About Leslie Leopold

Leslie Leopold is one of the Florida Keys’ most respected real estate professionals, widely trusted for representing some of Islamorada’s most significant waterfront properties and legacy estates while guiding clients through thoughtful investment decisions at every level.

With more than two decades as a top-producing agent in the Florida Keys, Leslie has earned the confidence of longtime homeowners and discerning buyers alike. Her business is built on longstanding relationships, repeat clients, and referrals — a testament to the trust she has cultivated within the community throughout her career.

Leslie has represented many of the region’s most significant residential transactions, including the sale of a newly constructed oceanfront compound that closed for $27,750,000 — the highest residential sale ever recorded in Florida Keys history. Her portfolio includes numerous landmark waterfront estates and luxury properties throughout Islamorada and the Upper Keys.

In 2020, during a period of unprecedented market change, Leslie was honored as the top-earning individual at Ocean Sotheby’s International Realty, Islamorada — an achievement she repeated again in 2025.

A Florida Keys resident for more than 30 years, Leslie’s connection to the community runs deep. She and her husband, a respected local fishing captain, raised their two daughters in the Upper Keys, where both now live and work as adults. Her daughter Annie Hagen has recently joined her in real estate, continuing the Leopold family’s legacy of serving Florida Keys homeowners.

Leslie is also deeply involved in the community and is proud to serve as the sponsorships liaison for the Fish for Holly Sailfish Tournament, a major Florida Keys fundraiser honoring Holly Given’s legacy while raising awareness for domestic violence and providing scholarships and community support. She has also served on the boards of Habitat for Humanity of the Upper Keys, Montessori Island Charter School, Mariners Hospital Foundation, and the Islamorada Foundation.

Beyond her professional achievements, Leslie remains committed to community service and charitable initiatives while maintaining an active lifestyle centered around wellness, tennis, strength training, and healthy living.

Approachable, knowledgeable, and deeply rooted in the Florida Keys, Leslie Leopold offers clients a trusted perspective on one of the most unique real estate markets in the world.

Meet Leslie Leopold | A Personal Introduction Video