When you buy an older home in Winter Park, much of what you're paying for is the land and the set of rules attached to it. Under some older homes, the land is worth several times as much as the house. So the price follows what the city will let the next owner build, split, keep or tear down. This fall, several of the decisions that set those limits are still open.
That matters if you're comparing Winter Park with suburbs where most homes went up in the last 25 years. Out there, comparable sales tell you most of the story. In Winter Park, comps tell you what the last buyer paid under the last set of rules.
The House Is Often the Smaller Number
Spectrum News reported in July 2026 that in some cases the land under an older Winter Park home is worth several times more than the structure. A local Realtor quoted in that story laid out the renovation math. "You invest $400,000," she said, "and then you remember it's still a house from 1950." Her point was that an older structure may not gain value the way a new one does, so even a big renovation leaves the owner with the same old ceilings and foundation.
The same report describes what builders like about an empty lot. With the old house gone, there's nothing to work around, and a custom home can start from zero.
Follow that logic and the house becomes a cost to remove, while the land becomes the thing being priced. Land in Winter Park is worth whatever the code, the commission and the Historic Preservation Board allow on it. That's why a few city meetings this year carry real weight for anyone pricing an older property.
Merrywood Shows What One Vote Can Add
The clearest example is at 1020 Palmer Ave. Merrywood is a nearly 90-year-old lakefront estate designed by James Gamble Rogers II, and it's listed in Florida's database of historic and cultural assets. Winter Park Voice reports that it sold in August for $15 million, the highest price ever paid in Winter Park. The new owner has asked the City Commission to split the lot in two.
According to the Voice, a split would make the property even more valuable, because part of it could be sold separately. Under the plan described at the meeting, the existing house would be at least partly demolished and turned into a guest house.
Here's how the decision has moved so far:
- June 2026. Commissioner Kris Cruzada, Mayor Sheila DeCiccio and Commissioner Craig Russell voted to approve a lot split with no preservation conditions.
- Aug. 26. The owner asked that the second reading be tabled until Oct. 14, and the item next came up on that date.
- Oct. 14. After a meeting that ran more than four hours, Cruzada changed his position and pushed for a compromise that would save part of the house in exchange for the split. The commission voted 5-0 to delay its decision until Nov. 11.
Commissioners discussed keeping only part of the façade, the front wall, and gutting the rest. "Just like a billboard?" Russell asked, according to the Voice.
As this post goes up, the Merrywood decision is still pending. Most buyers will never look at a $15 million estate, but one property's value now depends on a single vote about how much of an old house has to stay standing, and that question can come up on far smaller lots.
Designation Is Voluntary. The Rules That Follow Are Not.
By law, Winter Park can't force an owner to designate a home as historic, and the July reporting said city leaders aren't considering a change to that. Signing up is free. The city says designation and design review carry no fee. Exterior changes on a designated property have to be compatible and are subject to review. The Historic Preservation Board can grant variances for compatible additions, and interior remodeling isn't reviewed.
Once a property is designated, the rules get strict. In May 2025, the commission voted 4-1 to approve changes to the preservation code. Winter Park Voice reported that commissioners chose the version requiring exact reconstruction after unauthorized demolition or a major alteration, plus loss of any variances, over a proposed money fine. The city's ordinance draft describes restoration to the exact previous condition and materials. It also lets the board revoke variances and require full reconstruction as an authentic replica.
Those variances can be worth a lot. The same Voice story covered a College Quarter project at 965 Lakeview Drive, approved at 7,200 square feet. A builder estimated that losing the historic-district variances could cost that project $500,000 to $800,000.
Some incentives already exist. The city's preservation FAQ says designation doesn't affect a property's tax valuation. In May 2026, Winter Park Voice reported that the city code already allows tax exemptions for historic properties, though the city's planning and zoning director said no one appeared to be using them. She also said the city offers a 50 percent matching grant for qualifying renovation work, up to $18,000. How either applies to a particular address is a question for the city and a tax professional.
Those incentives are modest next to the variance costs above and the penalties now written into the code. The larger package meant to make designation more attractive hasn't been adopted.
The Incentive Package Is Still in Committee
On July 1, 2026, the Historic Preservation Board held a work session on ways to make preservation pay. Minutes from that session list grants, more funding, consultant support, lower permit fees, floor-area incentives, transfer of development rights, tax incentives, outreach and code changes.
The board's Sept. 9 agenda set the goal of finalizing those ideas for a joint work session with the commission on Sept. 24. The city's meeting portal lists that session as canceled. As of mid-October, the city meeting calendar also showed the board's Oct. 14 meeting as canceled, and no replacement joint session on incentives had been scheduled.
That gap affects price. If the owner of an older house compares keeping it with selling to a builder, the keep-it side has an $18,000 grant cap and a little-used exemption to point to, and nothing new. Betsy Rogers Owens, executive director of Friends of Casa Feliz, told Spectrum News that other cities use tools to share the cost of keeping historic homes with their owners. Casa Feliz itself was saved from demolition nearly 25 years ago, after donors raised several hundred thousand dollars. The broader tools the board discussed in July are still proposals.
Trees Are Next on the List
One more factor shapes what a lot can hold. On Sept. 24, 2026, Winter Park Voice reported final approval of a budget, starting Oct. 1, that cuts public tree planting by about $210,000. It also eliminates two vacant tree-related positions, including the tree-permit position. The story says officials proposed getting out of the residential tree-permit process.
The city's Urban Forestry page still says residential tree-removal permit rules and enforcement haven't changed. Protected trees still need a permit, except where state law overrides local authority. So the requirement still stands, even as the budget behind it shrinks.
Here's where each lever stood in mid-October 2026:
| Lever | What it decides about a lot | Status, mid-October 2026 |
|---|---|---|
| Lot splits | Whether one parcel can become two | Merrywood decision delayed to Nov. 11 |
| Historic designation penalties | Cost of unapproved demolition or alteration | Adopted May 2025 |
| Preservation incentives | Whether keeping an old house pays | Existing grant and exemption only, Sept. 24 workshop canceled |
| Residential tree permits | Whether protected trees limit what you can build | Rules unchanged, staff position cut in budget |
Pricing an Older Winter Park House With All This in Mind
Because the land carries so much of the value, the useful questions about an older Winter Park home are mostly about the parcel:
- Is the property on the historic register? The city's historic preservation page explains what designation involves and who reviews changes.
- Have any variances been granted? Under the 2025 rules, variances on a designated property can be revoked after unapproved work.
- Is anything nearby on a commission or board agenda? The city meetings page lists upcoming sessions, cancellations included.
- Are protected trees on the lot? The Urban Forestry page lays out the current permit rules.
Two similar-looking houses on the same brick street can sit under very different rules. A comparable sale only helps if the comp's lot carried the same rules as the one you're looking at.
FAQ
Can Winter Park make me designate my home as historic? No. Spectrum News reported in July 2026 that by law the city cannot force designation, and city leaders weren't considering a change.
Does designation restrict interior renovations? The city says the Historic Preservation Board doesn't review interior remodeling. Exterior changes are reviewed for compatibility.
When will the Merrywood lot split be decided? The commission delayed its vote until Nov. 11, 2026.
This post is general information, not legal, tax or financial advice. Before you rely on a rule for a specific property, confirm it with the City of Winter Park and the right professional.
If you own an older home in Winter Park and want to know what your lot is worth under today's rules, Ken Burningham can put together a valuation that weighs the parcel as carefully as the house. Get Your Free Home Valuation, and we'll walk you through it.
