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CEO/Broker Owner

  • Award-winning broker
  • Expertly guides clients through residential, commercial and investment acquisitions
  • Past CIREBA Board Member
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Sheena Conolly

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Our offices are located at:

Governor's Square
Seven Mile Beach, West Bay Road
Grand Cayman, Cayman Islands

Our postal address is:

PO Box 30567
Grand Cayman, Cayman Islands

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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.


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.

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Upcoming auction: Sotheby’s Modern & Contemporary Evening Auction will encompass over a century of pioneering artistic production. Beginning with the innovations of the Impressionists, it spans the birth of Modernism in the early 20th century through to the evolution of Abstract Expressionism and Contemporary abstraction and figuration.

Includes a group of works from the collection of Ralph I. Goldenberg and other highlights from Pablo Picasso, Jean Michel Basquiat, Paula Rego, and more.

#sothebysauction #artauction #sothebysauctionhouse #contemporaryart
#NewListing - Luxury Living At Lions Court, Britannia
2 bed | 2 bath | 1,696 ft2
Britannia has remained one of the Cayman Islands most popular real estate locations for over two decades and for obvious reasons. Minutes from Seven Mile Beach and sitting in a coveted position in the heart of the Seven Mile Beach corridor, Britannia Drive leads homeowners into a ninety-acre oasis set along one of the longest canals in the Cayman Islands, which provides boat access into the water playground of the North Sound

Listed at CI$1,135,000

For more information contact:
Jonathan at +1.345.525.3400 or Heather at +1.345.525.3600
MLS# 417804 | Member of CIREBA

#SevenMileBeachCorridor #CaymanRealEstate #CaymanProperty #GrandCayman #CaymanIslandsRealEstate #CaymanLife #NewListing #Cayman #CaymanSothebysRealty

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