Andy Weir Buys a Second Winnetka Home Off-Market. What Quiet Deals Mean for North Shore Buyers and Sellers

A second address in the same village. Andy Weir, the author of Project Hail Mary, has bought a $6.8 million home in Winnetka in an off-market deal, according to Crain's Chicago Business. The purchase gives Weir and his wife, Ashley, a second home in the village. It isn't a vacation house in another state.

The celebrity detail is the headline. The more useful part for our clients is the way the deal happened.

Off-market is how a lot of the North Shore trades at this level. In Winnetka, Kenilworth, Glencoe and the other lakefront villages, many owners at the top of the market value privacy as much as price. Some won't put their address, interior photos and showing schedule in front of the public. These sales often come together through relationships between agents, past clients and owners who would sell for the right offer even though they never planned to list.

What stands out about this purchase is the buyer's commitment to one place. Someone who already owns in Winnetka chose to add a second property there. That says something about how much demand for the best North Shore locations comes from people who already live there, and how little of that demand shows up on public search sites.

For buyers, waiting for a listing alert may not be enough. If you are looking for a specific street, lake access or a particular school attendance area, tell an agent exactly what you want and let them make quiet inquiries. Our team regularly approaches owners who aren't listed but might sell, in both Chicagoland and San Diego. The same pattern holds in La Jolla, Rancho Santa Fe and Del Mar.

For sellers, an off-market sale is a tradeoff, not a shortcut. A private sale protects your privacy and can save time. It can also leave money on the table, because fewer buyers see the home and compete for it. Off-market works best when the seller already has a qualified buyer in mind and a clear idea of value from recent comparable sales. If you don't have both, full exposure usually produces the stronger result.

There is a middle path. You can prepare the home, set the price using solid comps, and quietly show it to a short list of qualified buyers before deciding whether to go public. That keeps your options open.

If you own a home on the North Shore or along the San Diego coast and have wondered what a private sale might look like, our team is happy to walk you through the numbers in confidence.