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Leslie A Leopold

Leslie A Leopold
Real Estate Agent (Salesperson)
Islamorada FL

Salesperson (FL: 3071091)

23 years experience

REALTOR® 11 Active Listings Serves Monroe County, FL
View on Realtor.com

Contact Information

Brokerage
Ocean Sotheby's International Realty

Office Website
Office Address
81888 Overseas Hwy
Islamorada, FL  33036
(Monroe County)
Office Phone
305-712-8888
Office Fax
305-712-8889
Mobile
305-712-8888
Email
lleo****@********.com
Show Email for $5

Service Areas

Islamorada: FL Islamorada Village of Islands: FL North Key Largo: FL Key Largo: FL Key Colony Beach: FL Grassy Key: FL Duck Key: FL Marathon Shores: FL Marathon: FL Layton: FL Tavernier: FL

About Leslie Leopold

Leslie Leopold possesses a deep-rooted enthusiasm for the Florida Keys, a passion cultivated over three generations of her family’s fishing and diving traditions in the region. This love for the Keys inspired her relocation nearly three decades ago, where she has since dedicated herself to promoting the unique lifestyle that she cherishes.

With a nursing degree and extensive experience in the medical field, Leslie has developed a strong foundation for assisting clients in their quest for the ideal home. Since 2004, she has consistently ranked among the top real estate agents in the Florida Keys, a distinction she values greatly.

Leslie shares her life with her husband, a well-known fishing captain and president of the Islamorada Charter Boat Association, along with their two daughters. Together, they actively participate in a variety of local sports and activities, including tennis, soccer, volleyball, fishing, scuba diving, and horseback riding.

In addition to her professional endeavors, Leslie is committed to community service. She has held positions on the Board of Directors for several organizations, including Habitat for Humanity of the Upper Keys, Montessori Island Charter School, Mariner's Hospital Foundation, and the Islamorada Foundation.

Monroe County, FL Real Estate Market Analysis (Single Family Homes)

$2,566,329
Avg. Listing Price
From Leslie's portfolio
3.4 / 3.0
Avg. Beds/Baths
Typical property size
2,076 sf
Avg. Square Footage
Interior living space
1571
Active Listings
Current inventory

Monroe County, Florida represents one of the most unique real estate markets in the United States, stretching across the iconic Florida Keys archipelago from Key Largo to Key West. This tropical paradise market operates under extraordinary constraints that make it unlike any other coastal region, with limited land availability creating a supply-restricted environment that drives both opportunity and complexity for real estate professionals.

The county's real estate landscape is served by 2,309 actively licensed agents, all of whom maintain email contact information, reflecting the tech-savvy nature required to navigate this specialized market. These professionals must master everything from hurricane-resilient construction standards to complex flood zone regulations while serving clients ranging from local fishing families to international luxury buyers seeking their slice of Caribbean-style living just 90 miles from Cuba.

Major Monroe County, Florida Real Estate Markets

Key West anchors the county's luxury market as the southernmost city in the continental United States, where historic Conch Republic charm meets million-dollar waterfront estates. The island's limited 4.2 square miles support everything from quaint Old Town cottages near Duval Street to expansive harbor-front compounds, while Islamorada has emerged as the sportfishing capital with some of the highest per-square-foot values in Florida due to its exclusive resort atmosphere and world-class marina infrastructure.

The Upper Keys, including Key Largo and Tavernier, offer the most accessible entry points to Keys living while maintaining proximity to mainland Florida amenities. Marathon serves as the geographic and commercial heart of the Middle Keys, featuring the largest year-round population and most diverse housing stock, from affordable mobile home communities to luxury canal-front properties with deep-water access to both the Atlantic Ocean and Florida Bay.

Market Dynamics and Geographic Complexity

Monroe County's real estate market operates under the unique constraint of the Rate of Growth Ordinance (ROGO), which strictly limits new residential construction to preserve the fragile ecosystem and infrastructure capacity. This creates an unusual dynamic where teardown and renovation projects often represent the primary path to modern housing, driving construction costs significantly above mainland Florida averages while maintaining property values through scarcity.

Hurricane risk and flood insurance requirements add layers of complexity that separate experienced Keys agents from mainland practitioners. Properties must navigate FEMA flood zones, wind mitigation standards, and elevation requirements that can dramatically impact both insurability and marketability, creating a specialized knowledge base that makes local expertise invaluable for successful transactions.

Why Businesses Need Monroe County, Florida Agent Contact Data

Insurance companies, mortgage lenders, and construction contractors require direct access to Monroe County's agent network to navigate the specialized requirements of Keys real estate transactions. These professionals serve as essential liaisons for understanding flood zone determinations, wind mitigation credits, and hurricane-resistant construction standards that directly impact underwriting and project feasibility in this high-risk, high-value market.

Technology providers, luxury service companies, and marine industry businesses find Monroe County agents invaluable for identifying affluent property owners who represent prime prospects for high-end products and services. The concentration of vacation homes, investment properties, and luxury waterfront estates creates unique opportunities for businesses targeting sophisticated buyers who often maintain multiple residences and require premium services across various lifestyle categories.

Current Property Listings

As of 3/27/2026, Leslie Leopold has 11 properties for sale in Islamorada and surrounding areas. These are the top 10 listings.

$27,800,000

Listed 2025-08-05

89505 Old Hwy
Tavernier, FL  33070

Beds: 7.0
Baths: 6.5
Sq Ft: 8,988
Lot: 207,346 sf
Single Family Map
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$510,000

Listed 2025-10-20

140 Tavern Dr
Tavernier, FL  33070

Beds: 1.0
Baths: 1.0
Sq Ft: 506
Lot: 4,000 sf
Single Family Map
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$3,350,000

Listed 2025-12-17

236 Tarpon St
Tavernier, FL  33070

Beds: 3.0
Baths: 2.5
Sq Ft: 1,536
Lot: 13,068 sf
Single Family Map
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$8,490,000

Listed 2026-03-26

198 Lowe St
Tavernier, FL  33070

Beds: 5.0
Baths: 4.5
Sq Ft: 4,170
Lot: 62,291 sf
Single Family Map
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$5,950,000

Listed 2025-05-03

75851 Overseas Hwy
Islamorada, FL  33036

Beds: 5.0
Baths: 6.5
Sq Ft: 3,978
Lot: 37,462 sf
Single Family Map
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$7,800,000

Listed 2025-03-23

75931 Overseas Hwy
Islamorada, FL  33036

Beds: 5.0
Baths: 5.5
Sq Ft: 4,770
Lot: 60,113 sf
Single Family Map
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$3,995,000

Listed 2025-09-09

87445 Old Hwy
Islamorada, FL  33036

Beds: 5.0
Baths: 4.0
Sq Ft: 4,014
Lot: 79,279 sf
Single Family Map
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$2,890,000

Listed 2025-12-01

75055 Overseas Hwy
Islamorada, FL  33036

Beds: 3.0
Baths: 2.0
Sq Ft: 1,400
Lot: 7,100 sf
Single Family Map
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$6,490,000

Listed 2026-02-04

137 Sapodilla Dr
Islamorada, FL  33036

Beds: 5.0
Baths: 5.5
Sq Ft: 5,456
Lot: 17,860 sf
Single Family Map
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$6,750,000

Listed 2026-03-21

83407 Old Hwy
Islamorada, FL  33036

Beds: 6.0
Baths: 5.0
Sq Ft: 4,566
Lot: 24,829 sf
Single Family Map
View Full Details

Current Property Rentals

Leslie Leopold currently has no rental properties available in Islamorada and surrounding areas. Check back later.