Matt & Jenny Cannon are Sarasota real estate professionals with more than 31 years of experience helping buyers and sellers throughout Sarasota, Lakewood Ranch, Bradenton, and Florida's Gulf Coast barrier islands that include Anna Maria, Casey Key, Bird Key, Lido Key, Longboat Key and Siesta Key, and Venice. Sarasota residents for more than 22 years, they specialize in luxury homes, downtown Sarasota condos, waterfront properties and new construction. With a client first approach, Matt & Jenny combine extensive local market knowledge, responsive service and decades of experience to guide their clients through every step of buying or selling a home. Their impressive career has totaled more than 2,600 transactions with a sales volume over $1.5 Billion in Sales.
A native of Indiana, Matt moved to Florida in 2004. Matt started his real estate career in Indiana in 1995 with Cannon Real Estate and was one of the top agents and broker managers during his tenure with the Marion Area Board of Realtors. Matt's successful career transitioned him to Florida with a local real estate firm to represent a new condominium development on Lido Key, with prices that ranged from $1 million to over $5.2 million. He transitioned as a sales associate and later Director of Sales and Marketing for custom builder Lee Wetherington Homes, overseeing more than 15 different new home communities with prices that ranged from $350,000 to over $10 million. Matt joined a well respected real estate firm in 2009 and was consistently a top selling agent. Matt received his MBA from Indiana Wesleyan University and a BS in Management/Finance from Purdue University.
Jenny has worked with several National & Regional Home Builders throughout her career like Pulte Homes, DR Horton Custom Homes, Fortis Homes, and Shea Homes. A native of Texas, she relocated to Florida in 2006, where she specialized in new home sales with Neal Communities. In 2010 Jenny joined Matt to work as a team and they are a consistent top selling real estate team. Beyond a commitment to exceptional service, she engages the latest, most effective tools of technology while staying in tune with the trends that shape our local market.
Selling or buying a home is one of the most significant financial transactions you will ever make. We know you will have many important concerns and decisions to make along the way; and we are committed to making sure that your experience is positive. We would love to have the opportunity to sit down with you and discuss our business model and how it can benefit you.
Featured In Market Insights
With more than 31 years of real estate experience and over two decades in the Sarasota market, Matt Cannon has been featured by KeyCrew Media as a Sarasota real estate expert, providing insight on local housing trends, condominium ownership, insurance, pricing strategies, and changing buyer behavior.
Sarasota, Florida’s Housing Market Is Normalizing — And Long-Time Agents Say That’s a Good Sign
KeyCrew Media | June 2026
https://keycrew.co/journal/sarasota-floridas-housing-market-is-normalizing-and-long-time-agents-say-thats-a-good-sign/
Florida’s Condo Insurance Crisis Is Easing — But Not Evenly Across the State
KeyCrew Media | June 2026
https://keycrew.co/journal/floridas-condo-insurance-crisis-is-easing-but-not-evenly-across-the-state/
Matt & Jenny Cannon
Broker Associate
MBA,CRB,CRS,CIPS,GRI,ABR
941-228-2030
mattscannon@msn.com
www.finesarasotahomes.net
Home Types:
House, Condo, Lot/Land, Mobile Homes, Townhouse
Years of Experience:
31
Education:
MBA - Master of Business Administration
