The Town Files

The 25 Best Small Towns to Retire in Wisconsin

Ranked on The Town Files lifestyle rankings among 269 towns of 2,500–10,000 people in Wisconsin. #1 is Okauchee Lake, WI.

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Numbers match the ranking.
The 25 Best Small Towns to Retire in Wisconsin1. Okauchee Lake99th pct2. Williams Bay99th pct3. Minocqua98th pct4. Ladysmith98th pct5. Sevastopol98th pct6. Empire98th pct7. Bayside97th pct8. Fontana-on-Geneva Lake97th pct9. Oconomowoc96th pct10. Cedarburg96th pct11. Dunn96th pct12. Taycheedah96th pct13. Westport96th pct14. Pleasant Springs96th pct15. Middleton95th pct16. Erin95th pct17. Oakland95th pct18. Springfield95th pct19. Lake Wissota95th pct20. Mineral Point95th pct21. Brookfield94th pct22. Rib Mountain94th pct23. Farmington94th pct24. Lodi94th pct25. Delafield93rd pct
  1. 25Delafield, Wisconsin

    Better for retirees than 93% of Wisconsin towns

    8,095 people · Waukesha County · median home $613,300 · income $158,353 · Jan low 12°F · 37 in snow

  2. 24Lodi, Wisconsin

    Better for retirees than 94% of Wisconsin towns

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

  3. 23Farmington, Wisconsin

    Better for retirees than 94% of Wisconsin towns

    3,712 people · Waupaca County · median home $251,500 · income $83,244 · Jan low 8°F · 49 in snow

  4. 22Rib Mountain, Wisconsin

    Better for retirees than 94% of Wisconsin towns

    6,061 people · Marathon County · median home $255,900 · income $94,294 · Jan low 7°F · 64 in snow

  5. 21Brookfield, Wisconsin

    Better for retirees than 94% of Wisconsin towns

    6,477 people · Waukesha County · median home $374,500 · income $89,323 · Jan low 12°F · 37 in snow

  6. 20Mineral Point, Wisconsin

    Better for retirees than 95% of Wisconsin towns

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

  7. 19Lake Wissota, Wisconsin

    Better for retirees than 95% of Wisconsin towns

    2,830 people · Chippewa County · median home $334,600 · income $105,150 · Jan low 6°F · 52 in snow

  8. 18Springfield, Wisconsin

    Better for retirees than 95% of Wisconsin towns

    2,929 people · Dane County · median home $554,700 · income $135,216 · Jan low 10°F · 39 in snow

  9. 17Oakland, Wisconsin

    Better for retirees than 95% of Wisconsin towns

    3,231 people · Jefferson County · median home $353,900 · income $94,603 · Jan low 11°F · 42 in snow

  10. 16Erin, Wisconsin

    Better for retirees than 95% of Wisconsin towns

    3,825 people · Washington County · median home $442,800 · income $111,375 · Jan low 9°F · 36 in snow

  11. 15Middleton, Wisconsin

    Better for retirees than 95% of Wisconsin towns

    6,792 people · Dane County · median home $689,400 · income $203,646 · Jan low 10°F · 39 in snow

  12. 14Pleasant Springs, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    3,078 people · Dane County · median home $444,100 · income $119,273 · Jan low 10°F · 36 in snow

  13. 13Westport, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    4,191 people · Dane County · median home $418,700 · income $83,750 · Jan low 12°F · 52 in snow

  14. 12Taycheedah, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    4,554 people · Fond du Lac County · median home $354,000 · income $105,690 · Jan low 9°F · 38 in snow

  15. 11Dunn, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    4,880 people · Dane County · median home $447,300 · income $127,734 · Jan low 10°F · 36 in snow

  16. 10Cedarburg, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    6,162 people · Ozaukee County · median home $473,800 · income $124,121 · Jan low 17°F · 54 in snow

  17. 9Oconomowoc, Wisconsin

    Better for retirees than 96% of Wisconsin towns

    8,836 people · Waukesha County · median home $466,300 · income $114,782 · Jan low 11°F · 40 in snow

  18. 8Fontana-on-Geneva Lake, Wisconsin

    Better for retirees than 97% of Wisconsin towns

    3,120 people · Walworth County · median home $572,600 · income $106,750 · Jan low 13°F · 40 in snow

  19. 7Bayside, Wisconsin

    Better for retirees than 97% of Wisconsin towns

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

  20. 6Empire, Wisconsin

    Better for retirees than 98% of Wisconsin towns

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

  21. 5Sevastopol, Wisconsin

    Better for retirees than 98% of Wisconsin towns

    2,826 people · Door County · median home $430,200 · income $88,750 · Jan low 10°F · 57 in snow

  22. 4Ladysmith, Wisconsin

    Better for retirees than 98% of Wisconsin towns

    3,216 people · Rusk County · median home $124,200 · income $41,719 · Jan low 2°F · 52 in snow

  23. 3Minocqua, Wisconsin

    Better for retirees than 98% of Wisconsin towns

    5,062 people · Oneida County · median home $311,100 · income $69,112 · Jan low 2°F · 55 in snow

  24. 2Williams Bay, Wisconsin

    Better for retirees than 99% of Wisconsin towns

    2,953 people · Walworth County · median home $444,700 · income $84,113 · Jan low 15°F · 40 in snow

  25. 1Okauchee Lake, Wisconsin

    Better for retirees than 99% of Wisconsin towns

    5,094 people · Waukesha County · median home $497,500 · income $131,170 · Jan low 11°F · 40 in snow

Price vs ranking

Median home value vs ranking, Wisconsin towns0255075100$105K$213K$321K$429K$537KMedian home valuePercentile
Orange squares are the 25 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. Only towns better than 60% of their peers on this measure qualify, so lists can be shorter than 25. Sources: