Winter Park Voice reported that Cathy Gilmer told the Winter Park City Commission in June that a local historic designation "isn't ever going to be pursued." She was talking about Merrywood, the house her mother lived in from the mid-1970s until about a year earlier.
That one decision explains more about older homes in Winter Park than any architectural survey. Merrywood is a 1939 estate by James Gamble Rogers II on 3.67 acres overlooking Lake Osceola at 1020 Palmer Avenue. It is described as one of his largest and most ornate works. Even so, its protection came down to a single question. Was it on the city's local register? It was not. So anyone weighing an older Winter Park home should start with that question, before the floor plan or the roof age.
The Demolition Permit Was Already in Hand
Here's the detail that surprises people. When the commission took its first vote on Merrywood on June 24, a permit already in place would have allowed the home to be bulldozed any day. The only thing holding it back was a verbal agreement between the owners and the buyer under contract to wait for a second vote. The city then extended a demolition permit for the property in August. Winter Park Voice reported that officials have little power to require preservation, because the longtime owners never listed the house on the local register.
Lake Osceola Holdings LLC closed on the property in August for $15 million. As of September 30, the people behind that entity had not been publicly identified. Its attorney told the city the new owner wants to finish the lot split process. The second required commission vote is scheduled for October 14.
Two Lists With Very Different Powers
Winter Park keeps track of historic homes in two ways, and the difference between them decides what happens when someone files for a demolition permit.
| Florida Master Site File or historic survey only | Local landmark or local historic district | |
|---|---|---|
| What a demolition application triggers | A 90-day consideration period under Winter Park's ordinance | Review by the Historic Preservation Board |
| Can the board deny demolition? | No | Yes. Winter Park Voice reports that demolition needs board approval, or approval on appeal |
| Can the timeline be extended? | Another 60 days, for good cause and only with the owner's agreement | Contributing buildings in a district can't be demolished without an approved certificate of review |
| What happens during the wait | Staff and the board look at moving the house, a private or public purchase, or documenting and salvaging historic elements | Formal review of the request |
Merrywood was in the left column. Because it appears in the Florida Master Site File, a 90-day delay kicked in automatically when the owners, who inherited the estate from parents who bought it in 1977, filed a demolition application in early 2026. That 90 days bought time. It did not give the city the power to say no.
Age doesn't move a house into the right column either. The city says local designation generally requires a home to be at least 50 years old and to have architectural, aesthetic or historical value. Meeting that test only makes a home eligible. The owner still has to request designation, and Spectrum News reported in July that by law the city can't force owners to designate, and city leaders are not considering changing that. The city's register table lists 130 entries. Its locally designated districts include College Quarter and Virginia Heights East, and the city map separately labels Downtown and Interlachen as National Register districts.
What the Land Is Worth Without the House
Once a house can come down, the price is really about what can go up in its place. Commissioners heard that if Merrywood sold as one parcel, the house could be replaced with up to 56,000 square feet, based on the acreage and city code. That would be the largest single home in the city. The land alone was estimated at more than $10 million as the largest single lot on Winter Park's Chain of Lakes.
A few doors down, the current record shows what that math looks like when it plays out. Marc Hagle recently finished years of construction at 926 Palmer Avenue after tearing down an older home there. The result is a 31,000-square-foot residence, currently the city's largest.
The offers on Merrywood tell the same story. A buyer offered $10 million in August 2025 and later raised the offer to $12 million, saying he would like to see the house preserved. The property sold for $15 million. The house was handled as a pocket listing and never broadly advertised on the MLS. Betsy Owens, executive director of Friends of Casa Feliz and the architect's granddaughter, told commissioners Merrywood "has never truly been tested on the open market as a preservation opportunity."
The Lot Split Is Where Status Could Have Changed Hands
Winter Park normally prohibits splitting lakefront lots. That's why the original buyer under contract asked for a plan amendment that would apply only to 1020 Palmer. The commission approved it 3-2 on first reading with two conditions. The two new homes together could not exceed 30,000 square feet, and at least one would follow a style related to Gamble Rogers.
City planning staff had recommended a different deal: allow the split if the house is designated historic. They pointed to an earlier case on New York Avenue, where designating a lakefront Gamble Rogers house went along with carving out a new lot that is not on the lakefront, and selling the new lot helped pay to restore the historic home. The Planning & Zoning Board approved the split without that condition. Winter Park Voice reported that the clearest way left to keep the house standing is for the commission to approve the split on the condition that the home stays and is listed on the register. Planning Director Allison McGillis said she was told some portion of the estate might be preserved, but she has no details on the owner's plans.
For buyers, this means a home's protected status can be bargained for at the moment an owner wants something from the city.
Once a House Is Protected, the Rules Have Teeth
The left column of that table is loose. The right column got stricter in 2025. Winter Park Voice reported that Winter Park's preservation changes that year let the city require rebuilding with authentic exterior materials after an unauthorized demolition or major alteration of a protected structure, and revoke variances already granted for the project.
College Quarter has already seen a case. At 965 Lakeview Drive, most of a 1936 house was demolished when approval covered only removing its garage. The city ordered work to stop. The Historic Preservation Board and city staff later negotiated a $100,000 payment from the builder, which was paid the next day, and the project was allowed to continue. If you're buying in a designated district, check your renovation scope against what the Historic Preservation Board actually approved, line by line.
What Designation Costs and What It Gives
The protected column also comes with benefits that many owners may not know about:
- Review covers major exterior changes only. The City of Winter Park says the board reviews major changes to a home's facade and has no control over interior renovations. Designation doesn't require owners to restore anything.
- No city fees for designation, design review, or variances needed for alterations and additions.
- Variance flexibility and accessory dwelling units. Designated homes often get variances that wouldn't be allowed for a non-historic structure, and owners can add accessory dwelling units.
- A rehabilitation grant. The City of Winter Park grant guidelines say it matches up to 50% of eligible work, capped at $18,000 per property. Annual funding can run out.
- A property tax exemption exists in city code. In May 2026, McGillis said no one appeared to be using it. Ask a tax professional whether it applies to you.
The commission voted 4-0 in May to have the Historic Preservation Board come up with ways to encourage voluntary listing. At a July 1 work session, board members brainstormed transferable development rights, property appraiser flags, a longer demolition delay and renovation tax exemptions, among other ideas. None of those ideas has been adopted. A September commission workshop on the proposals was expected, but we haven't seen its outcome reported.
Before You Offer on an Older Winter Park House
- Find out whether the home is a local landmark, a contributing structure in a local district, or only listed in the Florida Master Site File. Each one leads to a different answer if someone files for demolition.
- Do the same check on the houses on either side of it. A neighboring estate with only a Master Site File listing can be replaced after a 90-day wait.
- If the home is protected, get the scope of any past approvals and compare it with what was actually built.
- If you plan a major exterior change, factor Historic Preservation Board review into your timeline, and look into the $18,000 grant before you sign with a contractor.
FAQ
Does a 1930s house in Winter Park automatically get a demolition delay? No. The 90-day period applies to buildings recorded in the Florida Master Site File and to historic survey properties identified as potential National Register candidates. The ordinance doesn't set a separate age cutoff for the delay.
Does local designation ban demolition outright? No. Requests go to the Historic Preservation Board, which has to approve them.
Is Merrywood's lot split final? Not yet. The first vote passed 3-2 in June, and the second vote is scheduled for October 14, 2026.
If you're looking at an older Winter Park home, or a lot next to one, call Eileen Winfrey or schedule a free consultation. We'll find out the property's register status and the approvals already on file before you write an offer, so you know whether the house is part of what you're buying.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
