David Simkins Flips Morningside Waterfront Home for $24.1M Record

David Simkins has sold his Morningside waterfront home for $24.1 million, a year after paying $16 million for it, setting a new sale record for the Miami neighborhood, according to The Real Deal. Simkins, who bought the property at 5725 North Bayshore Drive from prior owner David Wallack in September 2025, moved it to an undisclosed trust in an off-market deal that agents said took months to negotiate.

The 1969 house sits on nearly an acre with 125 feet of water frontage, a pool, a dock, a treehouse, a music studio and a 140-year-old gazebo, features The Real Deal cited as part of the sale’s appeal to a buyer who plans to tear it down and build new. Compass agent Maurice Boschetti and One Sotheby’s International Realty agent Jackie Diop represented the buyer.

Why it matters

The sale tops the previous Morningside benchmark, Barstool Sports founder Dave Portnoy’s $14 million purchase in 2021, by more than 70%, another marker of how far the Upper Eastside’s land value has run since national buyers started treating it as an extension of the coastal core. Track more of the trend at the South Florida hub. A tear-down commanding $24 million confirms the neighborhood is now being priced on lot and dock rights rather than the house sitting on it.

The numbers

Miami-Dade Property Appraiser records confirm Simkins closed on the property for $16,000,000 on September 5, 2025, deed recorded at Official Records Book 34945, Page 4347. The county’s 2026 assessed land value alone is $9.4 million against a 37,629-square-foot lot, before the newest sale price has flowed through to the tax roll. The $8.1 million gain over a roughly one-year hold works out to a 51% increase before carrying costs, insurance and transaction expense.

What’s next

The county record had not posted the $24.1 million deed as of this reporting, meaning the sale’s book and page, and the buyer’s identity behind the trust, remain to be confirmed once it is indexed. The new owner’s plan to demolish and rebuild will put the lot, not the 1969 house, to its next test.