Yesterday's Bar & Grill. Photo by Peter Leeman
Hough’s, view of downtown from Greenfield and Cooper Kettle Brewing Company (all photos by Pete Leeman)
Hough’s, view of downtown from Greenfield and Cooper Kettle Brewing Company (all photos by Pete Leeman)

Close to Pittsburgh’s most established neighborhoods, Greenfield is drawing a new generation of homeowners with affordable housing and a do-it-yourself ethic. 

Stats (from Niche)

  • Population: 10,039
  • Size: 0.773 sq. miles
  • Median Rent: $970
  • Median Home Value: $221,594

Don’t Miss

Take Copper Kettle Brewing Co. on Greenfield Avenue, for example: At the only brew-on-premises shop in Pennsylvania, you can create your own single batch one-of-a-kind beers. Next door at Hough’s Taproom and Brewpub, you’ll find what author and Greenfield resident Thomas Sweterlitsch calls the “social center” of Greenfield. And you can grab pizza pies as small as six inches and as gigantic as 28 inches at Rialto Pizza. Or if you’re craving farm-to-table eats with big flavor, head to Staghorn Garden Cafe for savory scones, breakfast tacos or individual quiches.

Further aloft in the shadow of the parkway is Big Jim’s, a legendary bare-bones, old Pittsburgh style bar with a loyal following. Down the street is Saint John Chrysostom Byzantine Catholic Church, where Andy Warhol was baptized.

Wedged between Hazelwood to the south, Oakland to the north and Squirrel Hill to the east, Greenfield’s hilly topography offers magnificent views of Downtown and Schenley Park. On foot or bike, it’s an easy jaunt from Greenfield to Squirrel Hill’s abundant eateries and shops.

The community is less pricey than many of its neighboring enclaves, but just as convenient to their amenities, so first-time homebuyers love it.

Greenfield’s got character to spare, from its colorful native sons to its fervent baseball fans to its steep hills and spider web of streets and steps. This gritty neighborhood spawned two beloved Pittsburgh mayors (Richard Caliguiri and Bob O’Connor) and a slew of national sports stars. Plus, rapper Pittsburgh Slim calls Greenfield home.

Green Bay Packers head coach Mike McCarthy grew up in Greenfield and attended neighborhood school Saint Rosalia Academy, which has closed. A legendary baseball, basketball and football hero around these parts, McCarthy still contributes thousands of dollars every year to his alma mater and to the Greenfield Baseball Association. Established in 1951, this long-running city youth league keeps the neighborhood’s love of baseball alive. Bud Hammer, a janitor from Saint Rosalia’s early days, taught baseball to local boys and now has a field in the neighborhood named for him.

Because Greenfield is mostly residential, its many single-lane, two-way streets typically avoid congestion. The main roads—Murray and Greenfield avenues and Beechwood Boulevard—send traffic to the neighborhood’s business districts and down to the Waterfront shopping district in Homestead. Greenfield also offers easy access to I-376 and to Downtown via Second Avenue.

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