Agent

Leslie Leopold | Ocean Sotheby's International Realty

Agency Ocean Sotheby's International Realty

Description

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, raising awareness of 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.

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Agency
Ocean Sotheby's International Realty

81888 Overseas Hwy, Islamorada, FL 33036 - 33036 Islamorada

List

9 listings

82

Detached House in Plantation Key, Monroe County
€ 23,754,700

881 m² 10 7

Escape to Palm Paradise, a one-of-a-kind oceanfront estate in Islamorada, Florida Keys, where luxury and privacy intertwine on 7.64 secluded acres. This magnificent property...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
68

Detached House in Islamorada, Monroe County
€ 5,767,800

424 m² 5 6

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
94

Detached House in Islamorada, Monroe County
€ 5,545,600

506 m² 6 5

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
72

Detached House in Plantation Key, Monroe County
€ 6,660,700

290 m² 5 5

San Roc is a stunning, gated oceanfront estate set on 2.34 lush tropical acres with 130 feet of direct ocean frontage. This exceptional new-construction residence, completed in...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
73

Detached House in Islamorada, Monroe County
€ 6,665,000

443 m² 6 5

Set on 1.38 acres of pristine oceanfront in the Florida Keys, this private estate offers the perfect blend of luxury, serenity, and tropical beauty. With an enormous 150-foot...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
50

Detached House in Key Largo, Monroe County
€ 7,254,600

387 m² 5 5

Welcome to Key Harbor--an exceptional oceanfront estate set on 1.5 acres of pristine, private grounds with sweeping, unobstructed open-water views. This beautifully restored...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
68

Detached House in Key Largo, Monroe County
€ 2,862,500

142 m² 3 3

Charming oceanfront cottage located in the historic district of Tavernier. This three-bedroom, two-and-a-half-bath residence features vaulted ceilings, French doors, and a...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
54

Detached House in Islamorada, Monroe County
€ 2,469,500

130 m² 2 3

Beach life simplicity perfectly describes this pristine three bedroom, two bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection
28

Detached House in Key Largo, Monroe County
€ 425,500

47 m² 1 1

Step back in time and experience the charm of Old Florida in this 1934 historic cottage, one of the oldest homes in the Old Tavernier subdivision. Lovingly maintained and...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Collection