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Boston is so packed full of historic buildings some get left behind and forgotten. When a city is so full of history there are actually underrated buildings, you know it’s a great place to be.

Whether you just relocated to Boston or you’ve been here all your life, discovering some of the most underrated buildings can be an amazing way to see the city. Here’s a look at some of the most underrated buildings in Boston.

Roslindale Substation

Known as one of the most iconic buildings in Roslindale, this substation often gets overlooked. It’s not a huge tourist attraction like some of the buildings in Boston, but it’s still rather unique and amazing.

The building dates back to 1911 and used to be without heat or plumbing. A recent revitalization upgraded the Roslindale Substation by adding new, yet historically accurate windows for better lighting, and upgrading to include many modern conveniences.

The ceiling in this substation stretches 46 feet, and it’s considered a cavernous building. Originally, the building was used for power distribution of street cars. Today, it’s home to popups, retailers, and breweries.

The Classical Revival style is one you won’t find everywhere in Boston. It was designed by Robert S. Peabody, and it’s certainly worth the trip for those looking to enjoy great architecture and some of the history found in Roslindale, MA.

The Roslindale Substation is found at 4228 Washington Street.


Another underrated building in Boston, Cyclorama was designed by Charles A. Cummings and William T. Sears. It dates back to the 1880s and provides a steel-trussed dome measuring 127 feet in diameter. This is another Classical revival building and has played host to boxing tournaments, rolling skating events and so much more.

Cyclorama is located at 539 Tremont Street.

Boston City Hall

It’s not iconic and doesn’t stick out due to ornate features, but the Boston City Hall offers something you don’t see every day. Some will say it’s one of the ugliest buildings in Boston, but it’s still worth a second look.

The building was first unveiled in 1969, and at the time, it was a bold architectural statement. While it’s not a pretty building, it did spark conversation as people still talk about this building today.

Boston City Hall is found at 1 City Hall Square.

South Station

It’s easy to miss the South Station even though it’s one of the busiest train and bus stations in the city. The building dates back to 1899 and was designed by Shepley, Rutan, and Coolidge. It’s one of the best examples of Classical Revival architecture in the city.

While it can easily be ignored, the South Station offers plenty of history and was designed for functionality, along with aesthetics. It’s located at 700 Atlantic Avenue #2.

Boston Public Library – East Boston Branch

The East Boston Branch of the library offers a unique building you simply cannot miss. It’s not old, but it’s still worth visiting. The building includes a glass facade, and it’s built like one huge room without any columns inside. Many say it’s the most beautiful of the branches of the Boston Public Library.

The East Boston Library Branch is found at 365 Bremen Street.

Bruce C. Bolling Municipal Building

Designed by Sasaki and Mecanoo, this building was the redevelopment of the Ferdinand Building found in Dudley Square. It was re-opened in 2015 as the headquarters of the Boston Public Schools.  The building is rather unique and offers plenty of history.

This Municipal Building is located at 2300 Washington Street.

 The Ritz-Carlton, Boston

Designed by Handel Architects, this building is one of the most significant for Boston real estate in recent years. It was opened in 2000 and helped to transform the housing market in the city.

The Ritz-Carlton was the first condo building to include luxury-hotel services and the first to get $1,000 per square foot for the homes inside.  In addition, it opened right on the edge of what some called the Combat Zone, which was a not so nice area of downtown Boston. The Ritz-Carlton helped to change that.

This building is located at 10 Avery Street in Boston.

Hibernian Hall

A building dating back more than 100 years, the Hibernian Hall was originally the home of the Irish-Catholic fraternal organization. It was designed by Edward T.P. Gram and Joseph M. Dolan and stands four stories tall.

The building is an art hub today and still shows off some of the changes Boston went through as a city. It’s located at 184 Dudley Street.

There are several underrated buildings in Boston. Some have plenty of historical significance, while others are simply unique. Check them out and find your new favorite.

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