From the Group Chat: A 2k-Acre Farm, a Geodesic Dome in Woodstock + a Treehouse in Hawaii

From $300k to $90 million: 5 homes with serious personality

Howdy, and happy Wednesday!

If you’ve been following our From the Group Chat series, you know we gravitate toward homes with character. Our small team doesn’t always share identical taste, but we overlap where it matters: character over cookie-cutter, architecture over trend, which makes for some lively real estate threads behind the scenes.

Over time, those text chains have turned into these roundups: ski houses, midcentury homes in Southern California, character-rich historic properties, and more. The common denominator is rarely price point or location, but personality.

This week, we leaned fully into that instinct, looking well beyond the Hudson Valley and Catskills, all the way to Hawaii. The lineup is as varied as it is surprising: a $90m compound spread across 2,000 acres in the Hudson Valley, a Bruce Goff–designed home tucked into a suburban OK neighborhood, a renovated blacksmith’s shop in central Philadelphia, a midcentury house with a geodesic dome in Woodstock, and an entirely off-grid Hawaiian treehouse.

If there’s an offbeat niche we should dig into next, tell us. A surprisingly robust collection of European castles waiting in the wings suggests we’re ready.

– Hannah + the EB Team