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Boston's 10 ugliest buildings, mapped

It’s not that all of these are aesthetically unpleasing necessarily, it’s that some are just plain boring

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It’s not that Boston’s 10 ugliest buildings are all aesthetically unpleasing necessarily. It’s more that some are just plain boring. Or at least that was the verdict of Curbed Boston readers, who helped devise this map.

Modern architecture came in for a particular drubbing, with that style's brutalist subset bearing the brunt of the criticism. What’d you think? (We think there are plenty of gorgeous modern buildigns in Boston.)

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1. Fenway Park

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4 Yawkey Way
Boston, MA 02215
(877) 733-7699
Visit Website

The home of the World Series champion Red Sox opened in early 1912, and that makes it the oldest ballpark in all of Major League Baseball.

The arena, which seats just over 37,000, is also one of MLB’s smallest.

Because of this size and age, it’s also not as sleekly striking as its younger MLB brethren; positively dowdy, in short.

A row of wooden seats in an open-air ballpark. Emma Krahmer/Shutterstock

2. The Clarendon Apartments

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400 Stuart St
Boston, MA 02116

The Robert A.M. Stern-designed condo opened in 2009, and has rankled residents ever since for its starkly utilitarian appearance.

The 107-unit spire could be even more obtrusive, though, so points for that.

Photo via Trulia

3. Tufts Medical Center

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800 Washington St
Boston, MA 02111
(617) 636-5000
Visit Website

One Curbed Boston reader described this complex as "the world's largest air-conditioner."

4. One Beacon Street

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1 Beacon St
Boston, MA 02108

Skidmore Owings & Merrill designed this office skyscraper, which went up in 1971.

The 37-story modern is representative of what one reader called "nothingness." Indeed, One Beacon is just kind of there and adds little aesthetically to the skyline.

Photo via Wikipedia Commons

5. Government Service Center

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50 New Sudbury St
Boston, MA 02114
(617) 227-0385

Another brutalist punching bag, this monolithic structure went up in the late 1960s and very early 1970s.

Paul Rudolph designed it as a way to kind of exhibit government at work, but for many it reigns instead as an eyesore downtown.

Photo via Wikipedia Commons

6. St. Anthony Shrine

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100 Arch St
Boston, MA 02110
(617) 542-6440
Visit Website

The Catholic parish and charity hub is something to look at on the inside, but outside readers described it as basically monolithic and forbidding.

The building dates from the early 1950s—any later and it might've looked worse.

Jim McIntosh/Flickr

7. Boston City Hall

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1 City Hall Sq.
Boston, MA 02201
(617) 635-4000
Visit Website

Boston's City Hall has been an architectural punching bag since its completion in 1968.

Kallmann, McKinnell & Knowles, then professors at Columbia, won an international competition to design the civic hub; and pivoted from more traditional fare as well as from sleek glassiness to a brutalist design that still perplexes and enrages the masses.

A large building with a concrete facade and a red pedestrian plaza in front. Jorge Salcedo/Shutterstock

8. 28 State Street

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85-87 Congress St
Boston, MA 02109

Emery Roth & Sons and Edward Larrabee Barnes Associates designed this skyscraper, which was constructed in the late 1960s.

The 40-story office building is definitely for modern architecture aficionados and nobody else.

Photo via Wikipedia Commons

9. One Federal Street

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1 Federal St
Boston, MA 02110

The Architects Collaborative was behind this 38-story skyscraper that went up in the early 1970s. It's another product of its time.

Photo via Wikipedia Commons

10. Harbor Towers

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65 E India Row
Boston, MA 02110

The pair of 40-story residential towers went up in the late 1960s and opened in 1971.

I.M. Pei designed them in the modern-slash-brutalist style popular at the time. They certainly stand out on the waterfront and not necessarily in a good way.

David Persson/Shutterstock

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1. Fenway Park

4 Yawkey Way, Boston, MA 02215
A row of wooden seats in an open-air ballpark. Emma Krahmer/Shutterstock

The home of the World Series champion Red Sox opened in early 1912, and that makes it the oldest ballpark in all of Major League Baseball.

The arena, which seats just over 37,000, is also one of MLB’s smallest.

Because of this size and age, it’s also not as sleekly striking as its younger MLB brethren; positively dowdy, in short.

4 Yawkey Way
Boston, MA 02215

2. The Clarendon Apartments

400 Stuart St, Boston, MA 02116
Photo via Trulia

The Robert A.M. Stern-designed condo opened in 2009, and has rankled residents ever since for its starkly utilitarian appearance.

The 107-unit spire could be even more obtrusive, though, so points for that.

400 Stuart St
Boston, MA 02116

3. Tufts Medical Center

800 Washington St, Boston, MA 02111

One Curbed Boston reader described this complex as "the world's largest air-conditioner."

800 Washington St
Boston, MA 02111

4. One Beacon Street

1 Beacon St, Boston, MA 02108
Photo via Wikipedia Commons

Skidmore Owings & Merrill designed this office skyscraper, which went up in 1971.

The 37-story modern is representative of what one reader called "nothingness." Indeed, One Beacon is just kind of there and adds little aesthetically to the skyline.

1 Beacon St
Boston, MA 02108

5. Government Service Center

50 New Sudbury St, Boston, MA 02114
Photo via Wikipedia Commons

Another brutalist punching bag, this monolithic structure went up in the late 1960s and very early 1970s.

Paul Rudolph designed it as a way to kind of exhibit government at work, but for many it reigns instead as an eyesore downtown.

50 New Sudbury St
Boston, MA 02114

6. St. Anthony Shrine

100 Arch St, Boston, MA 02110
Jim McIntosh/Flickr

The Catholic parish and charity hub is something to look at on the inside, but outside readers described it as basically monolithic and forbidding.

The building dates from the early 1950s—any later and it might've looked worse.

100 Arch St
Boston, MA 02110

7. Boston City Hall

1 City Hall Sq., Boston, MA 02201
A large building with a concrete facade and a red pedestrian plaza in front. Jorge Salcedo/Shutterstock

Boston's City Hall has been an architectural punching bag since its completion in 1968.

Kallmann, McKinnell & Knowles, then professors at Columbia, won an international competition to design the civic hub; and pivoted from more traditional fare as well as from sleek glassiness to a brutalist design that still perplexes and enrages the masses.

1 City Hall Sq.
Boston, MA 02201

8. 28 State Street

85-87 Congress St, Boston, MA 02109
Photo via Wikipedia Commons

Emery Roth & Sons and Edward Larrabee Barnes Associates designed this skyscraper, which was constructed in the late 1960s.

The 40-story office building is definitely for modern architecture aficionados and nobody else.

85-87 Congress St
Boston, MA 02109

9. One Federal Street

1 Federal St, Boston, MA 02110
Photo via Wikipedia Commons

The Architects Collaborative was behind this 38-story skyscraper that went up in the early 1970s. It's another product of its time.

1 Federal St
Boston, MA 02110

10. Harbor Towers

65 E India Row, Boston, MA 02110
David Persson/Shutterstock

The pair of 40-story residential towers went up in the late 1960s and opened in 1971.

I.M. Pei designed them in the modern-slash-brutalist style popular at the time. They certainly stand out on the waterfront and not necessarily in a good way.

65 E India Row
Boston, MA 02110