High-End Hospitality: Six Stylish Guesthouses

Whether in California, on the sugary sand in Palm Beach, or in the hills north of the historic Santa Fe Plaza, these welcoming guest houses allow visiting family and friends to unwind in style.

Flying Point Compound

Southampton, New York | Harald Grant & Bruce Grant, Sotheby’s International Realty – Southampton Brokerage

Minutes from beaches and Southampton Village, this gated three-acre compound includes a four-bedroom main residence, a swimming pool and spa, a tennis court, and a three-car garage. The 9,600-square-foot home tastefully updates and expands an 1850s farmhouse and is heated by solar and geothermal power. The 5,500-square-foot barn-style guesthouse offers four restful bedrooms, a stainless-steel kitchen, an airy living space opening to covered patios, and a finished lower level with a media or game room and a bar.

Elegant Retreat on the Beach

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

Enveloped in color and lush tropical greenery, this Palm Beach retreat was inspired by the classic beach houses of Bermuda. The property consists of a light-filled main residence with a library, a family room, and a three-car garage; a private beachfront cabana; and an inviting guest cottage with one bedroom, a walk-in closet, and a living area with a bar. Patios, a balcony, and a breezy loggia overlook the ocean and the alluring swimming pool.

Secluded Sonoma Serenity

Glen Ellen, California | Donald Van de Mark, Sotheby’s International Realty – Wine Country – East Napa Street Brokerage

On 10 acres on the shoulder of Sonoma Mountain, this tree-surrounded getaway designed by San Francisco–based architect Dan Phipps has a distinctly modern style, with light-filled spaces and abundant windows. Anchored by a very private pool and patio are a four-bedroom main residence and a guesthouse with a stylish kitchen; a sleeping loft; and an open, airy living and dining space with a wall of glass that opens to the alluring outdoors.

Casa Cielo Azul

Santa Fe, New Mexico | Ray Rush & Tim Van Camp, Sotheby’s International Realty – Santa Fe – Main Downtown Brokerage

The centerpiece of this elegant Southwestern estate in the hills north of Santa Fe is a distinctive three-bedroom main residence with an office, a gourmet kitchen, and plentiful spaces for indoor-outdoor living and entertaining, including a colorful garden courtyard and patios and portales facing mountains and sunsets in the west. Accommodating visitors in comfort and ease, the welcoming guesthouse features a charming kitchen, a living area with a warming gas fireplace, a cozy bedroom and bath, and its own mountain-view portal.

Grand Getaway in Greenwich

Greenwich, Connecticut | Helene Barre, Sotheby’s International Realty – Greenwich Brookerage

This luxurious 7.24-acre lakeside compound is located on a private peninsula in Greenwich. The focal point is a 10,418-square-foot Georgian manor designed by the illustrious Tony Ingrao. The backyard is a serene sanctuary that includes a sports facility with a tennis court, a gym, and a sports court and a pool and spa with a waterfall. The poolside guesthouse offers a spacious living and dining area and a quiet bedroom. In addition, a one-bedroom guest apartment is tucked on the upper level of the freestanding three-car garage.

Colorful Country Estate in Monterey County

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

Providing an ideal blend of elegance and comfort, this 4.3-acre estate includes a warm and welcoming three-bedroom main residence, a swimming pool, equestrian facilities, and a guesthouse. Ideal for gatherings large or small, expanses of colorful patios and terraces surround the inviting pool and offer serene views of the lovely natural surroundings. Short- or long-term visitors will appreciate the approximately 1,200-square-foot guesthouse, which affords living and dining space, a kitchen with stainless-steel appliances, two bedrooms, and one bath.

From the Principality of Andorra to the shores of Hawaii’s Big Island, discover more about the world’s most sought after destinations only with Sotheby’s International Realty