The 21 Best Affordable Small Towns to Retire in Maryland With Mild Winters

Ranked on The Town Files lifestyle rankings among 244 towns of 500–10,000 people in Maryland, scoring every town on all of these at once. #1 is Piney Point, MD.

1. 21Middletown, Maryland

   Retirement: 76th percentile · January average low (°F): 51st percentile · Home value ÷ income: 83rd percentile

   Middletown is a town of 4,943 people in Frederick County, Maryland. Homes have a median value of $554,800 against household income of $173,333; January lows average 27°F.

   4,943 people · Frederick County · median home $554,800 · income $173,333 · Jan low 27°F · 31 in snow

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

2. 20Kingstown, Maryland

   Retirement: 73rd percentile · January average low (°F): 60th percentile · Home value ÷ income: 87th percentile

   Kingstown is a community of 1,689 people in Queen Anne's County, Maryland. Homes have a median value of $293,000 against household income of $93,625; January lows average 27°F.

   1,689 people · Queen Anne's County · median home $293,000 · income $93,625 · Jan low 27°F · 17 in snow

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

3. 19Rock Hall, Maryland

   Retirement: 100th percentile · January average low (°F): 60th percentile · Home value ÷ income: 67th percentile

   Rock Hall is a town of 1,198 people in Kent County, Maryland. Homes have a median value of $262,000 against household income of $74,597; January lows average 27°F.

   1,198 people · Kent County · median home $262,000 · income $74,597 · Jan low 27°F · 17 in snow

   Full Rock Hall, Maryland profile: weather, storms, schools, jobs →

4. 18Sharptown, Maryland

   Retirement: 55th percentile · January average low (°F): 79th percentile · Home value ÷ income: 97th percentile

   Sharptown is a town of 691 people in Wicomico County, Maryland. Homes have a median value of $192,500 against household income of $85,938; January lows average 29°F.

   691 people · Wicomico County · median home $192,500 · income $85,938 · Jan low 29°F · 10 in snow

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

5. 17Butlertown, Maryland

   Retirement: 80th percentile · January average low (°F): 60th percentile · Home value ÷ income: 91st percentile

   Butlertown is a community of 520 people in Kent County, Maryland. Homes have a median value of $209,500 against household income of $72,991; January lows average 27°F.

   520 people · Kent County · median home $209,500 · income $72,991 · Jan low 27°F · 17 in snow

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

6. 16Preston, Maryland

   Retirement: 58th percentile · January average low (°F): 80th percentile · Home value ÷ income: 94th percentile

   Preston is a town of 673 people in Caroline County, Maryland. Homes have a median value of $267,000 against household income of $100,000; January lows average 29°F.

   673 people · Caroline County · median home $267,000 · income $100,000 · Jan low 29°F · 14 in snow

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

7. 15Galesville, Maryland

   Retirement: 87th percentile · January average low (°F): 88th percentile · Home value ÷ income: 57th percentile

   Galesville is a community of 623 people in Anne Arundel County, Maryland. Homes have a median value of $752,200 against household income of $205,205; January lows average 30°F.

   623 people · Anne Arundel County · median home $752,200 · income $205,205 · Jan low 30°F · 15 in snow

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

8. 14Riva, Maryland

   Retirement: 89th percentile · January average low (°F): 88th percentile · Home value ÷ income: 57th percentile

   Riva is a community of 4,257 people in Anne Arundel County, Maryland. Homes have a median value of $644,500 against household income of $176,094; January lows average 30°F.

   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 →

9. 13Galena, Maryland

   Retirement: 93rd percentile · January average low (°F): 60th percentile · Home value ÷ income: 83rd percentile

   Galena is a town of 539 people in Kent County, Maryland. Homes have a median value of $281,000 against household income of $88,958; January lows average 27°F.

   539 people · Kent County · median home $281,000 · income $88,958 · Jan low 27°F · 16 in snow

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

10. 12Shady Side, Maryland

    Retirement: 71st percentile · January average low (°F): 88th percentile · Home value ÷ income: 77th percentile

    Shady Side is a community of 5,806 people in Anne Arundel County, Maryland. Homes have a median value of $503,500 against household income of $153,661; January lows average 30°F.

    5,806 people · Anne Arundel County · median home $503,500 · income $153,661 · Jan low 30°F · 15 in snow

    Full Shady Side, Maryland profile: weather, storms, schools, jobs →

11. 11Lusby, Maryland

    Retirement: 59th percentile · January average low (°F): 84th percentile · Home value ÷ income: 93rd percentile

    Lusby is a community of 2,072 people in Calvert County, Maryland. Homes have a median value of $423,800 against household income of $151,711; January lows average 30°F.

    2,072 people · Calvert County · median home $423,800 · income $151,711 · Jan low 30°F · 13 in snow

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

12. 10Adamstown, Maryland

    Retirement: 99th percentile · January average low (°F): 51st percentile · Home value ÷ income: 87th percentile

    Adamstown is a community of 2,331 people in Frederick County, Maryland. Homes have a median value of $601,700 against household income of $195,625; January lows average 27°F.

    2,331 people · Frederick County · median home $601,700 · income $195,625 · Jan low 27°F · 32 in snow

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

13. 9Wildewood, Maryland

    Retirement: 66th percentile · January average low (°F): 84th percentile · Home value ÷ income: 89th percentile

    Wildewood is a community of 7,821 people in St. Mary's County, Maryland. Homes have a median value of $383,400 against household income of $126,890; January lows average 30°F.

    7,821 people · St. Mary's County · median home $383,400 · income $126,890 · Jan low 30°F · 13 in snow

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

14. 8Garrison, Maryland

    Retirement: 66th percentile · January average low (°F): 91st percentile · Home value ÷ income: 83rd percentile

    Garrison is a community of 9,487 people in Baltimore County, Maryland. Homes have a median value of $331,600 against household income of $102,423; January lows average 30°F.

    9,487 people · Baltimore County · median home $331,600 · income $102,423 · Jan low 30°F · 27 in snow

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

15. 7Hampton, Maryland

    Retirement: 90th percentile · January average low (°F): 91st percentile · Home value ÷ income: 61st percentile

    Hampton is a community of 5,180 people in Baltimore County, Maryland. Homes have a median value of $615,300 against household income of $170,688; January lows average 30°F.

    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 →

16. 6Cecilton, Maryland

    Retirement: 89th percentile · January average low (°F): 60th percentile · Home value ÷ income: 93rd percentile

    Cecilton is a town of 676 people in Cecil County, Maryland. Homes have a median value of $241,800 against household income of $87,813; January lows average 27°F.

    676 people · Cecil County · median home $241,800 · income $87,813 · Jan low 27°F · 18 in snow

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

17. 5Callaway, Maryland

    Retirement: 61st percentile · January average low (°F): 84th percentile · Home value ÷ income: 97th percentile

    Callaway is a community of 1,779 people in St. Mary's County, Maryland. Homes have a median value of $364,700 against household income of $160,341; January lows average 30°F.

    1,779 people · St. Mary's County · median home $364,700 · income $160,341 · Jan low 30°F · 13 in snow

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

18. 4Mount Vernon, Maryland

    Retirement: 66th percentile · January average low (°F): 80th percentile · Home value ÷ income: 100th percentile

    Mount Vernon is a community of 761 people in Somerset County, Maryland. Homes have a median value of $163,500 against household income of $113,938; January lows average 29°F.

    761 people · Somerset County · median home $163,500 · income $113,938 · Jan low 29°F · 9 in snow

    Full Mount Vernon, Maryland profile: weather, storms, schools, jobs →

19. 3Queenstown, Maryland

    Retirement: 99th percentile · January average low (°F): 78th percentile · Home value ÷ income: 83rd percentile

    Queenstown is a town of 705 people in Queen Anne's County, Maryland. Homes have a median value of $384,800 against household income of $122,031; January lows average 29°F.

    705 people · Queen Anne's County · median home $384,800 · income $122,031 · Jan low 29°F · 16 in snow

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

20. 2Crisfield, Maryland

    Retirement: 91st percentile · January average low (°F): 84th percentile · Home value ÷ income: 93rd percentile

    Crisfield is a city of 2,475 people in Somerset County, Maryland. Homes have a median value of $137,900 against household income of $50,139; January lows average 30°F.

    2,475 people · Somerset County · median home $137,900 · income $50,139 · Jan low 30°F · 8 in snow

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

21. 1Piney Point, Maryland

    Retirement: 82nd percentile · January average low (°F): 100th percentile · Home value ÷ income: 95th percentile

    Piney Point is a community of 980 people in St. Mary's County, Maryland. Homes have a median value of $336,600 against household income of $129,018; January lows average 30°F.

    980 people · St. Mary's County · median home $336,600 · income $129,018 · Jan low 30°F · 12 in snow

    Full Piney Point, Maryland profile: weather, storms, schools, jobs →

Price vs ranking

More Maryland rankings

• The 25 Best Small Towns to Retire in Maryland
• 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 25 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

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