Your Winter Park, FL Insurance Agent

We Insure Winter Park

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1950 Lee Road
Suite 100A
Winter Park, FL 32789

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Office Hours

M - F 9:00 a.m. - 5:00 p.m. 
S - S By Appointment Only 

Every coverage type for every type of customer

Brian Dearing


We Insure Winter Park is an independent insurance agency committed to the principles of service, integrity, and professionalism. We provide our valued clients the highest quality of service with the goal of exceeding their expectations while building a long-term relationship to help protect what they value 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. Please think of us for your insurance needs.

Your local We Insure reviews

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Charles Adolphe
Linda Rivera
Brian is just so awesome . He had always helped me with my insurance needs and always come through .
D Bryant
I highly recommend Brian. He is wonderful to work with. He has always helped with obtaining the best home and auto insurance. Very professional, responsive, proactive, and knowledgeable.
Alex Scures
Brian is extremely helpful!
Mario Ponce
Brian was real informative and professional during our transition moving to florida. Look forward to working w him in other areas after our move.
Justin Preppy
Been using Brian for 3 years now. Always find the best deal for me
Helen Deer
Brian was very prompt in his responses and made useful suggestions along the way while we were reviewing policies.
Nancy MacDonald
Professional, personable, good results!!
Rebecca Huffman
Brian was extremely helpful with getting us new home insurance! He was able to answer all my questions, and explain everything so that I understood the process.
Victoria Rigby
Brian is very knowledgeable and answered all my questions!! I'm very grateful to have had Brian help me and explain everything in detail :) We need more people like him! Thank you Brian!!!!
Thepdara Sepulveres
Brian was great and very knowledgeable. He got us a great price for our home insurance. Definitely would recommend Brian to my friends, family, and clients.
Timothy Russell
Brian was great , got our home policy done with what we needed
Justin Denicola
Been with Brian for 3 years now. Always find me the best deal
Danielle McNichol
By far the best experience I have ever had with insurance. From start to finish, Brian was responsive, knowledgeable and provided practical solutions to a tricky insurance market. I can't say enough good things about We Insure. I would highly recommend working with Brian. I know we sure will now and in the future.
Charlie Adolphe
Brian Dearing is my go-to insurance broker who has helped me find real estate insurance where others failed. He will go the extra mile! Call him.
Fred Liebenhaut
Brian was fantastic. Handled our homeowners and flood insurance with cit courtesy, knowledge, and professionalism.
Eduardo Vasquez
Amazing customer service, 2nd to none
Adam Leon
Excellent service.
My insurance was canceled and my agent could not find a new policy for me so he suggested I complete an online request through a website that would match me with agents that could help me. I had over ten companies contact me but only Brian took the time to walk me through the entire process step by step. He discussed all my options and answered my questions regarding the various coverages. He was very thorough and knowledgeable. But most of all he was very patient with me. We were on the phone for two days in a row for over an hour each time and he never once lost his patience or rushed me off the phone. Most of the agents who contacted me prepared quotes based on what they found online and didn't bother taking the time to talk to me. Brian was the utmost professional and he will now be my insurance agent for years to come. Thank you for actually caring about your customers!
Johan Lechevalier
Brian Dearing from We Insure Winter Park has been my agent since I purchased my home in March 2020. He is very responsive to phone calls and emails, very proactive with searching the best premiums for me. He pretty much takes care of everything and contacts all the different parties to ensure that I'm covered adequately. He also help my mom to get flood insurance coverage at a great price. I would definitely recommend him to anyone looking for exceptional customer service!