Walking the Colonialtown South Historic District: Brick Streets and Bungalows
Platted in 1883, built out from 1913, protected since 2000: a self-guided walk through Colonialtown South's Craftsman bungalows, revival styles and brick streets — plus the looser, unprotected north for contrast.
3 minute read
The best free attraction in Colonialtown is its own street grid. South of East Colonial Drive, the Colonialtown South Historic District preserves one of Orlando’s most intact early-20th-century residential landscapes — brick streets, mature live oaks and block after block of bungalows and revival-style houses — and it rewards exactly one mode of exploration: on foot, slowly, looking up. Here is how to walk it and what you are actually looking at.
The history under your feet
The district’s earliest subdivision was platted in 1883, making this one of the oldest platted residential areas in the city. Its largest area was developed starting in 1913, when developer H. Carl Dann Sr. was among the prominent builders shaping this side of Orlando, and the bulk of the housing rose during the 1920s Florida land boom and in the years between the Great Depression and World War II. Development here followed the traditional pattern — a developer platted the land, then individual buyers built their own homes or hired their own builders — which is why no two blocks repeat themselves. The city designated Colonialtown South a local historic district in 2000, and exterior alterations, additions and demolitions in the district now run through a Certificate of Appropriateness from the Historic Preservation Board. The protection is a large part of why the walk still works.
What to look for
The dominant language is the Craftsman bungalow — low-pitched roofs, deep porches, tapered columns — but the district’s pleasure is its variety. Within a few blocks you will pass Mission and Mediterranean Revival houses with stucco and tile, Tudor Revival cottages with steep gables, Prairie-influenced homes with wide eaves, and the Minimal Traditional houses that filled the later 1930s and 1940s lots. Brick streets survive on the residential grid, and the canopy does the rest: this is a neighborhood designed, a century ago, for shade. Streets like Shine Avenue and East Concord Street carry the full effect, and Shine has a working reward at the end of it — Maxine’s on Shine, a ranked, Michelin-selected restaurant operating out of one of the district’s own houses.
North of the Drive: the control group
Cross East Colonial Drive and you enter Colonialtown North, first platted in 1911 as Highland Grove. The bones rhyme — bungalows, cottages, the same era’s instincts — but North was never given the historic-district designation, so bright-painted cottages and contemporary infill sit side by side with the older stock. Walking both halves back to back is the whole lesson: South shows what preservation holds, North shows what a neighborhood does when it is left to improvise. Neither is a museum. Both are lived in, which is the point.
Walking it well
Go in the early morning or the golden hour, when the porches are occupied and the brick holds the light. Start anywhere along Shine Avenue, wander the grid without an agenda for forty minutes, then drift south toward Dickson Azalea Park and its 1926 Washington Street Bridge — the ravine park that anchors our Colonialtown parks guide — or north to the corridor for coffee and errands. You are a guest on residential streets: admire from the sidewalk, photograph the architecture rather than the residents, and let the neighborhood stay a neighborhood. When you are ready to see how the district’s houses work as a home base, our Colonialtown guide and the Orlando Top Spots Map pick up from there.
The verdict
Orlando sells its history in theme-park form all day long. Colonialtown South is the unscripted version — an 1883 plat, a 1913 building campaign, a 2000 act of preservation — still doing its original job of housing people beautifully. Walk it before dinner. You will arrive at the table understanding the city better.
Best for: architecture lovers, photographers, and anyone who thinks a neighborhood walk beats a gift shop.
Orlando Citizen by email
The weekly edition, in your inbox
One email, every Saturday: the week’s edition of Orlando Citizen — the week’s stories, rankings and winners, gathered in one place. Free, and you can unsubscribe at any time.
Related Stories
Editor’s Picks
Spotted an error? Tell us — corrections · How we rank