Best Places to Live in Wisconsin for Retirees: Our Picks
Jun 27, 2025
Choosing where to spend your retirement years plays a meaningful role in shaping your lifestyle. Whether it’s about connecting more deeply with nature, enjoying a lower cost of living, or finding a true sense of community, Wisconsin offers some of the best places to retire.
With its charming towns, accessible amenities, and proximity to scenic lakes and trails, the southeastern region of the state provides a uniquely rewarding retirement experience. If you’re looking for a retirement community where you can enjoy outdoor activities and live each day with purpose, this guide will help you explore your options.
Wauwatosa
Known locally as “Tosa,” Wauwatosa blends small-town charm with big-city access. It offers a walkable village center, highly rated healthcare options, and a vibrant dining table of local restaurants and cafes. Retirees appreciate the balance Wauwatosa strikes between city energy and peaceful residential areas.
While property taxes can be slightly above the national average, the value lies in the community infrastructure and abundant outdoor activities, including trails along the Menomonee River and easy access to parks and gardens. Wauwatosa appeals to retirees who seek culture and convenience—all within a welcoming environment.
Brookfield
Brookfield offers a peaceful yet connected lifestyle that makes it an appealing choice for seniors. With gently winding streets, access to excellent shopping and medical services, and a deep sense of local pride, Brookfield is ideal for those who want a quieter atmosphere without sacrificing amenities.
The town also supports an active retirement lifestyle with its many parks and hiking trails. Retirees often move here for the mix of privacy and connection, with a cost of living that remains reasonable, especially for those with moderate retirement income. Social Security benefits are not taxed in Wisconsin, and some are eligible for additional deductions, which helps ease financial planning.
Waukesha
Waukesha brings together natural beauty and a rich cultural heritage. Known for its historic downtown, riverwalk, and growing arts scene, it’s become a popular destination for retirees who want both vitality and tranquility.
The cost of living in Waukesha is slightly above the national average, but residents enjoy easy access to locally owned shops and community amenities. Waukesha also supports outdoor enthusiasts with ample green space, nearby forests, and paths for biking and walking. For retirees with a passion for creativity and community, Waukesha offers an inspired place to call home.
Milwaukee
As Wisconsin’s largest city, Milwaukee is full of life and opportunity for retirees. With renowned medical centers, the shores of Lake Michigan, and an engaging cultural scene, Milwaukee makes a compelling case as one of the best places to retire.
Yes, it’s a city, but with its beautiful lakes, miles of trails, and strong neighborhood identity, Milwaukee also offers a surprising sense of intimacy. For retirees interested in lifelong learning, the presence of a major university adds even more richness to daily life.
Pewaukee – The Heart of Lake Country
Among all the exceptional communities in southeastern Wisconsin, Pewaukee stands out as a true lakeside haven. Surrounded by sparkling lakes, open trails, and vibrant local shops, Pewaukee gives residents the peaceful lifestyle they’ve long expected—without feeling isolated. It offers the perfect balance between small-town charm and everyday convenience, making it an ideal home for those seeking meaningful connection in retirement.
At the center of this beautiful community is The Westerly Pewaukee, Lake Country’s newest senior living community. Offering various senior living options, The Westerly is rooted in a deep understanding of what matters most—connection, dignity, and choice.
Each private residence at The Westerly Pewaukee is designed for comfort and independence, featuring bright, contemporary layouts and thoughtful touches. Residents enjoy access to a wide range of amenities including a fitness center, indoor pool, golf simulator, rooftop patio, and on-site dining in the Swan Tea Room or Comet Club Social Bar. For those who love outdoor activities, The Westerly is ideally located near walking paths and natural beauty, allowing residents to stay active while remaining part of a close-knit community.
The Westerly Pewaukee is designed to feel like home—a place where comfort and a sense of belonging are part of everyday life. Here, you're supported in ways that celebrate who you are and how you choose to live.
Discover The Westerly Pewaukee
If you’re considering where to retire and want to find a community that offers support and a meaningful lifestyle, look no further than Pewaukee and The Westerly Pewaukee. Among the best places to live in Wisconsin for retirees, this lakeside town offers everything you need to thrive in your retirement years.
Contact us today to learn more about our community or schedule a personal tour. We would love to help you explore the next step in your journey.