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

Oct 21, 2026 | 10:00-11:00AM OR 2:00-3:00PM

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 Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

Nov 4, 2026 | 10:00-11:00AM

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 Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

Past Events

Sep 15, 2026 | 2:00-4:00PM

Music Bingo

Join us for an afternoon of fun, music and friendly competition! Instead of numbers your BINGO will feature popular songs and favorite hits from across the decades. Let’s connect, laugh, and bring back some great memories!

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

Aug 18, 2026 | 3:00-4:00PM

Dementia Caregiver Support Group

Caring for a loved one with dementia can be overwhelming at times, and it’s okay to need support. You are not alone. Our no-cost, registered dementia caregiver support group offers a welcoming space to connect with others who are walking a similar path. Through shared stories, understanding, and learning together, you’ll find comfort, perspective, and renewed strength—so you can continue caregiving with compassion for your loved one and yourself.

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

Aug 12, 2026 | 10:00AM OR 2:00PM

The Joy Factor: Supporting Mental Wellness

Finding moments of joy, even in the midst of life stress, can pack a serious punch for your mental and physical health. Just a few new habits, including reframing your perspective, can be the key to feeling more empowered in the good – and hard – times. Join us to learn more about how to add bright spots of joy, and all the benefits that go along with this approach, from our local expert. Here’s to making the most of what life offers, together.

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

Jul 8, 15 & 22, 2026 | 10:00AM

Now Showing: Join Us for a Summer Movie Series

Enjoy all three My Big Fat Greek Wedding movies (in order) and even better company right here in our community. Come ready to relax, make a few new friends, and enjoy the shows. We’ll have your seat waiting!

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

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