Office Hours
After Hours by Appointment
Insurance Products Offered
Auto, Homeowners, Condo, Renters, Personal Articles, Business, Life, Health, Pet
Other Products
Banking, Annuities
Bradley Blessing
Office Hours
After Hours by Appointment
Address
The Villages, FL 32159
Country Crossings Plaza
Would you like to create a personalized quote?
Would you like to create a personalized quote?
Office Info
Insurance Products Offered
Auto, Homeowners, Condo, Renters, Personal Articles, Business, Life, Health, Pet
Other Products
Banking, Annuities
Office Info
Simple Insights®
Understanding the insurance premium audit process
Understanding the insurance premium audit process
As a business owner, you may be contacted to complete an insurance premium audit. Learn what the insurance audit process entails and how to prepare.
Car maintenance tasks you can do yourself
Car maintenance tasks you can do yourself
To combat auto repair costs that keep climbing, some auto maintenance can be done at home. Here are ones that are usually do-it-yourself.
Rental car insurance coverage scenarios: Tips to help you decide what to consider
Rental car insurance coverage scenarios: Tips to help you decide what to consider
Discover how to choose rental car insurance based on your specific situation, such as renting with or without personal insurance, high-deductibles or renting abroad.
Social Media
Viewing team member 1 of 20
Caroline Blessing
Office Manager
License #E043147
Viewing team member 2 of 20
Ronda MacDonald
Agent's Assistant
License #P222993
Viewing team member 3 of 20
Matt Hoosac
Multiple Line Representative
License #W134358
Viewing team member 4 of 20
Braely Matthews
Account Manager
License #W542784
Viewing team member 5 of 20
Samantha Tallarico
Account Manager
License #W750989
Samantha joined the Bradley Blessing team in mid 2021. She currently is licensed in Auto, Fire, Life, Health, and Business insurance, holding her 2-15 and 2-20 licenses. Originally from a small town in Illinois, she moved to Florida in 2006. When not assisting our customers, you can find her spending time with her family, camping, kayaking, or watching sports. She is also an avid gardener and baker.
Viewing team member 6 of 20
Tyler Wilson
Multiple Line Representative
License #W928912
Tyler is a hometown employee having lived in the Belleview area for over 20 years after growing up in Marysville, Ohio. Tyler graduated from CTAE in 2011. He is currently licensed in Auto, Fire, Life, Health & Business Lines holding his 2-15 & 2-20 licenses. When not working, he enjoys spending time with his wife, Amber. Tyler’s favorite pastimes are gaming, reading, and playing the guitar.
Viewing team member 7 of 20
Madison Elliott
Account Manager
License #W842003
Madison joined the Bradley Blessing team in early 2022. She currently holds her 2-20 license in Auto, Fire, and Business Lines. She is a graduate of Pedro Menendez High School in St. Augustine. Madison has been a resident of Marion County for 3 years now. When not assisting our customers, you can find her spending time with her family and three fur babies.
Viewing team member 8 of 20
Halley Black
Account Manager
License #W876541
Halley joined the Bradley Blessing team in mid 2022 bringing 3+ years customer service and management experience. She is currently licensed in Auto & Fire holding her 4-40 license. When not assisting our customers, you can find her spending quality time with her family, and pups! She loves going on walks, spending time at the park, or just relaxing at home.
Viewing team member 9 of 20
Jessica Fladd
Office Representative
License #P040651
Viewing team member 10 of 20
Alisha Wilkins
Multiple Line Representative
License #W695404
Alisha joined the Bradley Blessing team in late 2024. She is currently licensed in Auto, Fire, Life, Health & Business Lines holding her 2-15 & 2-20 licenses. She was born in North Carolina but grew up in Clermont, Florida having graduated from Lake Minneola High School. Alisha loves spending time with her family and two dogs. She looks forward to anything outdoors, going to church each week, and that glorious cup of coffee each morning.
Viewing team member 11 of 20
Caleb Nichols
Multiple Line Representative
License #G027319
Caleb joined the Bradley Blessing team in late 2024 but is no stranger to the world of insurance. He currently holds his 2-14 & 4-40 licenses transacting in Auto, Fire, Life, & Health insurance. Prior to finding his passion to change lives through insurance, he had a successful career in construction. When not in the office you can find him spending time with his wife and kids. He loves being active in his local church, going to theme parks or just having a relaxing night at home.
Viewing team member 12 of 20
Laura Franklin
Office Representative
License #G206351
Laura joined the Bradley Blessing team in December 2024. She currently is licensed in Auto & Fire holding her 4-40 license. After her high school graduation, she went on to study surgical technology. Her three grown children, five grandchildren, & cats would say that family means everything to her. When not greeting all customers with a smile you can find her around classic cars, thinking of her next tattoo, hiking, at the beach, or in a botanical garden.
Viewing team member 13 of 20
Felicia Sweet
Account Manager
License #G226057
Viewing team member 14 of 20
Josh Cesarec
Multiple Line Representative
License #G251672
Josh joined the Bradley Blessing team in June of 2025. He currently holds his 4-40 and 2-15 licenses, focusing in Auto, Fire, Life, and Health. This Florida native earned his Bachelor's Degree from Walden University majoring in Business Administration. When he is not helping our customers, Josh enjoys taking on DIY projects, golfing, fishing, watching football, and spending time with his family.
Viewing team member 15 of 20
Drew Parker
Account Manager
License #G310499
Drew joined the Bradley Blessing Team in 2026! He is currently licensed in Auto and Fire holding his 4-40 license. He started his college career playing basketball at Florida College in Tampa and is now finishing his degree in Business and Finance at UNF. Born and raised in Ocala, Drew spends most of his time outside of work hunting, fishing, and golfing.
Viewing team member 16 of 20
Araceli Ramos Santana
Account Manager
License #G343965
Viewing team member 17 of 20
Nathan Williams
Account Manager
License #G345144
Viewing team member 18 of 20
Tori Firkins
Account Manager
License #W847767
Tori joined the Bradley Blessing team in 2026! She came to us with almost 4 years of previous State Farm experience and has been a great addition to our office. She currently has her 20-44 and 2-14 licenses in Auto, Fire, Health, and Life insurance. She was born and raised in Florida and loves to spend her free time reading, gaming, baking, being on the farm, and interacting with animals.
Viewing team member 19 of 20
Courtney Sowers
Account Manager
License #G320887
Courtney joined the Bradley Blessing Team in February of 2026! She currently holds her 4-40 license helping customers with Auto & Fire insurance. She was born and raised in Ohio but made her way to the sunshine state in 2022. Outside of work, she enjoys spending quality time with her husband, two step kids and their family dog. She also likes taking trips to the beach, trying new foods, and flying to her hometown to visit family.
Viewing team member 20 of 20
Jenn Rolls
Marketing Manager
Belleview - FL Full Time
The Villages - FL Full Time
Belleview - FL Full Time
Summerfield, FL Full Time
Belleview - FL Full Time
The Villages - FL Full Time
The Villages - FL Full Time
Belleview - FL Full Time