One of the benefits of owning a luxurious estate is being able to offer guests their own comfortable private space. Whether it’s a historic retreat in the Hamptons or a midcentury modern escape in California, these thoughtful guesthouses will help visitors relax and really unwind in style.
Midcentury Modern in Montecito
A paradigm of midcentury modern style, this delightful light-filled home features inviting open spaces with soothing natural design elements, desirable modern amenities, and windows that blur the line between indoors and out. In addition to a luxurious master suite, a gourmet kitchen, living and dining areas, a family room, and an office alcove, it offers a guest studio with a full kitchen and a versatile bonus room that, with a full bath and a kitchenette, could serve as additional guest quarters.
Offered at: $2,999,000
Location: 1211 East Valley Road, Montecito, CA 93108
Regal Refinement in Houston
At this stunning 3.7-acre estate in Houston’s exclusive Rivercrest community, every detail has been chosen to create a sophisticated, satisfying atmosphere, from the home’s dynamic open kitchen and living area to a billiards room with a wet bar, a majestic swimming pool, and a climate-controlled 1,000-bottle wine room. The estate also includes three-bedroom guesthouse that mirrors the main residence in refinement and offers living and dining rooms, a full kitchen with a breakfast area, a game room, a study, a terrace, and its own one-car garage.
Offered at: $14,500,000
Location: 6 West Rivercrest Drive, Houston, TX 77042
Sag Harbor Compound
Giving a respectful nod to the classic charm of Sag Harbor, this impressive new estate boasts a rare combination of a five-bedroom modern farmhouse, a freestanding cottage, and a gunite swimming pool with a timelessly styled pool house. Ideal for guests, the two-story cottage features two bedrooms, a spacious living room with a wall of windows, a dining room, a kitchen, ample closet space, a full basement, and access to a bluestone terrace.
Offered at: $3,295,000
Location: 56 Grand Street, Sag Harbor, NY 11963
Santa Fe Sanctuary
This secluded, sophisticated estate includes a luxurious five-bedroom residence with an inspiring owners’ suite, an office, a family room, a den or media room, and an eat-in kitchen as well as an attached guesthouse, which has an open living, dining, and kitchen area and one generous bedroom. Appreciation of Santa Fe’s four fabulous seasons is easy thanks to two traditional portales—one overlooking a koi pond—and a grand patio with a fire pit and mountain views.
Offered at: $3,600,000
Location: 1110 Old Santa Fe Trail, Santa Fe, NM 87505
Magnificent Mediterranean Style
This majestic 24,600-square-foot estate is a breathtaking example of Palm Beach style, combining European elegance and contemporary comfort. The rare 2.25-acre gated estate includes gorgeous terraces, a courtyard lush with bougainvillea, a heated swimming pool, and frontage on the Atlantic Ocean and Lake Worth. The eight-bedroom main residence features interiors crafted by world-renowned designer Juan Pablo Molyneux. Equally stylish, the freestanding guesthouse affords visitors peace and privacy beside the alluring pool.
Offered at: $56,000,000
Location: 1960 S Ocean Boulevard, Palm Beach, FL 33480
La Belle Vista
A truly grand estate, this gated 101.72-acre compound in the Santa Ynez Valley recalls a retreat in the Tuscan countryside, with sweeping romantic views of the surrounding vineyards and orchards. It includes an approximately 9,000-square-foot main residence, a certified-organic olive grove, a saltwater pool and spa, a six-car garage, a full-size tennis court, an eight-stall barn, and fenced and irrigated pastureland. The guesthouse has vaulted ceilings, two restful bedrooms, and an updated bath.
Offered at: $6,495,000
Location: 1920 Westerly Road, Santa Ynez, CA 93460
Historic Hamptons Hideaway
A picture-perfect setting for classic indoor-outdoor living and entertaining in the Hamptons, this delightful four-bedroom home dates to 1880 and is accompanied by lush garden-like landscaping, brick terraces, and a refreshing gunite swimming pool. The spacious two-bedroom guest cottage offers light-filled living and dining areas, a kitchen, and an expansive patio that includes an outdoor kitchen with a pizza oven and a grill. Beaches and village attractions are minutes away.
Offered at: $3,395,000
Location: 268 Hill Street, Southampton Village, NY 11968