Inside the Deals That Broke Records From Big Sur to the Caribbean

Lucía Torres · 2026-09-30

There's something about a closing that tells a story. Not just the numbers, but the people behind them, the moves they made, and the markets that shifted because of them. This past quarter, our network closed deals from the Caribbean to California, and a few of them rewrote the record books along the way. Let's walk through the ones that stood out. ### A Caribbean Move, Handled on Both Ends When a client needed to sell in Jamaica and buy in the Cayman Islands, Thomas Greenwell and Rebecca Stevenson split the work. Rebecca guided the sale of the client's home at The Argyle in Kingston, while Thomas represented the purchase of Southern Skies #10 in South Sound. Two markets, one seamless transition. That kind of coordination matters. Moving between islands isn't like moving between states. Timing, currency, and local regulations all come into play. ### Naples: $24.4 Million and a Rare Triple Lot In Olde Naples, Chris and Kara Resop represented the buyer in an all-cash closing at 225 4th Avenue N. The estate sold for $24.4 million, or about $3,251 per square foot, making it one of the top sales in the area this year. Here's what made it special: - A rare triple-lot property spanning about 0.96 acres, just four doors from the beach - Roughly 7,504 square feet across a main residence and detached guest house - Six bedrooms, seven full baths, one half bath, a wine room, bocce court, two outdoor summer kitchens, and a pool with a sun shelf - A full Savant smart-home system throughout Designed by Kukk Architecture & Design and built by The Williams Group, it's the kind of property that doesn't come up often. ### Wellington: A New Record in Olympia Paul Rabinowitz represented the sellers of 2186 Stotesbury Way, which closed at $2.125 million. That price set a new record as the highest sale ever in Olympia, one of Wellington's most sought-after communities. For a neighborhood, a record like that does more than make headlines. It resets expectations. ### Big Sur: The Highest New-Construction Sale in History Paul Lester and Daniel Stevenson represented the sale of 47730 Coast Ridge Road for $7.5 million. That transaction marked the highest-priced new-construction sale in Big Sur history, at more than $3,750 per square foot. Big Sur is a place where land is scarce and views are everything. A record like this says a lot about what buyers are willing to pay for new construction in a market known for its older homes. ### West Hollywood: $36 Million at Sierra Towers Blair Chang represented the buyer of the penthouse at 9255 Doheny Road in the iconic Sierra Towers. The deal closed at $36 million and earned Blair The Hollywood Reporter's 2026 Los Angeles Power Brokers Condo Sale of the Year award. > "A record-setting sale isn't just about the price. It's about what it says for everyone who owns nearby." That's the thing about penthouse deals. They lift the whole building. ### Pacifica: Coastal Living Above the Pacific Mara McCain represented the seller of 5 Ohlone Drive, a newly built coastal estate in one of the Bay Area's exclusive gated communities. Walls of floor-to-ceiling glass frame ocean and coastline views, and nearly every major room opens to terraces, gardens, or outdoor entertaining spaces. And the location? Just 16 minutes from SFO, 25 minutes from downtown San Francisco, and 30 minutes from Sand Hill Road and Stanford University. Privacy and access don't often come together like that. ### Los Angeles: $29 Million, Both Sides Represented At 1204 Chickory Lane, Santiago Arana and Griffin Riddle represented both sides of a $29 million sale. Santiago handled the listing and also represented the buyer. ### Dana Point: $12.15 Million at Monarch Bay Tony Maniaci represented the sale of 416 Monarch Bay Drive in Dana Point, which closed at $12.15 million. Another strong result in a coastal market that keeps drawing attention. ### What These Closings Tell Us Look across these deals and a pattern shows up. Records are falling in markets where inventory is tight and buyers are serious. From Big Sur to Wellington to West Hollywood, the theme is the same: when the right property comes up, it moves. And for anyone watching these markets, that's worth paying attention to.