On the Market: Three Gorgeous Properties with Guest-Friendly Configurations

As wonderful as it is to bring everyone in the family together at the holidays and beyond, the key to congenial gatherings may be a little privacy. Case in point: A Silicon Valley couple who live with their elderly parents, and who frequently host other relatives, sought out architecture firm Bohlin Cywinski Jackson to create a purpose-built family compound. Its two living areas and central courtyard allow them to accommodate everyone gracefully under one roof. “When our guests come here, they don’t feel like they are guests, we can be together but apart at the same time,” says the owner. We surveyed the market for homes with guest-friendly domestic configurations, perfect for those who have extended family or a multitude of visitors under their roof.

On the outskirts of the East Bay, larger parcels of land lend themselves to more expansive properties. Villa Toscana d’Oro is a Tuscan-inspired hilltop estate located on nearly two-and-a-half acres at the Blackhawk Country Club that was redesigned by its previous owners to accommodate their large family. With nine bedrooms in the main house and an additional bedroom in a two-level, 1,260-square-foot guesthouse, it certainly has room to spare. The $14 million listing is with Susan Bazinett of Sotheby’s

On the Peninsula, the standard lot size in Atherton is one acre, and homes with guesthouses are not uncommon. By press time, high-end residential developers Jeff and Katherine Wise should have brought their latest offering to market, a six-bedroom Colonial-style home at 190 Almendral. Represented by Rich Bassin at Dreyfus Sothebys, it also has a separate one-bedroom guesthouse that features an open floor plan with a full kitchen, dining and living room. Another property of note is on Bridle Court in Hillsborough. The original servants’ quarters of the Tobin Clark estate, the home was significantly expanded in 2003 to form three interconnected buildings. It has six bedrooms in total, but one bedroom suite is located over the garage and another bedroom suite is in the original brick building. “It’s one of the most versatile and flexible houses I’ve seen, and can be readily adapted to different living arrangements,” says Charlene Chang of Alain Pinel, who has the listing for $7.8 million. 

Within San Francisco city limits, check out 2529 Union Street, a Tudor-style house in Cow Hollow with three bedrooms plus a unique “penthouse” on the third floor. Designed as a home office, it has a half-bathroom and a roof deck with expansive Bay views. The only way to reach it is via an exterior staircase, giving it a sense of privacy and seclusion. “It’s superb for guests because they can be completely independent and come and go without going through the house,” says Janet Feinberg Schindler at Sotheby’s, who has the $5.25 million listing. “It offers the best of San Francisco. If you came to visit, why would you want to leave?”