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Monday 8:30am - 5pm Tuesday 8:30am - 5pm Wednesday 8:30am - 5pm Thursday 8:30am - 5pm Friday 8:30am - 5pm

Brightway Insurance, The Bailey and Associates Agency

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Winter Haven, FL
Brightway Insurance, The Bailey and Associates Agency

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We are a local insurance agency located in Winter Haven, FL. Providing all lines of personal and commercial insurance. Contact us today for a customized quote!

We proudly serve the insurance needs of our local communities as well as the entire state of Florida. As your Winter Haven insurance experts, we can provide you with multiple quotes from a variety of insurance companies to help you find the best coverage at the best price.

11/02/2026

When it comes to protecting what matters most, having the right insurance AND the right people on your side makes all the difference!

At Brightway Insurance – The Bailey & Associates Agency, we're proud to serve Winter Haven and the surrounding communities with personalized service and insurance options that fit your needs and budget.

✅ Homeowners Insurance
✅ Auto Insurance
✅ Flood Insurance
✅ Business Insurance
✅ Life Insurance
✅ And More!

Here's the BRIGHT side! ☀️ We work with multiple insurance companies to compare coverage options and help you find the right protection at a competitive price.

We're local, we're here to help, and we believe insurance should come with answers, not confusion!

10/31/2026

Happy Halloween! Wishing you a fun, safe, and spooky holiday from Brightway Insurance. 🎃

Whether you are carving pumpkins, dressing up in your favorite costume, or heading out to trick-or-treat, we hope your evening is filled with more treats than tricks! 🍬

10/30/2026

Be safe out there!
Happy Halloween! 🎃

10/29/2026

Chocolate and candy ingestion is one of the most common pet insurance claims during Halloween week.

Accidents happen. That's what we’re here for. 🐶

Keep your pet protected with coverage that's there for the unexpected: http://www.BrightwayBaileyAndAssociates.com

10/27/2026

Navigating your insurance policies shouldn't feel like getting lost in a maze. Let us guide the way! 🗺️

A brighter future starts today — contact us: http://www.BrightwayBaileyAndAssociates.com

10/26/2026

With little ghosts and goblins roaming the neighborhoods this Halloween, it's a good reminder to slow down, stay alert, and make sure your auto insurance is up to date.

At Brightway Insurance, Bailey & Associates, we believe insurance shouldn't be scary or confusing! We're your local Winter Haven team, here to help you understand your options and find coverage that fits your needs and budget.

🍬 Don't let an insurance surprise be your Halloween trick!

📞 Give us a call for an auto insurance review. We'd love to help!

10/22/2026

👻 Spooky Fact 👻

Halloween is one of the busiest nights for your homeowners liability coverage! With strangers walking through yards and up driveways, protecting yourself if a visitor gets hurt on your property is more important than ever.

Make sure you're covered before the trick-or-treaters arrive! http://www.BrightwayBaileyAndAssociates.com

10/21/2026

Join Brightway leaders for a series of webinars focused on now being "The Time to Win."

Despite falling insurance prices, which are great for our clients, it creates a softer market for agency owners. Learn how Brightway’s model and owners create opportunity and grow share even in a soft insurance market.

Live Webinar: Part One: Time to Win: Taking Share in a Soft Market.
Wednesday, Nov 4th 7pm E.T.

Register here: https://bit.ly/4yFSPAp

10/20/2026

Pick your favorite emojis — and discover your policy that needs reviewed! 👇

⚓🌊☀️: Boat Insurance
🌼🧺🖼️: Home Insurance
📍🛣️🍟: Car Insurance

Contact us TODAY to make sure you’re doing insurance the brighter way: http://www.BrightwayBaileyAndAssociates.com

10/19/2026

❤️ We never know what tomorrow will bring. But we can take steps today to help protect the people we love most.

Life insurance isn’t really about us. It’s about the people who count on us. It’s about helping your family pay the bills, cover final expenses, and maintain some financial stability if the unexpected happens.

You insure your home. You insure your car. But have you taken the time to think about protecting your family’s financial future?

Don’t wait for a life-changing moment to start the conversation. Let’s talk about your options and find coverage that fits your needs and budget.

📞 Reach out to Brightway, Bailey & Associates in Winter Haven to explore your life insurance options. Because the best time to plan for the unexpected is before it happens.

10/15/2026

Congrats to Brightway Insurance, The Wilson Agency with offices in Safety Harbor and the Nature Coast for acquiring Boca Bay Insurance Agency!

The Brightway M&A Team was happy to help find and facilitate the deal as well as fast-track due diligence for a smooth close. Boca Bay clients will be in wonderful hands with this Elite Brightway Agency! A win for everyone involved.

Learn more about Brightway’s unique agency transition models here, brightway.com/franchise/mergers-and-acquisitions

10/07/2026

It's official — meet our new local agencies! ✨

Learn more about becoming an agency owner: https://www.brightway.com/franchise?utm_source=linkedin&utm_medium=organic_social&utm_campaign=franchise_marketing

10/07/2026

Meet Chase! 👋 A recent college graduate ➡️ Solutions Specialist making his mark on our company!

Chase had a RECORD-BREAKING 33 sales in his first full month, and we couldn't be more proud! ✨

10/05/2026

⭐ Big news! ⭐ We're welcoming these Sales Producers to our local agencies!

Swipe to meet them! 👉

10/02/2026

Most independent agency owners don’t think about succession planning because nothing is forcing the issue.

However, succession risk still shapes an owner’s willingness to reinvest in the business and can ultimately suppress growth. 🫣

Read more here: www.brightway.com/news/what-happens-when-theres-no-clear-successor

10/02/2026

✨ Congratulating our October Fast Track agencies! ✨

Fast Track is our exclusive springboard for agencies in their earliest months, focused on helping owners grow revenue, build a strong renewal foundation, and move confidently toward Elite performance.

We can’t wait to see what else this group accomplishes as they continue to grow! ⭐ See less

10/01/2026

09/30/2026

"Seeing my agents happy, seeing them succeed, it's incredible to see." 🥹

A career as a producer at a Elite Agency is waiting for you: https://bit.ly/4cNmHTm

09/28/2026

Your business. Your time. Your growth. 🙌 That’s the brighter way to do insurance.

Become a agency owner today: https://bit.ly/4hcsRxE

Address

150 3rd Street SW, Suite 203
Winter Haven, FL
33880

Opening Hours

Monday	8:30am - 5pm
Tuesday	8:30am - 5pm
Wednesday	8:30am - 5pm
Thursday	8:30am - 5pm
Friday	8:30am - 5pm

Telephone

+18636141300

Website

https://www.brightway.com/agencies/FL/Winter-Haven/0529

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