Events

Join us for events that inspire connection and community. From informative talks and wellness programs to social gatherings that bring residents, families, and neighbors together, there’s always something meaningful to enjoy. Explore our upcoming calendar and see what’s happening at The Windsor.

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Upcoming Events

Nov 4, 2026 | 11:00AM-12:30PM

Unlocking VA Benefits: Clear Steps, Confident Choices

Veteran benefits can sometimes be complex, changing based on eligibility, type of service, and more. If you or your loved one is a Veteran, it is worth understanding more about the types of benefits that might be available to you. Join us as we welcome a local expert to walk us through the different types of VA benefits, including eligibility requirements, so that you can make your most confident decisions for the future.

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

Past Events

Oct 7, 2026 | 2:00-3:30PM

Get the Most from Medicare with Confidence

Do the choices that come with Medicare leave you feeling overwhelmed and a little frustrated? You aren’t alone! Most of us are not fully confident when it comes to making the most of our Medicare benefits. Choose to join us and learn more about Medicare so that you can be the one who is certain about your choices this year and every year following.

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

Sep 14 – 18, 2026 | Various Times

Shining Through The Years: National Assisted Living Week

Join us for a fun week of events and activities during National Assisted Living Week. Come to one or all of our special events. We invite you to bring a friend or family member!

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

Aug 20, 2026 | 11:30AM-2:45pm

Now Showing: Lunch & Movie

Enjoy a great movie and even better company right here in our community. Come ready to relax, make a few new friends, and share an afternoon. We’ll have your seat waiting! Feature presentation is I Can Only Imagine.

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

Jul 21, 2026 | 1:00-2:30PM

Live Longer, Live Secure: New Strategies for Lasting Health & Financial Security

Your retirement plan should support both financial security and overall well-being. Join us to learn steps toward a balanced, comprehensive retirement. Already retired? Discover simple ways to review your current plan and make small adjustments with confidence.

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

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