
Get to know Jaime Caballero
Real Estate Broker
If you are in the need of a vacation rental or have decided to move to Key West, let me help you. I am a native "conch"! I was born and raised in Key West. I have 30 years experience in property management industry.
We specialize in putting buyers with the perfect income producing property based on our years of property management experience.
I have been a Broker since 2009 when started my own company, KWVPR. I have been a real estate agent since 1...
Jaime Caballero's listings & sales (123)
For Sale (7)
Address | Bed/Bath | Listing price |
---|---|---|
![]() 413 Emma St #A Key West, FL 33040
| 2 Bed, 3 Bath | $2,700,000 |
![]() 3397 Northside Dr #4 Key West, FL 33040
| 2 Bed, 2 Bath | $560,000 |
![]() 1500 Seminary St APT 5A Key West, FL 33040
| 1 Bed, 1 Bath | $575,000 |
![]() 3312 Northside Dr APT 305 Key West, FL 33040
| 1 Bed, 1 Bath | $355,000 |
![]() 241 W Indies Dr Ramrod Key, FL 33042
| 4 Bed, 3 Bath | $1,475,000 |
Sold (116)
Address | Sold date | Closing price | Represented | Flag Sale |
---|---|---|---|---|
7/29/2025 | $300,000 | Buyer and Seller | ||
6/23/2025 | $577,000 | Buyer and Seller | ||
6/17/2025 | $750,000 | Seller | ||
2/7/2025 | $3,275,000 | Seller | ||
12/24/2024 | $340,000 | Seller |
Jaime Caballero's reviews (11)
Write a review- Highly likely to recommend||5.05.0
5/15/2018 - billmc42
Bought and sold a Single Family home in 2018 in Cudjoe key, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJaime and her team recently helped me locate and purchase my Florida Keys getaway. Her local knowledge and attention to detail are unsurpassed. She took an otherwise tedious process inn the current market and helped me sift down to the right areas an... - Highly likely to recommend||5.05.0
9/13/2016 - user5150358
Bought a Single Family home in 2015 in Trumbo point, Key west, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsI've worked with Jaime for several years now with both real estate purchases and vacation rental management in Key West. She is extremely responsive and her team is great. Would highly recommend her to anyone looking to purchase a property in Key W... - Highly likely to recommend||5.05.0
12/2/2013 - spg michael
Property managed a home.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJaime was a huge help marketing our property and getting rentals on a weekly/monthly basis. She treated our property as her own so we never had to worry if we weren't in town. I love Jaime and I continue to send people to her due to her professiona... - Highly likely to recommend||5.05.0
11/20/2013 - smhennry
Property managed a home in FL 33040.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJaime is a great property manager. I have worked with her for several years now and I have multiple properties she manages. She takes good care of my property as well as maximizes its income potential. She has also helped me with purchasing a prope... - Highly likely to recommend||5.05.0
11/19/2013 - rjtitus01
Bought and sold a Apartment home in 2013 in Upper duvall, Key west, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsI first met Jaime Caballero when she handled a rental house in Key West for me. That was about 10 years ago. In the meantime, she has also assisted me in buying a condominium, and selling the rental house. She continues to manage the condominium f...