Senior Living in Wisconsin, Reimagined

For many of us, there’s a time when we find ourselves with too much. Too much house. Too much home maintenance. And too many expensive repairs. For others, it’s simply time for a fresh start. Either way, retiring in Wisconsin as an Upside member could be exactly the change of pace you’re craving as an active adult with plenty of gas in the tank. So what makes Upside different from a typical 55+ community? Let’s explore.

Find Yourself. Retire in Wisconsin with Upside.

With us, retiring in Wisconsin is worlds apart from what most people think of when they picture a typical senior living community – and that’s by design. If you’ve been wondering about 55+ communities near Madison or Milwaukee, WI, you’ll love learning more about what differentiates Upside from typical senior living. Learn more about the benefits of Upside membership today.

It’s About Retiring, Not Expiring

Picture yourself in a cool apartment living in a neighborhood you love enjoying the best attractions, resources, and benefits Wisconsin has to offer. This is what retiring in Wisconsin is like when you’re an Upside member. Only Upside members get to choose from our exclusive selection of apartment homes in Madison and Milwaukee, which makes it fun and easy to find the perfect new digs. Plus, every member is paired with a personal Upside Manager, who is always on hand to connect you with activities, people, and resources.

Milwaukee truly is one of the great cities on the Great Lakes. It’s known as “Brew City,” but there’s way more to this town than bubbles and barley. For one, did you know Milwaukee was recently recognized by none other than National Geographic as one of THE best destinations in the world. That’s right, the world.That’s because Milwaukee is a city of treasures waiting to be discovered – from its museums and sports teams to its robust parks system beckoning outdoor enthusiasts of all kinds.

From bicycling along the lakefront to shopping and dining on State Street, it’s easy to fall “madly” in love with Madison, WI. This capital city offers culture galore, adventurous cuisine, and stunning architecture, including a convention center inspired by Frank Lloyd Wright. Meanwhile, you’ve got the amazing Overture Center for the Arts where you can catch performances by the always-astounding resident company, not to mention visiting Broadway performers.

Can’t get enough of Madison or Milwaukee? Retiring in Wisconsin as an Upside member is like having a VIP pass to the Midwestern cities you love. No matter where you decide to call home, retiring in Wisconsin with us is the fresh start you deserve.

All of the Care, None of the Stigma

With Upside+ Powered by TheKey, seniors live in their own apartment in a luxury building, not a sterile facility. But they still have access to support and living assistance from certified on-site care professionals. It’s the perfect solution for seniors who want care and community without the stigma or cost of senior living facilities—and with much more flexibility.

Upside Corporate Headquarters

6365 NW 6TH Way, Suite 200

Fort Lauderdale, FL 33309