Leslie Leopold

Leslie Leopold

Global Real Estate Advisor

Leslie Leopold has a genuine passion for the Florida Keys lifestyle derived from three generations of her family fishing and diving in the Keys. This passion prompted her to move here over 30 years ago and sell the lifestyle she so whole-heartedly loves. Leslie's degree in nursing and previous medical field experience has been a natural foundation for her real estate career. It shows her ability to care for people, listen to people, and ultimately help people find their perfect home in an authentic and humanly way. Leslie has been a top-producing real estate agent in the Florida Keys since 2004, which she considers a true honor. In 2020, Leslie succeeded in the pandemic's unprecedented obstacles, adapted to a new "virtual" way of life, and was the top-earning individual throughout all three Ocean Sotheby's International Realty offices. 


Leslie and her husband, a prominent fishing Captain, raised their two daughters in the Upper Keys. Both girls live and work here as adults, enjoying the Keys peaceful environment, healthy work/life balance, and the vast options offered here. The entire Leopold family is involved in many local sports and activities including tennis, soccer, volleyball, fishing, scuba-diving, and horseback riding. These small-town communities of the Keys provide a sense of togetherness and, most importantly, encourages giving back to those not as fortunate. One of Leslie's most significant achievements is her role in the Holly Given Fund and the annual Fish for Holly Sailfish Tournament, a non-profit foundation honoring Holly Given's memory by helping others in the community. In addition, Leslie is an active community member having served on the Board of Directors of Habitat for Humanity of the Upper Keys, Montessori Island Charter School, Mariner's Hospital Foundation, and the Islamorada Foundation.


Leslie is local, approachable, and has deep roots in the community she serves. 


Meet Leslie Leopold | A Personal Introduction Video 

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Featured Listings


75831 Overseas Highway

Welcome to 'Ocean Oasis,' a private oceanfront estate with a sandy walk-in beach, pool, outdoor bar, and a hammock retreat where you may enjoy rocking your cares away under the coconut palms while ...

1227 Mockingbird Road

Large (.85 acres) partially cleared buildable parcel with 40' canal frontage. Peak ocean view straight down the canal. Beautiful ocean views from the future 3rd floor of the home. Plans for three b...

1303 Almay Street

In the community of Rock Harbor Estates, sits this well-constructed newly refreshed spacious family home. The entry foyer showcases an interior stairway that leads to an open great room and spaciou...

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320 Key Honey Lane

Welcome to the classic old world charm of Villa Montelepre, a ten bedroom, nine and one half bath, gated bayfront compound situated on approximately 2 acres with over 7,900 sf of living space. Turn...

89635 Old Highway

Nestled on over 2.5 acres, this private gated oceanfront estate offers a quiet escape for resort-style luxury living with four-bedroom, three and one-half baths in the main home & one bedroom, ...

82698 Overseas Highway, Islamorada FL

Timeless Classic. This one-of-a-kind private estate is nestled on 3.48 acres in downtown Islamorada with over 300 feet on the Bay. This enchanting property offers four large bedrooms & four bat...

87429 Old Highway, Islamorada FL

A multitude of opportunities arises at this incredible gated oceanfront property. The existing 2 bedroom/2 bath home is a legal duplex and has been adoringly restored with a beautiful pool, spa, an...

87431 Old State Highway, Islamorada FL

Come home to Turtle Key. This offering includes 2.65 beautifully landscaped acres with 4 adorable cottages, boat basin, an oceanfront pool with 2 gated winding sand driveways and more. This propert...

77001 Overseas Highway, Islamorada FL

Tucked away on two exquisite oceanfront acres with sandy beach is this perfect island retreat. Lush tropical gardens with tall coconut palms cocoon the five-bedroom, five and one-half baths, 4, 700...

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