PHOTOS BY 360 CAPTURES

While many of Pittsburgh’s hillsides and valleys were becoming developed in the late 1800s, Squirrel Hill remained lush and rural as the city grew up around it.

Murdoch Farms, a vibrant dairy farm and nursery, was one of the last properties to have stately homes for the elite built on it. Because electric trolleys connected Squirrel Hill to the rest of the city, the verdant tracts of land were attractive to the millionaires of Pittsburgh’s industrial age.

In 1914, the Sterrett family, who at the time owned a large swath of land in the community, built one such impressive manse at 5558 Aylesboro Ave. in Squirrel Hill North. The powerful local family included Pennsylvania Supreme Court Justice James Patterson Sterrett; Pittsburgh Sterrett 6-8, a neighborhood school and partial Classical Academy Magnet school in Point Breeze, still bears his name.

Sterrett’s nephew, lawyer James Ralston Sterrett, who is buried in Homewood Cemetery, built the 7,500-square-foot-estate in the Murdoch Farms enclave. In addition to his family, the estate housed four servants, a nurse and a live-in butler.

Today, the crew living there is smaller — but the home’s elegance remains.

Current owner Georgia Rossi says it took her family over a year to find just the right home after relocating to Pittsburgh in 2018. They focused their search on Squirrel Hill because of its proximity to Downtown and walkability to restaurants, schools and Schenley Park.

“Our main criteria were a welcoming home where friends and family could gather, a large flat lot so kids could play and run around, with modern amenities,” she says. “We found this was a tall order to fill in Squirrel Hill.”

Their persistence paid off, though, and 5558 Aylesboro Ave. checked every one of Rossi’s boxes. Measuring more than half an acre, the backyard was perfect for the Rossi family’s active children.

The home’s eight bedrooms and six bathrooms also made it easy for Rossi to host gatherings of any size. The historical charm of the home served as the perfect backdrop; Rossi says she has always loved greeting her guests in the grand foyer.

“It features elegant details like high ceilings, intricate moldings and statement lighting with an impressive sweeping staircase,” she says.

The home’s custom original details are present in every room, including the ornate, wood-paneled vestibule. Arched doorways, wainscotting and grand chandeliers showcase Pittsburgh’s turn-the-of-century opulence. Despite the age of the home, impeccable care has maintained all its original details.

Although modern HVAC keeps things toasty (or cool) year-round, 10 intricately detailed mantles and hearths that once heated the large brick home are still in place today.

Also still in place is the dining room’s striking original wallpaper. Manufactured in Paris, the panoramic wood block print wallpaper is composed of 25 panels designed by Carle Vernet. The print is titled “Les Chasses de Compiègne” and is found in only five homes across the world.

The dining room also was used to film a scene in 2021 for the Netflix drama “The Chair,” starring Sandra Oh.

At the heart of the home is a kitchen housing high-end appliances, including a stunning cobalt blue Viking range, and ceiling-height white cabinetry. Featuring warm wood tones and a prep sink, the oversized island is a welcoming space to gather while the host is preparing a meal. A butler pantry with an additional sink, wall oven and refrigerator adds to the ease of hosting at the grand home.

Beyond the main floor, each of the eight bedrooms has their own unique features. The primary suite is expansive and includes both a bathroom and a dressing room. The remaining bathrooms and bedrooms are all bright, updated and well-maintained.

“A home of such grandeur and magnitude in a premier location, and in prime condition, is a rare treasure in Pittsburgh in 2025,“ says Julie Rost of Berkshire Hathaway HomeServices.

Rost now has the property listed for $4.25 million. While no stranger to luxury listings, Rost’s favorite feature of the home is somewhat surprising.

“I can’t resist a good third floor, in general,” she says. “The privacy, ‘nook-and-cranny’ spaces, the lines of the ceilings…but this one takes the cake.”

Rost says from the moment one rounds the corner of the staircase, light begins streaming down from the upper level.

“There is room after room…a home gym, a guest suite, billiards hall and a game room — all done to match the style and caliber of the first and second levels,” Rost says.

That half-acre lot is another gem in the city neighborhood. With a large paved pad for basketball or wheeled toys, the built-in trampoline, and a two-story garage with bays on two sides, the yard’s possibilities are endless for entertainment and recreation.

“We love the back porch overlooking the private lot surrounded by tall arborvitae trees,” Rossi says. “It has a wonderful flat backyard where my kids and friends played lacrosse, basketball and jumped.”

About: Squirrel Hill North (shuc.org)
Population: 11,879 (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.