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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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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
14Townsend, Massachusetts
Better for first-time buyers than 95% of Massachusetts towns

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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
3Brookfield, Massachusetts
Better for first-time buyers than 99% of Massachusetts towns

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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns. -
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 →
The Town Files lifestyle rankings, percentile vs Massachusetts towns.
Price vs ranking
More Massachusetts rankings
- The 25 Best Small Towns to Retire in Massachusetts
- 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 24 Best Affordable Small Towns for Remote Workers in Massachusetts
Same ranking, other places
- The 50 Best Small Towns for First-Time Home Buyers in America
- The 25 Best Small Towns for First-Time Home Buyers in Pennsylvania
- The 25 Best Small Towns for First-Time Home Buyers in New York
- The 25 Best Small Towns for First-Time Home Buyers in Michigan
- The 25 Best Small Towns for First-Time Home Buyers in Texas
- The 25 Best Small Towns for First-Time Home Buyers in California
- The 25 Best Small Towns for First-Time Home Buyers in New Jersey
- The 25 Best Small Towns for First-Time Home Buyers in Florida
- The 25 Best Small Towns for First-Time Home Buyers in Wisconsin
- The 25 Best Small Towns for First-Time Home Buyers in Ohio
- U.S. Census Bureau, American Community Survey 5-year estimates (2020–2024)
- U.S. Census Bureau, 2020 Census and 2025 Gazetteer (2020 / 2025)
- NOAA NCEI U.S. Climate Normals (1991–2020)
- NOAA NCEI Storm Events Database (1950–2026)
- FEMA OpenFEMA Disaster Declarations (this product uses the FEMA OpenFEMA API but is not endorsed by FEMA) (1953–2026)
- NCES Common Core of Data (2023–24)
- BLS Quarterly Census of Employment and Wages; USDA ERS county unemployment (BLS LAUS) (2000–2024)
- The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025)