Meet Jason
Jason Sklar brings a rare and powerful combination of legal expertise, financial acumen, and real-world real estate experience to every transaction. He earned his degree in Accounting from the University of Maryland in 1988 and went on to receive his Juris Doctor from the University of Baltimore.
For 27 years, Jason practiced real estate law in Maryland, during which time he founded and built one of the nation’s largest title companies. Over the course of his career, he has been directly involved in the closing of more than 150,000 residential real estate transactions, giving him an unmatched understanding of contracts, negotiations, risk mitigation, and deal structure.
Beyond the legal side of real estate, Jason has extensive experience in the mortgage lending space and has personally fixed and flipped over 1,500 properties. This hands-on investment background allows him to see value, identify opportunity, and anticipate issues long before they arise. Known as a highly skilled negotiator, Jason has saved buyers millions of dollars while consistently helping sellers achieve top-of-market results.
In 2020, Jason and his family relocated to Tampa, Florida. He officially obtained his Florida real estate license in 2024, bringing decades of national-level experience to the Tampa Bay market.
Outside of real estate, Jason is a former NFL agent and proudly represented three players on the 2012 Super Bowl Champion Baltimore Ravens. He is passionate about sports, fitness, and—most importantly—spending time with his family, children, and grandchildren.
Jason’s clients benefit from his unique ability to combine legal precision, financial strategy, and market insight—delivering confidence, clarity, and results in every transaction.