When you watch The Fresh Prince of Bel-Air and hear Will Smith sing “West Philadelphia, born and raised,” you can thank the Overbrook neighborhood for inspiring the oft-repeated line.

Overbrook anchors an end of the Main Line, an old commuter railroad corridor that gave rise to distinguished suburban communities in the early 20th century. “The housing in Overbrook is very good and attracts a lot of people who work for the city as police officers, firefighters, teachers and attorneys,” says Michael Cohen, a Philadelphia native and real estate agent with Keller Williams Realty. “It’s an attractive area with tree-lined streets. It sells very well.”

Overbrook sits on the city’s western boundary, where dense residential streets with attached row houses and duplexes start giving way to larger single-family homes on the other side of City Avenue in Montgomery County. Clay red brick and slate grey stone form most of the homes designed a century ago in Victorian, Tudor and Colonial styles that help give the neighborhood its historical feel. With commuter rail service still an essential feature of the area, the sound of clanging train bells and rolling steel bisects the community and parallels the homes and neighborhood businesses along Lancaster Avenue, the main thoroughfare that leads to Center City Philadelphia about 5 miles away.

Cohen says home prices in the neighborhood are competitive but still affordable for many households, making it a desirable place for those who want to be in the city without feeling overcrowded. According to Homesnap, the median sales price as of March 2023 was $194,000, about 20% below the city’s median home price. Listings at the time included a 3-bedroom, 1.5-bathroom row home with an asking price of $185,000. While owners of recently renovated row houses typically ask for bids over $200,000, duplex units can approach $300,000 or more. At the highest end, stately single-family homes at the neighborhood’s edge and near the campus of St. Joseph’s University can range from $400,000 to $800,000.

Inside the halls of the castle-like Overbrook High School, one of the neighborhood’s historic landmarks, teachers and coaches have helped mold superstars like Will Smith, NBA champion Wilt Chamberlin and Guion Bluford Jr., the first African American in space. The area also includes several charter schools and private institutions like St. Donato and the Harambee Institute of Science and Technology, giving families additional options for where to send their children.

While most of the neighborhood is in an urban environment, you can quickly enter a more natural, wooded setting by walking the trails at Morris Park or driving past Haddington Woods on Landsdowne Avenue. If you’re trying to shoot some hoops, you won’t have difficulty finding the neighborhood’s signature purple-and-gold basketball court at the Tustin Recreation Center, which also features a weight room and multi-purpose spaces inside.

There are various places to shop and dine in and around Overbrook, as there are suburban shopping centers and neighborhood retailers throughout the community. Overbrook Pizza, a hole-in-the-wall-type establishment near the train station, is an example of a neighborhood-oriented spot. On City Avenue, residents walk or drive to get groceries from the Aldi in the strip-mall shopping center that includes an Applebees, a Ross clothing store and various local and franchise businesses. Past the train station and St. Joseph’s in the other direction, the Bala Cynwyd shopping center offers a broader selection of stores and restaurants two miles away from the neighborhood.

With its comfortable setting, Overbrook is easily where you can spend most of your days chillin’ out, relaxin’ all cool.