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Waterfield Sotheby's International Realty
48 Mt Vernon St Suite One
Winchester, Massachusetts 01890

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Stylish Guest Houses | High-End Hospitality

Whether you're hosting family out in the Hamptons or friends down in Palm Beach, a tastefully appointed guest house is the epitome of high-end hospitality for those visiting from near and far.


Enter this luxurious 7.24 acre lakeside compound in Greenwich, Connecticut. Located on a private peninsula, the 10,418 square foot Georgian manor designed by Tony Ingrao offers a tranquil and private sanctuary for visitors in the poolside guest house. This elegantly decorated suite is fully equipped with a spacious living / dining area, as well as a quiet bedroom. Friends and family can also enjoy a sports facility with a tennis court, a gym, playing court, and a pool / spa featuring a flowing waterfall.

Greenwich, Connecticut | Helene BarreSotheby’s International Realty – Greenwich Brokerage


Over on the West Coast, this guest house provides the perfect blend of elegance and comfort to visitors as it sits alongside the three-bedroom main residence on 4.3 acres in Monterey County. Perfectly suited for gatherings both large and small, the colorful patios and terraces surrounding the property give way to the inviting pool and offer serene views of the beautiful natural surroundings and equestrian facilities. Family and friends will fully appreciate the 1,200-square-foot guest house, which offers a living and dining space, a kitchen with stainless-steel appliances, two bedrooms, and one bath.

Corral De Tierra, California | Mick Pfaff & Robert FontecchioSotheby’s International Realty – Carmel Ocean Avenue Brokerage


As you make your way back east, pay a visit to New Mexico where you can kick your feet up and stay a while in this guest house abutting an elegant Southwestern estate in the hills north of Santa Fe. The grounds include indoor-outdoor spaces for living and entertaining, a colorful garden courtyard, and patios with views of sweeping mountains and beautiful sunsets in the west. The welcoming guest house features a kitchen, a living area with gas fireplace, one bedroom and bath, and its own mountain-view portal.


Stay a while in Palm Beach, where this lush and tropical retreat inspired by the classic beach houses of Bermuda offers a serene and peaceful escape. The estate consists of a light and airy primary residence fully equipped with a library, a family room, and a three-car garage, as well as a private beachfront cabana. The inviting guest cottage boasts a breezy bedroom, a walk-in closet, and a living area with a bar. Guests can enjoy the patios and balconies overlooking the ocean and the refreshing swimming pool.

Palm Beach, Florida | Maryann ChoppSotheby’s International Realty – Palm Beach Brokerage


Ready to provide your guests with the ultimate experience? Reach out today for a free buyer consultation.

Originally featured in the Dec. 7 Extraordinary Living Blog by Sotheby's Realty