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High-End Hospitality: 4 Welcoming Guesthouses


Whether in California’s wine country or on the rolling plains outside historic Santa Fe, these estates offer guesthouses that allow visitors to unwind in seclusion and consummate style.

Quintessential Wine Country Retreat


Holly Bennett | Sotheby’s International Realty – Sonoma Brokerage

This 5.96-acre Kenwood retreat was designed for quintessential wine country living. Behind a redwood façade, the single-level interiors of the main residence boast a great room and cook’s kitchen with beamed cathedral ceilings, four bedroom suites, a family room, and a soft soothing palette. The verdant landscaped grounds feature an inviting pool, a bocce court, and a one-bedroom guesthouse with a similar rustic yet elegant aesthetic, a luxurious bath that includes a soaking tub and a shower, and covered and open-air patios.

Grand Greenwich Getaway


Leslie McElwreath | Sotheby’s International Realty – Greenwich Brokerage 

Recalling the summer getaways of the Adirondacs, this majestic 21.9-acre estate in Conyers Farm overlooks 140-acre Converse Lake. The Shingle-style main residence features six bedrooms; living, dining, music, and billiards rooms; a library; a solarium; a conservatory; a gym; a sauna; a family room with a bar and a wine cellar; an indoor pool; and a four-car garage. The grounds include a tennis court, a fire pit, a floating dock, and a charming two-bedroom guesthouse with a kitchen, a dining room, and a garage.

Seaside Sanctuary


Ellen Valentgas | Sotheby’s International Realty – Osterville Brokerage

Glorious natural light illuminates the elegant millwork and other classical details that pervade this magnificent seaside home on Nantucket Sound. Every room of the main residence—including the six bedrooms—enjoys a view of the water. The freestanding guesthouse—which is adjoined by the estate’s six-bay garage—offers two bedroom suites, a kitchen, and living and dining spaces. The nine-acre sanctuary also boasts 1,855 feet of pristine sandy beach with a panoramic view.

Sophisticated Santa Fe Compound


Abigail Davidson | Sotheby’s International Realty – Santa Fe Brokerage

Privy to a kaleidoscope of majestic mountains, dramatic sunsets, colorful gardens, and sparkling night skies, this enchanting 11-acre compound on the rugged outskirts of Santa Fe was built for luxurious living and entertaining in distinctive Southwestern style. In addition to a hacienda-style main residence, the property features an art studio, office, or gym; a well-equipped horse barn with easy access to trails; and a stylish guest casita with a living room, a full kitchen, one bedroom and bath, and a wraparound covered patio.

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