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Matthew J Sheehan

Matthew J Sheehan
Real Estate Agent (Broker Sales)
Key West FL

Broker Sales (FL: 3400684)

8 years experience

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

Contact Information

Brokerage
Ocean Sotheby's International Realty
Office Address
3433 Riviera Dr
Key West, FL  33040
(Monroe County)
Office Phone
305-294-1117
Office Fax
Mobile
305-849-9233
Email
matt*********@*****.com
Show Email for $5
Website

Service Areas

Big Coppitt Key: FL Stock Island: FL Key West: FL East Rockland Key: FL Little Torch Key: FL Middle Torch Key: FL Cudjoe Key: FL Summerland Key: FL Sugarloaf: FL Lower Sugarloaf Key: FL Ramrod Key: FL Upper Sugarloaf Key: FL Big Torch Key: FL Sugarloaf Key: FL Big Pine Key: FL

About Matthew Sheehan

Matt Sheehan has been a resident of Key West for 15 years. Transitioning from a successful career in the restaurant industry, he has embraced a full-time role as a realtor. This change allows him to dedicate more time to his family while enjoying the laid-back lifestyle that the Florida Keys offer. Matt values the tranquility of sandy shores and the satisfaction that comes from a day spent on the water.

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

$2,566,329
Avg. Listing Price
From Matthew'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, Matthew Sheehan has 11 properties for sale in Key West and surrounding areas. These are the top 10 listings.

$1,324,000

Listed 2026-01-01

1712 Laird St
Key West, FL  33040

Beds: 3.0
Baths: 2.0
Sq Ft: 1,378
Lot: 5,285 sf
Single Family Map
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$1,499,000

Listed 2025-03-03

132 N Indies Dr
Duck Key, FL  33050

Beds: 4.0
Baths: 4.0
Sq Ft: 3,298
Lot: 7,500 sf
Single Family Map
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$1,449,000

Listed 2026-01-16

1614 Dennis St
Key West, FL  33040

Beds: 7.0
Baths: 4.0
Sq Ft: 2,699
Lot: 5,056 sf
Multi Family Map
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$2,250,000

Listed 2026-01-21

1209 Packer St
Key West, FL  33040

Beds: 4.0
Baths: 4.0
Sq Ft: 2,150
Lot: 4,986 sf
Multi Family Map
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$1,050,000

Listed 2025-01-21

1106 17th St
Key West, FL  33040

Beds: 3.0
Baths: 2.5
Sq Ft: 1,943
Lot: 8,550 sf
Single Family Map
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$1,949,000

Listed 2025-09-26

2827 Harris Ave
Key West, FL  33040

Beds: 5.0
Baths: 5.0
Sq Ft: 3,086
Lot: 5,041 sf
Single Family Map
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$310,000

Listed 2025-10-02

201 Coppitt Rd Apt 202C
Big Coppitt, FL  33040

Beds: 1.0
Baths: 1.0
Sq Ft: 536
Condos Map
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$985,000

Listed 2026-02-25

21855 Spain Blvd
Cudjoe Key, FL  33042

Beds: 3.0
Baths: 2.0
Sq Ft: 1,467
Lot: 44,075 sf
Single Family Map
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$1,049,000

Listed 2025-08-02

206 Truman Ave
Key West, FL  33040

Beds: 4.0
Baths: 1.0
Sq Ft: 1,343
Lot: 4,729 sf
Single Family Map
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$999,000

Listed 2025-06-19

60 Golf Club Dr
Key West, FL  33040

Beds: 3.0
Baths: 2.5
Sq Ft: 1,203
Lot: 3,998 sf
Townhomes Map
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Current Property Rentals

Matthew Sheehan currently has no rental properties available in Key West and surrounding areas. Check back later.