8 Of The Best Affordable Towns To Retire In Wisconsin

All of Wisconsin experiences all four seasons, although the intensity and timing can differ slightly depending on the region. But that's a tiny fraction of what this friendly Midwestern state offers. Wisconsin typically ranks third for the most ski hills in the whole country, and has well-known surfing destinations like Sheboygan, endearingly called the “Malibu of the Midwest.” It is also relatively affordable. A median listing price of only $346,633 means you can snap up a decent lakefront property and remain with a modest amount to set yourself up for peak comfort. The good news is that some towns are even cheaper. If you find this unbelievable, continue reading to discover the 8 affordable towns to retire in Wisconsin.

Monroe

A median listing price of $257,850 is too good to overlook, especially if you add the fact that Monroe is just 50 minutes away from Madison, the second-largest city in Wisconsin. The "Cheese Capital of America" offers some of Wisconsin’s finest cheese products, a decent number of stunning green spaces (like Lincoln Park), and the Monroe Golf Club, which provides enough challenge to perfect one's golfing skills. Residents often look forward to the Green County Cheese Days Festival, a cherished tradition celebrating Monroe's cheese-making legacy with a variety of cheeses to sample. To allay concerns about healthcare access, SSM Health Monroe Hospital is a highly rated medical facility in the area and has previously been recognized for the Patient Safety Excellence Award. Movie lovers are not left out, either. Goetz Sky-Vu Drive-In has been showing films outdoors since the 1950s.

Sheboygan

Sheboygan’s position right on Lake Michigan and its median listing price of $267,933 make it a fantastic retirement choice. Madison is an easy two hours on the road, and you have plenty of cool things going on. This includes the Midsummer Festival of the Arts, typically held in July, and Brat Days, a beloved local tradition centered around the world-famous Sheboygan bratwurst, featuring food, live music, games, and contests. When it comes to outdoor recreation, especially surfing, it speaks volumes that Sheboygan is often referred to as the “Malibu of the Midwest.”

Up until the early 2010s, Sheboygan hosted the Dairyland Surf Classic, one of the largest freshwater surfing competitions in the world. You can regularly visit North Point Park and enjoy the relaxing sound of the waves lapping at the shore, or Kohler-Andrae State Park, a stunning space with the perfect mix of dunes, beach, and forest. Keep in mind that there are 16 courses within a 15-mile radius of Sheboygan, including PGA-level destinations like Whistling Straits. In terms of healthcare, Aurora Medical Center Sheboygan County received an “A” Hospital Safety Grade from The Leapfrog Group in Fall 2024, a national distinction for excellence in patient safety.

Stevens Point

A vibrant college town with riverside access, Stevens Point has been increasingly attracting retirees due to its livability and affordability. Houses fetch a median listing price of $283,267, which is significantly better than the statewide median of $346,633, according to the latest on Zillow. Residents have immediate access to the 406-acre University of Wisconsin-Stevens Point campus, as well as a satellite campus for Mid-State Technical College. Besides offering courses that some retirees can find relevant, these two places imbue the town with a mist of vibrancy and cultural flair.

The town has two hospitals: Aspirus Stevens Point Hospital, named one of the 2025 Top 100 Rural & Community Hospitals by The Chartis Center for Rural Health, and Aspirus Plover Hospital, previously recognized as one of the nation’s 15 Top Health Systems by IBM Watson HealthTM. The highly rated Dimensions Living Stevens Point, one of several assisted-living facilities in the area, has friendly staff that pays close attention to the individual needs of those in their care. Also, Rogers Cinema 7, known for its comfortable seats and ample legroom, is a great place to occasionally catch a matinee. Pfiffner Pioneer Park offers fabulous views and peaceful walking paths, and there's the Wisconsin River, another awesome recreational site to take note of.

Elkhorn

Elkhorn, the administrative heart of Walworth County, sits just 45 miles southwest of Milwaukee, a location that strikes a rare balance between accessibility and tranquility. This prime positioning offers easy access to big-city amenities while preserving the charm of small-town living. With a median home listing price of about $324,833, slightly below Wisconsin’s statewide median, Elkhorn stands out as a compelling value for retirees. Add its serene landscapes and storybook streetscapes, and it’s easy to see why the town has earned the affectionate nickname “Christmas Card Town,” and why it makes a strong case for being one of Wisconsin’s best small towns to retire in.

The Elkhorn Antique Flea Market, which typically features more than 500 vendors, is held four times a year. Additionally, the Walworth County Fair, one of the country's oldest and most renowned county fairs, attracts approximately 100,000 people annually. The fair features everything from local crafts and youth 4-H projects to a variety of modern agribusiness displays. Aurora Medical Center Summit, about 30 minutes down the road, received an “A” Hospital Safety Grade from The Leapfrog Group in Fall 2024, a national distinction recognizing excellence in patient safety. Geneva Lake, Delavan Lake, and Lake Como offer a variety of epic outdoor recreational opportunities.

Manitowoc

Money often talks when it comes to picking a retirement destination, but it is not as loud in Manitowoc, a beautiful mid-sized city on Lake Michigan at the mouth of the Manitowoc River. Manitowoc checks many boxes in the retirement ecosystem, starting with a median listing price of just $224,950, which is certainly less than the state median. The town also hosts a population of about 35,000, which strikes the sweet spot between high and low, and exceptional scenery with countless pleasure spots. In town, you'll find a public library that usually has events going on for all ages throughout the year, and Strand Adventures, a family-oriented entertainment complex where you can take grandkids to play and burn energy.

Keep in mind that Froedtert Holy Family Memorial Hospital, right at your doorstep, earned the American Heart Association (AHA) Commitment to Quality award in 2025. Felician Village is an assisted-living facility known for its home-like atmosphere, and there is a regional campus of UW-Green Bay, which offers bachelor’s degree opportunities and community programs right in Manitowoc.

Viroqua

Viroqua is also a lovely choice to consider for retirement, especially for pensioners seeking to escape the financial hamster wheel without compromising their quality of life. Houses in Viroqua fetch a median listing price of $271,267, a value-packed package that comes with epic festivals like The Driftless Music Festival in Eckhart Park, typically held the second Saturday in July. Viroqua is also home to the Vernon Memorial Hospital, which has previously earned Healthgrades recognition for Outstanding Patient Experience and Joint Replacement Excellence, and the Viroqua Hills Golf Course, one of the highest-rated golf courses in the area.

The course is renowned for its scenic fairways and a welcoming layout that is ideal for both beginners and seasoned golfers. The Historic Temple Theatre of Viroqua, centrally located on Main Street, is a beautifully restored venue that has been entertaining area residents since 1922. Finally, Viterbo University, a private Catholic institution located in nearby La Crosse (approximately 25 miles north), offers undergraduate and graduate programs.

Superior

Superior is a small town of about 26,000 residents, yet it has plenty to offer beyond routine trips to the local Walmart. You're no more than 15 minutes from some of the best hiking trails in the world, especially with well-known names such as the Superior Hiking Trail (SHT), the trails that meander through Superior Municipal Forest, and Pattison State Park Trails, which offer multiple hiking paths, including routes to Big Manitou Falls, Wisconsin’s tallest waterfall. Meanwhile, the Lake Superior Ice Festival is a vibrant, family-friendly celebration that brings the entire community together to experience the beauty and magic of winter through food, ice racing, and a variety of other fun-filled activities.

There's Essentia Health St. Mary’s Hospital-Superior, a 25-bed critical-care access hospital with an emergency room and several outpatient services. Larger hospitals in the area include St. Luke’s Hospital in Duluth, Minnesota, just across the state border. Don't forget that Superior is incredibly easy to get around and that it has genial and friendly residents. Houses in Superior fetch a median listing price of only $225,050.

Baraboo

Tucked into the rolling hills of south-central Wisconsin, Baraboo is the kind of town anyone would want to settle in, let alone retirees. The Baraboo River winds right through the heart of town, and it is ringed by a well-maintained riverwalk and trail system, offering an easy, scenic place for morning strolls, bike rides, or simply soaking up the nice, peaceful scenery. Minutes away is Devils Lake State Park, widely regarded as Wisconsin’s crown jewel. Towering quartzite cliffs, crystal-clear water, and miles of hiking trails make it a year-round outdoor playground, whether it’s summer swimming and kayaking, memorable fall foliage hikes, or winter snowshoeing. Also, despite its relaxed pace, Baraboo never feels isolated, especially with Madison just less than an hour away.

This means quick access to big-city amenities, including approximately hospitals, universities, and an international airport. Not to be outdone, downtown Baraboo is lively and welcoming, with a historic square doubling as a gathering place, reinforcing the town’s strong sense of community. Tumbled Rock Brewery & Kitchen is a favorite local hangout for craft beer and casual fare. If you need urgent medical attention, SSM Health St. Clare Hospital-Baraboo received a Top 20 Rural and Community Hospital ranking in 2024 by the National Rural Health Association. It was the only hospital in Wisconsin to receive such an award. The median listing price in Baraboo is $306,633.

So, if you can't wait to start your retirement life and are looking for a beautiful and convenient place to move to, start taking Wisconsin seriously. The Badger State is known for easy-going folks who seem always happy to chat and seek your welfare, and an outdoor landscape that most Americans would enjoy feasting their eyes on. Still, one of Wisconsin's selling points is affordability. A median listing price of $346,633 is wickedly tempting, regardless of the criteria.