The Best of Island Living

Turquoise waters, breezy sea air, sun soaked beaches and lush greenery are part and parcel for the idyllic island jaunt, but there are tropical escapes, and then there are tropical escapes.

Once you decide to own a slice of paradise, the details of island living become that much more nuanced. It becomes about sun and shade cycles, open-air living, a welcome dose of privacy, and views whenever possible. Warm wood adds a beach-hut feel, sweeping white walls offset pops of topical color, and washed stones evoke nearby shorelines. Couple those trappings of good taste with resort-like amenities and you may never leave the island.

Castillo Caribe, Grand Cayman

$39,950,000 USD | Grand Cayman, Cayman Islands | Cayman Islands Sotheby’s International Realty

The Caribbean’s year-round sunshine and bright culture are nearly eclipsed by the oceanfront majesty of this Cayman Island retreat.

Castillo Caribe’s boutique hotel–like features make it an unforgettable spot to retreat with friends. A grand front hall presents woven-style ceiling details, recessed lighting, and a sweeping wood staircase, all of which get a splash of the island’s natural elements via indoor palms and two-story floor-to-ceiling windows.

Here, classical features and decor outshine typical nods to beach living: a long table dining hall with elegant chandeliers, an expansive chef’s kitchen with multiple prep areas, and a master bedroom with beautiful wood ceiling inlay. Then there’s the wine cellar, games room, home theatre, gym, outdoor pool and private grotto. Cap that off with the Cayman Islands’ tax-neutral environment for the ultimate break from normalcy.

Makena, Maui

$26,995,000 USD | Makena, Hawaii | Island Sotheby’s International Realty

Look out across the endless Pacific Ocean from one of the most beautifully constructed, custom-detailed homes in Maui. Perched upon one acre of land, this 10,500-square-foot residence is an exemplary model of indoor-outdoor living.

Custom wood detailing runs through every area, including the eight bedrooms. Rippling fountains keep relaxation dialed, and a home theater is at the ready when you need a break from the sun. Or maybe you’ll prefer to soak up that movie in the open night air—an outdoor theater rises from the pool deck.

The nearby pool house accommodates any additional guests, and the nearly 4000-square feet of deck is perfect for large celebrations and star-gazing alike.

Sentosa Cove, Singapore

$19,900,000 SGD | Singapore | List Sotheby’s International Realty

Incredible modern architecture defines this rare oceanfront residence in Singapore. The lure of a marina resort meets high residential integrity here—a marriage of raw wood, polished steel, fair-faced concrete, and tropical sea air.

Views of the water rush into grand rooms at the rear of the home, while front rooms face the waterway. Flow, light, and open space are abundant, as is indoor-outdoor living. A timber bridge intersects the main staircase, giving way to a covered terrace so you can comfortably enjoy the local climate out of the sun’s rays (a dip in the pool will also do nicely). Sliding and folding glass doors expand the living and dining spaces for breakfasts and dinners al fresco. Whether you’re upstairs in a private, inviting bedroom or taking in the tranquility of the courtyard, this Sentosa Cove stunner is open and alive.

Mahoe Bay, Virgin Gorda

$23,000,000 USD | Virgin Gorda, British Virgin Islands | British Virgin Islands Sotheby’s International Realty

Beachfront living just doesn’t get any better than this. Stunning local stonework, warm woods, Travertine marble, and sandy shades of upholstery line the rooms of the villas at Aquamare.

Three 8,000-square-foot villas, equipped with 30-foot vaulted ceilings and beautiful indoor-outdoor detailing—including hammock seating—can house up to 12 guests each. Each also has its own private waterfront infinity pool with clear views of Drake’s Channel and upscale beachside lounging. A manager’s villa is partnered with the property, making large celebrations and group gatherings easy.

Elevated island homes offer the ideal blend of private retreat and resort living, where tempos slow and lapping waves provide the soundtrack to your days—your own personal paradise.

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