Ultimately, my goal is to use my drive, energy and exceptional brand wisely. This underpins my overriding desire to spread happiness in everything I do for my clients, customers, family & friends.
Local expertise. Global connections.
ABOUT SHEENA
A consummate professional within the industry who is highly regarded by her peers, Sheena Conolly began heading Cayman Islands Sotheby’s International Realty in December 2005 when the firm approached her to take on their master franchise in the Cayman Islands. Sheena had already built up a successful real estate business at that time, using her extensive background in the hospitality industry and her background as a student of Cornell University to create a successful independent real estate business.
A former board member of the Cayman Islands Real Estate Brokers Association, Sheena has helped the Sotheby's International Realty brand further its global reach by establishing what has become an award-winning branch of Sotheby's International Realty, by assisting its clientele to purchase some of the Caribbean’s finest homes right here in the Cayman Islands.
As a testament to the heights Cayman Islands Sotheby’s International Realty has been able to climb under Sheena’s leadership, she and her team were present at the Sotheby's International Realty inaugural summit at the Waldorf Astoria in New York and, since then, both the company and the brand have seen phenomenal growth, now represented in more than 1000 offices in 75 countries worldwide. Today, Sotheby's International Realty is the number one choice for buyers and sellers looking for real estate representation in the Cayman Islands and worldwide.
Awards and accolades include Cayman Islands Sotheby’s International Realty proudly receiving the International Property Awards (Americas) ‘Best Real Estate Agency Cayman Islands’ in 2012. In 2013 it was again highly commended for 'Real Estate Agency Marketing'. In addition, Sheena has been selected to participate in a wide range of panel discussions for Sotheby’s International Realty in numerous leadership forums and global networking events. Cayman Islands Sotheby’s International Realty is the only company to have been awarded ‘Best Real Estate Company in the Cayman Islands’ by AIPP at the International Property Awards.
A charismatic and highly knowledgeable professional, Sheena has helped to place luxury Cayman Islands property firmly on the global real estate stage, having been featured on various television programmes, including House Hunters International, the BBC’s Travel Channel, A Place in the Sun, and HGTV’s Million Dollar Room. Her commitment to client service, marketing innovation and agent development has earned her professional recognition throughout the Caribbean region.
On The Bay 208 Beautiful ocean views, peaceful North Side living, and short-term rental approval already in place. With property management already arranged, this is an easy option for island living, holiday use, or generating rental income when you’re not there.
Listed at US$625,000 For more info contact Cathy at +1.345.927.8095 MLS# 420579 | Member of CIREBA
Kool Kai, Cayman Kai 🌴 A spectacular 3-bedroom, 3-bath beachfront estate encompassing 5,083 square feet of refined island living in the exclusive community of Cayman Kai, Grand Cayman.
Perfectly positioned on a stretch of pristine white sand, the home enjoys breathtaking, unobstructed sunset views over the Caribbean Sea - a daily masterpiece from your own backyard.
Listed at US$6,500,000 To arrange a viewing contact Patty at +1.345.525.3003 MLS# 420530 | Member of CIREBA
Rum Point Club Residences 203 Residence 203 at Rum Point Resort features just under 2,250 sq. ft. of living space with an easy, open flow from the kitchen to the dining and living areas, and out to a large covered balcony. The kitchen is designed for both everyday living and entertaining, with high-end appliances, generous counter space, and a full dining area.
Listed at US$2,000,000 To arrange a viewing contact @britt.slade.cayman.realtor at +1.345.323.9783 MLS# 420520 | Member of CIREBA
Before there were luxury handbags, there were Louis Vuitton trunks.
Originally designed for the golden age of travel, these iconic trunks became symbols of status, craftsmanship and a life well-travelled. More than 170 years later, they remain some of the most recognisable luxury objects in the world.
One of the most spectacular beachfront parcels in the Cayman Islands, and the kind we see rarely come to market.
Set on 3.75 acres in peaceful Pease Bay, this pristine beachfront site offers approx. 390 ft of beach frontage, 500 ft deep with beautiful swimmable water, magnificent views, and flexible Beach/Hotel zoning. Utilities are already in place, and an existing residence on site gives you an immediate foothold while plans take shape. Recently repriced, a rare opportunity to secure substantial beachfront acreage of this caliber.
US$5,750,000 | MLS# 419686
Contact Sheena Conolly, Broker/Owner for full details.
Our Cayman Cottage ✨ Perched on the bluff of Queen’s Highway, this 8,759 sq. ft. four-story estate offers breathtaking panoramic views of the Caribbean Sea. Enjoy over 2,000 sq. ft. of covered outdoor space, a vanishing edge pool & spa, and a private beach with crystal-clear, reef-protected waters—perfect for snorkeling, kayaking, and paddleboarding.
Listed at US$3,999,000 For more details, contact @patty.nugent.cayman.realtor at +1.345.525.3003 MLS# 418642 | Member of CIREBA
