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Governor's Square
Seven Mile Beach, West Bay Road
Grand Cayman, Cayman Islands
PO Box 30567
Grand Cayman, Cayman Islands
KY1-1203
Heather grew up in Cobourg, Ontario, Canada, a small town just outside of Toronto, and realised very early on that the cold winters were not for her, even though she spent a very active childhood in cold arenas as a figure skater or on the ski slopes. After graduating, Heather spent over 15 years in hospitality management with Canadian Pacific Hotels in four and five-star hotels and resorts across Canada. She caught the travel bug during this time and decided it was time to see the world, so she spent two years traveling, hiking, and working throughout Australia, Southeast Asia, India and Nepal. When she thought she still wasn’t ready to settle down, she accepted the Director of Sales position with the Westin Grand Cayman, thinking the Cayman Islands would be a great spot to enjoy for a couple of years before her next adventure. Twenty four years later, she is still calling the Cayman Islands home and plans to do so for many years to come.
Heather moved from hotel management to real estate sales in 2005, starting with Sheena Conolly Real Estate, which transitioned to Cayman Islands Sotheby’s International Realty shortly after. She has been a successful top producing agent every year since. She was awarded Cayman Islands Real Estate Associations (CIREBA) Agent of The Year by her peers in 2009, sat on the Association’s Board of Directors for five years and recently sold the highest priced single family home ever in the Cayman Islands in 2020.
Exceptional customer service is Heather’s number one priority. She is dedicated to exceeding her clients’ expectations while making the real estate process a carefree experience for them. Listening to clients’ needs while focusing on their experience has allowed her to not only be very successful in building a wonderful repeat and referral network, it has allowed her to match hundreds of happy buyers and sellers over the years and, most importantly, meet a lot of wonderful people she calls friends to this day. She can’t imagine anything she’d rather be doing or anywhere else in the world she’d rather being doing it.
#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
🔗 Link in bio
#CaymanPropertyRentals #CaymanRentals #GrandCayman
#CaymanLongTermRental #CaymanIslands #CaymanProperty
Dec 9
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!
#CaymanIslandsMarathon #TeamSIR #MarathonRunner #CaymanIslands #ProudTeam #RunCayman #WeRunCayman
Dec 8
#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
🔗 Link in bio
#CaymanBrac #CaymanIslands #CaymanBracRealEstate #CaymanBracProperty #CaribbeanProperty #CaribbeanRealEstate
#BeachfrontLiving #CaymanIslandsRealEstate
Dec 7
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
🔗 Link in bio
#CaymanSothebysRealty #CaymanRealEstate #CaymanIslands #CaymanKai #Kaibo #LuxuryRealEstate #WaterfrontLiving #BeachfrontHome #CaribbeanRealEstate #LuxuryProperty
Dec 7
Open House this weekend.
Join Sheena at this 2 bedroom end unit townhome in Southampton Gardens. Located in the heart of the Seven Mile Beach corridor and sharing several amenities including a gym, pool, and tennis court.
12pm - 2pm
Southampton Gardens 1
CIREBA MLS#419973
Sheena +1 345 525-3333
#openhouse #caymanrealestate #caymansothebysrealty
Dec 4
Rare Opportunity on Midsummer Drive 🌴
Discover a prime piece of land in one of the island’s most desirable neighbourhoods — private and just minutes from town.
Build your dream home on high, dry terrain or combine two adjoining lots for an even grander retreat.
Listed at CI$595,000
For more details contact @karinamcdermot at +1.345.925.3800
MLS# 418590 | Member of CIREBA
🔗 Link in bio
#CaymanRealEstate #SothebysRealty #CaymanIslands #CaymanIslandsLand #MidsummerDrive #CaymanLand #DreamHomeCayman #CaymanIslands
Dec 3
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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