The Town Files

The 19 Best Affordable Small Towns to Retire in Wisconsin With Mild Winters

Ranked on The Town Files lifestyle rankings among 269 towns of 2,500–10,000 people in Wisconsin, scoring every town on all of these at once. #1 is Bayside, WI.

Map of the 19 towns12345678910111213141516171819
Numbers match the ranking.
The 19 Best Affordable Small Towns to Retire in Wisconsin With Mild Winters1. Baysidescore 922. Kewauneescore 873. Ottawascore 844. Oostburgscore 845. Winneconnescore 826. Juneauscore 797. Mineral Pointscore 798. Lodiscore 779. Wilsonscore 7710. Peshtigoscore 7711. Fox Pointscore 7612. Plymouthscore 7613. Oregonscore 7614. Seymourscore 7615. East Troyscore 7516. Empirescore 7417. Columbusscore 7218. Waterlooscore 7219. Algomascore 71
  1. 19Algoma, Wisconsin

    Retirement: 85th percentile · January average low (°F): 74th percentile · Home value ÷ income: 55th percentile

    6,866 people · Winnebago County · median home $334,400 · income $107,290 · Jan low 10°F · 39 in snow

  2. 18Waterloo, Wisconsin

    Retirement: 54th percentile · January average low (°F): 78th percentile · Home value ÷ income: 83rd percentile

    3,492 people · Jefferson County · median home $230,600 · income $87,776 · Jan low 11°F · 42 in snow

  3. 17Columbus, Wisconsin

    Retirement: 84th percentile · January average low (°F): 78th percentile · Home value ÷ income: 55th percentile

    5,540 people · Columbia County · median home $230,600 · income $75,427 · Jan low 11°F · 42 in snow

  4. 16Empire, Wisconsin

    Retirement: 98th percentile · January average low (°F): 63rd percentile · Home value ÷ income: 62nd percentile

    2,774 people · Fond du Lac County · median home $378,600 · income $125,185 · Jan low 9°F · 38 in snow

  5. 15East Troy, Wisconsin

    Retirement: 74th percentile · January average low (°F): 88th percentile · Home value ÷ income: 62nd percentile

    3,992 people · Walworth County · median home $369,300 · income $123,804 · Jan low 12°F · 39 in snow

  6. 14Seymour, Wisconsin

    Retirement: 61st percentile · January average low (°F): 74th percentile · Home value ÷ income: 92nd percentile

    3,546 people · Outagamie County · median home $184,600 · income $80,602 · Jan low 10°F · 57 in snow

  7. 13Oregon, Wisconsin

    Retirement: 82nd percentile · January average low (°F): 83rd percentile · Home value ÷ income: 62nd percentile

    3,125 people · Dane County · median home $455,600 · income $150,536 · Jan low 11°F · 39 in snow

  8. 12Plymouth, Wisconsin

    Retirement: 86th percentile · January average low (°F): 88th percentile · Home value ÷ income: 55th percentile

    8,932 people · Sheboygan County · median home $213,300 · income $68,038 · Jan low 12°F · 45 in snow

  9. 11Fox Point, Wisconsin

    Retirement: 77th percentile · January average low (°F): 97th percentile · Home value ÷ income: 55th percentile

    6,934 people · Milwaukee County · median home $444,700 · income $141,467 · Jan low 14°F · 40 in snow

  10. 10Peshtigo, Wisconsin

    Retirement: 71st percentile · January average low (°F): 63rd percentile · Home value ÷ income: 96th percentile

    3,420 people · Marinette County · median home $140,300 · income $66,990 · Jan low 9°F · 49 in snow

  11. 9Wilson, Wisconsin

    Retirement: 62nd percentile · January average low (°F): 94th percentile · Home value ÷ income: 74th percentile

    3,484 people · Sheboygan County · median home $296,400 · income $104,632 · Jan low 13°F · 49 in snow

  12. 8Lodi, Wisconsin

    Retirement: 94th percentile · January average low (°F): 64th percentile · Home value ÷ income: 74th percentile

    3,189 people · Columbia County · median home $328,200 · income $117,584 · Jan low 10°F · 44 in snow

  13. 7Mineral Point, Wisconsin

    Retirement: 95th percentile · January average low (°F): 59th percentile · Home value ÷ income: 83rd percentile

    2,581 people · Iowa County · median home $212,200 · income $81,000 · Jan low 9°F · 41 in snow

  14. 6Juneau, Wisconsin

    Retirement: 91st percentile · January average low (°F): 57th percentile · Home value ÷ income: 90th percentile

    2,658 people · Dodge County · median home $186,700 · income $77,708 · Jan low 9°F · 41 in snow

  15. 5Winneconne, Wisconsin

    Retirement: 90th percentile · January average low (°F): 74th percentile · Home value ÷ income: 83rd percentile

    2,544 people · Winnebago County · median home $218,100 · income $82,411 · Jan low 10°F · 42 in snow

  16. 4Oostburg, Wisconsin

    Retirement: 86th percentile · January average low (°F): 92nd percentile · Home value ÷ income: 74th percentile

    3,056 people · Sheboygan County · median home $246,900 · income $87,857 · Jan low 12°F · 49 in snow

  17. 3Ottawa, Wisconsin

    Retirement: 93rd percentile · January average low (°F): 86th percentile · Home value ÷ income: 74th percentile

    3,646 people · Waukesha County · median home $425,900 · income $153,018 · Jan low 11°F · 51 in snow

  18. 2Kewaunee, Wisconsin

    Retirement: 68th percentile · January average low (°F): 94th percentile · Home value ÷ income: 98th percentile

    2,837 people · Kewaunee County · median home $159,600 · income $82,028 · Jan low 12°F · 48 in snow

  19. 1Bayside, Wisconsin

    Retirement: 97th percentile · January average low (°F): 100th percentile · Home value ÷ income: 79th percentile

    4,482 people · Milwaukee County · median home $431,900 · income $160,096 · Jan low 17°F · 47 in snow

Price vs ranking

Median home value vs ranking, Wisconsin towns0255075100$105K$213K$321K$429K$537KMedian home valuePercentile
Orange squares are the 19 towns on this list; green dots are other towns on The Town Files in Wisconsin.

More Wisconsin rankings

Same ranking, other places

Methodology. We ranked 269 towns of 2,500–10,000 people in Wisconsin (2020 Census population; towns with 2,500+ people have pages so far). Lifestyle measures are The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025), shown as percentiles. The combined score is the average of the percentiles shown for each town; a town must be above the middle on every one. Only towns better than 60% of their peers on this measure qualify, so lists can be shorter than 25. Sources: