High-End Hospitality: Seven Stylish Guesthouses

Whether it’s a serene Southwestern getaway near the Rio Grande, a charming cottage on the water in Cape Cod, or a quiet retreat on an impeccable equestrian estate, these unique guesthouses encourage visiting family and friends to relax and stay a while.

Georgian Estate in Midcountry Greenwich


This magnificent 24,039-square-foot, six-bedroom residence on 5.34 acres in midcountry Greenwich displays a dedication to Georgian elegance and quality, yet the finest in modern living is accommodated with ease thanks to a host of amenities and conveniences. Across the lush emerald lawn and beside the generous swimming pool, the guest and pool house offers two bedrooms and three baths along with a comfortable great room that includes a fireplace and well-outfitted kitchen space.

Offered at: $24,995,000
Location: 110 Clapboard Ridge Road, Greenwich, CT 06830
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Connecticut’s Double H Farm


Northeast of Manhattan in Ridgefield, Connecticut, Double H Farm is an exceptional 87-acre equestrian estate offering top-tier facilities for up to 43 horses—including two Olympic-caliber barns, indoor and outdoor rings, riding paths, and groomed paddocks—a main residence, beautiful gardens with a koi pond, a pool and spa, a party barn, a sports court, and a seven-car garage. Affording comfort and privacy for visitors are a four-bedroom “lower house,” a three-bedroom guesthouse, and a farmhouse with multiple apartments.

Offered at: $33,000,000
Location: 7-11 Old Stagecoach Road & 40 Neds Lane, Ridgefield, CT 06877
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Cape Cod Oasis

Ideally located in Osterville’s East Bay, this welcoming 3.09-acre waterfront estate combines tranquility, luxury, superior quality, refreshing sea breezes, and mesmerizing water views. In addition to a spectacular main residence offering more than 4,700 square feet of timeless gathering spaces and restful private quarters, it includes tall trees, tasteful landscaping, a dock for fishing and boating, and a charming guest cottage secluded on a separate lot.

Offered at: $5,795,000
Location: 52 Caillouet Lane, Osterville, MA 02655
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Sophisticated Sagaponack Compound


A stately tree-lined drive introduces this enviable gated compound, which features a chic main residence, a restored 250-year-old barn, a tennis court, a gunite swimming pool, two pergolas, unparalleled views, and 7.5 acres of consummate privacy. Augmenting the spaces for living and entertaining are a pool house with a sitting room, a fireplace, a kitchenette, and two bedroom suites as well as a two-bedroom carriage house with a sitting room, a kitchenette, a living room, and a three-car garage.

Offered at: $29,900,000
Location: Sagaponack, NY 11962
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Rare Pastoral Property in Studio City


Designed by esteemed area architect Gus Duffy, this modern half-acre compound in coveted Colfax Meadows is a rare find, secluded and private and enveloped by mature trees. Anchoring the estate is a light-filled five-bedroom residence with a fabulous chef’s kitchen, a patio, and a balcony overlooking the grounds. Across an expansive green lawn are a transformed barn ideal for office space, a recording studio, or a car collection and a stylish one-bedroom guesthouse.

Offered at: Price Upon Request
Location: 4107 Troost Avenue, Studio City, CA 91604
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Exceptional Santa Fe Estate


This exciting hillside compound in the exclusive Las Campanas community has fabulous views of the Jack Nicklaus Sunset Golf Course, the Jemez Mountains, and sunsets. Highlights include a cook’s kitchen, informal living and dining areas, a luxurious master suite, a media room, a library and office, a three-car garage, generous storage space, and extraordinary outdoor entertaining areas. The two-bedroom, two-bath guesthouse boasts refined finishes similar to those in the main house and offers a great room and a kitchen.

Offered at: $3,900,000
Location: 17 Storm View Lane, Santa Fe, NM 87506
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Old World Inspiration by the Rio Grande


Thoughtfully designed and thoroughly updated, this exquisite 5.84-acre compound is located in pastoral Los Poblanos Estates, near the banks of the Rio Grande northwest of Albuquerque. It includes a vineyard, livestock pastures and quarters, gardens, a bell tower, lush landscaping, a waterfall, a koi pond, a rose-lined path, and a pool. Accompanying the 5,040-square-foot four-bedroom home is a carefully crafted 2,340-square-foot casita with a great room, a full kitchen, one bedroom, an office, and a wine cellar and tasting room.

Offered at: $3,200,000
Location: 2021 Los Poblanos Place, Albuquerque, NM 87107
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ARE YOU ON THE LIST?
Subscribe for a weekly digest of house tours, luxury real estate market news and design inspiration.
ARE YOU ON THE LIST ?
ARE YOU ON THE LIST ?
Subscribe for a weekly digest of house tours, luxury real estate market news and design inspiration.