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.
Modern Ranch Style Home on Jacada Place This bright and stylish modern ranch sits on a spacious, private lot with lush landscaping and mature fruit trees.
The home features a sleek contemporary kitchen with stainless steel appliances and an open-plan dining and living area with quality finishes throughout — perfect for modern family living.
Listed at CI$2,150,000 To schedule a viewing contact Sheena on +1.345.525.3333 MLS# 417490 | Member of CIREBA
#NewRental ✨ Vela Phase 3 This 3 bedroom home is located in the gated community of Vela that is a family friendly complex with an Olympic size swimming pool. Other amenities include a tennis and pickleball courts, and gym. There are two bedrooms and two bathrooms on the 2nd floor and the third floor has an additional bedroom and bathroom. Pets will be considered but must be approved by the owner.
Available February 1, 2026 | KYD $5,400 PCM For more details contact Cathy at +1.345.927.8095 RMLS# 6199 | Member of CIREBA
Congratulations to our very own Karina! @karinamcdermot 🏃♀️🏅 She crushed it at the @caymanmarathon yesterday with a 5:00:43 finish—earning 2nd place in her age group, 20th among all women, and 65th overall. We couldn`t be prouder!
#NewListing Carib Sands Cayman Brac - Relaxed Beachfront Living 🌴 Nestled along the unspoiled shoreline of Cayman Brac, this penthouse condo offers an inviting coastal retreat in one of the most scenic corners of the Cayman Islands.
Known for its rugged natural beauty, active pursuits like deep-sea fishing, world-class diving and snorkeling, and iconic landmarks such as the Bluff—famous for rock climbing—Cayman Brac epitomizes relaxed island living blended with adventure. It’s an ideal hideaway for those seeking a laid-back lifestyle with access to the natural wonders of Cayman Islands real estate.
Listed at US$325,000 For more details contact Jonathan, @caymanislands_realtor at +1.345.525.3400 MLS# 420037 | Member of CIREBA
Go Bragh – Kaibo Beachfront Home with Dock ✨ Imagine beginning each day with the sound of the sea and west-facing views stretching across the Caribbean. Go Bragh is more than a home — it is a rare opportunity to own along one of Cayman’s most sought-after stretches of beachfront.
Positioned in the desirable Kaibo area near Rum Point, this property offers exceptional privacy, direct beach access, and a private dock — an ideal combination for effortless boating and truly relaxed coastal living.
Listed at US$3,950,000
For more details contact Jonathan: @caymanislands_realtor at +1.345.525.3400 or Caroline at @carolinethorburn1 at +1.345.916.4858 MLS# 419806 | Member of CIREBA
