Most Akron neighborhoods are defined by what was built there decades ago. Highland Square is one of the few defined by what it's deciding to do next.
It's the most walkable neighborhood in the city — a reputation it earned back in the 1920s, when the streets were laid out so you could live, shop, eat, and catch a movie without ever getting in a car. A century later, that bet is paying off in a way most Akron neighborhoods can only envy. But the Square isn't coasting on it — right now the neighborhood is actively organizing around its own future, and if you own a home here, that's worth understanding.
What's happening in Highland Square right now
A new Special Improvement District. The City of Akron has been standing up a Special Improvement District in Highland Square — where property owners inside the footprint pay into a shared fund for extra services: added security, litter pickup, beautification, gathering spaces. It's what a neighborhood does when the people who own there decide to invest in it rather than wait on the city. That's a signal about direction.
The commercial strip is fighting to stay full. The city, business owners, and Akron Police have been working together to keep West Market's storefronts occupied and manage the late-night friction that comes with a busy entertainment district. New ownership at the beloved Mary Coyle ice cream shop has been held up as proof the strip can turn empty spaces back into anchors.
The theater is still the anchor it's always been. The Highland Theatre has been showing movies since 1938 — 600-plus seats, refreshed art deco, and a concession stand that now pours beer and wine alongside the popcorn. A single-screen neighborhood theater that's survived nearly ninety years is not a small thing. It's the reason people still say they're “going to the Square.”
The community organizes around its problems instead of leaving. Like a lot of dense, walkable districts, Highland Square has wrestled with safety and late-night issues — and the response has been residents and business owners organizing, pushing for action, and standing up that improvement district. A neighborhood that fights for itself is a very different thing from one that empties out.
Why the houses here are worth what they're worth
Highland Square's housing is mostly 1910s–1930s — real architectural character, on tree-lined streets, walkable to Market. That combination commands a premium nationally, and here it's baked into the original layout in a way you simply can't retrofit into a subdivision. Inventory is tight; when a house comes up, it tends to move. The median sits well above the Akron average — north of $150,000 — and it's held that position more consistently than almost any neighborhood in the city, because the people who own here tend to be owner-occupants who stay.
What this means if you own a house here
If you've owned a Highland Square home for years, you're holding something in short supply: a walkable, architecturally intact house in a neighborhood the market has never stopped wanting. That's leverage — and it means the buyer you choose matters. A rough flip that guts the original details takes value out of a place whose value is the details.
We're a local, family-owned team that buys houses in cash across Summit County, and we don't flip and we don't wholesale. Every property we buy, we renovate properly — working with the character that's already there, not stripping it out — and keep. If you're weighing a sale, you might also read our piece on neighboring West Akron, just south and west of the Square.
If you want a confidential cash offer on a Highland Square home, our Highland Square page has the details, or call or text us at (330) 661-9885. We respond within one business day.
