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Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm

Winston Financial

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Madison, WI
Winston Financial

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Welcome to Winston Financial. Madison's home for retirement planning, Medicare expertise, and financial advice. What sets us apart from other insurance brokers?

Welcome to Winston Insurance Group,
Madison's most trusted insurance brokers. We are a husband wife duo with a strong team working towards the same goal. Winning for our clients! We aim to provide insurance to our clients based on their needs and what makes the most sense for them. Winston Insurance Group is looking forward to helping you gain peace of mind. Insurance products we offer:
Medicare
Health / Dental / Vision / Hearing
Mortgage Protection
Life Insurance
Retirement
Annuities

and more!

10/29/2026

Your retirement should reflect the life you want to live. 🐾 Winston Financial knows it starts with a plan—and a team that takes the time to understand you.

Let’s talk about your next chapter. Call or text 608-358-3612.

10/26/2026

Beasley’s taking a closer look—and your investment risk deserves one, too. 👓🐾

Does your portfolio fit your goals, timeline, and comfort with market changes? Let’s review how much risk you’re taking and whether it still makes sense for you.

Call or text 608-358-3612.

09/23/2026

AEP is coming! 🍂 Medicare plans can change from year to year, so now is the time to start thinking ahead.

At Winston Financial, we’re here to help make the Medicare review process easier and ensure you understand your options for 2027.

📅 Annual Enrollment Period: October 15 – December 7

Questions about your coverage? Give our office a call or text at 608-358-3612.

09/22/2026

🍂 Hello, Fall! 🍎

We kicked off the first day of fall with a fun Winston Financial team lunch! Everyone brought different ingredients, we put it all together, and enjoyed some good food and even better company. 🧡🍁

P.S. Jason was here too 😂 He was with a client when the pictures were being taken!

09/09/2026

It’s never too late to improve your muscle health! 💪

Join Winston Financial and Fitness Specialists on September 29th for a special fitness class designed for adults 60+.

⚠️ Only 8 spots per class — RSVP to save yours!

09/07/2026

Happy Labor Day from Winston Financial! 💙

We hope everyone enjoys a well-deserved day off with good food, good company, and a little time to relax! ☀️🐾

07/16/2026

🐾 Meet July's Pet of the Month... Etta! 💙

This sweet Border Terrier has stolen our hearts with her friendly personality, love for people, and adorable stubborn streak. Congratulations to Senn on having Etta selected as our July Pet of the Month! Be sure to read her story below.

Think your furry friend should be featured next? We'd love to meet them! 🐶🐱

📧 [email protected]
📱 608-358-3612

07/15/2026

🎶 Opera in the Park is almost here! 🎶

We're stocking up on all the goodies for our Client Appreciation Event, and we can't wait to spend the evening with everyone!

🧀 Charcuterie boards
🥤 Drinks & snacks
🎲 Games

Just bring a lawn chair, and we'll take care of the rest!

There's still time to RSVP! Call or text 608-358-3612 or email [email protected] to join us.

P.S. Bringing your own drinks? Please remember no glass containers—plastic only!

For event details and park rules, visit: https://www.operainthepark.org

07/10/2026

Let's be honest... insurance and retirement paperwork isn't exactly everyone's idea of a good time. 😅

That's why we do our best to make the process simple, answer every question, and help take the stress off your shoulders.

Thank you, Tim, for trusting Winston Financial and for sharing your experience! Reviews like yours remind us why we love what we do. ⭐⭐⭐⭐⭐

07/08/2026

📅 Hello, July! ☀️

A new month means new opportunities to learn, connect, and plan with confidence.

Here's what's happening at Winston Financial this month:

🎆 July 4 – Happy Independence Day!
🎶 July 18 – Client Appreciation Event at Opera in the Park
🛡️ July 21 – Long-Term Care Planning Workshops
💰 July 28 – Social Security Workshops
🍽️ July 28–30 – Medicare 101 Dinner Workshops

Whether you're planning for retirement, navigating Medicare, or simply looking to learn more, we're here to help every step of the way.

📞 Questions or ready to reserve your spot?
Call or text us at 608-358-3612.

We hope you have a wonderful, safe, and fun-filled July! ❤️🤍💙

Address

34 Schroeder Court Suite 260
Madison, WI
53711

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Website

http://winstoninsurancegroup.com/

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