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.
A rare opportunity to own prime land on Midsummer Drive! Nestled in a secluded, upscale neighbourhood just minutes from town, this stunning piece of land offers the perfect setting for your dream home. The property is ready for building, providing peace of mind and endless possibilities.
Listed at CI$595,000 Contact @karinamcdermot at +1.345.925.3800 MLS# 418590 | Member of CIREBA
Known for being a particularly intimidating course, is currently hosting the 2025 US Open, and our very own Tana Kelly is front row today supporting Cayman`s Justin Hastings, as he started today`s round.
From luxury homes with private putting greens to golf course views that never get old — discover the ultimate properties designed for golf lovers. Whether you`re a serious player or just enjoy the lifestyle, these homes are on par with perfection ⛳
Seabreeze offers rare privacy and true beachfront living on world-renowned Seven Mile Beach — just nine luxury residences with uninterrupted Caribbean views.
This 4-bedroom, 4.5-bathroom condo with a den spans nearly 3,000 sq. ft., featuring resort-style amenities, direct elevator access, two underground parking spaces, and snorkeling right outside your door.
Listed at US$4,950,000 For more details, contact Cathy at +1.345.927.8095 MLS# 418407 | Member of CIREBA
#NewRental 72 Vista Del Mar - Luxury 4-Executive Family Home
Welcome to your dream rental in one of Grand Cayman’s most exclusive gated communities — Vista del Mar. This elegant 4- bedroom + den, 4.5-bathroom estate offers the ultimate in privacy, comfort, and Caribbean luxury.
US$15,500 per month For more details contact Karina at +1.345.925.3800 RLS# 5487 | Member of CIREBA
