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.
The Islands welcomed almost 289,000 stayover visitors in the first half of 2026, up 11.3% year-on-year, with particularly strong growth from Canada and Europe alongside expanded air connections.
More visitors, more flights and growing international interest in Cayman 🇰🇾
Rum Point Beach Front Lot ✨ Discover one of the finest beachfront opportunities in the prestigious enclave of Cayman Kai. This exceptional half-acre homesite boasts outstanding elevation, offering peace of mind while showcasing breathtaking panoramic views across the Caribbean`s world-famous turquoise waters.
Listed at US$2,200,000 For more details contact @patty.nugent.cayman.realtor at +1.345.525.3003 MLS# 420971 | Member of CIREBA
#TravelTuesday - Published in Architectural Digest, this grand Spanish-style home stands in a private, lushly landscaped setting with distant views of Los Angeles. Presented by our colleague Sonia Cole and Sotheby`s International Realty - Los Feliz
From island life and community to the practicalities of making Cayman home, here are ten things worth knowing about living in one of the Caribbean’s most unique places.
100 Acres | High Rock Drive | Low Density Residential ✨ A significant 100-acre land opportunity in a low-density residential area, located on both sides of High Rock Drive, north of Sea View Road.
The property offers approximately 1,500 linear feet of road frontage across both sides of the parcel, with sealed road access, street lighting and direct vehicular access.
The terrain is generally dry and rocky with native bush. Mains power and water services are available in the vicinity.
Listed at CI$8,000,000 For more details contact Sheena at +1.345.525.3333 MLS# 420704 | member of CIREBA
The Wreck of the Ten Sail is one of Cayman’s best-known stories — but where does history end and legend begin?
Revisit the dramatic events of 1794, exploring the stories of princes, pirates and tax-free promises, and the remarkable oral histories that kept the tale alive for generations.
