In July 2024, Winter Park's city commission voted to swap the brick paving planned for several S.R. 426 corridor intersections, including Chase and Ollie avenues, Cortland Avenue, Trismen Terrace, Sylvan Drive, and Phelps Avenue, for cheaper asphalt, redirecting the savings toward a traffic signal at Cortland Avenue that residents had requested. The decision didn't sit well with everyone. By February 2025, pushback over the traffic signal itself had commissioners reconsidering the whole trade, with a resolution on the table that could reopen the door to bringing the bricks back. Construction on the corridor was expected to begin the following spring.
That back-and-forth says more about the economics of brick streets in Winter Park than almost any listing description ever will. When the city is the one paying, brick and asphalt compete on cost, and a fight over a few blocks of pavement can occupy a commission agenda for more than a year. When a homeowner ends up paying instead, the calculation changes, and so does who's making the decision.
Two Kinds of Pavement, Two Different Wallets
Winter Park treats brick and asphalt as two separate financial systems, not two finishes on the same road. The distinction is spelled out in the city's Street Brick Policy, adopted by the City Commission in June 2001 and still in effect today.
Routine asphalt resurfacing comes out of the city's general Public Works budget. Brick is different. Under the policy, any project that upgrades an asphalt street to brick, or fully reclaims an existing brick street where the underlying road base has failed, gets billed to the property owners with frontage on that street. The city calculates the net cost and assesses it based on linear footage of frontage, a method the policy itself ties to Chapter 170 of the Florida Statutes, the state law governing municipal special assessments.
Here's how the two systems break down in practice:
| Type of work | Who pays | Funding source |
|---|---|---|
| Asphalt resurfacing, pothole repair, curb fixes | The city | General Public Works budget |
| Spot repairs to existing brick (settling, minor depressions) | The city | General Public Works budget |
| Upgrading an asphalt street to brick | Adjacent property owners | Frontage-based special assessment |
| Full reclamation of a deteriorated brick street (removing and rebuilding the road base) | Adjacent property owners | Frontage-based special assessment |
The line between the two columns matters more than it looks. A homeowner on a brick street that just needs a few settled bricks reset isn't on the hook for anything beyond their property taxes. A homeowner on a street where the sandy base underneath has shifted enough to require full reclamation, or a homeowner whose neighbors petition to convert an asphalt street to brick, is looking at a different kind of bill entirely.
What the Premium Is Actually Paying For
None of this would matter much if brick streets were just a curiosity. They aren't. Recent 2026 market analysis of Winter Park's core 32789 zip code found that homes within roughly a half mile of Park Avenue, inside what's sometimes called the brick-street triangle between Park Avenue, Interlachen Avenue, and Fairbanks Avenue, sell for something like 15 to 25 percent more per square foot than comparable homes in the city's outer neighborhoods.
That premium isn't paying for the bricks themselves. It's paying for what the bricks signal: walkable access to Park Avenue's restaurants and galleries, proximity to Rollins College, and, in neighborhoods like the historic Interlachen district, closeness to Interlachen Country Club, whose 18-hole course was originally designed by Joe Lee in 1985 and redesigned by Steve Smyers in 2007. Buyers aren't shopping for pavement. They're shopping for a walk score that a subdivision built in 1995 can't replicate no matter how much landscaping money gets thrown at it.
That's also why the premium has held up. Winter Park's brick-street inventory is fixed. The city isn't laying new historic brick streets in new subdivisions, and the ones that exist can't be manufactured elsewhere in Central Florida. Scarcity plus walkability is a durable combination, and it's the reason these blocks have stayed firm in price even when broader Orlando-area segments have softened.
The Backlog That's Forcing the Question
The tension between wanting brick streets and paying for brick streets isn't theoretical. It showed up directly in Winter Park's 2027 budget discussions this past summer. A city survey drew roughly 800 resident responses, and street quality, brick and asphalt alike, came back as one of the top concerns. The city's own budget memorandum acknowledged that funding "has been insufficient to keep pace with the level of street deterioration and the cost of repairs," and commissioners added an extra $500,000 to the roads budget as a result.
Winter Park has also been falling short of its own maintenance targets for years, typically completing 4 or 5 lane miles of repaving annually against a stated goal of 9, with the city now resetting that goal to a more achievable 7.5 lane miles per year. A deferred-maintenance backlog on ordinary asphalt streets is a budget headache. A deferred-maintenance backlog on brick streets, where the eventual fix triggers a frontage assessment rather than a line item in the city's general fund, is a different kind of problem, and it's one that lands on whoever owns the property when the petition finally goes through.
Public Works Director Charles Ramdatt captured the emotional split residents feel about the streets themselves during a 2023 city commission update on brick repair planning.
"Some people really love them the way they are, some people really hate them. There's hardly anyone in the middle."
The financial split is less emotional and more mechanical, but it's just as real.
Repair Versus Rebuild: Why Old England Avenue Isn't a Warning Sign
It's worth being precise here, because not every brick street with visible wear is headed toward an assessment. Old England Avenue, a one-way historic brick street in Winter Park, has had documented depressions from age, and the city has funded spot repairs there through its regular Streets Division budget, the same pool of money used for work on Pennsylvania Avenue and Lake Sue Avenue in recent years. That's routine maintenance. It doesn't trigger the Brick Street Policy's assessment provisions.
What does trigger those provisions is a full reclamation, the kind the policy describes for streets where "the condition of the road base underlying the brick surface has deteriorated" to the point that the existing bricks and asphalt need to come out entirely and get rebuilt from the ground up. That's a materially bigger project, and it's the one that gets billed to frontage rather than absorbed by the city.
A buyer looking at a home on a brick street shouldn't assume every visible pothole means a bill is coming. But a buyer should know the difference exists, because the answer changes what due diligence looks like.
What to Ask Before You Write an Offer or List Your Home
For anyone actively transacting in the Via district, Interlachen, Old England Avenue, or any of Winter Park's other brick-lined pockets, a few questions are worth asking before signing anything:
- Has the street had any recent brick reclamation work, and is there a petition pending with the city's Public Works and Transportation Department?
- Is there a recorded special assessment lien on the property? Once a brick assessment is approved, it typically becomes a lien tied to the property, similar to other Florida non-ad valorem assessments, and a standard title search before closing should surface anything already on record.
- If a petition is in an earlier stage, has it been voted on by the city commission yet? Petitions that haven't reached a final assessment hearing may not show up in a title search at all.
The city's Public Works and Transportation Department takes resident questions and repair requests directly by email at [email protected] or by phone at 407-599-3233. For a transaction with real money on the line, a direct call to confirm the status of a specific street is worth the ten minutes it takes.
FAQ
Does this mean every brick street in Winter Park carries hidden costs? No. Routine maintenance on existing brick streets is funded by the city like any other road repair. The assessment only applies to a street-level upgrade from asphalt to brick or a full reclamation of a deteriorated brick street.
Can I find out if a street has an active petition before I buy? Yes. The city's Public Works and Transportation Department can confirm the status of any pending brick petitions or scheduled reclamation projects for a specific address.
Does the assessment affect the whole neighborhood or just certain lots? It's calculated by linear footage of frontage on the specific street named in the petition, so it applies to the properties that actually front that street, not the broader subdivision.
The Takeaway for Buyers and Sellers
The brick streets that make Winter Park's core neighborhoods worth a premium are the same streets that carry a distinct, city-defined cost structure the moment they need real work. That's not a reason to avoid the Via district or Interlachen. It's a reason to ask sharper questions before an offer goes in, and to understand, if you're selling, exactly what story your street's condition is telling a buyer's agent who's done this homework.
If you're weighing a purchase or a listing in one of Winter Park's brick-street neighborhoods and want a straight read on what a specific address is actually worth, and what it might owe, Florida One Real Estate can walk through it with you street by street. Get Your Instant Home Valuation to start the conversation.
