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Ten Great Estates for Creative Home Entertaining

These estates have something for everyone, from elegant bars to outdoor hot tubs, private lakes and beaches, and more

The word “entertaining” might conjure images of elegantly set dining tables and cookbooks full of recipes ideal for a crowd, but the fine art of hosting friends can include much more, from a dip in an outdoor hot tub under the stars, to a ski outing on nearby snow-covered slopes, to a swim in the ocean on a secluded private beach. The inspired designs of these estates all include amenities for festive fun, indoors and out. No two are quite alike, but each offers its own unique brand of welcome for friends and visitors.

Rural Idyll
Cambridge, Vermont

Birchwood wouldn’t look out of place in a 19th-century New England landscape painting. Architect Sam Scofield’s masterful interpretation of traditional timber-frame architecture is ideally suited to this rural setting, where snow-covered Mount Mansfield is visible in winter months. This four-bedroom estate is a skier’s paradise due to its very close location to the popular slopes of Smugglers’ Notch. The interior is as cozy and inviting as a traditional ski cabin, with details like post-and-beam construction and locally sourced stone adding to the overall ambience. The exquisitely crafted fireplace provides the ideal setting for an après-ski hot chocolate or cocktail.

Rooftop Tropical Paradise        
Honolulu, Hawaii

This elegant penthouse boasts ample space for entertaining and floor-to-ceiling windows that offer breathtaking views of the ocean from almost every room. On top of the spacious eat-in kitchen and elegant dining and living rooms, the ultimate entertaining space in this apartment is actually outside: the 2,800-square-foot enclosed multi-use lounge area with open-air hot tub and roof deck. With ocean breezes and total privacy, this outdoor oasis is perfect for enjoying a sunset or relaxing under the stars.

Georgica Pond Gem
East Hampton, New York

Briar Patch sits on picturesque Georgica Pond in East Hampton—one of the East End’s most idyllic settings. Only three families have owned this Georgian Revival estate in its 80-year history, and it is included on the National Register of Historic Places. Recently redesigned by legendary architect Peter Marino, the interior is a deft blend of classic Long Island design with inspired updates. Highlights include reclaimed floorboards, hand-stenciled ceilings, handmade wallpaper, coffered ceilings, and French doors. With 10,000 square feet of living space and lush, landscaped grounds, the estate is sure to please each and every guest. Tennis courts and an outdoor sundeck, large pool, swimming and sailing in the pond, and ample space for large dinner parties or intimate gatherings make this the ideal spot for entertaining.

Starlit Soirées
Greenwich, Connecticut

Conyers Farm is one of Greenwich, Connecticut’s most impressive and beautiful historic estates. Situated on 80 acres, it was once a working farm and still offers stables, paddocks, an apple orchard, and cherry hedge. Converted into a gated community in the 1980s, the farm retains its secluded atmosphere and bucolic landscape. One of the estate’s most enchanting features is known as “the ruins”: the remnants of a barn made of monumental stone walls that are now covered in lush Virginia Creeper vines. Lit by night, the ruins stand open to the sky, providing a spectacular setting for a summer bash under the stars. Guests can enjoy the local riding trails and polo grounds, too.

Perfect Private Beach
Grand Cayman, Cayman Islands

Twin Coves, an eight-bedroom estate on the exclusive northern side of Grand Cayman, boasts views of the Caribbean Sea and more than 10,000 square feet of elegant living space. Entertaining here couldn’t be easier: from the back of the house, two stone staircases descend onto two private beaches that form a secluded swimming cove. The natural coral shoreline and clear waters make the cove perfect for snorkeling and swimming. Seagrape trees line every path of this estate’s grounds while indoors, custom elevators make each floor readily accessible. Right between the main house and the guesthouse sits a heated pool with its own warmed deck and elegant gazebo to provide shade at any time of day. For swimming, sunning, or simply enjoying the pristine views, Twin Coves is unique and spectacular.

Ski Easy
Telluride, Colorado

The majestic mountains of Telluride, Colorado, form the setting for this spacious and inviting estate, which boasts a ski room in addition to many other features. Located just outside the Mountain Village Core, this home combines its feeling of airy freedom with its convenient proximity to the restaurants, shops, and attractions of a charming town. Perched on a hillside in a dense patch of trees, it offers stunning mountain views, and its interior includes amenities for all kinds of fun including a deluxe theater room for movie nights, family room, wet bar, and large fireplace to warm cozy gatherings.

Green Lawns, Pink Beach
Paget Parish, Bermuda

The gentle pace of Bermuda is a tonic for the soul, and Chelston in Paget Parish embodies the elegance and ease of this enchanting island. The main residence enjoys 10,000 square feet of living space on 14 beachfront acres, and three additional guest cottages, a pool house, and staff cottage round out the property. With its balmy weather, Bermuda is an ideal place for outdoor pursuits, and this home boasts ample space and amenities that include a croquet lawn, zero-edge pool, the pink sand of Grape Bay Beach, and an outdoor pavilion overlooking the water with its own wood-burning pizza oven.

Downtown Dinner Parties
East 11th Street, New York

Located on a leafy street just off Fifth Avenue, this stately seven-bedroom, five-story row house offers 9,000 square feet of living space and gracious, well-proportioned interiors throughout. A beautifully designed garden provides a green retreat at the back of the house, and two terraces plus a large roof deck offer ample additional outdoor space. With a temperature-controlled wine cellar and proximity to some of New York’s finest gourmet shops, this home is ideal for hosting dinner parties. The spacious and modern eat-in kitchen also opens onto the garden—perfect for an al fresco meal under the stars.

Canyon Views
Beverly Hills, California

This expansive estate on five acres in Beverly Hills boasts 22,000 square feet of living space and a design inspired by the opulent interiors of a French château. Perched high up in the hills with breathtaking canyon views, the home offers an array of amenities ideal for entertaining. Not surprising for this region of California, there’s a professional-quality screening room and a large wine cellar and adjacent tasting room. The gym and spa feature state-of-the-art equipment, and the outdoor pool is situated next to the barbeque. Interior finishes include marble, Venetian plaster, walnut floors, and sumptuous touches of glass, gold, and crystal.

South Florida Perfection
Coral Gables, Florida

This six-bedroom estate in the Snapper Creek Lakes community of Coral Gables combines everything that makes South Florida such a coveted place in which to relax. Lakeside and surrounded by mature oak trees, traditional Spanish-style architectural elements include a terracotta tile roof and terraces with wrought-iron balustrades. A large pool with natural stone surround blends seamlessly into the landscape. Inside, a gourmet kitchen and well-appointed living and dining rooms are ideal for formal entertaining, while the private balcony is perfect for grilling or cocktails overlooking the pool.