Fenway has world-class public transportation and about 25 bus, 3 rail, 1 subway and 1 light rail lines passing through it.

The Fenway–Kenmore area was formed by land annexed from neighboring Brookline in the 1870s as part of the Brookline-Boston annexation debate of 1873 as well as from land filled in conjunction with the creation of landscape architect Frederick Law Olmsted parks in the 1890s When planned, it was thought that the buildings built upon the Fenway parkway would house high-wealth residents and that the whole area would be a high-class neighborhood. As property values rose, however, it was educational institutions that sprung up along the Fenway’s route. By 1907, there were twenty-two educationally focused organizations, including nine college and universities which had made their homes on the Fenway. Residential buildings that were built needed their frontages to be approved by the Park Board so that a “poor looking building [did not] depreciate the value of the whole neighborhood”.

In the last few years, development in Fenway has picked up, particularly from developer Samuels and Associates. Recent developments include the renovation of the Landmark Center; the 2003 addition of Hotel Commonwealth on the site of the Rathskeller bar; and the 576-unit, 17-floor Trilogy apartment building on Brookline Avenue and Boylston Street. 1330 Boylston, a second high-rise apartment building, was completed in 2008 and contains 210 apartments, 85,000 square feet of office space contained within 10 floors and the new home of Fenway Health.

Planned developments include a 24-story mixed use development at the confluence of Boylston Street and Brookline Avenue, likely including retail, dining, and luxury hotel/apartments. Other plans include the renovation of the Howard Johnson motel on Boylston Street, to be rehabbed as an upscale hotel. Additionally, developer John Rosenthal is planning to build a complex named One Kenmore over the Mass Pike alongside the Beacon Street Bridge, comprising 525 units in one 17 floor tower and one 20 floor tower. Concerning infrastructure, in 2007 the MBTA renovated the Fenway Green Line stop, and is planning to renovate the nearby Yawkey Way Commuter Rail Station. Finally, the Museum of Fine Arts, Boston recently completed a $425 million expansion, and the Isabella Stewart Gardner Museum completed construction of a second building.

There are about 297 restaurants, bars and coffee shops in Fenway, making it a hot destination for night life even when the Red Sox aren’t in town! People in Fenway can walk to an average of 16 restaurants, bars and coffee shops in 5 minutes.

East Fenway has a large student population due to its proximity to area colleges and universities, while West Fenway, formerly known as a student haven, has seen rising interest from young professionals, doctors, Longwood Medical Area employee’s and families. The Kenmore Square area is mainly commercial with many residential units now owned by Boston University and used as on-campus housing for students.

It is the home of Fenway Park, the famous Citgo sign, Kenmore Square, The Art Institute of Boston, The Forsyth Institute, Massachusetts College of Pharmacy and Health Sciences, Northeastern University, the New England Conservatory, portions of Boston University (including the Myles Standish Residence Hall), portions of the Harvard Medical School, Berklee College of Music, The Boston Conservatory, Massachusetts College of Art, Wentworth Institute of Technology, Simmons College, Wheelock College, Emmanuel College, New England School of Photography, Holy Trinity Orthodox Cathedral, the Isabella Stewart Gardner Museum and the Museum of Fine Arts, Boston

The neighborhood is ringed by the MBTA Orange Line Ruggles subway station and the following MBTA Green Line trolley stops:

Yawkey Station on the Framingham/Worcester Line of the MBTA Commuter Rail is located near Fenway Park and Kenmore Square and provides limited inbound and outbound stops for commuters during rush hour. Fenway–Kenmore is also served by a number of MBTA buses connecting it to the city proper and the surrounding neighborhoods and communities.

As for roadways, Fenway and Park Drive circulate around the Fens. Boylston Street is a major east-west route, as are Beacon Street (MA 2) and Commonwealth Avenue (U.S. 20), which intersect at Kenmore Square. Brookline Avenue begins in Kenmore Square at this intersection and proceeds southwest. Huntington Avenue (MA 9) is on the southern border, while Massachusetts Avenue forms the eastern border, and is a major north-south route. Although the Massachusetts Turnpike cuts through the neighborhood, there are no access points to it except westbound only at Massachusetts Avenue and Newbury Street.