We Insure Winter Park
Consultative coverage reviews and straight answers for Winter Park households - without the usual price-only quoting.

We work with trusted insurance companies.
Home, Auto, Flood, and More
Common policy types reviewed for clients in Winter Park and nearby communities
Ways We Help
Ways To Meet
Find Us
Areas Served
Based in Winter Park, serving clients across the greater Winter Park area.
About the Owner
We Insure Winter Park is an independent insurance agency committedto the principles of service, integrity, and professionalism. We provide ourvalued clients the highest quality of service with the goal of exceeding theirexpectations while building a long-term relationship to help protect what theyvalue most. We have an award-winning service team, cutting edge technology, and access to dozens of top-rated carriers that will help meet our client's needs. Pleasethink of us for your insurance needs.
How this office works
Owner started this office to give Winter Park clients a more consultative insurance experience instead of a quick price-only conversation. The office focuses on: Taking time to ask better questions, understanding what matters to each household, and recommending coverage that actually fits the risk.
What stands out
Consultative coverage reviews instead of price-only quoting
Transparent when another solution is the better fit
Meet the Winter Park Team

Brian Dearing
Licensed Insurance Broker

Bailey Spangler
Producer
What homeowners in Winter Park often miss
A common mistake is assuming flood risk only exists in high-risk zones. In the Winter Park area, the better conversation is understanding the actual risk, the flood zone, and what the policy would do before a storm ever shows up.
What to review
Check flood, wind, and deductible details before storm season instead of waiting until a claim.
Review deductibles, water damage limits, and optional coverages before renewal so nothing important gets missed.
Rated ★★★★★ By Neighbors
Local roots in Winter Park
This office has deep Winter Park roots, with team members who have lived and worked in the community for years. We understand the local market and the unique insurance needs of Winter Park residents.
Community involvement includes:
Chamber and local business networking
Community charitable organizations
Local school and youth programs