The 25 Best Small Towns to Retire in New York

Ranked on The Town Files lifestyle rankings among 707 towns of 500–10,000 people in New York. #1 is Rhinebeck, NY.

1. 25Heritage Hills, New York

   Better for retirees than 97% of New York towns

   Heritage Hills is a community of 4,511 people in Westchester County, New York. It also ranks better for first-time buyers than 92% of New York towns and more upscale than 91% of New York towns.

   4,511 people · Westchester County · median home $524,800 · income $105,546 · Jan low 17°F · 40 in snow

   Full Heritage Hills, New York profile: weather, storms, schools, jobs →

2. 24Ulysses, New York

   Better for retirees than 97% of New York towns

   Ulysses is a town of 4,890 people in Tompkins County, New York. It also ranks hipper than 87% of New York towns and more of a college town than 81% of New York towns.

   4,890 people · Tompkins County · median home $274,500 · income $71,400 · Jan low 14°F · 62 in snow

   Full Ulysses, New York profile: weather, storms, schools, jobs →

3. 23North Salem, New York

   Better for retirees than 97% of New York towns

   North Salem is a town of 5,243 people in Westchester County, New York. It also ranks more upscale than 97% of New York towns and better for families than 95% of New York towns.

   5,243 people · Westchester County · median home $670,600 · income $178,750 · Jan low 18°F · 45 in snow

   Full North Salem, New York profile: weather, storms, schools, jobs →

4. 22Highland, New York

   Better for retirees than 97% of New York towns

   Highland is a community of 6,385 people in Ulster County, New York. It also ranks better for cycling than 99% of New York towns and better for young professionals than 98% of New York towns.

   6,385 people · Ulster County · median home $415,900 · income $101,917 · Jan low 19°F · 53 in snow

   Full Highland, New York profile: weather, storms, schools, jobs →

5. 21Philipstown, New York

   Better for retirees than 97% of New York towns

   Philipstown is a town of 9,831 people in Putnam County, New York. It also ranks more upscale than 91% of New York towns and better for families than 84% of New York towns.

   9,831 people · Putnam County · median home $615,000 · income $140,557 · Jan low 21°F · 36 in snow

   Full Philipstown, New York profile: weather, storms, schools, jobs →

6. 20Clarence, New York

   Better for retirees than 98% of New York towns

   Clarence is a community of 2,733 people in Erie County, New York. It also ranks better for young professionals than 92% of New York towns and better for cycling than 88% of New York towns.

   2,733 people · Erie County · median home $338,800 · income $88,269 · Jan low 19°F · 95 in snow

   Full Clarence, New York profile: weather, storms, schools, jobs →

7. 19Bedford Hills, New York

   Better for retirees than 98% of New York towns

   Bedford Hills is a community of 3,239 people in Westchester County, New York. It also ranks better for young professionals than 96% of New York towns and better for first-time buyers than 88% of New York towns.

   3,239 people · Westchester County · median home $487,300 · income $94,024 · Jan low 17°F · 40 in snow

   Full Bedford Hills, New York profile: weather, storms, schools, jobs →

8. 18Copake, New York

   Better for retirees than 98% of New York towns

   Copake is a town of 3,346 people in Columbia County, New York. It also ranks quieter than 92% of New York towns and better for a vacation home than 91% of New York towns.

   3,346 people · Columbia County · median home $325,000 · income $113,611 · Jan low 14°F · 50 in snow

   Full Copake, New York profile: weather, storms, schools, jobs →

9. 17Cutchogue, New York

   Better for retirees than 98% of New York towns

   Cutchogue is a community of 3,437 people in Suffolk County, New York. It also ranks better for a vacation home than 99% of New York towns and more seaside character than 97% of New York towns.

   3,437 people · Suffolk County · median home $917,800 · income $143,472 · Jan low 23°F · 27 in snow

   Full Cutchogue, New York profile: weather, storms, schools, jobs →

10. 16Livingston, New York

    Better for retirees than 98% of New York towns

    Livingston is a town of 3,628 people in Columbia County, New York. It also ranks better for cycling than 99% of New York towns and better for a vacation home than 92% of New York towns.

    3,628 people · Columbia County · median home $309,100 · income $54,024 · Jan low 18°F · 31 in snow

    Full Livingston, New York profile: weather, storms, schools, jobs →

11. 15Northwest Harbor, New York

    Better for retirees than 98% of New York towns

    Northwest Harbor is a community of 4,637 people in Suffolk County, New York. It also ranks better for a vacation home than 99% of New York towns and more seaside character than 95% of New York towns.

    4,637 people · Suffolk County · median home $1,573,300 · income $160,375 · Jan low 23°F · 27 in snow

    Full Northwest Harbor, New York profile: weather, storms, schools, jobs →

12. 14North Hills, New York

    Better for retirees than 98% of New York towns

    North Hills is a village of 5,464 people in Nassau County, New York. It also ranks more upscale than 98% of New York towns and better transit than 87% of New York towns.

    5,464 people · Nassau County · median home $1,228,800 · income $173,315 · Jan low 27°F · 19 in snow

    Full North Hills, New York profile: weather, storms, schools, jobs →

13. 13Skaneateles, New York

    Better for retirees than 99% of New York towns

    Skaneateles is a village of 2,533 people in Onondaga County, New York. It also ranks more upscale than 86% of New York towns and better for families than 83% of New York towns.

    2,533 people · Onondaga County · median home $647,100 · income $125,625 · Jan low 15°F · 106 in snow

    Full Skaneateles, New York profile: weather, storms, schools, jobs →

14. 12Coxsackie, New York

    Better for retirees than 99% of New York towns

    Coxsackie is a village of 2,746 people in Greene County, New York. It also ranks better for young professionals than 96% of New York towns and more of a college town than 89% of New York towns.

    2,746 people · Greene County · median home $300,300 · income $70,500 · Jan low 18°F · 31 in snow

    Full Coxsackie, New York profile: weather, storms, schools, jobs →

15. 11Sag Harbor, New York

    Better for retirees than 99% of New York towns

    Sag Harbor is a village of 2,772 people in Suffolk County, New York. It also ranks better for a vacation home than 100% of New York towns and more seaside character than 96% of New York towns.

    2,772 people · Suffolk County · median home $1,615,900 · income $129,821 · Jan low 23°F · 27 in snow

    Full Sag Harbor, New York profile: weather, storms, schools, jobs →

16. 10North East, New York

    Better for retirees than 99% of New York towns

    North East is a town of 2,971 people in Dutchess County, New York. It also ranks better for first-time buyers than 99% of New York towns and better for a vacation home than 92% of New York towns.

    2,971 people · Dutchess County · median home $334,000 · income $84,757 · Jan low 14°F · 54 in snow

    Full North East, New York profile: weather, storms, schools, jobs →

17. 9Otsego, New York

    Better for retirees than 99% of New York towns

    Otsego is a town of 3,641 people in Otsego County, New York. It also ranks better for a vacation home than 97% of New York towns and hipper than 96% of New York towns.

    3,641 people · Otsego County · median home $352,600 · income $72,891 · Jan low 14°F · 86 in snow

    Full Otsego, New York profile: weather, storms, schools, jobs →

18. 8Washington, New York

    Better for retirees than 99% of New York towns

    Washington is a town of 4,522 people in Dutchess County, New York. It also ranks hipper than 95% of New York towns and better for young professionals than 81% of New York towns.

    4,522 people · Dutchess County · median home $532,300 · income $102,303 · Jan low 16°F · 56 in snow

    Full Washington, New York profile: weather, storms, schools, jobs →

19. 7Skaneateles, New York

    Better for retirees than 99% of New York towns

    Skaneateles is a town of 7,112 people in Onondaga County, New York. It also ranks more upscale than 87% of New York towns and better for families than 84% of New York towns.

    7,112 people · Onondaga County · median home $457,800 · income $103,545 · Jan low 15°F · 106 in snow

    Full Skaneateles, New York profile: weather, storms, schools, jobs →

20. 6Piermont, New York

    Better for retirees than 100% of New York towns

    Piermont is a village of 2,517 people in Rockland County, New York. It also ranks hipper than 100% of New York towns and better for young professionals than 97% of New York towns.

    2,517 people · Rockland County · median home $652,900 · income $140,450 · Jan low 23°F · 33 in snow

    Full Piermont, New York profile: weather, storms, schools, jobs →

21. 5Woodstock, New York

    Better for retirees than 100% of New York towns

    Woodstock is a community of 2,521 people in Ulster County, New York. It also ranks hipper than 99% of New York towns and better for a vacation home than 99% of New York towns.

    2,521 people · Ulster County · median home $675,600 · income $52,091 · Jan low 12°F · 86 in snow

    Full Woodstock, New York profile: weather, storms, schools, jobs →

22. 4Rhinebeck, New York

    Better for retirees than 100% of New York towns

    Rhinebeck is a village of 2,697 people in Dutchess County, New York. It also ranks hipper than 99% of New York towns and more vibrant than 91% of New York towns.

    2,697 people · Dutchess County · median home $492,600 · income $70,496 · Jan low 11°F · 61 in snow

    Full Rhinebeck, New York profile: weather, storms, schools, jobs →

23. 3Caroline, New York

    Better for retirees than 100% of New York towns

    Caroline is a town of 3,334 people in Tompkins County, New York. It also ranks better for young professionals than 96% of New York towns and better for first-time buyers than 94% of New York towns.

    3,334 people · Tompkins County · median home $234,200 · income $80,855 · Jan low 13°F · 63 in snow

    Full Caroline, New York profile: weather, storms, schools, jobs →

24. 2Woodstock, New York

    Better for retirees than 100% of New York towns

    Woodstock is a town of 6,287 people in Ulster County, New York. It also ranks hipper than 99% of New York towns and better for a vacation home than 99% of New York towns.

    6,287 people · Ulster County · median home $604,700 · income $92,118 · Jan low 12°F · 86 in snow

    Full Woodstock, New York profile: weather, storms, schools, jobs →

25. 1Rhinebeck, New York

    Better for retirees than 100% of New York towns

    Rhinebeck is a town of 7,596 people in Dutchess County, New York. It also ranks hipper than 91% of New York towns and more upscale than 81% of New York towns.

    7,596 people · Dutchess County · median home $521,800 · income $93,284 · Jan low 11°F · 60 in snow

    Full Rhinebeck, New York profile: weather, storms, schools, jobs →

Price vs ranking

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Same ranking, other places

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