The Town Files

The 25 Best Small Towns for First-Time Home Buyers in Massachusetts

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

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Numbers match the ranking.
The 25 Best Small Towns for First-Time Home Buyers in Massachusetts1. Sagamore100th pct2. Winchendon99th pct3. Brookfield99th pct4. Ashby99th pct5. Monument Beach99th pct6. Salisbury98th pct7. Groveland98th pct8. Salisbury98th pct9. Cheshire97th pct10. Sandwich97th pct11. Plympton97th pct12. Athol96th pct13. Rochester96th pct14. Townsend95th pct15. Kingston95th pct16. Dennis Port95th pct17. Halifax94th pct18. Yarmouth Port94th pct19. Forestdale93rd pct20. Plymouth92nd pct21. Pinehurst92nd pct22. Littleton Common92nd pct23. Warren91st pct24. Adams90th pct25. Millis-Clicquot90th pct
  1. 25Millis-Clicquot, Massachusetts

    Better for first-time buyers than 90% of Massachusetts towns

    4,499 people · Norfolk County · median home $545,600 · income $146,853 · Jan low 17°F · 52 in snow

  2. 24Adams, Massachusetts

    Better for first-time buyers than 90% of Massachusetts towns

    5,466 people · Berkshire County · median home $197,400 · income $48,775 · Jan low 14°F · 76 in snow

  3. 23Warren, Massachusetts

    Better for first-time buyers than 91% of Massachusetts towns

    4,975 people · Worcester County · median home $333,700 · income $66,082 · Jan low 16°F · 43 in snow

  4. 22Littleton Common, Massachusetts

    Better for first-time buyers than 92% of Massachusetts towns

    3,065 people · Middlesex County · median home $558,200 · income $135,074 · Jan low 15°F · 60 in snow

  5. 21Pinehurst, Massachusetts

    Better for first-time buyers than 92% of Massachusetts towns

    7,368 people · Middlesex County · median home $623,800 · income $146,250 · Jan low 18°F · 59 in snow

  6. 20Plymouth, Massachusetts

    Better for first-time buyers than 92% of Massachusetts towns

    7,667 people · Plymouth County · median home $446,800 · income $81,703 · Jan low 22°F · 38 in snow

  7. 19Forestdale, Massachusetts

    Better for first-time buyers than 93% of Massachusetts towns

    4,116 people · Barnstable County · median home $490,200 · income $108,158 · Jan low 20°F · 30 in snow

  8. 18Yarmouth Port, Massachusetts

    Better for first-time buyers than 94% of Massachusetts towns

    5,403 people · Barnstable County · median home $604,900 · income $110,304 · Jan low 24°F · 22 in snow

  9. 17Halifax, Massachusetts

    Better for first-time buyers than 94% of Massachusetts towns

    7,749 people · Plymouth County · median home $481,500 · income $118,556 · Jan low 17°F · 34 in snow

  10. 16Dennis Port, Massachusetts

    Better for first-time buyers than 95% of Massachusetts towns

    3,487 people · Barnstable County · median home $523,900 · income $70,094 · Jan low 25°F · 22 in snow

  11. 15Kingston, Massachusetts

    Better for first-time buyers than 95% of Massachusetts towns

    5,700 people · Plymouth County · median home $589,900 · income $150,886 · Jan low 22°F · 38 in snow

  12. 14Townsend, Massachusetts

    Better for first-time buyers than 95% of Massachusetts towns

    9,127 people · Middlesex County · median home $433,200 · income $121,528 · Jan low 15°F · 75 in snow

  13. 13Rochester, Massachusetts

    Better for first-time buyers than 96% of Massachusetts towns

    5,717 people · Plymouth County · median home $599,100 · income $120,273 · Jan low 20°F · 31 in snow

  14. 12Athol, Massachusetts

    Better for first-time buyers than 96% of Massachusetts towns

    8,486 people · Worcester County · median home $248,700 · income $67,394 · Jan low 14°F · 52 in snow

  15. 11Plympton, Massachusetts

    Better for first-time buyers than 97% of Massachusetts towns

    2,930 people · Plymouth County · median home $517,800 · income $126,736 · Jan low 20°F · 38 in snow

  16. 10Sandwich, Massachusetts

    Better for first-time buyers than 97% of Massachusetts towns

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

  17. 9Cheshire, Massachusetts

    Better for first-time buyers than 97% of Massachusetts towns

    3,258 people · Berkshire County · median home $268,200 · income $69,803 · Jan low 14°F · 76 in snow

  18. 8Salisbury, Massachusetts

    Better for first-time buyers than 98% of Massachusetts towns

    5,629 people · Essex County · median home $465,900 · income $92,469 · Jan low 17°F · 62 in snow

  19. 7Groveland, Massachusetts

    Better for first-time buyers than 98% of Massachusetts towns

    6,752 people · Essex County · median home $610,900 · income $141,487 · Jan low 17°F · 67 in snow

  20. 6Salisbury, Massachusetts

    Better for first-time buyers than 98% of Massachusetts towns

    9,236 people · Essex County · median home $478,700 · income $93,361 · Jan low 16°F · 62 in snow

  21. 5Monument Beach, Massachusetts

    Better for first-time buyers than 99% of Massachusetts towns

    2,784 people · Barnstable County · median home $559,900 · income $77,167 · Jan low 22°F · 37 in snow

  22. 4Ashby, Massachusetts

    Better for first-time buyers than 99% of Massachusetts towns

    3,193 people · Middlesex County · median home $390,500 · income $115,598 · Jan low 15°F · 75 in snow

  23. 3Brookfield, Massachusetts

    Better for first-time buyers than 99% of Massachusetts towns

    3,439 people · Worcester County · median home $341,900 · income $81,250 · Jan low 16°F · 64 in snow

  24. 2Winchendon, Massachusetts

    Better for first-time buyers than 99% of Massachusetts towns

    4,160 people · Worcester County · median home $276,300 · income $55,809 · Jan low 12°F · 51 in snow

  25. 1Sagamore, Massachusetts

    Better for first-time buyers than 100% of Massachusetts towns

    3,851 people · Barnstable County · median home $575,700 · income $108,315 · Jan low 20°F · 37 in snow

Price vs ranking

Median home value vs ranking, Massachusetts towns0255075100$196K$463K$730K$998K$1265KMedian home valuePercentile
Orange squares are the 25 towns on this list; green dots are other towns on The Town Files in Massachusetts.

More Massachusetts rankings

Same ranking, other places

Methodology. We ranked 181 towns of 2,500–10,000 people in Massachusetts (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: