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.
Burgundy has a way of transforming a room. Deep, warm and timeless, this rich shade is finding its place in luxury interiors again, adding depth, character and a touch of drama.
Discover how burgundy can bring a new dimension to your home.
Discover Tropical Haven 16, a beautifully maintained and fully furnished 2-bedroom + den, 2.5-bathroom townhome for sale in Grand Cayman, offering an exceptional combination of comfort, privacy, and relaxed Caribbean living. Located in the established community of Tropical Gardens, this move-in-ready Cayman Islands property features spacious interiors, valuable energy-efficient upgrades, and a peaceful tropical setting.
Join Heather on Saturday from 12pm - 2pm Tropical Haven 16 Member of CIREBA MLS421342
As wealth shifts around the world, so does the question of where people choose to live, invest and build. Explore the changing picture of global wealth and the places attracting attention.
#NewListing Turnkey Island Living | Energy-Efficient Upgrades | Private End Unit | Lush Tropical Surroundings
Discover Tropical Haven 16, a beautifully maintained and fully furnished 2-bedroom, 2.5-bathroom townhome for sale in Grand Cayman, offering an exceptional combination of comfort, privacy, and relaxed Caribbean living. Located in the established community of Tropical Gardens, this move-in-ready Cayman Islands property features spacious interiors, valuable energy-efficient upgrades, and a peaceful tropical setting.
Listed at CI$499,000 To arrange a viewing contact Heather at (345) 525-3600 MLS# 421342 | Member of CIREBA
The Cayman Islands is the highest-ranked Caribbean island in @patrician.ch 100, a 2026 ranking of the best places in the world to live for high earners.
George Town placed 26th of 100 worldwide, ahead of Bermuda, Turks and Caicos, the Bahamas, Barbados and the BVI. Cayman also ranked 9th in the world for Wealth, alongside Monaco, Dubai, Singapore and Zug in the top 10.
What sets Cayman apart: - Zero income tax and no capital gains tax - One of the world`s leading financial centres - Strong schools and a safe, welcoming community - And, of course, Seven Mile Beach on your doorstep
Thinking about making Cayman home? Let’s discuss what’s possible.
As reported by @cayman_compass https://www.caymancompass.com/2026/10/19/george-town-ranked-26th-best-place-to-live-globally/
Read the ranking: https://patrician.ch/rankings/world/
Our team was delighted to be there over the weekend, and proud to serve as title sponsor of this special fundraiser for @jasminepalliativecare at the Harquail Theatre.
Congratulations to everyone involved, and thank you to all who came along 💙
