Affordable-ish Housing in Pittsburgh: Good vs. bad nostalgia edition (2025)

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Photo: Courtesy of Zillow

331 Hoffman Rd.

The other day, a pop song from my childhood leapt into my brain as it spilled out of a passing car, and suddenly time reversed for a few seconds.

It wasn’t even a song I really liked as a kid; it was simply part of the soundscape of daily life, like the symphony of crickets serenading a suburban dusk. Now, however, it’s a dopamine rush of pure nostalgia, and I’m transported to a time of pizza parties with sticky floors and greasy napkins, riding bikes to the arcade, collecting loose change to buy baseball cards and comic books, and hoping my favorite jam was up next on the radio.

I'm glad that I grew up in a time and place before life moved online. Describing it to my son makes me feel like an archaeologist describing the lost civilization of the Olmecs or something.

As a city, Pittsburgh’s nostalgia-industrial complex is fairly unique, and it helps create a strong, shared culture of collective memory that helps bind us together, even if the transient nature of modern life pushes us apart. Nostalgia can be good, but it can also be a trap.

Change isn’t good or bad, it’s just constant, and relentless, and coming for us all. The main driving force in American life right now seems to be a kind of toxic nostalgia for a time (the 1950s, mostly), that wasn’t all that great to begin with. Well, it was great if you were a white man coming home from the war to free college via the GI Bill, a unionized job at the mill, and abundant housing from the postwar building boom. For others, not so much.

GOOD NOSTALGIA: Go ahead, grab a Skyscraper Cone at the new/old Isaly’s. Pine for the days of the Steel Curtain (the defense, not the ride), and imagine an outfield anchored by Barry Bonds before he discovered steroids. Cheer the preservation/renewal of historic properties (like the New Granada Theater, Crawford Grille, National Negro Opera Company, etc.).

BAD NOSTALGIA: Bring back days when housing was cheap in Pittsburgh (because jobs were scarce and crime was not). Preserve this historic parking lot, abandoned dive bar, etc., to keep unwanted change (especially new housing) out.

For sale: 331 Hoffman Rd., Shaler, $249,900
Speaking of nostalgia, I spent the first year of my life in Shaler. I remember, uh, not much. Seems like an OK place, even though Route 8 is technically an outer ring of Hell. The suburbs were once full of places like this 1940 Cape Cod, before the great square-footage inflation of the ‘70s, and it was pretty good. You can still find some of these in Pittsburgh’s older inner-ring suburbs and a few scattered farther out. There should be a market for this — smaller families, starter homes — but they barely build anything this size (1,000 square feet) anymore.

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Photo: Courtesy of Oak Hill Apartments

Oak Hill Apartments, 475 Garner Ct.

For rent: Oak Hill Apartments, 475 Garner Ct., Oakland, $1,275-1,795/month
Speaking of nostalgia (pt. 2), I think I was watching (on TV) in this exact building when Marc-Andre Fleury stood on his head to bring the Stanley Cup back to Pittsburgh, because my brother lived here at the time. Yes, that seems like ancient history, but Fleury and Sidney Crosby are both still in the league, so what is time, anyway? This development was still new then, bridging the upper Pitt campus and the Hill District with a quiet, attractive, if somewhat bland mixed-income community. I haven’t been up there since then, but it still seems like a good place to live if you value walkability and proximity to transit.

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Photo: Courtesy of Zillow

1234 High St.

For sale: 1234 High St., Troy Hill, $239,000
“No, officer, I’m completely sober. Where do I live? Uh, 1234 High Street.” Definitely an answer a not-high person would give. Troy Hill is an enclave of old-school unpretentious urbanism without the stratospheric prices that usually commands nowadays. Up here on the mountain, Scratch and Penn Brewery are great places to eat and hang out, and you can actually feel like you’re looking down upon the skyscrapers Downtown.

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Photo: Courtesy of Zillow

214.5 Watson Blvd.

For rent: 214.5 Watson Blvd., Perry North, $1,000/month
This two-bedroom, two-bath yellow brick rowhouse on the North Side “includes a $9.95/month Resident Benefit Package” to sweeten the pot. What does that mean? What can $10 a month even get you nowadays? Replacement wood paneling for the basement? Lotto scratch-offs? A parking chair (plastic, gently used)? I’m curious to know how this works.

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Photo: Courtesy of Kaufmann's

Kaufmann’s, 434 Fifth Ave.

For rent: Kaufmann’s, 434 Fifth Ave., Downtown, $1,539/month
Speaking of nostalgia (pt. 3), remember Kaufmann’s department store? This is something that was indisputably better back in the day — the era of grand, elegant city-within-a-city department stores, at the nexus of streetcar lines and passenger rail. I caught the twilight of this era, and it was still pretty great. But it’s never coming back, killed by Walmart and the cult of ample parking. Oh, you can live here now, and there’s even a small Target in this building, as a better-than-nothing consolation prize. Most of these apartments are considerably more expensive, but the 672-square-feet studios aren’t too bad. (Oh, there’s a movie room? You have my attention.)

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Photo: Courtesy of Zillow

660 Chester Ave.

For sale: 660 Chester Ave., Perry South, $115,000
Very little housing was built in Pittsburgh for the entire decade of the ‘80s, which is kind of a wash, because that means there’s a lot less heinous ‘80s houses/apartments to look at. That said, these townhouses aren’t bad and even come with porthole windows (so nautical!), and a red-and-white-colored kitchen that’s oddly appealing. Usually, 100K gets you something with 100 years of wallpaper and soot stains to sort out, so (relative) newness has its advantages.

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Affordable-ish Housing in Pittsburgh: Good vs. bad nostalgia edition (2025)
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