A hidden gem of Bermuda, the restored former pirate fortress, Sandymount is Bermuda’s newest addition to the luxury vacation rental market.

The two-and-a-half acre Bailey’s Bay property sits on a peninsula encompassing a historic fort site that has unobstructed panoramic views of the north shore all the way from Dockyard to Ferry Reach.

Both inside and outside of the home there are many artifacts of Bermuda’s nautical history, including harpoons, a fish pot, old maps, and diving helmets.

The original house was built in the 1600s and has been owned by a who’s who of Bermudians over the centuries. In 1980, Wendell Hollis, who is a descendant of the original owners, purchased the dilapidated property. He sought advice from a multitude of architects to try to restore the home to its former glory but was told it would be better to tear it down and start anew.



He finally, found one who had the imagination to see the possibilities in restoration. After four years of meticulous and loving work in using Bermuda stone and cedar, the result was an award from the Bermuda National Trust.

Rachel Sawden, property manager, said Mr Hollis saw an opportunity after the last tenant left. She said for those looking for an extraordinary experience the property is available as a vacation rental and can be booked for exclusive private events. “He loved the property so much, he wanted to share it with more people,” Ms Sawden said. “He wanted more people to see it and experience it.”

It has already hosted a gala wedding providing the bride and groom a vista as an accompaniment to their nuptials. “It was an absolutely stunning night,” Ms Sawden said. “We had a wedding arbor that overlooked north shore. It was a perfect one-stop shop for them as we did the ceremony, pictures, cocktails, and the reception in one spot so they didn’t have to move the wedding party around to different venues.” The property has the ability to both house the couple, plus family members or friends and host all the events onsite, which is ideal for those traveling to Bermuda to host a destination wedding.


Photo by Gavin Howarth


She enthused life could even be more comfortable for newlyweds if they rent the villa, stay in the upstairs master bedroom while other family members retire to one of the three additional bedrooms. “They could then have their rehearsal dinner the night before, the wedding the next day, and other festivities the day after without ever having to leave the property. It is a perfect location for those coming in from overseas.”


Photo by Gavin Howarth


Ms Sawden added there are very few villas in Bermuda which can house up to nine people, and Sandymount is in that elite tier of rental properties. “This helps fill that niche for luxury travelers, those people who want to stay on a beautiful compound of a property.” A benefit of the large-scale of the property and home, Sandymount is perfect for larger groups, especially multiple couples coming to Bermuda for vacation, or a large family with multiple generations looking to stay together while on-island.



It has also hosted several corporate events, and cocktail parties where guests mingled on the grounds dotted whimsical reflections of Bermuda’s past. Ms Sawden says Sandymount provides an exclusive experience that can’t be found anywhere else on the island.

Although steeped in Bermuda’s past, Sandymount is not without its modern amenities as it has chargers for Twizys for people who decide that they want the electric rental cars to traverse the island. For those who choose to partake of a vacation, one of the unique features of Sandymount includes a wine cellar that was converted from a water tank.


Drone footage by John Singleton


Ms Sawden also functions as a concierge so she can make dinner reservations, book tours, arrange for a private yoga instructor, or help book a private chef to come in to provide a personal dining experience. Sandymount is the perfect private retreat for those looking for seclusion in a picturesque location but are also looking for experiences and amenities tailored to their liking. With Sawden on-board as the property manager and concierge, there’s really no need for guests to ever leave the property if total relaxation is what they’re after.


Photo by Paul Sawden


Those looking to take a deep dive into Bermuda’s pristine waters will relish in the waterfront property that boasts a private dock and beach access. Guests can be collected by boat directly from the property for a sunset cruise or fishing trip and snorkeling off the property is a worthwhile excursion as one can easily spot groups of beautiful parrotfish swimming nearby as well as turtles grazing on patches of sea grass. Sandymount really is the ultimate ocean-lovers dream.



“This is an exceptional property,” Ms Sawden said. “It is one of Bermuda’s hidden secrets, and I didn’t know what was up here until my first visit. It’s spectacular. Bailey’s Bay offers that perfect Bermuda turquoise with the beautiful indigo sea out to the horizon.” Sawden also recommends taking in the sunset from the property as you really won’t find a better location for it on-island. With unobstructed views of the North Shore, Sandymount offers an incomparable piece of the Bermudian lifestyle that everyone should experience, at least for a little while.

The property may be viewed at www.sandymountbermuda.com.