High-End Hospitality: 4 Estates With Welcoming Guesthouses

One of the benefits of owning an expansive estate is being able to offer visitors their own truly private quarters. From Sagaponack to Sonoma, these guesthouses are secluded spaces to relax in comfort and style.

Stylish Sonoma Oasis

On Sonoma’s desirable east side, just blocks from the historic plaza, this modern estate epitomizes chic wine country living. The private 2.5-acre property includes a light-flooded three-bedroom main residence with stunning vineyard and mountain views, 1.5 acres of recently planted pinot noir hobby vineyards, a refreshing pool and spa, covered and open-air spaces for alfresco dining and lounging, an outdoor kitchen, and an inviting guesthouse with a living area, a thoughtful kitchenette, and one stylish bedroom and bath.

Eagle Wing Estate

On the banks of Lake Houston, this majestic estate is surrounded by trees on 2.17 forest-like acres. The idyllic property includes a unique pool with a waterfall, a spa, a pond, a waterfront gazebo, the lake’s largest boat house, a lighted basketball court, and a five-bedroom main residence with elegant living and entertaining areas, an elevator, and a five-car garage. The European-inspired casita enjoys its own covered patio, a well-appointed kitchen, and other versatile spaces.

Southern California Villa

Occupying a tranquil corner lot in a prestigious gated Westlake Village enclave, this 3.16-acre estate is a timeless, stylish retreat with mountain and golf course views. In addition to a single-level Mediterranean-inspired main residence with a four-car garage, a pool with a casita, two spas, a pergola, and other outdoor entertaining areas, the compound offers a spacious guesthouse featuring a private courtyard, a living room with a fireplace, kitchen and laundry facilities, and one bedroom and bath.

Sagaponack’s Winnecoma Estate

This bucolic compound of approximately four acres—which includes some 1.4 acres of conservation land and specimen trees—is the site of one of Sagaponack’s first summer homes. Dating to 1899, when it was a summer getaway and horse farm, it features a timeless gambrel-style main residence, a three-bedroom carriage house with a two-car garage, a woodshop created from the property’s former stables, and a one-bedroom, one-bath guesthouse with its own charming living and dining area as well as studio space for the artist.

This article was originally published in Sotheby’s International Realty’s Extraordinary Living Blog in Nov 2022.