Matt Cannon

Matt and 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 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

Matt Cannon shares his perspective on Sarasota’s changing real estate market, including inventory, pricing, buyer opportunities, and why a more balanced market can be a positive development for both buyers and sellers.

Read the full KeyCrew article: Sarasota, Florida's Housing Market Is Normalizing - And Long Time Agents Say That's a Good Sign

Florida’s Condo Insurance Crisis Is Easing — But Not Evenly Across the State
KeyCrew Media | June 2026

Matt discusses Florida’s evolving condominium market, including insurance costs, reserves, building age, and the considerations Sarasota condo buyers should understand when evaluating a property.

Read the full KeyCrew article: Florida's Condo Insurance Crisis Is Easing - But Not Evenly Across the State

For buyers and sellers navigating Sarasota, Lakewood Ranch, downtown Sarasota condos, luxury homes, and waterfront properties, Matt Jenny Cannon combine decades of real estate experience with extensive knowledge of the Sarasota area.

Matt and Jenny Cannon

941-228-2030

Broker Associate

MBA,CRB,CRS,CIPS,GRI,ABR

mattscannon@msn.com

www.finesarasotahomes.net