Michael's Highland Park Perspective

I’ve lived in Highland Park for over 30 years and have helped buyers and sellers throughout Pittsburgh’s East End discover what makes this neighborhood so special.

A Suburb Within the City

I grew up in Squirrel Hill and Shadyside. When I told friends I was moving to Highland Park, I'd joke that I was moving to the suburbs. It wasn't a neighborhood we walked to. It was a neighborhood we drove to. I've always described Highland Park as a suburb within the city. You still get everything that makes Pittsburgh special, but life just feels a little different here. The homes have yards, front porches, and tree- lined streets and one of Pittsburgh's greatest parks becomes part of your everyday life.

The Park & The Porch

Life here revolves around two major anchors: the 380-acre park itself and the legendary front porches that line every street. It’s a place where Saturday mornings start at the reservoir and end with neighbors chatting over coffee on a wide stone veranda.

People don’t gather around shopping. They gather around green space.

The proximity to the Pittsburgh Zoo and the diverse Bryant Street business district creates an ecosystem where everything you need is within a ten-minute walk through tree-lined boulevards.

A Neighborhood for Growing Up

One of the biggest differences between Highland Park, Shadyside, and East Liberty is something you still see on the neighborhood streets: school-age kids riding bikes, playing together, and moving from block to block.

That was one of the original reasons we moved here 30 years ago. We wanted our children to have the independence to leave the house, find friends nearby, and move through the neighborhood together.

There is safety in numbers, but there is also something important about growing up knowing the families around you and feeling connected to more than your own block.

Thirty years later, I can still walk around Highland Park and see kids having that same experience.

More House. More Character. More Neighborhood.

One of the things I’ve always appreciated as a Realtor is that Highland Park gives buyers more house, more character, and more neighborhood than they often expect for their money.
The neighborhood offers tree-lined residential streets, substantial older homes, front porches, usable yards, and immediate access to the park all while remaining part of Pittsburgh’s East End.

The Park Side

Homes directly adjacent to the park's greenery, often featuring some of the most prestigious addresses and views in the neighborhood.

North of Hampton

Characterized by larger lots and grand Victorian structures, this area feels like a quiet, historic residential retreat.

South of Hampton

Bringing you closer to the Bryant Street business district, this area offers a slightly more urban, walkable feel with diverse housing styles.

Market Context

One Intertwined Housing Market

Understanding the Highland Park Housing Market

While geography creates different vibes, the market acts as one cohesive unit. Demand remains consistently high across all sectors, driven by the neighborhood’s unique value proposition.

VOLUME

66

Annual Transactions

MEDIAN PRICE

$500k

Reflecting strong property values.

ACTIVE LISTINGS

14

Low inventory keeps market competitive.

You Honestly Don't Need to Leave the Neighborhood

Reservoir Regulars

The local community of runners and walkers who consider the reservoir loop their daily meditation.

Urban Safari

A neighborhood tradition of exploring the hidden architectural gems and secret gardens of the side streets.

The Pub

Referring to the local gathering spots on Bryant Street where everyone truly knows your name.

Sunset at the Upper Reservoir

The definitive Highland Park experience—watching the sky change colors over the water as the city lights begin to twinkle.

The Personal Note

Growing Up Between the Blocks

“I’ve spent three decades walking these streets, and every season brings a new appreciation for the architecture and the people here. We call ourselves ‘Reservoir Regulars’—those of us who find peace in the daily loop around the water.”

“Highland Park isn’t just where I work; it’s where my kids grew up, where I’ve seen ‘Urban Safaris’ turn into community festivals, and where the houses aren’t just properties—they’re pieces of Pittsburgh history.”

“A Personal Measure of Highland Park: To me, the neighborhood is measured by the number of familiar faces you see between your front door and Bryant Street.”

Final Thought: Highland Park has a way of wrapping itself around you like an old favorite sweater.

Highland Frequently Asked Questions

What is Highland Park like as a neighborhood?

Highland Park feels like a suburb within the city—tree-lined streets, front porches, and yards, all centered around one of Pittsburgh’s greatest parks. It is a porch community where neighbors get to know one another, and many residents remain for decades rather than moving every few years.

Yes. Bryant Street covers many daily needs within walking distance, including groceries, coffee, restaurants, haircuts, and even auto repair. Many residents also walk around the reservoir each day, and it has become one of the neighborhood’s natural gathering places.
One of Highland Park’s most distinctive sights is school-age children riding bikes, playing together, and moving from block to block. Its residential streets and access to green space help make that kind of neighborhood experience possible.
Highland Park is quieter and more residential—a suburb within the city—while Shadyside and East Liberty offer more concentrated retail and denser day-to-day activity. Highland Park’s identity centers on the park itself and the neighborhood streets surrounding it rather than on a large commercial district.
Pricing varies by size, condition, architecture, and renovation quality, but well-maintained homes throughout the neighborhood now command strong prices. Top-tier properties can reach the $800,000 to $1 million range in any section of Highland Park.
Historically, the area near the park—north of Stanton Avenue and east of Highland Avenue—was considered the most desirable. Today, the market has become more intertwined, and strong, renovated homes command premium prices across all sections, although Highland Park remains a street-by-street and house-by-house market.
Michael DiFiore has lived in Highland Park for 30 years and specializes in Pittsburgh’s East End. That experience gives him direct, on-the-ground knowledge of the neighborhood’s submarkets, pricing trends, housing differences, and character from block to block.

Ready to find your place?

Leverage 30 years of local insight to navigate the Highland Park market with confidence.