Over my professional 25 years as a specialist working in the Luxury Real Estate industry, I have heard a lot of questions, concerns, seen up markets, down markets, and everything in between. I have been writing the following as a bit of a memoir and way to share what Ive learned in a way that I normally only get to express one on one and face to face. My initial thought with this article was to publish it only as a part of listing brochures and property descriptions, not necessarily for the general public. It's even cut into simple to grasp bite sized ideas that are part of a larger longer term thinking plan. Given the market events of this past week, it seems timely to share my decades of direct and two generations of Luxury Real Estate knowledge.
Part 1. The Timeless Appeal of Second Homes, Cabins, Resorts, and Retreats
The allure of second homes and luxury retreats among the world’s most successful individuals dates back centuries. Historically, affluent families have sought out private estates and resort properties as symbols of wealth, leisure, and exclusivity. From European aristocrats building countryside chateaus to 19th-century American industrialists escaping to mountain lodges, the idea of a second home has long been intertwined with success and prestige.
During the early 20th century, luxury vacation properties became a key asset for business magnates and cultural elites. The emergence of exclusive resort destinations—such as the Hamptons, Aspen, and the French Riviera—cemented the trend of high-net-worth individuals acquiring real estate in serene and picturesque locales. Over time, ski resorts, tropical islands, and private retreats have only increased in desirability, driven by both lifestyle aspirations and financial prudence.
