Market Appraisals
General Enquires
Press Enquires
Investment & New Homes
  • United Kingdom
  • United States
  • Spain
    • Majorca
    • Ibiza
  • Italy

Chestertons Cayman Islands

100 Owen Roberts Drive, Grand Cayman

With our extensive real estate experience, our agents make finding and buying the perfect property in Cayman easy and hassle free. We will guide you around the distinctive communities and various idyllic lifestyles, so you can choose between beachfront or canal-front property. By staying in sync with the market, we can assist you to build and manage your property portfolio.

As an additional tool, we offer an all-encompassing and personalised property search of every suitable property available for sale on Cayman’s Multiple Listing System powered by CIREBA and when necessary, we introduce you to other professionals to facilitate your purchase. We frequently welcome newcomers to the Cayman Islands and are able to play a vital role in helping many familiarise themselves with the island and settling into all aspects of Cayman life and culture.

The Wreck Bar & Grill in Rum Point is reported to be the place where the delicious mudslide cocktail was invented 

Michel Chossudovsky - Canadian economist and author

Office Location

100 Owen Roberts Drive, Grand Cayman, Cayman Islands


+1 345 9269926

Our Team

Sophie Miles
CEO, Cayman Islands

Sophie grew up in rural England and started her career in 1993, soon after she made the move to prime central London. In 1999 Sophie transitioned to property investments again in the capital's most dynamic postcodes. Wanting a change of pace she relocated to Cayman in 2001, specialising in Cayman's most exclusive residences, developments, and HNWI's relocation.

Area Guide

The Cayman Islands offer far more than just some of the world’s best beaches. What was once a small seafaring cluster of islands, established itself primarily as a tax-free jurisdiction in the 1960’s. Recently, Cayman has emerged as a first class tourism destination and one of the top offshore banking centres in the world, with all of the associated industries to support it, the synergy of which has endured global economic crises and arisen to a highly liveable Caribbean island. Thus, the Cayman real estate market remains strong and continues to grow. This British Overseas Territory is now internationally recognised as a ‘safe haven’, offering one of the best offshore lifestyles in a safe and stable environment for high net worth investors.

There is a vast variety of lifestyles available in Cayman, which has been internationally recognised by Forbes and HSBC among others as ranking highly in the lifestyle leagues. With endless beaches and surrounded by the warm Caribbean Sea, activities on and under the water are obvious, but there are numerous other sporting and cultural pursuits and events for the whole family to enjoy. There are charitable organisations and service clubs who always welcome new members. There is something for everyone to relish...but even if you want to relax and do very little, just being in Cayman is a real pleasure.

New Instruction
2 bedroom house, Cayman Islands

New to the Cayman real estate market is this charming 2 bedroom 2 bathroom detached cottage in popular North Side beachfront community located a short drive from Rum Point and Cayman Kai. The property has been the subject to a plethora of sympathetic upgrades, to include new kitchen and bathrooms, whilst maintaining the intrinsic character of a beachfront cottage with an island vibe. The fabulous kitchen includes KitchenAid stainless steel appliances package, Shaker-style wood cabinets, and quartz countertops and backsplash, all enhanced by the plantation window shutters. The cottage also benefits from a covered front porch, large ground trellis covered ocean view patio spanning the width of the property, and accessible from living room and master bedroom. The property also has the potential to be extended further into the large attic space to create further bedrooms / bathrooms should these be desirable, especially as a luxury Cayman villa rental investment. This serene reef protected beachfront complex comprises of seven individual villas that all the share common amenities including swimming pool and deck, large outdoor gazebo, and lush gardens, all adding to the quality beach life on offer to owner occupiers and holiday makers alike. 

  • 2
  • 2
  • 0
2 bedroom condominium, Cayman Islands

Number 12 Grand Palms is an upper floor 2 bed / 2 bath unit, currently rented and well maintained, this condo is ready for an investor or owner occupier, to move into with high-gloss Neff kitchen cabinets, granite counters and a separate utility/laundry room. Good quality furniture package, large elevated balcony, and fabulous pool and grounds complete the offerings at this exclusive South Sound condo complex. Grand Palms is situated on over an acre of prime South Sound Road land. A traditional Step Well is a natural, and free source of water to the strata's luscious landscaping. There is ample parking. A brick paved pathway meanders around the complex serving the salt-water 40ft pool and the private entrances to all the units. Conveniently located only minutes east from George Town on South Sound, this community is a well established condo development consisting of 14 executive level, and over-sized 2 bedroom apartments either side of the 40ft freeform pool and jetted tub, encircled by grand palms and dense landscaping. There are two pedestrian gates to South Sound, so that residents benefit from easy access to the 3.5 acre oceanfront Dart Family Park, with its cabanas and playground and a short walk to the beautiful beach at Smith's Cove. Grand Palms Features: Standing Seem metal Roof 10ft+ AMSL Private entrance Living room with doors to patio/balcony High ceilings Patio/balcony overlooking the pool and gardens High gloss white Neff kitchen cabinetry (German made, with metal casings) Granite counter tops and full Appliance package Laundry/utility room Two master sized bedrooms, each with their own bathrooms & wardrobes Linen cupboard

  • 2
  • 2
  • 0
4 bedroom house, Cayman Islands

As Old Prospect Point is one of the Cayman Islands’ most coveted addresses, a quiet residential road lined with private beachfront homes and upscale condo’s, perfect for evening walks with the dog or kids, this is a sweet spot elevated to catch the captivating sunsets, with vistas over the reef protected beach and the bay of South Sound beyond. New to the Cayman real estate market, Sugar Reef has been completely renovated and transformed into a super stylish, contemporary beachfront villa with vintage touches, which now thrives as a luxury villa rental, sleeping a maximum of 15 guests. The bespoke walnut and white KW Wood works kitchen with integrated Thermador, Gaggenau & Bosch appliances from  Bon Vivant , with the luxury of a built in coffee machine and tall wine cellar that serves the dining area. The custom designed  Artisan Metal Works  spiral staircase is framed by a double volume picture window. Open concept entertaining areas are defined by tray ceiling details, and spill out onto the shaded terrace & sundeck, a zero-edge pool, and steps down to the sugary sand beach. An exceptional master suite with its own private balcony, boasts customised bathroom of Hansgrohe hardware and a Victoria + Albert freestanding bath, plus a fully fitted walk-in wardrobe. Adjacent to the master is a den, which can double as a nursery. The second bedroom suite has its own study/nook and balcony too. The spacious third and forth bedrooms also have en-suite bathrooms. Two stories of solidly built steel reinforced concrete block with an engineered & fully insulated roof truss system, plus a slab elevation of 10ft AMSL - the property is protected by seawall. Hurricane rated Rehau 'tilt and turn' windows are great for pets and families, allowing you to tilt the windows open to enjoy the sea breezes. A full shutter package is included for double protection with electric roll down shutters to the front and Bahama shutters for aesthetics. Surrounding the infinity edge pool is a raw marble terrace, laid in French pattern which seamlessly transitions into a wooden deck, both of which have steps down to the coral beach below. A louvered pergola helps escape from the Caribbean sun for alfresco dining with the adjacent barbecue and bar. To the front of the home is a sweeping driveway with an abundance of blooms and foliage for privacy. Contact us  today for more information or to arrange a viewing......for more showcase photo's click here!

  • 4
  • 5
  • 0
4 bedroom condominium, Cayman Islands

After an impressive sell out of phases I & II, Milestone Properties are most pleased to announce  Davenport's latest phase of VELA, completion of phase III is anticipated early 2020 and we are taking reservations for the remaining few now! Now even more spacious, these family sized 4 bedroom, 3.5 bathroom totaling 2650 sq ft of useable space have been enlarged - over the three storey villa with a feature roof terrace and private patio, master suite balcony and front courtyard. The larger floor plan offers the capacity for an extended second master on the top floor.To upgrade this top floor room into a full bedroom suite will cost from CI$11,000 See below floor plans or contact us at Milestone for further details, and availability.   Like a sail, these contemporary villas are designed to catch the cool sea breezes of the reef protected South Sound, and characteristic of all Davenports developments there will be a strong emphasis on the outdoor environment with immense roof terraces and private patios over looking the luscious landscaping. Also true to form will be the structurally solid and energy efficient ICF building technology used in all Davenport Developments. Many of these villas will enjoy sublime views over the private South Sound beach frontage (scroll down for map), and all residents will benefit from the heavenly resort style comforts of an outstanding Olympic length pool, fully equipped gymnasium, tennis courts, on-site property management office and concierge service.

  • 4
  • 3
  • 0

Need property advice in Cayman Islands? 
Thinking of investing in Cayman Islands?

Service Finder