The 25 Best Small Towns to Retire in Maryland

Ranked on The Town Files lifestyle rankings among 124 towns of 2,500–10,000 people in Maryland. #1 is Darnestown, MD.

1. 25Paramount-Long Meadow, Maryland

   Better for retirees than 81% of Maryland towns

   2,658 people · Washington County · median home $374,200 · income $122,262 · Jan low 22°F · 31 in snow

2. 24Chester, Maryland

   Better for retirees than 81% of Maryland towns

   5,003 people · Queen Anne's County · median home $487,400 · income $102,399 · Jan low 29°F · 15 in snow

3. 23Derwood, Maryland

   Better for retirees than 82% of Maryland towns

   2,535 people · Montgomery County · median home $719,800 · income $118,194 · Jan low 27°F · 23 in snow

4. 22National Harbor, Maryland

   Better for retirees than 84% of Maryland towns

   5,509 people · Prince George's County · median home $472,500 · income $109,707 · Jan low 27°F · 14 in snow

5. 21Chevy Chase, Maryland

   Better for retirees than 85% of Maryland towns

   2,904 people · Montgomery County · median home $1,670,600 · income $250,001 · Jan low 26°F · 6 in snow

6. 20Chestertown, Maryland

   Better for retirees than 86% of Maryland towns

   5,532 people · Kent County · median home $344,000 · income $54,346 · Jan low 27°F · 17 in snow

7. 19Leisure World, Maryland

   Better for retirees than 86% of Maryland towns

   9,215 people · Montgomery County · median home $274,800 · income $62,011 · Jan low 27°F · 16 in snow

8. 18Fallston, Maryland

   Better for retirees than 86% of Maryland towns

   9,306 people · Harford County · median home $562,300 · income $154,688 · Jan low 25°F · 30 in snow

9. 17Stevensville, Maryland

   Better for retirees than 87% of Maryland towns

   7,442 people · Queen Anne's County · median home $481,200 · income $115,357 · Jan low 29°F · 16 in snow

10. 16Braddock Heights, Maryland

    Better for retirees than 88% of Maryland towns

    3,075 people · Frederick County · median home $537,700 · income $124,000 · Jan low 27°F · 31 in snow

11. 15Maugansville, Maryland

    Better for retirees than 89% of Maryland towns

    3,669 people · Washington County · median home $321,800 · income $79,019 · Jan low 25°F · 31 in snow

12. 14Riva, Maryland

    Better for retirees than 89% of Maryland towns

    4,257 people · Anne Arundel County · median home $644,500 · income $176,094 · Jan low 30°F · 16 in snow

13. 13West Ocean City, Maryland

    Better for retirees than 89% of Maryland towns

    4,952 people · Worcester County · median home $423,700 · income $97,165 · Jan low 28°F · 8 in snow

14. 12Hampton, Maryland

    Better for retirees than 90% of Maryland towns

    5,180 people · Baltimore County · median home $615,300 · income $170,688 · Jan low 30°F · 27 in snow

15. 11Poolesville, Maryland

    Better for retirees than 90% of Maryland towns

    5,742 people · Montgomery County · median home $752,300 · income $205,919 · Jan low 25°F · 28 in snow

16. 10Friendship Heights Village, Maryland

    Better for retirees than 91% of Maryland towns

    5,360 people · Montgomery County · median home $484,300 · income $119,384 · Jan low 26°F · 6 in snow

17. 9Ashton-Sandy Spring, Maryland

    Better for retirees than 91% of Maryland towns

    5,746 people · Montgomery County · median home $809,200 · income $174,063 · Jan low 26°F · 16 in snow

18. 8Brookmont, Maryland

    Better for retirees than 92% of Maryland towns

    3,751 people · Montgomery County · median home $1,361,100 · income $247,150 · Jan low 26°F · 6 in snow

19. 7La Vale, Maryland

    Better for retirees than 92% of Maryland towns

    4,201 people · Allegany County · median home $170,800 · income $77,500 · Jan low 23°F · 29 in snow

20. 6Herald Harbor, Maryland

    Better for retirees than 94% of Maryland towns

    2,869 people · Anne Arundel County · median home $598,600 · income $147,778 · Jan low 30°F · 19 in snow

21. 5Jarrettsville, Maryland

    Better for retirees than 94% of Maryland towns

    2,888 people · Harford County · median home $476,800 · income $146,635 · Jan low 25°F · 29 in snow

22. 4Pleasant Hills, Maryland

    Better for retirees than 96% of Maryland towns

    3,998 people · Harford County · median home $532,900 · income $166,339 · Jan low 25°F · 29 in snow

23. 3Kingsville, Maryland

    Better for retirees than 96% of Maryland towns

    4,358 people · Baltimore County · median home $567,400 · income $128,563 · Jan low 25°F · 25 in snow

24. 2Solomons, Maryland

    Better for retirees than 97% of Maryland towns

    2,650 people · Calvert County · median home $436,800 · income $94,963 · Jan low 30°F · 13 in snow

25. 1Darnestown, Maryland

    Better for retirees than 98% of Maryland towns

    6,723 people · Montgomery County · median home $958,200 · income $232,135 · Jan low 27°F · 27 in snow

Price vs ranking

More Maryland rankings

• The 25 Quietest Small Towns in Maryland
• The 25 Most Affordable Small Towns in Maryland
• The 25 Best Small Towns for Families in Maryland
• The 19 Best Quiet, Affordable Small Towns to Retire in Maryland
• 25 Small Towns in Maryland With the Cheapest Homes
• 25 Small Towns in Maryland With the Mildest Winters
• The 25 Most Walkable Small Towns in Maryland
• 25 Small Towns in Maryland With the Fewest Tornadoes Since 1950
• The 25 Best Small Towns for First-Time Home Buyers in Maryland
• The 18 Best Affordable Small Towns for Remote Workers in Maryland

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 New York
• 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