Lockwood\u2019s attorney Jason Searl told commissioners Lockwood was open to discussions. But earlier in the meeting,\u00a0he said Lockwood\u2019s plan for the land involved tearing Merrywood<\/a> down without further delays.<\/p>\n \u201cWhat happens if we receive a no vote today on this request? A no vote is the demolition application filed with the city to be performed,\u201d Searl said initially.<\/p>\n Wednesday\u2019s commission meeting was the latest twist in the tortuous path to Merrywood\u2019s ultimate fate, which still remains uncertain. The 7,300-square-foot Spanish-style home built in 1939 is the largest residence designed by the city\u2019s famed architect,\u00a0James Gamble Rogers II. The city said 50 buildings designed by him \u2014 commercial and residential \u2014 remain standing in Winter Park.<\/p>\n Lockwood, who last year bought Orlando-founded drinkware brand Corkcicle, <\/a>purchased the property on Lake Osceola in August for $15 million from siblings Cathy and Raymond Gilmer. He initially bought the property secretly through a mystery corporation, Lake Osceola Holdings LLC, and the later revelation of the transaction stunned those who\u2019ve been working for many months to save the house from demolition<\/a>.<\/p>\n The Merrywood sale, the largest-ever for a single lot in city history, could potentially allow Lockwood to build a 55,991-square-foot house on the land under existing ordinances. The city\u2019s current largest home is about 40,000 square feet.<\/p>\n Searl said Lockwood\u2019s initial vision involves dividing the land into two lakefront lots where he and a friend could both build homes for their families. Searl said two reports filed Monday with the city attest to the mansion\u2019s significant structural damage, necessitating demolition.<\/p>\n But in pursuit of the needed city comprehensive plan amendment to split the lot, he said Lockwood was willing to, at his own expense, work to save or restore part of the existing structure where feasible. A section of Merrywood could then be incorporated into a new structure on the property, such as a guest house or pool house.<\/p>\n Commissioner Elizabeth Ingram, arguably the commission\u2019s most vocal advocate for saving Merrywood, said she wasn\u2019t willing to rely on Lockwood\u2019s \u201cgood-faith effort\u201d to save part of it.<\/p>\n \u201cOur comprehensive plan is not just a collection of suggestions that we set aside when someone presents us with a compelling financial opportunity for themselves or an alarming hypothetical scenario,\u201d Ingram said.<\/p>\n She said she\u2019s never been categorically opposed to dividing the property, but wants legally binding protections stating what parts of the home and how much square footage would be saved.<\/p>\n Commissioner Craig Russell, however, said that while he\u2019s all for historic preservation \u2014 and believes Merrywood can be renovated \u2014 he\u00a0is also a strong supporter of property rights.<\/p>\n \u201cThere\u2019s a lot of pocket-watching going on around here,\u201d Russell said. \u201cWho am I to tell anybody how to spend their money?\u201d<\/p>\n Vice Mayor Kris Cruzada said he supported adding language to the proposal requiring partial preservation and defining exactly what that is.<\/p>\n \u201cI\u2019m trying to find a path to some level of preservation or lose it all together,\u201d Cruzada said. \u201cWe\u2019re in an unfortunate set of circumstances.\u201d<\/p>\n Allison McGillis, director of the city\u2019s Planning & Zoning department, also suggested language specifying the square footage or percentage of the existing structure that would be retained and maintained by current and future owners through a deed restriction.<\/p>\n But Searl said he and Lockwood couldn\u2019t support it.<\/p>\n They instead returned with a printout of a photo of Merrywood showing two portions surrounded by blue lines from a pen.<\/p>\n \u201cSteve and his family are willing to make a good-faith attempt to save the front facade, a minimum of these two areas,\u201d Searl said, referring to the image on the screens, \u201cif the policy is approved and the split goes in place tonight.\u201d<\/p>\n He said if at any point during that effort it becomes impractical, impossible, part of the house falls down or the family doesn\u2019t like the way it will look, Searl would bring the issue back the commission.<\/p>\n Commissioners could then rescind, withdraw or waive it under the presumption that Lockwood had made a good-faith attempt, he argued, and if the split is denied he\u2019d have to wait a year to apply again for it under city codes.<\/p>\n Ardaman advised commissioners they could make the lot split contingent upon preserving a portion of the front \u2014 and if Lockwood is not able to accomplish that, he doesn\u2019t get his lot split.<\/p>\n But Commissioner Warren Lindsey, another consistent proponent of saving Merrywood, said he couldn\u2019t vote for such a vaguely-worded proposal.<\/p>\n![\"Steve](\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2026\/10\/TOS-L-merrywood-owner-1015.jpg\")
Steve Lockwood, left, the new owner of the land where the iconic Merrywood mansion sits, speaks toward Betsy Rogers Owens, executive director of Friends of Casa Feliz and granddaughter of James Gamble Rogers II, during the Winter Park City Commission meeting on Wednesday, Oct. 14, 2026. Next to him is Jason Searl, an Orlando real estate attorney. (Brian Bell\/Orlando Sentinel)<\/p>\n![\"Orlando](\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2026\/10\/TOS-L-merrywood-meeting-1015.jpg\")
Orlando real estate attorney Jason Searl writes on a printed image of the Merrywood mansion in Winter Park displayed on screens during the Winter Park City Commission meeting on Wednesday, Oct. 14, 2026. Searl was doing it during discussions on saving the center part of the home and attempt to save the other part on behalf of the new owner, Steve Lockwood. (Brian Bell\/Orlando Sentinel)<\/p>\n