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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.

4 bedroom apartment, Cayman Islands

Turn-key and move-in ready, so don't wait for Cayman property prices to go up any more! This fantastically finished, four-bedroom townhouse with three and a half bathrooms set over 3 storeys has picturesque views over the North Sound towards the Cayman Islands Sailing Club and mouth of the Grand Harbour canal. This family home is also flexible in that the spacious ground floor suite can be self-contained, and can easily include what is currently the garage to form some additional income or accommodation. The light-filled entertaining spaces enjoy a wide and deep terrace with ever-present breezes off the Sound, for those that love to cook and entertain, the kitchen and bar areas have been fitted with a modern soft close Shaker-style cabinets, Ceasarstone counters and KitchenAid appliance package with the added benefit of gas. The over sized master bedroom suite boasts its own private balcony and deep walk-in wardrobe, two further bathrooms that share a full bathroom and conveniently located laundry are all placed on the top floor. Adding to the fantastic finishes, Ocean Crest individual docks, a family-style pool with an ideal shallow area and tropical planting around the pool deck, lawn and 'beach' area for shade and privacy for the residents. The well-established developer has put an emphasis on Energy Efficiency, including but not limited to Solar Panels, ICF construction, gas range, water heater and dryer, so expect very low outgoings to top it off!

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5 bedroom house, Cayman Islands

Tucked away, but just moments from the world renowned Seven Mile Beach and the hussle and bustle of the West Bay Road 'strip' is this charming family home in the residential enclave of Whitehall Estates - equidistant from Camana Bay and George Town, capital of the Cayman Islands. Approached from the quiet turning circle, and having undergone more recent additions and improvements since it's construction in the early 1980's, this unique property offers approximately 4,000 square feet of flexible living and entertaining accommodation. Comprising four bright and airy reception rooms with valuted ceiling details, and easy flow between the spaces. Three of the four bedrooms are upstairs off the galleried landing, including the master bedroom with ensuite bathroom, and the family bathroom. The ground floor guest suite could have its own access and courtyard garden for the purchaser looking for a helpers quarters / granny flat / rental income. There is also a welcoming entry hall and study/5th bedroom with guest powder room (could be converted to shower room), utility room, and a two car garage. Sitting on a generous lot, with ample setbacks from the parcel boundaries, the property gives the feeling of space with its mature landscaping, family friendly swimming pool with waterfall, and large tiled deck for entertaining. The garden is also pet freindly, having a various fenced-off areas. With such low inventory of family homes, and with this level of charm and character on the Cayman Real Estate market, contact Nick Sellars today to arrange a viewing of this rare find.

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3 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 3 bedroom, 3.5 bathroom totaling 2550 sq ft of useable space have been enlarged over the three storeys, the villa features a front courtyard, private patio, master suite balcony and terrific top floor roof terrace, with the capacity for a second master on the top floor. To upgrade and covert the top floor terrace into a second master suite or den starts in cost from CI$35,000. See below floor plans or contact us at Milestone for further details, and availability.   All residents will benefit from the heavenly resort style comforts of 2 fully equipped gyms with a Club House, 3 spectacular Olympic length swimming pools, 2 lit tennis courts, boat trailer parking, storage lockers, Concierge and onsite property management services. Inspired by the Catboats of Cayman’s seafaring past, and a constellation of the Southern Sky, VELA (meaning Sail) is dynamic and modern in its styling. Like a sail, these contemporary villas are designed to catch the cooling sea breeze, 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.

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1 bedroom condominium, Cayman Islands

VERY LIMITED AVAILABILITY OF THESE ONE BEDROOM OFFERINGS: BOTH ENTERED THROUGH THEIR OWN PRIVATE GATE AND COURTYARD, THERE IS A RAISED GROUND FLOOR CONDO, AND A SECOND AND THIRD STOREY 'MAISONETTE' STYLE DUPLEX, WITH VOLUMINOUS HIGH CEILINGS, AND AN OVERSIZED TERRACE, THESE ARE AN IDEAL ENTRY LEVEL CONDO AND/OR RENTAL INVESTMENT WITH LOW OUTGOINGS AND HIGH DEMAND - RESERVE NOW! WITH CHOICES OF PORCELAIN TILES, EUROPEAN STYLE CABINETRY TO THE KITCHEN AND BATHROOMS, QUALITY COUNTERTOPS AND AN INTEGRATED BOSCH APPLIANCE PACKAGE, YOUR STYLE OF MODERN LUXURY IS ENSURED. ONE BEDROOM CONDO CI$350,000; ONE BEDROOM MAISONETTE WITH DEN/SECOND BEDROOM CI$505,000; Maisonette - diminutive of maison (French) or house; Self-contained living accommodation, with its own front door and often occupying two floors   SPECIFICATIONS ICF construction with 2.5 inches of insulation either side of the core industrial grade, steel re-inforced concrete FLOORS & ROOF engineered with metal frames with over 5 inches of poured concrete. Slab elevation is anticipated to be +/- 9ft AMSL WINDOWS - Induplan of Spain and are insulated impact windows.  An important feature is the Low-E glass WHICH comes with a 'Neat & Preserve' coat similar to self-cleaning windows on the HS glass. TILES Italian Marrazzi porcelain tiles throughout KITCHENS & BATHROOMS European and contemporary style cabinets and hardware with high-quality form, finish and function. BOSCH APPLIANCES Fully equipped with 30” cook-top, a wall mounted oven and microwave combo, an extra large French Door fridge/freezer with high efficiency dishwasher. HVAC SYSTEM Air conditioning shall be Split level/ Multi Zone A/C from Lennox, supplied and installed by OTIS AIR. The HVAC system will be controlled by the NEST Thermostat (www.nest.com) SMART WIRING Home wired with ‘smart wiring’ Cat 6 cables for the discerning purchaser to program their home for the future. All Homes will be ‘Fibre Ready’ for fibre in all living areas. SECURITY Each Home comes with a complete security system from Island Electronics Ltd. A video entry system from C3 will also be available.

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