Darrin McCutcheon

A Naples property owner since the early 2000s, Darrin McCutcheon brings an unmatched depth of local knowledge and a refined client-focused approach to his role as a global real estate advisor with Premier Sotheby's International Realty's Southeast Naples office. With a deep appreciation for the area's signature golf course communities and coastal lifestyle, Darrin specializes in luxury properties throughout Lee and Collier counties, including Greyhawk at Golf Club of the Everglades, Twin Eagles Club, and Quail Creek Country Club.



An accomplished former insurance executive with multi-state licensure and leadership experience, Darrin has built a career on analyzing data and understanding what truly matters to his clients. His mission is simple: serve the client first, not the sale. Whether advising a buyer seeking the perfect second home or helping a seller secure top dollar, Darrin is known for fostering trust, delivering clarity, and negotiating with fairness and integrity.



With strong ties to the Naples community and a personal passion for golf and lifestyle-driven living, Darrin offers a seamless and elevated real estate experience. His past role as president of a large insurance agent network in the Washington, D.C. region further enhances his ability to work with clients from diverse backgrounds and navigate complex transactions with ease.



Darrin's unique background comes with skillsets and local vendor relationships to create a hassle-free way to sell homes faster and at a higher price, enhancing the real estate journey and elevating the experience of working with him.