The 25 Best Small Towns to Retire in Massachusetts

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

1. 25East Sandwich, Massachusetts

   Better for retirees than 88% of Massachusetts towns

   East Sandwich is a community of 3,669 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 95% of Massachusetts towns and better for cycling than 94% of Massachusetts towns.

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

   Full East Sandwich, Massachusetts profile: weather, storms, schools, jobs →

2. 24East Harwich, Massachusetts

   Better for retirees than 89% of Massachusetts towns

   East Harwich is a community of 5,250 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 95% of Massachusetts towns and easier by car than 92% of Massachusetts towns.

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

   Full East Harwich, Massachusetts profile: weather, storms, schools, jobs →

3. 23West Concord, Massachusetts

   Better for retirees than 89% of Massachusetts towns

   West Concord is a community of 6,320 people in Middlesex County, Massachusetts. It also ranks better for young professionals than 97% of Massachusetts towns and better for cycling than 96% of Massachusetts towns.

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

   Full West Concord, Massachusetts profile: weather, storms, schools, jobs →

4. 22Hatfield, Massachusetts

   Better for retirees than 90% of Massachusetts towns

   Hatfield is a town of 3,352 people in Hampshire County, Massachusetts. It also ranks more of a college town than 97% of Massachusetts towns and hipper than 84% of Massachusetts towns.

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

   Full Hatfield, Massachusetts profile: weather, storms, schools, jobs →

5. 21Lenox, Massachusetts

   Better for retirees than 90% of Massachusetts towns

   Lenox is a town of 5,095 people in Berkshire County, Massachusetts. It also ranks better for cycling than 93% of Massachusetts towns and better for a vacation home than 89% of Massachusetts towns.

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

   Full Lenox, Massachusetts profile: weather, storms, schools, jobs →

6. 20Williamsburg, Massachusetts

   Better for retirees than 91% of Massachusetts towns

   Williamsburg is a town of 2,504 people in Hampshire County, Massachusetts. It also ranks quieter than 95% of Massachusetts towns and better for a vacation home than 92% of Massachusetts towns.

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

   Full Williamsburg, Massachusetts profile: weather, storms, schools, jobs →

7. 19East Dennis, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   East Dennis is a community of 2,585 people in Barnstable County, Massachusetts. It also ranks easier by car than 91% of Massachusetts towns and better for a vacation home than 90% of Massachusetts towns.

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

   Full East Dennis, Massachusetts profile: weather, storms, schools, jobs →

8. 18Sandwich, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   Sandwich is a community of 2,998 people in Barnstable County, Massachusetts. It also ranks better for first-time buyers than 97% of Massachusetts towns and more seaside character than 94% of Massachusetts towns.

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

   Full Sandwich, Massachusetts profile: weather, storms, schools, jobs →

9. 17Sheffield, Massachusetts

   Better for retirees than 92% of Massachusetts towns

   Sheffield is a town of 3,327 people in Berkshire County, Massachusetts. It also ranks better for a vacation home than 90% of Massachusetts towns and easier by car than 90% of Massachusetts towns.

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

   Full Sheffield, Massachusetts profile: weather, storms, schools, jobs →

10. 16Mattapoisett Center, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    Mattapoisett Center is a community of 3,190 people in Plymouth County, Massachusetts. It also ranks better for a vacation home than 93% of Massachusetts towns and more seaside character than 88% of Massachusetts towns.

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

    Full Mattapoisett Center, Massachusetts profile: weather, storms, schools, jobs →

11. 15Nahant, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    Nahant is a community of 3,334 people in Essex County, Massachusetts. It also ranks more of a college town than 99% of Massachusetts towns and more seaside character than 99% of Massachusetts towns.

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

    Full Nahant, Massachusetts profile: weather, storms, schools, jobs →

12. 14Scituate, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    Scituate is a community of 5,620 people in Plymouth County, Massachusetts. It also ranks better for cycling than 97% of Massachusetts towns and more seaside character than 96% of Massachusetts towns.

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

    Full Scituate, Massachusetts profile: weather, storms, schools, jobs →

13. 13Mattapoisett, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    Mattapoisett is a town of 6,508 people in Plymouth County, Massachusetts. It also ranks better for a vacation home than 93% of Massachusetts towns and more seaside character than 88% of Massachusetts towns.

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

    Full Mattapoisett, Massachusetts profile: weather, storms, schools, jobs →

14. 12Chatham, Massachusetts

    Better for retirees than 93% of Massachusetts towns

    Chatham is a town of 6,594 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 99% of Massachusetts towns and more seaside character than 90% of Massachusetts towns.

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

    Full Chatham, Massachusetts profile: weather, storms, schools, jobs →

15. 11West Tisbury, Massachusetts

    Better for retirees than 94% of Massachusetts towns

    West Tisbury is a town of 3,555 people in Dukes County, Massachusetts. It also ranks better for a vacation home than 100% of Massachusetts towns and better for first-time buyers than 85% of Massachusetts towns.

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

    Full West Tisbury, Massachusetts profile: weather, storms, schools, jobs →

16. 10Wellfleet, Massachusetts

    Better for retirees than 95% of Massachusetts towns

    Wellfleet is a town of 3,566 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 97% of Massachusetts towns and quieter than 93% of Massachusetts towns.

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

    Full Wellfleet, Massachusetts profile: weather, storms, schools, jobs →

17. 9Orleans, Massachusetts

    Better for retirees than 96% of Massachusetts towns

    Orleans is a town of 6,307 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 94% of Massachusetts towns and hipper than 91% of Massachusetts towns.

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

    Full Orleans, Massachusetts profile: weather, storms, schools, jobs →

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

    Better for retirees than 97% of Massachusetts towns

    Manchester-by-the-Sea is a town of 5,395 people in Essex County, Massachusetts. It also ranks more upscale than 98% of Massachusetts towns and more seaside character than 98% of Massachusetts towns.

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

    Full Manchester-by-the-Sea, Massachusetts profile: weather, storms, schools, jobs →

19. 7Lincoln, Massachusetts

    Better for retirees than 97% of Massachusetts towns

    Lincoln is a town of 7,014 people in Middlesex County, Massachusetts. It also ranks more upscale than 97% of Massachusetts towns and better for young professionals than 93% of Massachusetts towns.

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

    Full Lincoln, Massachusetts profile: weather, storms, schools, jobs →

20. 6Berlin, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    

    Berlin is a town of 3,158 people in Worcester County, Massachusetts. It also ranks quieter than 85% of Massachusetts towns and more upscale than 75% of Massachusetts towns.

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

    Full Berlin, Massachusetts profile: weather, storms, schools, jobs →

21. 5Falmouth, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    Falmouth is a community of 3,818 people in Barnstable County, Massachusetts. It also ranks hipper than 99% of Massachusetts towns and better for cycling than 98% of Massachusetts towns.

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

    Full Falmouth, Massachusetts profile: weather, storms, schools, jobs →

22. 4Williamstown, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    Williamstown is a community of 4,308 people in Berkshire County, Massachusetts. It also ranks better for young professionals than 99% of Massachusetts towns and better for cycling than 94% of Massachusetts towns.

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

    Full Williamstown, Massachusetts profile: weather, storms, schools, jobs →

23. 3Williamstown, Massachusetts

    Better for retirees than 98% of Massachusetts towns

    

    Williamstown is a town of 7,513 people in Berkshire County, Massachusetts. It also ranks better for young professionals than 99% of Massachusetts towns and better for cycling than 95% of Massachusetts towns.

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

    Full Williamstown, Massachusetts profile: weather, storms, schools, jobs →

24. 2Rockport, Massachusetts

    Better for retirees than 99% of Massachusetts towns

    Rockport is a community of 5,010 people in Essex County, Massachusetts. It also ranks more seaside character than 98% of Massachusetts towns and hipper than 95% of Massachusetts towns.

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

    Full Rockport, Massachusetts profile: weather, storms, schools, jobs →

25. 1Rockport, Massachusetts

    Better for retirees than 99% of Massachusetts towns

    Rockport is a town of 6,992 people in Essex County, Massachusetts. It also ranks more seaside character than 98% of Massachusetts towns and hipper than 92% of Massachusetts towns.

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

    Full Rockport, Massachusetts profile: weather, storms, schools, jobs →

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
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• 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