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Sheena
Conolly

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
KY1-1203

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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.

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.

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More Canadians are choosing Cayman, and getting here is about to become even easier. 🇨🇦

Canadian stayover arrivals to the Cayman Islands rose 41% during the first nine months of 2026, contributing almost a quarter of the overall visitor growth.

This winter, a record 15 weekly flights from Canada will offer greater choice through Air Canada, WestJet and Porter Airlines, strengthening the connection between the two countries.

Reposted from @paxnews

🔗 Link in bio

#CaymanIslands #CanadaToCayman #CaymanLiving #CaymanRealEstate #CaribbeanLiving
#NewListing
High Rock - 1.75 Acres With Ocean View
Elevated Views. Expansive Possibilities. An Exceptional Opportunity.

Imagine creating your own private Caribbean sanctuary, where sweeping ocean views, natural beauty, and the tranquillity of Grand Cayman's East End provide the perfect backdrop for your dream home.

Set within the peaceful High Rock area, this impressive 1.75-acre parcel offers a rare combination of space, privacy, and potential. Whether your vision is a spectacular custom-built residence, a secluded island retreat, or a strategic investment for the future, this substantial parcel provides an exciting blank canvas to bring that vision to life.

Listed at US$750,000
For more information contact Nikki at +1 (345) 938-0600
MLS# 421415 | Member of CIREBA

🔗 Link in bio

#CaymanLandListings #CaymanRealEstate #CaymanLand #BuildingInCayman #CaymanLandForSale #CaymanIslands #CaribbeanRealEstate #GrandCaymanLand
A jewel with a story spanning empire, revolution and Cartier. 💙

The Romanov Sapphire, a remarkable 197.80-carat unheated Ceylon sapphire, is expected to achieve up to £1.5 million when it is offered at Sotheby’s Royal & Noble Jewels sale in Geneva.

One of the few identifiable gemstones to survive from the Russian Crown Jewels, it was worn by Dowager Empress Maria Feodorovna at the legendary Winter Palace Ball of 1903. Following the Russian Revolution, it passed through the Soviet dispersal sales, the collection of opera singer Ganna Walska and the hands of Cartier.

A rare gemstone made even more extraordinary by its history.

Read more via @the.independent 
🔗 Linkin bio

#Sothebys #RomanovSapphire #RoyalJewels #FineJewellery #JewelleryAuction #TheArtOfCollecting
#NewlyPriced ✨
Northern Lights 1 & 2 🌴
Slow mornings, uninterrupted Caribbean Sea views and days spent by the water. Island living at your own pace.

With access to a secluded beach, private boat dock and swimming pool just steps from the spacious screened-in patio, Northern Lights offers a relaxed coastal lifestyle in a peaceful oceanfront community of just ten residences.

A rare opportunity to own two neighbouring beachfront residences in Grand Cayman, with the flexibility of a permanent home, island retreat or investment property.

Listed at US$999,000

For more details, contact @carolinethorburn1 at +1 345 916 4858 or @patty.nugent.cayman.realtor at +1 345 525 3003
MLS# 420691 | Member of CIREBA

🔗 Link in bio

#CaymanIslandsProperty #CaymanIslandsRealEstate #CaribbeanRealEstate #CaymanProperty #IslandLife #CaymanRealEstate #OceanViews #CaymanIslands

What Our
Clients Say

Whether you want to buy, sell or invest in a property in the Cayman Islands, our skills and experience make us your ideal partner.

Discover what our clients have said about their experience of working with us.

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