Chestnut Hill is bounded on the northwest by Northwestern Avenue; on the west by the Wissahickon Gorge (part of Fairmount Park) (beyond which lie Upper Roxborough and Andorra); on the northeast by Stenton Avenue (a county line and city limit, beyond which lie Erdenheim and Wyndmoor, Springfield Township); and on the southeast by the Cresheim Valley (part of Fairmount Park) (beyond which lies Mount Airy).

The village of Chestnut Hill was part of the German Township laid out by Francis Daniel Pastorius and came to include the settlements originally known as Sommerhausen and Crefeld, as well as part of Cresheim. It served as a gateway between Philadelphia and the nearby farmlands. During the American Revolutionary War era (late 18th century), the area was one of many summer vacation spots due to its higher elevation, 400–500 feet (120 to 150 m) above sea level, and cooler temperatures than the historic Center City. Chestnut Hill is still stereotypically known as one of the more affluent sections of Philadelphia.

From the mid-19th century through the mid-20th, the neighborhood served as the functional equivalent of both a "railroad suburb" and a "streetcar suburb" of Center City; although it was part of Philadelphia, and not a suburb, it was a leafy outlying part functioning much like a commuter town. (It still serves this function, although the streetcars are gone.) The neighborhood contains a wide variety of 19th and early 20th century residential buildings by many of the most prominent Philadelphia architects.

Today, designated as a National Historic District, the community includes an extraordinary mix of impressive stone mansions, 19th century farmhouses, and more modest rowhomes. Charming shops and a multitude of cultural resources abound. Local attractions include the Water Tower, Stagecrafters, Valley Green, the Woodmere Art Gallery, or any of some 20 delightful restaurants clustered along Germantown Avenue.