If you love cities, you’ll probably love Pittsburgh.
Of course, lots of people hate cities for many reasons, and they seem to be disproportionately represented in elected office and talk radio. You’re not going to convert anyone who prioritizes parking above all else, or doesn’t want to be around those people (take your pick). That “alpha male” podcaster bro who’s too scared to walk around Downtown Pittsburgh without a gun (these people exist, sadly) is probably a lost cause.
But if you like cities in all their messy, contradictory, serendipitous glory, then Pittsburgh might be for you.
That seems to be the case for Rob Delahanty, a West Coast-based YouTuber known as “CityNerd,” who combs through a lot of data about cities, transit, urban planning, walkability, affordability, and other urbanist predilections. He noticed everything kept coming up Pittsburgh. So, he came to visit and made a lengthy video about what he found. It’s called “Pittsburgh: The Affordable Urbanism Mecca?” — and that question mark is just for effect. It totally is.
We try to parse the meaning in a lot of clickbait listicles, which are almost always less than meets the eye. So, it’s pretty nice to see what happens when somebody who knows what he is looking at, and observes it accurately, still seems overjoyed to be here. The synopsis “RIDICULOUSLY UNDERVALUED” sums it up, but how he arrives at that conclusion is fascinating.
Anyway, watch the video. It’s great, and I promise to never recommend a YouTuber again.
For sale: 6833 Meade St., Point Breeze, $279,900.
I have had to pass through Point Breeze almost every weekday for two years, and I find new things to like all the time. It’s just a beautiful neighborhood, whose only flaw seems to be proximity to Squirrel Hill, which grabbed 95% of the good restaurants and shops. But it’s also the rare Pittsburgh neighborhood where not a lot really qualifies for inclusion in this column. Except, well, this nice condo, with an unusual (creamsicle?) paint job, beautiful floors and woodwork, and a lot of healthy trees in the vicinity.
For rent: 2711 Cobden St., South Side Slopes, $950/month.
Coming to Pittsburgh with few preconceived notions about the place, CityNerd loved the South Side, which he ranked number one of all his favorite Pittsburgh neighborhoods. I wouldn’t go that far, but Pittsburghers are way too down on the South Side, which has lost much of its heat to Lawrenceville and the Strip, and has a reputation for drunken mayhem that’s only occasionally deserved. Sure, two nights a week it’s a nightlife district, slightly past its prime but still fairly healthy. Every other time of day it’s pretty quiet, with one of the country’s longest intact stretches of Victorian commercial architecture on Carson Street, housing everything from coffee shops and restaurants to vintage clothiers and hardware stores. The housing stock is just as solid, with a ton of restored rowhouses interspersed with historic apartments. Even SouthSide Works seems to have turned a corner; CityNerd inexplicably loves Cheesecake Factory, but we agree on Pins Mechanical (“kind
of like an urbanist’s Dave & Buster’s”).
For rent: 130 22nd St., South Side, $1,200/month.
It’s always nice when schools look like schools — places where important things like educating children taking place — and not featureless concrete bunkers for warehousing youth. But if there just aren’t enough children for a school, the next best thing is turning the former St. Casimir High School into housing. As saints go, St. Casimir is a deep cut; I don’t even know if he’s known enough to feature in the book of burning saints my wife got for her confirmation (instead of, like, a Nintendo). Housing prices on the South Side are somewhat (relatively) elevated, but nice rentals like this are still pretty common.
For sale: 410 W. Swissvale Ave., Swissvale, $147,500.
Sure, every Pittsburgh neighborhood (except maybe two or three) is “RIDICULOUSLY UNDERVALUED” when compared to the usual high-end coastal enclaves. But what neighborhood is ridiculously undervalued for Pittsburgh? Well, the entirety of the Mon Valley for starters, but Edgewood and Swissvale are the closest to the city and have the nicest homes, like this freshly painted example. No, I’m not going to get into litigating where Edgewood, Wilkinsburg, Regent Square, Swissvale and Pittsburgh begin and end, because life is too short for that. However, I did just have an excellent meal at nearby Bombay To Burgh, and have definitely chosen places to live for worse reasons than that.
For sale: 5636 Rural St., Garfield, $180,000.
Maybe this street was rural back when George Washington was sipping Iron Cities at the Graveyard Grille (perhaps the last time it was open), but that’s not the case today. Then, there’s that window situation — what are we even doing here? Is the house squinting at me? Is it winking? I get that a lot of decisions made in the ‘60s, like this 1965 townhouse, can be blamed on the drugs. But I’m not sure that other explanations are even plausible.
For sale: 603 Whitney Ave., Wilkinsburg, $199,000.
I’ve noticed that Little Free Libraries seem to be catching some strays in the tedious “everyone-is-a-gentrifier (but me)” discourse, and I want to condemn that shameful display with the utmost vehemence. Who gets mad at free books for kids? You can put Audre Lorde or Frantz Fanon in there; there aren’t any rules. At any rate, this house’s listing features its Little Free Library in a picture, and that’s fine. If there’s a culture war afoot, I’m on the side of the libraries, little or otherwise.
This article appears in Jul 2-8, 2025.
