The 25 Best Small Towns to Retire in New York

Ranked on The Town Files lifestyle rankings among 707 towns of 2,500–10,000 people in New York. #1 is Rhinebeck, NY.

1. 25Heritage Hills, New York

   Better for retirees than 97% of New York towns

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

2. 24Ulysses, New York

   Better for retirees than 97% of New York towns

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

3. 23North Salem, New York

   Better for retirees than 97% of New York towns

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

4. 22Highland, New York

   Better for retirees than 97% of New York towns

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

5. 21Philipstown, New York

   Better for retirees than 97% of New York towns

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

6. 20Clarence, New York

   Better for retirees than 98% of New York towns

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

7. 19Bedford Hills, New York

   Better for retirees than 98% of New York towns

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

8. 18Copake, New York

   Better for retirees than 98% of New York towns

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

9. 17Cutchogue, New York

   Better for retirees than 98% of New York towns

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

10. 16Livingston, New York

    Better for retirees than 98% of New York towns

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

11. 15Northwest Harbor, New York

    Better for retirees than 98% of New York towns

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

12. 14North Hills, New York

    Better for retirees than 98% of New York towns

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

13. 13Skaneateles, New York

    Better for retirees than 99% of New York towns

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

14. 12Coxsackie, New York

    Better for retirees than 99% of New York towns

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

15. 11Sag Harbor, New York

    Better for retirees than 99% of New York towns

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

16. 10North East, New York

    Better for retirees than 99% of New York towns

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

17. 9Otsego, New York

    Better for retirees than 99% of New York towns

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

18. 8Washington, New York

    Better for retirees than 99% of New York towns

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

19. 7Skaneateles, New York

    Better for retirees than 99% of New York towns

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

20. 6Piermont, New York

    Better for retirees than 100% of New York towns

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

21. 5Woodstock, New York

    Better for retirees than 100% of New York towns

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

22. 4Rhinebeck, New York

    Better for retirees than 100% of New York towns

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

23. 3Caroline, New York

    Better for retirees than 100% of New York towns

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

24. 2Woodstock, New York

    Better for retirees than 100% of New York towns

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

25. 1Rhinebeck, New York

    Better for retirees than 100% of New York towns

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

Price vs ranking

More New York rankings

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• The 25 Best Small Towns for Families in New York
• The 25 Best Quiet, Affordable Small Towns to Retire in New York
• 25 Small Towns in New York With the Cheapest Homes
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• The 25 Best Small Towns for First-Time Home Buyers in New York
• The 24 Best Affordable Small Towns to Retire in New York With Mild Winters

Same ranking, other places

• The 50 Best Small Towns to Retire in America
• The 25 Best Small Towns to Retire in Pennsylvania
• The 25 Best Small Towns to Retire in Michigan
• The 25 Best Small Towns to Retire in Texas
• The 25 Best Small Towns to Retire in California
• The 25 Best Small Towns to Retire in New Jersey
• The 25 Best Small Towns to Retire in Florida
• The 25 Best Small Towns to Retire in Wisconsin
• The 25 Best Small Towns to Retire in Ohio
• The 25 Best Small Towns to Retire in Illinois