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 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

    Millis-Clicquot is a community of 4,499 people in Norfolk County, Massachusetts. It also ranks more of a college town than 83% of Massachusetts towns and better for families than 78% of Massachusetts towns.

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

    Full Millis-Clicquot, Massachusetts profile: weather, storms, schools, jobs →

    Millis-Clicquot lifestyle rankingsFirst-time buyers90th pctFamilies78th pctYoung professionals70th pctQuiet46th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  2. 24Adams, Massachusetts

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

    Adams is a community of 5,466 people in Berkshire County, Massachusetts. It also ranks hipper than 98% of Massachusetts towns and better for cycling than 95% of Massachusetts towns.

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

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

    Adams lifestyle rankingsFirst-time buyers90th pctFamilies2th pctYoung professionals55th pctQuiet29th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  3. 23Warren, Massachusetts

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

    Warren is a town of 4,975 people in Worcester County, Massachusetts. It also ranks easier by car than 95% of Massachusetts towns.

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

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

    Warren lifestyle rankingsFirst-time buyers91th pctFamilies24th pctYoung professionals26th pctQuiet42th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  4. 22Littleton Common, Massachusetts

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

    Littleton Common is a community of 3,065 people in Middlesex County, Massachusetts. It also ranks better for families than 95% of Massachusetts towns and more upscale than 81% of Massachusetts towns.

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

    Full Littleton Common, Massachusetts profile: weather, storms, schools, jobs →

    Littleton Common lifestyle rankingsFirst-time buyers92th pctFamilies95th pctYoung professionals67th pctQuiet58th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  5. 21Pinehurst, Massachusetts

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

    Pinehurst is a community of 7,368 people in Middlesex County, Massachusetts. It also ranks better for families than 95% of Massachusetts towns and better transit than 92% of Massachusetts towns.

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

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

    Pinehurst lifestyle rankingsFirst-time buyers92th pctFamilies95th pctYoung professionals7th pctQuiet54th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  6. 20Plymouth, Massachusetts

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

    Plymouth is a community of 7,667 people in Plymouth County, Massachusetts. It also ranks more seaside character than 99% of Massachusetts towns and more vibrant than 96% of Massachusetts towns.

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

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

    Plymouth lifestyle rankingsFirst-time buyers92th pctFamilies6th pctYoung professionals87th pctQuiet16th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  7. 19Forestdale, Massachusetts

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

    Forestdale is a community of 4,116 people in Barnstable County, Massachusetts. It also ranks easier by car than 97% of Massachusetts towns and better for families than 78% of Massachusetts towns.

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

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

    Forestdale lifestyle rankingsFirst-time buyers93th pctFamilies78th pctYoung professionals10th pctQuiet61th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  8. 18Yarmouth Port, Massachusetts

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

    Yarmouth Port is a community of 5,403 people in Barnstable County, Massachusetts. It also ranks better for a vacation home than 83% of Massachusetts towns and quieter than 82% of Massachusetts towns.

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

    Full Yarmouth Port, Massachusetts profile: weather, storms, schools, jobs →

    Yarmouth Port lifestyle rankingsFirst-time buyers94th pctFamilies41th pctYoung professionals22th pctQuiet82th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  9. 17Halifax, Massachusetts

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

    Halifax is a town of 7,749 people in Plymouth County, Massachusetts. It also ranks better transit than 89% of Massachusetts towns and easier by car than 85% of Massachusetts towns.

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

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

    Halifax lifestyle rankingsFirst-time buyers94th pctFamilies80th pctYoung professionals8th pctQuiet64th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  10. 16Dennis Port, Massachusetts

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

    Dennis Port is a community of 3,487 people in Barnstable County, Massachusetts. It also ranks hipper than 94% of Massachusetts towns and more seaside character than 84% of Massachusetts towns.

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

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

    Dennis Port lifestyle rankingsFirst-time buyers95th pctFamilies8th pctYoung professionals50th pctQuiet38th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  11. 15Kingston, Massachusetts

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

    Kingston is a community of 5,700 people in Plymouth County, Massachusetts. It also ranks more seaside character than 82% of Massachusetts towns and quieter than 74% of Massachusetts towns.

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

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

    Kingston lifestyle rankingsFirst-time buyers95th pctFamilies61th pctYoung professionals34th pctQuiet74th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  12. 14Townsend, Massachusetts

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

    Townsend, Massachusetts
    Photo: Marcbela (Marc N. Belanger) (public domain, Wikimedia Commons)

    Townsend is a town of 9,127 people in Middlesex County, Massachusetts. It also ranks easier by car than 92% of Massachusetts towns.

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

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

    Townsend lifestyle rankingsFirst-time buyers95th pctFamilies69th pctYoung professionals40th pctQuiet63th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  13. 13Rochester, Massachusetts

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

    Rochester is a town of 5,717 people in Plymouth County, Massachusetts. It also ranks easier by car than 100% of Massachusetts towns and better for families than 92% of Massachusetts towns.

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

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

    Rochester lifestyle rankingsFirst-time buyers96th pctFamilies92th pctYoung professionals44th pctQuiet66th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  14. 12Athol, Massachusetts

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

    Athol is a community of 8,486 people in Worcester County, Massachusetts. The median home is worth $248,700 (typical Massachusetts town: $510,150).

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

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

    Athol lifestyle rankingsFirst-time buyers96th pctFamilies13th pctYoung professionals7th pctQuiet40th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  15. 11Plympton, Massachusetts

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

    Plympton is a town of 2,930 people in Plymouth County, Massachusetts. It also ranks better for families than 97% of Massachusetts towns and quieter than 70% of Massachusetts towns.

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

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

    Plympton lifestyle rankingsFirst-time buyers97th pctFamilies97th pctYoung professionals16th pctQuiet70th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  16. 10Sandwich, Massachusetts

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

    Sandwich is a community of 2,998 people in Barnstable County, Massachusetts. It also ranks more seaside character than 94% of Massachusetts towns and 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

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

    Sandwich lifestyle rankingsFirst-time buyers97th pctFamilies26th pctYoung professionals85th pctQuiet81th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  17. 9Cheshire, Massachusetts

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

    Cheshire is a town of 3,258 people in Berkshire County, Massachusetts. It also ranks easier by car than 96% of Massachusetts towns and quieter than 92% of Massachusetts towns.

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

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

    Cheshire lifestyle rankingsFirst-time buyers97th pctFamilies50th pctYoung professionals5th pctQuiet92th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  18. 8Salisbury, Massachusetts

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

    Salisbury is a community of 5,629 people in Essex County, Massachusetts. It also ranks better for young professionals than 83% of Massachusetts towns and more seaside character than 83% of Massachusetts towns.

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

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

    Salisbury lifestyle rankingsFirst-time buyers98th pctFamilies22th pctYoung professionals83th pctQuiet61th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  19. 7Groveland, Massachusetts

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

    Groveland is a town of 6,752 people in Essex County, Massachusetts. It also ranks better for families than 95% of Massachusetts towns and quieter than 71% of Massachusetts towns.

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

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

    Groveland lifestyle rankingsFirst-time buyers98th pctFamilies95th pctYoung professionals13th pctQuiet71th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  20. 6Salisbury, Massachusetts

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

    Salisbury is a town of 9,236 people in Essex County, Massachusetts. It also ranks better for young professionals than 80% of Massachusetts towns and more seaside character than 79% of Massachusetts towns.

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

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

    Salisbury lifestyle rankingsFirst-time buyers98th pctFamilies29th pctYoung professionals80th pctQuiet62th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  21. 5Monument Beach, Massachusetts

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

    Monument Beach is a community of 2,784 people in Barnstable County, Massachusetts. It also ranks easier by car than 99% of Massachusetts towns and more seaside character than 92% of Massachusetts towns.

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

    Full Monument Beach, Massachusetts profile: weather, storms, schools, jobs →

    Monument Beach lifestyle rankingsFirst-time buyers99th pctFamilies19th pctYoung professionals40th pctQuiet48th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  22. 4Ashby, Massachusetts

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

    Ashby is a town of 3,193 people in Middlesex County, Massachusetts. It also ranks quieter than 94% of Massachusetts towns and better for families than 90% of Massachusetts towns.

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

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

    Ashby lifestyle rankingsFirst-time buyers99th pctFamilies90th pctYoung professionals10th pctQuiet94th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  23. 3Brookfield, Massachusetts

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

    Brookfield, Massachusetts
    Photo: Unknown authorUnknown author (public domain, Wikimedia Commons)

    Brookfield is a town of 3,439 people in Worcester County, Massachusetts. It also ranks easier by car than 99% of Massachusetts towns and more of a college town than 92% of Massachusetts towns.

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

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

    Brookfield lifestyle rankingsFirst-time buyers99th pctFamilies62th pctYoung professionals11th pctQuiet66th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  24. 2Winchendon, Massachusetts

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

    Winchendon is a community of 4,160 people in Worcester County, Massachusetts. It also ranks more walkable than 85% of Massachusetts towns and more vibrant than 82% of Massachusetts towns.

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

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

    Winchendon lifestyle rankingsFirst-time buyers99th pctFamilies14th pctYoung professionals33th pctQuiet6th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.
  25. 1Sagamore, Massachusetts

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

    Sagamore is a community of 3,851 people in Barnstable County, Massachusetts. It also ranks more seaside character than 90% of Massachusetts towns and more vibrant than 84% of Massachusetts towns.

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

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

    Sagamore lifestyle rankingsFirst-time buyers100th pctFamilies29th pctYoung professionals58th pctQuiet34th pct
    The Town Files lifestyle rankings, percentile vs Massachusetts towns.

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 500–10,000 people in Massachusetts (2020 Census population). 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: