The 25 Best Small Towns to Retire in Maryland

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

1. 25Paramount-Long Meadow, Maryland

   Better for retirees than 81% of Maryland towns

   Paramount-Long Meadow is a community of 2,658 people in Washington County, Maryland. The median home is worth $374,200 (typical Maryland town: $412,300).

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

   Full Paramount-Long Meadow, Maryland profile: weather, storms, schools, jobs →

2. 24Chester, Maryland

   Better for retirees than 81% of Maryland towns

   Chester is a community of 5,003 people in Queen Anne's County, Maryland. It also ranks more seaside character than 92% of Maryland towns and easier by car than 85% of Maryland towns.

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

   Full Chester, Maryland profile: weather, storms, schools, jobs →

3. 23Derwood, Maryland

   Better for retirees than 82% of Maryland towns

   Derwood is a community of 2,535 people in Montgomery County, Maryland. It also ranks better for young professionals than 99% of Maryland towns and more vibrant than 97% of Maryland towns.

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

   Full Derwood, Maryland profile: weather, storms, schools, jobs →

4. 22National Harbor, Maryland

   Better for retirees than 84% of Maryland towns

   

   National Harbor is a community of 5,509 people in Prince George's County, Maryland. It also ranks better for first-time buyers than 100% of Maryland towns and better for young professionals than 95% of Maryland towns.

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

   Full National Harbor, Maryland profile: weather, storms, schools, jobs →

5. 21Chevy Chase, Maryland

   Better for retirees than 85% of Maryland towns

   

   Chevy Chase is a town of 2,904 people in Montgomery County, Maryland. It also ranks more upscale than 99% of Maryland towns and better for cycling than 99% of Maryland towns.

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

   Full Chevy Chase, Maryland profile: weather, storms, schools, jobs →

6. 20Chestertown, Maryland

   Better for retirees than 86% of Maryland towns

   Chestertown is a town of 5,532 people in Kent County, Maryland. It also ranks more seaside character than 99% of Maryland towns and hipper than 97% of Maryland towns.

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

   Full Chestertown, Maryland profile: weather, storms, schools, jobs →

7. 19Leisure World, Maryland

   Better for retirees than 86% of Maryland towns

   

   Leisure World is a community of 9,215 people in Montgomery County, Maryland. It also ranks hipper than 98% of Maryland towns and better for first-time buyers than 78% of Maryland towns.

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

   Full Leisure World, Maryland profile: weather, storms, schools, jobs →

8. 18Fallston, Maryland

   Better for retirees than 86% of Maryland towns

   Fallston is a community of 9,306 people in Harford County, Maryland. It also ranks better for families than 96% of Maryland towns and more of a college town than 89% of Maryland towns.

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

   Full Fallston, Maryland profile: weather, storms, schools, jobs →

9. 17Stevensville, Maryland

   Better for retirees than 87% of Maryland towns

   

   Stevensville is a community of 7,442 people in Queen Anne's County, Maryland. It also ranks more seaside character than 89% of Maryland towns and easier by car than 84% of Maryland towns.

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

   Full Stevensville, Maryland profile: weather, storms, schools, jobs →

10. 16Braddock Heights, Maryland

    Better for retirees than 88% of Maryland towns

    

    Braddock Heights is a community of 3,075 people in Frederick County, Maryland. It also ranks better for first-time buyers than 96% of Maryland towns and better for families than 91% of Maryland towns.

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

    Full Braddock Heights, Maryland profile: weather, storms, schools, jobs →

11. 15Maugansville, Maryland

    Better for retirees than 89% of Maryland towns

    Maugansville is a community of 3,669 people in Washington County, Maryland. It also ranks hipper than 90% of Maryland towns and better for first-time buyers than 72% of Maryland towns.

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

    Full Maugansville, Maryland profile: weather, storms, schools, jobs →

12. 14Riva, Maryland

    Better for retirees than 89% of Maryland towns

    Riva is a community of 4,257 people in Anne Arundel County, Maryland. It also ranks better for families than 94% of Maryland towns and more seaside character than 93% of Maryland towns.

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

    Full Riva, Maryland profile: weather, storms, schools, jobs →

13. 13West Ocean City, Maryland

    Better for retirees than 89% of Maryland towns

    West Ocean City is a community of 4,952 people in Worcester County, Maryland. It also ranks better for a vacation home than 99% of Maryland towns and more seaside character than 87% of Maryland towns.

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

    Full West Ocean City, Maryland profile: weather, storms, schools, jobs →

14. 12Hampton, Maryland

    Better for retirees than 90% of Maryland towns

    Hampton is a community of 5,180 people in Baltimore County, Maryland. It also ranks better for families than 94% of Maryland towns and more upscale than 93% of Maryland towns.

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

    Full Hampton, Maryland profile: weather, storms, schools, jobs →

15. 11Poolesville, Maryland

    Better for retirees than 90% of Maryland towns

    Poolesville is a town of 5,742 people in Montgomery County, Maryland. It also ranks better for families than 98% of Maryland towns and more upscale than 94% of Maryland towns.

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

    Full Poolesville, Maryland profile: weather, storms, schools, jobs →

16. 10Friendship Heights Village, Maryland

    Better for retirees than 91% of Maryland towns

    Friendship Heights Village is a community of 5,360 people in Montgomery County, Maryland. It also ranks better for young professionals than 100% of Maryland towns and more vibrant than 100% of Maryland towns.

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

    Full Friendship Heights Village, Maryland profile: weather, storms, schools, jobs →

17. 9Ashton-Sandy Spring, Maryland

    Better for retirees than 91% of Maryland towns

    Ashton-Sandy Spring is a community of 5,746 people in Montgomery County, Maryland. It also ranks more upscale than 90% of Maryland towns and better for young professionals than 77% of Maryland towns.

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

    Full Ashton-Sandy Spring, Maryland profile: weather, storms, schools, jobs →

18. 8Brookmont, Maryland

    Better for retirees than 92% of Maryland towns

    Brookmont is a community of 3,751 people in Montgomery County, Maryland. It also ranks more upscale than 99% of Maryland towns and better for families than 93% of Maryland towns.

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

    Full Brookmont, Maryland profile: weather, storms, schools, jobs →

19. 7La Vale, Maryland

    Better for retirees than 92% of Maryland towns

    La Vale is a community of 4,201 people in Allegany County, Maryland. It also ranks quieter than 88% of Maryland towns and easier by car than 84% of Maryland towns.

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

    Full La Vale, Maryland profile: weather, storms, schools, jobs →

20. 6Herald Harbor, Maryland

    Better for retirees than 94% of Maryland towns

    Herald Harbor is a community of 2,869 people in Anne Arundel County, Maryland. It also ranks more seaside character than 92% of Maryland towns and quieter than 85% of Maryland towns.

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

    Full Herald Harbor, Maryland profile: weather, storms, schools, jobs →

21. 5Jarrettsville, Maryland

    Better for retirees than 94% of Maryland towns

    Jarrettsville is a community of 2,888 people in Harford County, Maryland. It also ranks better for families than 94% of Maryland towns and quieter than 90% of Maryland towns.

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

    Full Jarrettsville, Maryland profile: weather, storms, schools, jobs →

22. 4Pleasant Hills, Maryland

    Better for retirees than 96% of Maryland towns

    Pleasant Hills is a community of 3,998 people in Harford County, Maryland. It also ranks better for families than 94% of Maryland towns and quieter than 85% of Maryland towns.

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

    Full Pleasant Hills, Maryland profile: weather, storms, schools, jobs →

23. 3Kingsville, Maryland

    Better for retirees than 96% of Maryland towns

    Kingsville is a community of 4,358 people in Baltimore County, Maryland. It also ranks better for families than 92% of Maryland towns and quieter than 89% of Maryland towns.

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

    Full Kingsville, Maryland profile: weather, storms, schools, jobs →

24. 2Solomons, Maryland

    Better for retirees than 97% of Maryland towns

    Solomons is a community of 2,650 people in Calvert County, Maryland. It also ranks quieter than 79% of Maryland towns and better for young professionals than 78% of Maryland towns.

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

    Full Solomons, Maryland profile: weather, storms, schools, jobs →

25. 1Darnestown, Maryland

    Better for retirees than 98% of Maryland towns

    Darnestown is a community of 6,723 people in Montgomery County, Maryland. It also ranks better for families than 97% of Maryland towns and more upscale than 95% of Maryland towns.

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

    Full Darnestown, Maryland profile: weather, storms, schools, jobs →

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

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• 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