One of the benefits of owning an expansive estate is the ability to offer visiting family and friends a comfortable private space. Whether it’s a former carriage house in the Hamptons, a unique modern space north of Santa Fe, or a freestanding retreat with a stargazing observatory, these stylish guesthouses will encourage visitors to relax and stay awhile.

1 of 8 | Unprecedented East Hampton Equestrian Compound

1 of 8 | Unprecedented East Hampton Equestrian Compound


Minutes from East Hampton Village, this rare estate assembles 11 parcels in a stunning private haven totaling approximately 23 acres and including horse stables with paddocks, a tennis court, and vibrant landscaping by the revered Edmund Hollander. On-site are an approximately 18,000-square-foot Cotswold-inspired main residence, a stylish six-bedroom “carriage house,” two delightful guest cottages, a one-bedroom pool house with a full kitchen, a bluestone terrace surrounding the pool, and an outdoor kitchen.

$35,000,000 | 172 Cedar Street East Hampton, NY 11932 | VIEW LISTING

2 of 8 | Corte Madera Compound

2 of 8 | Corte Madera Compound


This remarkable Bay Area home honors its location, displaying a reverence for both ecological responsibility and sophisticated style. It comprises a unique 9,725-square-foot residence designed by Sim Van der Ryn, a sun-swept pool, an open-air spa, sports courts, and 11 acres planted with towering eucalyptus trees, flower and vegetable gardens, and an orchard. Guests will appreciate the serenity of the separate two-bedroom guesthouse, which accommodates with the utmost seclusion and comfort.

$25,000,000 | Corte Madera, CA 94925 | VIEW LISTING

3 of 8 | “Xanadu East”

3 of 8 | “Xanadu East”


This private 5.13-acre oasis encompasses two homes on two contiguous lots, both enjoying sweeping views stretching out toward the majestic Atlantic. The stately traditional main residence offers five bedrooms; while the delightful guest cottage, accessible via a private drive, includes four bedrooms, three baths, a living room with a striking conical glass ceiling, a dining area, and a country kitchen. A heated infinity-edge pool and spa, a tennis court, specimen trees, rolling lawns, and landscaped gardens create an impressive backdrop.

$9,999,000 | 972 Noyac Path Water Mill, NY 11976 | VIEW LISTING

4 of 8 | Stargazing in Sonoma

4 of 8 | Stargazing in Sonoma


Designed by a noted San Francisco architect as his own private oasis, this Sonoma County estate is a paradigm of modernism with views of Mount Diablo and San Pablo Bay. The 20-acre property features an approximately 4,980-square-foot residence, a swimming pool, and an approximately 840-square-foot guesthouse that includes a professional-caliber observatory for stargazing. The style of the guesthouse echoes that of the main home, with stone, timber, steel, abundant glass, soaring ceilings, and an open, airy, decidedly chic ambience.

$6,250,000 | 5340 Grove St, Sonoma, CA 95476 | VIEW LISTING

5 of 8 | Cape Cod Getaway

5 of 8 | Cape Cod Getaway


On a very private west-facing site in desirable Oyster Harbors, this estate features an exquisitely detailed five-bedroom residence accompanied by a charming two-bedroom guesthouse with its own living, dining, and kitchen area and stone fireplace. A deck, a swimming pool surrounded by a gloriously green lawn and other colorful landscaping, and an outdoor kitchen and bar transform this stately property into a truly enviable Cape Cod getaway.

$4,750,000 | 440 Grand Island Drive, Osterville, MA 02655 | VIEW LISTING

6 of 8 | Modern Wine Country Farmhouse

6 of 8 | Modern Wine Country Farmhouse


Located on a serene cul-de-sac, this wine country retreat was designed for consummate indoor-outdoor living and entertaining. Sets of black-framed Fleetwood glass pocket doors open from multiple rooms in the new three-bedroom residence as well as the living space of the intimate one-bedroom guesthouse, seamlessly linking both with the enticing swimming pool, spa, patio, alfresco dining space, and uniquely landscaped grounds. The guesthouse could also easily serve as a stylish poolside party venue.

$3,995,000 | 1212 Apple Tree Ct Sonoma, CA 95476 | VIEW LISTING

7 of 8 | Updated Old World Sanctuary in Los Feliz

7 of 8 | Updated Old World Sanctuary in Los Feliz


French Colonial refinement meets sophisticated modern style at this thoughtfully maintained and tastefully renovated estate in Los Feliz. In addition to the majestic four-bedroom residence, alluring outdoor entertaining spaces, a swimming pool and spa, and manicured mature landscaping, it includes a detached one-bedroom guesthouse, connected by a delightful breezeway. This peaceful sanctuary offers visitors an open, light-filled living area, views of downtown Los Angeles, and proximity to Griffith Park and other amenities and attractions.

$2,995,000 | 2529 Commonwealth Avenue Los Angeles, CA 90027 | VIEW LISTING

8 of 8 | Inspired Southwestern Contemporary

8 of 8 | Inspired Southwestern Contemporary


A tour de force of contemporary architecture, this remarkable five-bedroom home and its freestanding guesthouse have been imbued with modern style and ancient inspiration. On 13.58 gated private acres near the renowned Santa Fe Opera, both homes are filled with a welcoming warmth created by a generous use of stacked Anasazi stone, a pleasing circular theme, clean contemporary lines, vibrant color, and plentiful windows and outdoor entertaining spaces designed for appreciation of the stunning Southwestern setting.

$2,950,000 | 12 Calle De Luz, Santa Fe, NM 87506 | VIEW LISTING

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