The 25 Best Small Towns to Retire in Massachusetts

Ranked on The Town Files lifestyle rankings among 181 towns of 2,500–10,000 people in Massachusetts. #1 is Rockport, MA.

1. 25East Sandwich, Massachusetts

   Better for retirees than 88% of Massachusetts towns

   3,669 people · Barnstable County · median home $689,000 · income $115,000 · Jan low 20°F · 22 in snow

2. 24East Harwich, Massachusetts

   Better for retirees than 89% of Massachusetts towns

   5,250 people · Barnstable County · median home $638,900 · income $111,508 · Jan low 26°F · 25 in snow

3. 23West Concord, Massachusetts

   Better for retirees than 89% of Massachusetts towns

   6,320 people · Middlesex County · median home $904,200 · income $183,228 · Jan low 15°F · 59 in snow

4. 22Hatfield, Massachusetts

   Better for retirees than 90% of Massachusetts towns

   3,352 people · Hampshire County · median home $440,800 · income $89,005 · Jan low 14°F · 37 in snow

5. 21Lenox, Massachusetts

   Better for retirees than 90% of Massachusetts towns

   5,095 people · Berkshire County · median home $466,700 · income $106,080 · Jan low 13°F · 68 in snow

6. 20Williamsburg, Massachusetts

   Better for retirees than 91% of Massachusetts towns

   2,504 people · Hampshire County · median home $403,100 · income $104,792 · Jan low 14°F · 46 in snow

7. 19East Dennis, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   2,585 people · Barnstable County · median home $694,000 · income $103,654 · Jan low 25°F · 22 in snow

8. 18Sandwich, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   2,998 people · Barnstable County · median home $584,300 · income $117,321 · Jan low 20°F · 37 in snow

9. 17Sheffield, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   3,327 people · Berkshire County · median home $409,400 · income $92,120 · Jan low 14°F · 57 in snow

10. 16Mattapoisett Center, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    3,190 people · Plymouth County · median home $651,900 · income $105,500 · Jan low 22°F · 33 in snow

11. 15Nahant, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    3,334 people · Essex County · median home $748,800 · income $112,762 · Jan low 23°F · 49 in snow

12. 14Scituate, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    5,620 people · Plymouth County · median home $821,600 · income $124,549 · Jan low 22°F · 45 in snow

13. 13Mattapoisett, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    6,508 people · Plymouth County · median home $681,600 · income $130,241 · Jan low 22°F · 33 in snow

14. 12Chatham, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    6,594 people · Barnstable County · median home $942,800 · income $85,167 · Jan low 25°F · 25 in snow

15. 11West Tisbury, Massachusetts

    Better for retirees than 94% of Massachusetts towns

    3,555 people · Dukes County · median home $1,302,100 · income $182,750 · Jan low 23°F · 25 in snow

16. 10Wellfleet, Massachusetts

    Better for retirees than 95% of Massachusetts towns

    3,566 people · Barnstable County · median home $855,300 · income $117,938 · Jan low 26°F · 23 in snow

17. 9Orleans, Massachusetts

    Better for retirees than 96% of Massachusetts towns

    6,307 people · Barnstable County · median home $957,000 · income $102,335 · Jan low 26°F · 25 in snow

18. 8Manchester-by-the-Sea, Massachusetts

    Better for retirees than 97% of Massachusetts towns

    5,395 people · Essex County · median home $942,000 · income $206,389 · Jan low 18°F · 51 in snow

19. 7Lincoln, Massachusetts

    Better for retirees than 97% of Massachusetts towns

    7,014 people · Middlesex County · median home $1,208,200 · income $175,117 · Jan low 18°F · 59 in snow

20. 6Berlin, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    3,158 people · Worcester County · median home $616,600 · income $121,336 · Jan low 15°F · 55 in snow

21. 5Falmouth, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    3,818 people · Barnstable County · median home $837,900 · income $68,227 · Jan low 23°F · 29 in snow

22. 4Williamstown, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    4,308 people · Berkshire County · median home $439,300 · income $97,917 · Jan low 14°F · 68 in snow

23. 3Williamstown, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    7,513 people · Berkshire County · median home $437,100 · income $106,650 · Jan low 14°F · 67 in snow

24. 2Rockport, Massachusetts

    Better for retirees than 99% of Massachusetts towns

    5,010 people · Essex County · median home $748,200 · income $86,250 · Jan low 18°F · 49 in snow

25. 1Rockport, Massachusetts

    Better for retirees than 99% of Massachusetts towns

    6,992 people · Essex County · median home $746,100 · income $96,250 · Jan low 18°F · 50 in snow

Price vs ranking

More Massachusetts rankings

• The 25 Quietest Small Towns in Massachusetts
• The 25 Most Affordable Small Towns in Massachusetts
• The 25 Best Small Towns for Families in Massachusetts
• The 19 Best Quiet, Affordable Small Towns to Retire in Massachusetts
• 25 Small Towns in Massachusetts With the Cheapest Homes
• 25 Small Towns in Massachusetts With the Mildest Winters
• The 25 Most Walkable Small Towns in Massachusetts
• 25 Small Towns in Massachusetts With the Fewest Tornadoes Since 1950
• The 25 Best Small Towns for First-Time Home Buyers in Massachusetts
• The 24 Best Affordable Small Towns for Remote Workers in Massachusetts

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