We Insure

PERSONAL INSURANCE

Proven solutions to drive your business forward.

Explore Business

We Insure Winter Park

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

We Insure Winter Park in Winter Park
Address
1950 Lee Road, Suite 100A, Winter Park, FL 32789
Contact
Hours
M - F 9:00 a.m. - 5:00 p.m.  S - S By Appointment Only 

We work with trusted insurance companies.

Progressive
Allstate
Nationwide
Travelers
Liberty Mutual
Geico

Home, Auto, Flood, and More

Common policy types reviewed for clients in Winter Park and nearby communities

Home Insurance icon

Home Insurance

Protects your home, belongings, and liability.

Learn More
Auto Insurance icon

Auto Insurance

Coverage for cars, trucks, and daily drivers.

Learn More
Flood Insurance icon

Flood Insurance

Separate coverage not included in standard home policies.

Learn More
Condo Insurance icon

Condo Insurance

Coverage for your condo, personal property, and liability.

Learn More
RV Insurance icon

RV Insurance

Coverage for motorhomes and travel trailers.

Learn More
Renters Insurance icon

Renters Insurance

Protection for belongings and personal liability.

Learn More
Boat Insurance icon

Boat Insurance

Protection for boats and personal watercraft.

Learn More
Motorcycle Insurance icon

Motorcycle Insurance

Coverage for motorcycles.

Learn More

Ways We Help

1
Annual Policy Reviews
2
Multi-Carrier Quote Comparisons
3
New Homebuyer Consultations
4
Flood Zone Determinations

Ways To Meet

Phone
+1-407-753-1824
Hours
M - F 9:00 a.m. - 5:00 p.m.  S - S By Appointment Only 

Areas Served

Based in Winter Park, serving clients across the greater Winter Park area.

Downtown
North Side
South Side
East Side
West Side
Surrounding Areas

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

Brian Dearing

Licensed Insurance Broker

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

"Brian is great. Solves all my insurance needs from home to car business and boat. Always answers or calls back fast when I need him."

Jose Blanco

"Best insurance agent ever! Brian is so kind and helpful. Thanks for taking care of my home, business and personal insurance needs 😉"

Iveliz

"Brian Dearing assisted me with securing new insurance on my families home. Was very diligent in his services, and broke down every aspect of the insurance plan to make sure I knew exactly what we were getting. Very pleasant agent to work with and will use him for our future insurance needs going forward."

Joshua Neuville

"Great Service and very competitive pricing!"

Franklin ussery

"Brian is very helpful in finding us great coverage and at renewal time he is always great at shopping around."

Cindy Johnston

"I had a great experience working with Brian. He helped me with my home, flood, and auto insurance, and made the entire process incredibly smooth. He was always clear in his communication, took the time to answer all my questions, and made everything easy to understand. On top of that, he’s very approachable, friendly, and genuinely easy to work with. You can tell he really cares about his clients and making sure they feel comfortable and informed every step of the way. Highly recommend — 5 stars all the way."

Gustavo Diaz

"Our existing home insurance policy was up for renewal and our premium was increasing 40%! I called several different providers and was not successfully able to find anyone willing to cover us due to our existing plumbing. I found We Insure through Google [excellent reviews] and decided to reach out. Brian followed up almost immediately to get the ball rolling. His communication throughout the entire process was literally perfect. Any follow up questions we had were answered within minutes. He was able to land us coverage despite the plumbing issues at a significant savings compared to our existing provider. We are currently in the process of moving our RV and car insurance over with Brian as well. He is that good. 💯 recommend. 5 stars. 10 out of 10."

Eddy Witham

"Brian is an absolute professional. He took the time to find the perfect policy for my family and worked beyond your typical 9-5 employee. His above and beyond approach to the field was welcoming. I will 100 percent recommend him to anyone in need of insurance needs."

Jason Berry

"Mr. Dearing had made the search for a policy a wonderful experience. He explained everything that he was doing. He answered all of my questions. After the process, I definitely came out with a better understanding of homeowner's insurance policies. I will continue to work with him and will refer others to him."

Mackenzy Pierre-Francois

"Excellent service from start to finish! Brian Dearing was responsive, knowledgeable, and truly cared about finding the best insurance option for us. He made the process easy and stress-free and found the perfect car insurance to fit our needs. Thank you for the outstanding service!"

Odette Torres

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