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

Ranked on The Town Files lifestyle rankings among 132 towns of 500–10,000 people in Connecticut. #1 is Stepney, CT.

1. 25Sprague, Connecticut

   Better for first-time buyers than 80% of Connecticut towns

   Sprague is a town of 2,967 people, Connecticut. It also ranks easier by car than 94% of Connecticut towns and quieter than 80% of Connecticut towns.

   2,967 people · median home $273,500 · income $92,850 · Jan low 21°F · 28 in snow

   Full Sprague, Connecticut profile: weather, storms, schools, jobs →

2. 24New Milford, Connecticut

   Better for first-time buyers than 81% of Connecticut towns

   New Milford is a community of 7,160 people, Connecticut. It also ranks better for cycling than 86% of Connecticut towns and more of a college town than 75% of Connecticut towns.

   7,160 people · median home $331,900 · income $83,235 · Jan low 21°F · 47 in snow

   Full New Milford, Connecticut profile: weather, storms, schools, jobs →

3. 23Groton, Connecticut

   Better for first-time buyers than 81% of Connecticut towns

   Groton is a city of 9,387 people, Connecticut. It also ranks hipper than 98% of Connecticut towns and more walkable than 93% of Connecticut towns.

   9,387 people · median home $306,600 · income $79,577 · Jan low 23°F · 25 in snow

   Full Groton, Connecticut profile: weather, storms, schools, jobs →

4. 22Terryville, Connecticut

   Better for first-time buyers than 82% of Connecticut towns

   Terryville is a community of 5,202 people, Connecticut. It also ranks more walkable than 75% of Connecticut towns.

   5,202 people · median home $243,800 · income $72,813 · Jan low 17°F · 39 in snow

   Full Terryville, Connecticut profile: weather, storms, schools, jobs →

5. 21Branford Center, Connecticut

   Better for first-time buyers than 82% of Connecticut towns

   Branford Center is a community of 6,026 people, Connecticut. It also ranks hipper than 100% of Connecticut towns and more seaside character than 100% of Connecticut towns.

   6,026 people · median home $330,600 · income $74,150 · Jan low 23°F · 34 in snow

   Full Branford Center, Connecticut profile: weather, storms, schools, jobs →

6. 20Woodstock, Connecticut

   Better for first-time buyers than 83% of Connecticut towns

   Woodstock is a town of 8,221 people, Connecticut. It also ranks easier by car than 90% of Connecticut towns and more of a college town than 81% of Connecticut towns.

   8,221 people · median home $417,200 · income $112,011 · Jan low 15°F · 39 in snow

   Full Woodstock, Connecticut profile: weather, storms, schools, jobs →

7. 19Harwinton, Connecticut

   Better for first-time buyers than 85% of Connecticut towns

   Harwinton is a town of 5,484 people, Connecticut. It also ranks easier by car than 91% of Connecticut towns and quieter than 78% of Connecticut towns.

   5,484 people · median home $352,100 · income $129,643 · Jan low 15°F · 59 in snow

   Full Harwinton, Connecticut profile: weather, storms, schools, jobs →

8. 18Ashford, Connecticut

   Better for first-time buyers than 86% of Connecticut towns

   Ashford is a town of 4,191 people, Connecticut. The median home is worth $334,800 (typical Connecticut town: $376,000).

   4,191 people · median home $334,800 · income $121,926 · Jan low 19°F · 39 in snow

   Full Ashford, Connecticut profile: weather, storms, schools, jobs →

9. 17Colchester, Connecticut

   Better for first-time buyers than 86% of Connecticut towns

   Colchester is a community of 4,700 people, Connecticut. It also ranks better for retirees than 81% of Connecticut towns.

   4,700 people · median home $294,600 · income $86,760 · Jan low 18°F · 32 in snow

   Full Colchester, Connecticut profile: weather, storms, schools, jobs →

10. 16Long Hill, Connecticut

    Better for first-time buyers than 87% of Connecticut towns

    Long Hill is a community of 3,948 people, Connecticut. It also ranks better for young professionals than 99% of Connecticut towns and better for cycling than 99% of Connecticut towns.

    3,948 people · median home $175,600 · income $84,201 · Jan low 24°F · 25 in snow

    Full Long Hill, Connecticut profile: weather, storms, schools, jobs →

11. 15Watertown, Connecticut

    Better for first-time buyers than 88% of Connecticut towns

    Watertown is a community of 3,938 people, Connecticut. It also ranks more walkable than 71% of Connecticut towns.

    3,938 people · median home $293,300 · income $103,200 · Jan low 19°F · 47 in snow

    Full Watertown, Connecticut profile: weather, storms, schools, jobs →

12. 14Danielson, Connecticut

    Better for first-time buyers than 88% of Connecticut towns

    Danielson is a borough of 4,155 people, Connecticut. It also ranks better for cycling than 93% of Connecticut towns and more walkable than 81% of Connecticut towns.

    4,155 people · median home $224,600 · income $64,050 · Jan low 19°F · 62 in snow

    Full Danielson, Connecticut profile: weather, storms, schools, jobs →

13. 13Southwood Acres, Connecticut

    Better for first-time buyers than 89% of Connecticut towns

    Southwood Acres is a community of 7,879 people, Connecticut. It also ranks easier by car than 71% of Connecticut towns.

    7,879 people · median home $267,900 · income $110,286 · Jan low 19°F · 52 in snow

    Full Southwood Acres, Connecticut profile: weather, storms, schools, jobs →

14. 12Jewett City, Connecticut

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

    Jewett City is a borough of 3,328 people, Connecticut. It also ranks more walkable than 78% of Connecticut towns.

    3,328 people · median home $196,900 · income $55,530 · Jan low 21°F · 38 in snow

    Full Jewett City, Connecticut profile: weather, storms, schools, jobs →

15. 11Thompson, Connecticut

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

    Thompson is a town of 9,189 people, Connecticut. It also ranks quieter than 91% of Connecticut towns and easier by car than 81% of Connecticut towns.

    9,189 people · median home $291,900 · income $93,629 · Jan low 15°F · 39 in snow

    Full Thompson, Connecticut profile: weather, storms, schools, jobs →

16. 10Oxoboxo River, Connecticut

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

    Oxoboxo River is a community of 2,955 people, Connecticut. The median home is worth $246,200 (typical Connecticut town: $376,000).

    2,955 people · median home $246,200 · income $69,167 · Jan low 21°F · 28 in snow

    Full Oxoboxo River, Connecticut profile: weather, storms, schools, jobs →

17. 9Sandy Hook, Connecticut

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

    Sandy Hook is a community of 9,114 people, Connecticut. It also ranks better for families than 80% of Connecticut towns and more upscale than 77% of Connecticut towns.

    9,114 people · median home $501,200 · income $160,814 · Jan low 18°F · 49 in snow

    Full Sandy Hook, Connecticut profile: weather, storms, schools, jobs →

18. 8Winsted, Connecticut

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

    Winsted is a community of 7,192 people, Connecticut. It also ranks easier by car than 89% of Connecticut towns and better for a vacation home than 88% of Connecticut towns.

    7,192 people · median home $218,900 · income $64,871 · Jan low 14°F · 51 in snow

    Full Winsted, Connecticut profile: weather, storms, schools, jobs →

19. 7Thomaston, Connecticut

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

    Thomaston is a town of 7,442 people, Connecticut. It also ranks easier by car than 94% of Connecticut towns.

    7,442 people · median home $282,600 · income $103,218 · Jan low 17°F · 48 in snow

    Full Thomaston, Connecticut profile: weather, storms, schools, jobs →

20. 6North Canaan, Connecticut

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

    North Canaan is a town of 3,211 people, Connecticut. It also ranks hipper than 73% of Connecticut towns.

    3,211 people · median home $267,300 · income $71,976 · Jan low 14°F · 75 in snow

    Full North Canaan, Connecticut profile: weather, storms, schools, jobs →

21. 5Oronoque, Connecticut

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

    Oronoque is a community of 3,790 people, Connecticut. It also ranks hipper than 92% of Connecticut towns.

    3,790 people · median home $355,600 · income $72,417 · Jan low 18°F · 34 in snow

    Full Oronoque, Connecticut profile: weather, storms, schools, jobs →

22. 4Northwest Harwinton, Connecticut

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

    Northwest Harwinton is a community of 3,158 people, Connecticut. It also ranks easier by car than 98% of Connecticut towns and quieter than 75% of Connecticut towns.

    3,158 people · median home $330,500 · income $109,458 · Jan low 15°F · 59 in snow

    Full Northwest Harwinton, Connecticut profile: weather, storms, schools, jobs →

23. 3Long Hill, Connecticut

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

    Long Hill is a community of 8,039 people, Connecticut. It also ranks more walkable than 80% of Connecticut towns and more upscale than 78% of Connecticut towns.

    8,039 people · median home $487,800 · income $178,456 · Jan low 24°F · 34 in snow

    Full Long Hill, Connecticut profile: weather, storms, schools, jobs →

24. 2Lordship, Connecticut

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

    Lordship is a community of 2,954 people, Connecticut. It also ranks quieter than 95% of Connecticut towns and more seaside character than 95% of Connecticut towns.

    2,954 people · median home $465,200 · income $84,606 · Jan low 24°F · 34 in snow

    Full Lordship, Connecticut profile: weather, storms, schools, jobs →

25. 1Stepney, Connecticut

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

    Stepney is a community of 4,280 people, Connecticut. It also ranks more upscale than 75% of Connecticut towns and better for families than 74% of Connecticut towns.

    4,280 people · median home $475,800 · income $153,966 · Jan low 18°F · 44 in snow

    Full Stepney, Connecticut profile: weather, storms, schools, jobs →

Price vs ranking

More Connecticut rankings

• The 25 Best Small Towns to Retire in Connecticut
• The 25 Quietest Small Towns in Connecticut
• The 25 Most Affordable Small Towns in Connecticut
• The 25 Best Small Towns for Families in Connecticut
• The 21 Best Quiet, Affordable Small Towns to Retire in Connecticut
• 25 Small Towns in Connecticut With the Cheapest Homes
• 25 Small Towns in Connecticut With the Mildest Winters
• The 25 Most Walkable Small Towns in Connecticut
• 25 Small Towns in Connecticut With the Fewest Tornadoes Since 1950
• The 15 Best Affordable Small Towns for Remote Workers in Connecticut

Same ranking, other places

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• 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