Living in Chestnut Hill: A Neighborhood Guide

Between the Wissahickon and “The Ave,” you’ll want for nothing in this neighborhood at the top of the city.

Chestnut Hill

Market at the Fareway / Photograph by Jeff Fusco

Ne Plus Ultra

That’s Latin for “nothing’s higher,” and that applies to Chestnut Hill — literally. Originally called “Wissahickon Heights,” the neighborhood includes the highest point in Philly and is home to some of its most affluent residents. The Wissahickon Valley borders Chestnut Hill on its west, and residents consider the city’s great urban wilderness one of the chief selling points.

Like its just-down-the-hill neighbor, Mt. Airy, Chestnut Hill started out as a summer retreat. In fact, the Germans who were the first white settlers up this way called the village they established at Germantown Township’s upper end “Sommerhausen.”

And like in Mt. Airy, the coming of the railroads — to its east side in 1854 and to its west side 30 years after that — brought with it a year-round population. The latter railroad also brought with it the man who built it, Pennsylvania Railroad baron Henry Howard Houston. His “Wissahickon Heights” development brought the upper crust to the top of the city, and the upper middle class followed when George Woodward began to build his European-inspired rental houses.

You’ll still find plenty of bluebloods in Chestnut Hill, but they no longer set the tone for the neighborhood, for a younger generation has discovered its charms and made it their own. Drawn to it by assets like the Wissahickon Valley and one of the city’s classiest shopping districts, they have brought the neighborhood up to date while preserving its cherished history.

Park and Shop

In addition to exploring the neighborhood’s greenery, which includes Morris Arboretum & Gardens (100 East Northwestern Avenue), residents “keep it on the Hill” by patronizing the busy shopping district on Germantown Avenue. Truly local boutiques that cover you from head to toe include Serendipity (8506 Germantown Avenue), Style by Blain (8433 Germantown Avenue), and TC Unlimited Boutique (8518 Germantown Avenue), while Isabella Sparrow (8433 Germantown Avenue) has you covered at home. Must-visit eateries include McNally’s (8634 Germantown Avenue), home of the legendary “Schmitter” sandwich; Mexi-chic El Poquito (8201 Germantown Avenue); and Chestnut Hill Brewing Co., in the Market at the Fareway farmers’ market (8221 Germantown Avenue), a craft beer garden and taproom with a large pub menu.

Options Abound

Sure, a neighborhood as affluent as Chestnut Hill will have lots of multimillion-dollar homes. But, says Michael Sivel of the Sivel Group at BHHS Fox & Roach, you can also find much more affordable digs: “We have lower-price rowhomes to really expensive condos to grand estate homes on multiple acres bordering the park.” He adds that you could buy into this neighborhood for as little as $300,000.

What You Can Buy in Chestnut Hill For …


Chestnut Hill

Photograph by Gary Schempp

455-461 West Chestnut Hill Avenue. Cope and Stewardson designed this grand Jacobean Revival manor, built from 1903 to 1906, for a member of the Biddle family, and it’s still grand today.  8 BR, 4/1 BA, 11,360 sq. ft. Janice Manzi, Elfant Wissahickon Realtors, 215-680-7616.


Chestnut Hill

Photograph by Alcove Media

8215 Shawnee Street. This brand-new luxe townhouse faces Pastorius Park, home to a popular summer concert series. It’s also a short walk  from Germantown Avenue.  5 BR, 3/2 BA, 3,258 sq. ft. Mark Malfara, BHHS Fox & Roach Realtors, 215-327-8416.


Chestnut Hill

Photograph by Brian James

109 Rex Avenue. This light-filled 1884 farmhouse has  a gorgeous rear garden and has been totally updated  for the way we live now.  3 BR, 1/1 BA, 2,030 sq. ft. Rob Lamb, Compass Real Estate, 215-370-6798.


Published as “Living in Chestnut Hill” in the October 2023 issue of Philadelphia Magazine.