PHOTOS BY SARAH STALLINGS

After touring endless houses robbed of character thanks to painted-over millwork, shoddy updates and strange design choices, Carole Bailey vividly remembers the first moments she stepped inside 5427 Forbes Ave. nearly three decades ago.

While the massive, 5,000-square-foot brick home in Squirrel Hill had escaped the mishaps of bad renovations, it still needed quite a bit of an overhaul to be ready for Bailey’s family of five.

“We said, ‘Oh, we love this house, this is our forever home and we love everything about it,’” says Bailey. “And then we changed everything about it.”

That’s a bit of an exaggeration, as Bailey, her husband and three children thoughtfully brought the home into the modern era with renovations that honor its past. Still, it was a massive undertaking to update the home, which was built in 1901.

The first floor contained a captive room that was once a kitchen, though it had been removed by a previous owner. Multiple other captive rooms were carpeted, and the flooring underneath required refinishing and some updated wood inlay.

Today, the foyer floor pattern echoes the original leaded glass windows still surrounding the grand front door.

“We did one big overhaul, and the rest was bit by bit over the last 27 years,” Bailey says of the renovations.

The grand staircase in the ornate foyer is flanked by an elevator that was installed in the 1930s — and still works. When the family called first the manufacturer to have it serviced (and a safety shutoff added), the crew showed up with an index card listing all of the maintenance they’d completed on the elevator since originally installing it.

“It’s great for when you’re going on a trip and need to carry your bags down, or for laundry,” says Bailey.

The Baileys opened up some walls, but kept the historical charm intact. Clear sightlines between the kitchen and living room were more conducive to life with three young kids, who are all now adults.

The family loves to cook, and Bailey says the kitchen was laid out with flow and efficiency in mind. She adds buying a home without a kitchen was a risky choice, but it also gave her a blank slate to work with.

The family also replaced a bay window on the first floor with doors repurposed from portions of the original windows; the doors now lead to an outdoor kitchen with a pizza oven.

A three-stall garage in the carriage house was updated to include a single bay and a double bay to accommodate larger cars. A tidy apartment above the carriage house has a tenant living in it, which Bailey says has always been a positive experience, as well as an additional source of income.

Overall, the home has five bedrooms and seven bathrooms as well as a powder room, all of which have all been updated since Bailey first purchased the home. Space also was borrowed from an adjoining bedroom to create a nicely appointed bath in the primary suite.

With its soaring ceilings and exposed beams, the third floor, once a caretaker’s apartment, was reimagined as a game room and family space. Bailey says some of her fondest memories involve that third floor being packed with a gaggle of her kids’ friends.

“We built the third floor out, and that became their room,” she says. “They would have friends over all the time; it would easily sleep eight to 10 kids, so it was the place where the kids liked to hang out.”

With the kids now grown and living on their own, Bailey has listed the home with Julie Rost of Berkshire Hathaway HomeServices for $3.35 million.

“Given its vintage, it’s the perfect combination of everything you would expect from a home of that era — incredible woodwork, big rooms, a porte cochere and that historic elevator,” says Rost, who also loves the thoughtfully opened walls and the game room.

She’s drawn in by the home’s fascinating story, too.

“This house is so steeped in Pittsburgh history, from the owner lineage, events held on site, and the local materials used to construct it,” she says.

Throughout the years, Bailey has dug into the history of her grand old home and its ties to the surrounding Squirrel Hill community. Originally built by the Singer family more than a century ago, Bailey is only the home’s sixth owner.

The large lot and those around the home were subdivided in the mid-20th century, so the home is surrounded by smaller homes built around that time. Renowned dance instructor Genevieve Allen used to teach ballroom dancing in the expansive third-floor space and even hosted dancers traveling to Pittsburgh for local performances. Allen is credited in part with bringing modern dance to Pittsburgh.

Just influential in a different way, former resident Elizabeth Thaw founded the Birth Control League of Allegheny County, which later became the city’s first Planned Parenthood location.

In honor of her home’s history and her own passions, Bailey has served on Pittsburgh’s Planned Parenthood board for the last 18 years — even hosting its 60th anniversary gala at her home, where meeting minutes from an early gathering of the organization were printed and distributed to attendees as a way to bring history to life.

“This work was so important during the era of the railroads, coal and steel in this city. Men would get hurt and no longer be able to work, but their wives kept having babies — but they didn’t have enough money because no one could work,” Bailey says of the organization’s early mission. “They developed the league so they could actually have a life.”

Thaw’s half-brother, Pittsburgher Harry Thaw, was the defendant in what became known as the “Trial of the Century” for the 1906 shooting of architect Stanford White in front of a crowd at Madison Square Garden, which White had designed. The dispute was over Thaw’s wife, famed showgirl and Tarentum native Evelyn Nesbit — though he was found not guilty by reason of insanity. Parts of the tale are told in the musical Ragtime.

Despite the wild and storied history of her house, Bailey says when she thinks of moving on and downsizing, the most vibrant memory of her home is raising her family there. Walking to local eateries and the Squirrel Hill Farmers Market, enjoying relationships with other families in the community and watching her kids blossom into young adults was a joy, she says.

“To me, this is just where my kids grew up,” she says.

About: Squirrel Hill (North) (shuc.org)
Population: 11,907 (North)
Planes, Trains & Automobiles: 40 minutes to the airport; walking community, public transportation, bike lanes, rideshare.
Schools: City of Pittsburgh (pghschools.org)
Neighborhood: One of the most highly sought after neighborhoods in the East End, Squirrel Hill’s overall borders touch Greenfield, Oakland, Shadyside and Frick Park. Housing includes some of the area’s most historical grand mansions, Craftsmen and simple row houses. The community is diverse with a mix of students, families and immigrants from the world over; several historical districts are within its borders.