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Five Incredible Caribbean Homes Waiting for a New Owner

DATE POSTED:May 22, 2020
Many people dream of living in the Caribbean. Villas like Little Hill in Jamaica make us dream even bigger.
Many people dream of living in the Caribbean. Villas like Little Hill in Jamaica make us dream even bigger. (Christie’s International Real Estate/)

There’s a very good reason that television shows like House Hunters International and My Lottery Dream Home are so popular. They respectively showcase our daydreams of one day living on a tropical island and owning the biggest, most extravagant home on the beach. These things may never happen, but the dream is what matters, as it stems from our quenchless thirst for tropical travel and spending as much time as possible dipping our toes in crystal blue water.

It is also a ton of fun to online shop for island real estate, looking at the galleries of stunning pictures and imagining what it would be like to live like Prince or Bruce Willis in a Caribbean compound fit for a royal family. There’s nothing wrong with perusing listings and throwing a penny in a wishing well, because you never know when that lucky lottery ticket might end up in your hand.

If you need a little inspiration, we can start with these five incredible Caribbean properties that are ready to fulfill someone’s wildest dreams.

The Cascade Villa, Turks and Caicos

 $7.5 million
Named for its awesome cascading pool, the Cascade Villa is one of the most extravagant properties available on Turks and Caicos. Listing Price: $7.5 million (Christie’s International Real Estate/)

When it comes to Caribbean dream homes, Turks and Caicos has long been a sought-after destination for retirees and A-listers alike. Some of those dreams have come to fruition, while others are still a work in progress, but a property like the Cascade Villa takes the dream to another level.

Built in 2015 by award-winning architect R.A. Shaw, this home stands out on an island where almost everything seems too good to be true. Set on a little more than a half-acre of property inside Princess Alexandra National Park, this 9,800-sq. ft. villa boasts six bedrooms and six bathrooms, as well as a chef’s kitchen, but the inside is somehow nothing compared to the exterior.

With multiple levels, every guest has his or her pick of paradise, including an upper deck with plenty of space for catching rays and a cascading pool that rains down on two additional pools below. One of which is a wading pool for children or, really, anyone who wants to stay wet while working on a tan, and the other features a swim-up bar, because why wouldn’t it?

But this is Turks and Caicos, so pools will always be second fiddle to the gorgeous beach, of which the Cascade Villa offers 100-feet. Snorkelers will be especially thrilled with the location, but it’s hard to imagine anything being a disappointment at this property.

The Castle, St. Croix

 $9.95 million
Sometimes a name says it all. Listing Price: $9.95 million (Christie’s International Real Estate/)

You’ve undoubtedly heard the phrase “live like royalty,” and you’d certainly expect such a description of a property named “The Castle,” but this exceeds expectations. In fact, looking at the aerial view of this property, located on St. Croix in the U.S. Virgin Islands, you might think it has a name like “The Entire Island” or “A Totally Different Planet.” At the very least, with the way the Castle looks like an old fortress from Game of Thrones, you would live like Dornish royalty.

But this amazing home is hardly old. The Castle was built in 1989 by the Bulgarian Contessa Nadia Farber in 1989, and she drew architectural inspiration from her homeland, but the property also features Moorish and East Asian influence from her travels. It is also massive, if that’s not already clear. The home is more than 10,000-sq. ft., offering six bedrooms and bathrooms, as well as a sprawling deck with a pool that allows guests to enjoy the incredible landscaping. There’s even a separate gatekeeper’s cottage.

What makes this 102-acre estate even more spectacular is that it was once home to Farleigh Dickinson University's West Indies Marine Lab, so the roads and infrastructure are still in place, as is the long pier. Oh, and we should probably mention the beautiful palm-lined beach. That’s pretty great, too.

Little Hill, Jamaica

 $6.5 million
Looking Little Hill has hosted a bevy of celebrities. Listing Price: $6.5 million (Christie’s International Real Estate/)

The first home ever built in the Tryall Club, Little Hill is also the centerpiece, sitting stop a large hill and captivating its guests with panoramic views of Jamaica’s natural beauty. And, again, when we speak about “living like royalty,” Little Hill’s most famous guest was the late Queen Elizabeth The Queen Mother, so a new owner will be in historic company.

Renovated and refurnished in 2012, this 10,000-sq. ft. villa features a two-bedroom master suite with three bedrooms and an office, while the guest suite offers three bedrooms and three bathrooms, all of which surrounds a circular swimming pool. On one side, a covered terrace provides a dining experience for up to 24 people (in case you’re hosting the Super Bowl champions), and the other side has a covered terrace for cocktails and snacks by the pool.

There’s even tennis court with covered viewing area, in case another round of golf on the Tryall Club’s championship course seems monotonous.

Petite Saline, St. Barth

 Price Available Upon Request
It’s hard not to imagine spending every evening looking at the sunsets over Lorient Bay. Listing Price: Price Available Upon Request (Christie’s International Real Estate/)

For some, the idea of living in the Caribbean invokes a theme of subtle elegance. We rely on classic luxury inspired by the region and islands, allowing history and culture to influence architecture and design more than anything else. Featuring design elements like stone walls, dark wood and terracotta floors, Petite Saline is precisely that type of property, seemingly built as a tribute to the island’s natural majesty.

What really makes this property so appealing—aside from the breathtaking views of Lorient Bay—is how its layout promotes a strong sense of privacy. It’s almost like a small resort, blending charm with function, while allowing the owner to welcome guests to the compound but not necessarily into the home. The buildings are spread out over three acres, with beautiful tropical gardens in between the guest units and master villa, as well as the tennis court and gym.

But that’s not to say you wouldn’t want everyone to gather in the lounge and experience the infinity pool. At least not all the time.

Point House, Turks and Caicos

 $15 million
It might be tucked away and hidden by Parrot Cay’s vegetation, but Point House is impossible to ignore. Listing Price: $15 million (Christie’s International Real Estate/)

When it comes to private islands, Parrot Cay has quickly risen to gold standard status in the Caribbean, thanks to the luxurious brilliance of Como Parrot Cay, a resort widely regarded as one of the best in Turks and Caicos, and the dozen private estates that could collectively qualify as literal heaven on Earth. That isn’t hyperbole, certainly not once you’ve been introduced to Point House.

Tucked away in lush vegetation, almost as if it’s hiding from the rest of the world, this villa is a modern masterpiece designed by architect Cheong Yew Kuan. Between the high ceilings and large windows, this estate feels much larger than its 7,000-sq. ft., as if that’s possible, but every last detail of the five bedrooms and five bathrooms appears somehow both brilliant and simple, as if Point House was simply wished into existence.

Most remarkably, the exterior’s wood and glass components seem as if they’re framing the rectangle pool—which was made with lava stone imported from Bali—and its vast deck space. Again, every little detail seems so remarkable and yet so unassuming, and that’s why this is easily one of the most captivating properties in all of the Caribbean.