Winter Park’s City Commission is staring down a high-stakes choice next week that could decide whether Merrywood, a sprawling James Gamble Rogers II estate on Lake Osceola, is saved or cleared for new lakefront construction. The 3.7-acre parcel is under contract, and a hotly debated plan to split the property has already cleared the Planning & Zoning Board, setting the stage for a decisive commission vote.
Historic house, big lot
Merrywood, also known as the Caroline Griggs Plant House, was completed in 1939 and is widely regarded as one of James Gamble Rogers II’s most significant residential commissions in Winter Park. The home and its lakefront parcel are documented by preservation groups and are listed in the city’s historic resources survey, though the property is not formally designated on Winter Park’s local historic register. According to Casa Feliz, the house’s craftsmanship and lakeside siting make it a rare surviving example of the city’s architectural heritage.
Buyer wants a split
The property is under contract to attorney Tara Tedrow, who has asked the city to amend its comprehensive plan so the unusually large lakefront lot can be split. Her proposal would allow her family to build a new home on one piece while marketing the remaining parcel, which includes the existing house, to a preservation-minded buyer. That strategy, and the political storm swirling around it, is detailed in reporting by WKMG ClickOrlando.
Demolition permit opens a 90-day clock
A demolition application tied to Merrywood was filed earlier this year by the siblings who inherited the estate, and Tedrow says she helped facilitate the permit to create a short window for preservation talks to play out. That application launches a 90-day review period under local practice tied to the state’s Florida Master Site File process, a procedural wrinkle first reported by the Winter Park Voice.
Preservationists press their case
Friends of Casa Feliz and other local preservation advocates have been working to identify buyers willing to restore Merrywood. They argue that losing the house would chip away at the character that draws residents and visitors to Winter Park in the first place. “People do continue to flock here because they sense that je ne sais quoi,” longtime preservationist Betsy Rogers Owens said in recent coverage, underscoring the cultural and economic case for saving landmark homes. WKMG ClickOrlando and local preservation groups have been public about outreach to potential buyers.
A policy test for lakefront rules
At the center of the fight is a fundamental policy question: whether Winter Park will break from its long-standing rule against splitting lakefront lots. The Planning & Zoning Board voted 4-2 to recommend a comprehensive plan amendment that would allow the split, a move critics blasted as a “special favor” for the buyer. City planning staff had urged a more limited alternative that would tie any lot-split allowance to the preservation and formal designation of pre-1950 homes, a position outlined by the Winter Park Voice.
Legal and practical stakes
Because Merrywood is not listed on Winter Park’s local historic register, the city does not currently have clear authority to block demolition. The property’s presence in state records gives advisory bodies only a short delay to seek alternatives. The city’s resource survey confirms the house’s significance while also noting that it lacks the protective local designation that would require additional approvals before demolition. See the city’s historic resources survey and local reporting for how that legal gap shapes the options officials have.
What happens next
The final call now rests with the Winter Park City Commission at a hearing next Wednesday, when commissioners are expected to decide whether to allow the lot split and, indirectly, set Merrywood’s fate. Preservationists, neighbors, and the buyer all say they plan to press their cases at the meeting, leaving only a brief window for a new buyer or a policy compromise to emerge before the clock on the property runs out. For background on how the commission date was set and earlier coverage of the dispute, see WESH and the local reporting cited above.
