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Winston Financial 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!

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

🍂 Hello, Fall! 🍎We kicked off the first day of fall with a fun Winston Financial team lunch! Everyone brought different ...
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!

It’s never too late to improve your muscle health! 💪Join Winston Financial and Fitness Specialists on September 29th fo...
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!

Happy Labor Day from Winston Financial! 💙We hope everyone enjoys a well-deserved day off with good food, good company, a...
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! ☀️🐾

🐾 Meet July's Pet of the Month... Etta! 💙This sweet Border Terrier has stolen our hearts with her friendly personality, ...
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

🎶 Opera in the Park is almost here! 🎶We're stocking up on all the goodies for our Client Appreciation Event, and we can'...
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

Let's be honest... insurance and retirement paperwork isn't exactly everyone's idea of a good time. 😅That's why we do ou...
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. ⭐⭐⭐⭐⭐

📅 Hello, July! ☀️A new month means new opportunities to learn, connect, and plan with confidence.Here's what's happening...
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! ❤️🤍💙

🇺🇸 We hope everyone had a wonderful Independence Day weekend! ❤️🤍💙Whether you spent the holiday with family, friends, ne...
07/06/2026

🇺🇸 We hope everyone had a wonderful Independence Day weekend! ❤️🤍💙

Whether you spent the holiday with family, friends, neighbors, or your four-legged companions, we hope it was filled with laughter, great memories, and a little time to relax.

From all of us (and our furry friends 🐾) at Winston Financial, thank you for being part of our community. We wish you a safe, happy, and healthy summer!

❤️ Walter • Mable • Winston • Sammy • Charlie • Beasley

Helping people feel informed, supported, and confident is always our goal. ❤️Know someone preparing for retirement or Me...
06/17/2026

Helping people feel informed, supported, and confident is always our goal. ❤️

Know someone preparing for retirement or Medicare? Share this post with them.

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

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