The 25 Best Small Towns to Retire in Connecticut

Ranked on The Town Files lifestyle rankings among 132 towns of 2,500–10,000 people in Connecticut. #1 is Sharon, CT.

1. 25Bethlehem, Connecticut

   Better for retirees than 85% of Connecticut towns

   3,385 people · median home $410,900 · income $108,929 · Jan low 15°F · 47 in snow

2. 24Killingworth, Connecticut

   Better for retirees than 85% of Connecticut towns

   6,174 people · median home $446,200 · income $140,655 · Jan low 19°F

3. 23Litchfield, Connecticut

   Better for retirees than 86% of Connecticut towns

   8,192 people · median home $391,900 · income $102,609 · Jan low 15°F · 54 in snow

4. 22Redding, Connecticut

   Better for retirees than 86% of Connecticut towns

   8,765 people · median home $706,300 · income $186,060 · Jan low 18°F · 49 in snow

5. 21Barkhamsted, Connecticut

   Better for retirees than 87% of Connecticut towns

   3,647 people · median home $368,000 · income $123,544 · Jan low 14°F · 51 in snow

6. 20Beacon Falls, Connecticut

   Better for retirees than 87% of Connecticut towns

   6,000 people · median home $350,300 · income $101,516 · Jan low 18°F · 45 in snow

7. 19Chester, Connecticut

   Better for retirees than 88% of Connecticut towns

   3,749 people · median home $442,200 · income $109,191 · Jan low 19°F · 26 in snow

8. 18Essex, Connecticut

   Better for retirees than 88% of Connecticut towns

   6,733 people · median home $552,000 · income $104,395 · Jan low 23°F · 26 in snow

9. 17Collinsville, Connecticut

   Better for retirees than 89% of Connecticut towns

   3,721 people · median home $395,500 · income $94,815 · Jan low 17°F · 39 in snow

10. 16Goshen, Connecticut

    Better for retirees than 90% of Connecticut towns

    3,150 people · median home $482,400 · income $152,093 · Jan low 14°F · 75 in snow

11. 15Washington, Connecticut

    Better for retirees than 90% of Connecticut towns

    3,646 people · median home $660,200 · income $101,549 · Jan low 21°F · 47 in snow

12. 14Old Lyme, Connecticut

    Better for retirees than 90% of Connecticut towns

    7,628 people · median home $484,200 · income $131,899 · Jan low 23°F · 26 in snow

13. 13Westbrook, Connecticut

    Better for retirees than 91% of Connecticut towns

    6,769 people · median home $434,300 · income $91,202 · Jan low 23°F · 25 in snow

14. 12West Simsbury, Connecticut

    Better for retirees than 92% of Connecticut towns

    2,521 people · median home $503,100 · income $201,397 · Jan low 14°F · 51 in snow

15. 11Niantic, Connecticut

    Better for retirees than 92% of Connecticut towns

    3,194 people · median home $396,000 · income $81,250 · Jan low 23°F · 25 in snow

16. 10Deep River Center, Connecticut

    Better for retirees than 93% of Connecticut towns

    2,765 people · median home $334,600 · income $71,447 · Jan low 23°F · 26 in snow

17. 9Deep River, Connecticut

    Better for retirees than 93% of Connecticut towns

    4,415 people · median home $362,200 · income $90,253 · Jan low 19°F · 26 in snow

18. 8Salisbury, Connecticut

    Better for retirees than 95% of Connecticut towns

    4,194 people · median home $763,700 · income $124,256 · Jan low 14°F · 62 in snow

19. 7Woodbury, Connecticut

    Better for retirees than 95% of Connecticut towns

    9,723 people · median home $469,900 · income $131,480 · Jan low 21°F · 47 in snow

20. 6Sherman, Connecticut

    Better for retirees than 96% of Connecticut towns

    3,527 people · median home $497,300 · income $116,000 · Jan low 16°F · 52 in snow

21. 5Essex Village, Connecticut

    Better for retirees than 97% of Connecticut towns

    2,583 people · median home $751,900 · income $102,885 · Jan low 23°F · 26 in snow

22. 4Mystic, Connecticut

    Better for retirees than 98% of Connecticut towns

    4,348 people · median home $538,800 · income $152,559 · Jan low 24°F · 25 in snow

23. 3Heritage Village, Connecticut

    Better for retirees than 98% of Connecticut towns

    5,091 people · median home $243,100 · income $62,059 · Jan low 21°F · 47 in snow

24. 2Kent, Connecticut

    Better for retirees than 99% of Connecticut towns

    3,019 people · median home $470,900 · income $96,064 · Jan low 16°F · 56 in snow

25. 1Sharon, Connecticut

    Better for retirees than 100% of Connecticut towns

    2,680 people · median home $590,700 · income $100,518 · Jan low 14°F · 62 in snow

Price vs ranking

More Connecticut rankings

• The 25 Quietest Small Towns in Connecticut
• The 25 Most Affordable Small Towns in Connecticut
• The 25 Best Small Towns for Families in Connecticut
• The 21 Best Quiet, Affordable Small Towns to Retire in Connecticut
• 25 Small Towns in Connecticut With the Cheapest Homes
• 25 Small Towns in Connecticut With the Mildest Winters
• The 25 Most Walkable Small Towns in Connecticut
• 25 Small Towns in Connecticut With the Fewest Tornadoes Since 1950
• The 25 Best Small Towns for First-Time Home Buyers in Connecticut
• The 15 Best Affordable Small Towns for Remote Workers in Connecticut

Same ranking, other places

• The 50 Best Small Towns to Retire in America
• The 25 Best Small Towns to Retire in Pennsylvania
• The 25 Best Small Towns to Retire in New York
• The 25 Best Small Towns to Retire in Michigan
• The 25 Best Small Towns to Retire in Texas
• The 25 Best Small Towns to Retire in California
• The 25 Best Small Towns to Retire in New Jersey
• The 25 Best Small Towns to Retire in Florida
• The 25 Best Small Towns to Retire in Wisconsin
• The 25 Best Small Towns to Retire in Ohio