Winston Financial

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!

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.

🐾 June's Pet of the Month: Meet Bear! 🐾This month's featured pet belongs to Victoria Helvey, and we couldn't be more exc...
06/15/2026

🐾 June's Pet of the Month: Meet Bear! 🐾

This month's featured pet belongs to Victoria Helvey, and we couldn't be more excited to spotlight Bear!

Don't let the innocent face fool you! Bear may look like a stuffed animal, but this 6-pound ball of fluff is part watchdog, part service dog, and full-time drama king. 👑

Whether he's riding in style in his stroller, keeping a watchful eye on his owner, or turning down perfectly good food because he's "not in the mood," Bear always keeps life entertaining. ❤️

🐶 Want your pet featured next?

📸 Send us a favorite photo and a short description of their personality, funny habits, or special story.

📧 [email protected]
📱 608-358-3612

🪪 Social Security decisions can impact your retirement income for years to come.Join us on Tuesday, July 28th for our So...
06/12/2026

🪪 Social Security decisions can impact your retirement income for years to come.

Join us on Tuesday, July 28th for our Social Security Workshop and learn how to make more confident decisions about your future.

📍 Winston Financial
🕛 Lunch & Learn – 12:00 PM
🍷 Wine & Wisdom – 6:00 PM

Reserve your seat here:
https://preview.mailerlite.io/forms/2034558/187106662014781090/share

Questions? Call or text us at 608-358-3612 or email us at [email protected].

We’re grateful for the opportunity to help clients navigate Medicare and retirement planning with confidence. ⭐Tag someo...
06/10/2026

We’re grateful for the opportunity to help clients navigate Medicare and retirement planning with confidence. ⭐
Tag someone who may need guidance navigating their options.

🎶 Join Winston Financial for a relaxing summer evening filled with great music and good company!We're excited to host ou...
06/08/2026

🎶 Join Winston Financial for a relaxing summer evening filled with great music and good company!

We're excited to host our Client Appreciation Event at Madison's beloved Opera in the Park. Bring a blanket or lawn chair and enjoy charcuterie boards, refreshments, and a wonderful night with the Winston Financial family.

📍 Garner Park
🗓️ Saturday, July 18th
🕡 Arrive anytime after 6:30 PM
🎵 Concert begins at 8:00 PM

Reserve your spot:
https://preview.mailerlite.io/forms/2034558/187086227595331284/share

Tag a friend you'd bring along! ❤️

🛡️ Long-Term Care Planning isn't just about protecting your savings — it's about protecting your independence.Join us fo...
06/05/2026

🛡️ Long-Term Care Planning isn't just about protecting your savings — it's about protecting your independence.

Join us for our upcoming Long-Term Care Planning Workshop and learn what Medicare does (and doesn't) cover, the real costs of care, and strategies to help you plan ahead with confidence.

Reserve your seat today — spots are limited!
https://preview.mailerlite.io/forms/2034558/187086227595331284/share

Educational, welcoming, and pressure-free — exactly what Winston Financial workshops are designed to be. ❤️Follow our pa...
06/03/2026

Educational, welcoming, and pressure-free — exactly what Winston Financial workshops are designed to be. ❤️

Follow our page to stay updated on upcoming workshops and events.

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

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