself as nothing more than utilitarian—a garden shed with tracks.

But South Station—which dates from 1899 and which Shepley, Rutan, and Coolidge (now Shepley Bulfinch) designed—is an excellent example of Classical revival architecture.

Better yet, that architecture sheaths a vibrant and evolving complex—design and functionality helping to get you to points north, west, and south with (relative) ease.

A giant brown building. There is a street intersection in the foreground with people. Abdullah Al-Eisa/Getty Images

Cyclorama

A two-story, monolithic-like building extending for most of a city block. Boston Globe via Getty Images

William T. Sears and Charles A. Cummings designed this building in the early 1880s to host views of cyclorama paintings. It’s currently an arts hub (the picture herein is from 1974).

Its salient feature—a steel-trussed dome 127 feet in diameter—makes the Cyclorama worth a second look on its own.

But the Classical revival building is also an excellent reminder of how Boston buildings can evolve.

It hosted everything from boxing tournaments to roller skating after the cyclorama craze died down; and then became the site of auto-body shops and spark-plug concerns before ending up for decades as the hub of the city’s flower trade.

A two-story, monolithic-like building extending for most of a city block. Boston Globe via Getty Images

Bruce C. Bolling Municipal Building

A capacious lobby with tall floor-to-ceiling windows and a big staircase in the middle. Boston Globe via Getty Images

Architecture firms Sasaki and Mecanoo designed this redevelopment of the old Ferdinand Building in Dudley Square. The City of Boston was the developer.

The building opened in 2015, and houses the headquarters of Boston Public Schools. Capacious and light-filled, it’s a slam-dunk design-wise.

As Globe architecture critic Robert Campbell so memorably put it: “Compared with the clueless architecture often produced by the private real estate market, the Bolling is a Taj Mahal. It is a good place to work, and it is equally good as a piece of the city.”

A capacious lobby with tall floor-to-ceiling windows and a big staircase in the middle. Boston Globe via Getty Images

Hibernian Hall

Edward T.P. Graham and Joseph M. Dolan designed this four-story building 106 years ago as a hall for an Irish-Catholic fraternal organization.

Its fortunes have ebbed and flowed over the ensuing century-plus, and Hibernian Hall is now used as an arts hub. The building stands as a reminder of the changes in Boston itself during that time.

Roslindale substation

A sort of monolithic-looking brick building with large arched windows in the front and on the side. Photo courtesy of Roslindale.net

This cavernous building dating from 1911—its ceiling stretches to 46 feet—was originally built to convert converted AC to DC for localized distribution of electricity to power street cars. Hence the dimensions.

It fell into disrepair for decades beginning in the 1970s, but has taken on new life since 2017 as a location for popup and permanent retailers.

So the Classical revival building is an excellent example of the re-purposing of bits of Boston beyond downtown. But its sheer bulk and Robert S. Peabody design make it worth a second look.

A sort of monolithic-looking brick building with large arched windows in the front and on the side. Photo courtesy of Roslindale.net