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Jaime M Caballero

Jaime M Caballero
Real Estate Agent (Broker)
Key West FL

Broker (FL: 3047867)

23 years experience

REALTOR® 10 Active Listings Serves Monroe County, FL
View on Realtor.com

Contact Information

Brokerage
Key West Vacation Properties & Realty Llc (kw)

Office Website
Office Address
915 Eisenhower Dr Key W
Key West, FL  33040
(Monroe County)
Office Phone
305-296-6667
Office Fax
305-712-6712
Mobile
305-296-6667
Email
jaim*@*****.com
Show Email for $5

Service Areas

Big Coppitt Key: FL Stock Island: FL Key West: FL East Rockland Key: FL

About Jaime Caballero

A native of Key West, this seasoned real estate professional brings over 30 years of experience in property management to the table. With a deep understanding of the local market, they specialize in investment properties and can provide tailored recommendations to suit your needs, whether you're looking for a vacation rental or a second home.

Since becoming a licensed Broker in 2009 and founding KWVPR, they have consistently demonstrated expertise in real estate, having been an agent since 2003 and a property manager since 1989. For property owners seeking management services in Key West, their comprehensive approach ensures your investment is well cared for.

In addition to property management, they offer a range of vacation accommodations, from one-bedroom to four-bedroom options, perfect for family visits or short getaways. For those in search of long-term rentals or looking to buy or sell a property, both this professional and their daughter, Alexandria, who is also a licensed real estate agent, are available to assist.

For personalized guidance and to explore your options, feel free to reach out at any time.

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

$2,566,329
Avg. Listing Price
From Jaime'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, Jaime Caballero has 10 properties for sale in Key West and surrounding areas.

$625,000

Listed 2026-01-24

2601 S Roosevelt Blvd Apt 204A
Key West, FL  33040

Beds: 1.0
Baths: 1.0
Sq Ft: 754
Lot: 320,000 sf
Condos Map
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$515,000

Listed 2025-05-20

1500 Seminary St Unit 5A
Key West, FL  33040

Beds: 1.0
Baths: 1.0
Sq Ft: 525
Condos Map
View Full Details

$1,350,000

Listed 2025-08-19

1718 United St
Key West, FL  33040

Beds: 3.0
Baths: 2.5
Sq Ft: 1,477
Lot: 5,200 sf
Single Family Map
View Full Details

$850,000

Listed 2025-10-29

1720 United St
Key West, FL  33040

Beds:
Baths:
Sq Ft:
Lot: 5,200 sf
Land Map
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$949,000

Listed 2026-02-02

2012 Roosevelt Dr
Key West, FL  33040

Beds: 3.0
Baths: 2.0
Sq Ft: 1,515
Lot: 3,528 sf
Single Family Map
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$315,000

Listed 2026-02-03

201 Coppitt Rd Apt 104C
Big Coppitt, FL  33040

Beds: 1.0
Baths: 1.0
Sq Ft: 536
Condos Map
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$875,000

Listed 2026-02-23

5 El Monte Ln
Big Coppitt, FL  33040

Beds: 3.0
Baths: 3.0
Sq Ft: 1,545
Lot: 2,800 sf
Single Family Map
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$587,000

Listed 2026-03-03

2601 S Roosevelt Blvd Apt 108B
Key West, FL  33040

Beds: 1.0
Baths: 1.0
Sq Ft: 754
Lot: 320,000 sf
Condos Map
View Full Details

$540,000

Listed 2025-06-24

3397 Northside Dr Unit 4
Key West, FL  33040

Beds: 2.0
Baths: 2.0
Sq Ft: 952
Lot: 755 sf
Townhomes Map
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$205,000

Listed 2024-08-25

5555 College Rd Lot KF7
Key West, FL  33040

Beds:
Baths:
Sq Ft:
Land Map
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Current Property Rentals

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