Islamorada · Florida Keys · Ocean Sotheby's International Realty

Two
Generations.
One Home.

20+
Years Top Producer · Upper Keys
2×
Top-earning individual (2020 & 2025)
#1
Office in the Upper Keys, Ocean Sothebys
Leslie Leopold & Annie Hagen

Rooted here for thirty years and still counting.

Leslie has been a top-producing agent in the Florida Keys since 2004 — the year she turned a personal passion for this place into a career that has shaped the Upper Keys luxury market. Her record-breaking sales and three decades of community roots tell the story of an agent who leads with care and delivers extraordinary results.
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Now her daughter Annie has joined her. Born and raised in Islamorada, Annie brings the same deep community roots alongside a background in psychology. She is the natural continuation of a family legacy this market has come to trust.
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Together, they offer something this market rarely finds: a team that is both fiercely accomplished and genuinely at home here — in the community, on the water, and by your side through every step of the process.

As Seen in

Island Roots. Global Reach.

Most buyers searching for Florida Keys property begin somewhere else — New York, Chicago, São Paulo, London. Reaching them takes more than a listing on the MLS. Through Ocean Sotheby's International Realty and the worldwide Sotheby's International Realty network, every property we represent is placed in front of an audience that no independent brokerage can assemble.

Community

Giving Back

Leslie and Annie don't just work in this community — they are woven into it. From nonprofit boards to annual fundraising tournaments, their commitment to Islamorada goes far beyond real estate.

Fish for Holly Sailfish Tournament
Habitat for Humanity · Upper Keys
Mariner's Hospital Foundation
Islamorada Foundation
Mangrove tree with green leaves and exposed roots reflected in calm water.
Metal lighthouse structure in the ocean during a cloudy sunrise with sun rays over the horizon.
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Leslie didn't just sell our home — she understood what this place meant to our family. After forty years on Islamorada, we needed someone who could honor that story while delivering real results. She did both, effortlessly.

Courtney M.
Seller · Islamorada · 40 years in the Keys
We interviewed three agents before choosing Leslie. There was simply no comparison — her knowledge, her honesty, and her patience made the entire process a genuine pleasure.
Jim & Carol · Buyers · Upper Matecumbe Key
I've purchased several multimillion-dollar properties in the Keys. Leslie is the only agent I will ever use. Polished, motivated, and completely trustworthy.
T.N. · Repeat Buyer · Florida Keys
Local Knowledge

The Keys to the Islands

Let's Talk

Ready to find your place in the Keys?

Buying, selling, or simply curious what your property is worth. No pressure — just honest conversation from people who know this place better than anyone.

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