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Single-Family Homes in Leonardtown, MD
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3 bedsNew constructionWith a pool

Single-Family Homes in Leonardtown, MD

Single-Family Homes in Leonardtown, MD

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24 of 25 Listings
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Single-Family Homes in Leonardtown, MD

24 of 25 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 43146 N Megan Ln — photo14Active

    $319,000

    3 bd · 1 ba · 2,068 sqft

    43146 N Megan Ln, Leonardtown, MD

    Lewie A Aldridge III · Berkshire Hathaway HomeServices PenFed Realty

  2. 21395 Fairwood Ct — photo74Active

    $690,000

    4 bd · 4 ba · 4,066 sqft

    21395 Fairwood Ct, Leonardtown, MD

    Lauren Coble Garner · EXP Realty, LLC

  3. 44450 Schumann Way — photo74Active

    $695,000

    5 bd · 3 ba · 2,953 sqft

    44450 Schumann Way, Leonardtown, MD

    Jesieryl U Hartzer · CENTURY 21 New Millennium

  4. 23444 Lindsay Dr — photo43Active

    $639,900

    4 bd · 4 ba · 3,340 sqft

    23444 Lindsay Dr, Leonardtown, MD

    Natalya P. Ford · RE/MAX One

  5. 22601 Avenmar Dr — photoPrice Reduced91Active

    $699,000

    5 bd · 4 ba · 5,484 sqft

    22601 Avenmar Dr, Leonardtown, MD

    Jennifer L Goddard · CENTURY 21 New Millennium

  6. 40659 Klear Ct — photoPrice Reduced54Active

    $449,500

    4 bd · 3 ba · 2,774 sqft

    40659 Klear Ct, Leonardtown, MD

    Christopher W Blondin · Baldus Real Estate, Inc.

  7. 23354 Lindsay Dr — photoPrice Reduced1Active

    $609,900

    4 bd · 4 ba · 2,736 sqft

    23354 Lindsay Dr, Leonardtown, MD

    Dorothy M Bistransin · Redfin Corp

  8. 41524 Fairwood Ct — photo28Active

    $600,000

    4 bd · 3 ba · 3,793 sqft

    41524 Fairwood Ct, Leonardtown, MD

    William Rabbitt · The Southside Group Real Estate

  9. 40751 Merlin Way — photoPrice Reduced44Active

    $635,000

    5 bd · 3 ba · 2,601 sqft

    40751 Merlin Way, Leonardtown, MD

    Tracy A Trammel · Metro City Realty

  10. 20410 Chingville Rd — photo28Active

    $450,000

    4 bd · 3 ba · 2,604 sqft

    20410 Chingville Rd, Leonardtown, MD

    William Rabbitt · The Southside Group Real Estate

  11. 41888 Jenkins Ct — photo41Active

    $550,000

    4 bd · 4 ba · 2,562 sqft

    41888 Jenkins Ct, Leonardtown, MD

    Wayne A Floyd · RE/MAX One

  12. 23214 Dairy Barn Dr — photo44Active

    $695,000

    5 bd · 4 ba · 4,084 sqft

    23214 Dairy Barn Dr, Leonardtown, MD

    Wanda White · CENTURY 21 New Millennium

  13. 18937 Hodges Ln — photo74Active

    $699,900

    3 bd · 2 ba · 1,834 sqft

    18937 Hodges Ln, Leonardtown, MD

    Ingrid H Butler · CENTURY 21 New Millennium

  14. 25375 Loveville Rd — photo94Active

    $680,000

    4 bd · 2 ba · 2,388 sqft

    25375 Loveville Rd, Leonardtown, MD

    Kandy M. Moore · RMG Realty

  15. 42096 Wildflower Dr — photo45Active

    $619,900

    4 bd · 3 ba · 2,976 sqft

    42096 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  16. 42108 Wildflower Dr — photo31Active

    $614,900

    4 bd · 3 ba · 3,072 sqft

    42108 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  17. 42102 Wildflower Dr — photo72Active

    $609,900

    4 bd · 3 ba · 2,701 sqft

    42102 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  18. 41462 Culpepper Way — photoPrice Reduced75Active

    $624,900

    4 bd · 4 ba · 3,314 sqft

    41462 Culpepper Way, Leonardtown, MD

    Heather Leigh Foster · RE/MAX One

  19. 23636 Gunnell Dr — photoPrice Reduced40Active

    $559,900

    4 bd · 3 ba · 2,948 sqft

    23636 Gunnell Dr, Leonardtown, MD

    Marie Hankinson · EXP Realty, LLC

  20. 23628 Belmar Dr — photoPrice Reduced90Active

    $715,000

    5 bd · 4 ba · 4,834 sqft

    23628 Belmar Dr, Leonardtown, MD

    Heather Leigh Foster · RE/MAX One

  21. 22393 Saint Clements Ave — photoPrice Reduced56Active

    $738,997

    4 bd · 4 ba · 2,097 sqft

    22393 Saint Clements Ave, Leonardtown, MD

    Alyson Anderson I · Allfirst Realty, Inc.

  22. 42084 Wildflower Dr — photo33Active

    $629,900

    4 bd · 3 ba · 3,072 sqft

    42084 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  23. 40115 Combs Creek Way — photoPrice Reduced89Active

    $1,590,000

    5 bd · 4 ba · 2,993 sqft

    40115 Combs Creek Way, Leonardtown, MD

    Diana Washabaugh · CENTURY 21 New Millennium

  24. 20798 Waterside Dr — photoPrice Reduced33Active

    $450,000

    2 bd · 1 ba · 1,018 sqft

    20798 Waterside Dr, Leonardtown, MD

    Connie M. Fitzgerald · RE/MAX One

12

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-19 19:46:24 UTC
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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Leonardtown, MD community profile

    Population
    4,615
    Median income
    $125,466
    Housing units
    1,635
    People per sq. mi.
    43.8
    Area
    105.3 sq. mi.

    Source: HJN community data

    Leonardtown housing market

    August 2026 · This period is still settling

    Leonardtown 12-month median sale price trend

    Selling at 100.8% of asking price

    Buyers here are paying above asking. MLS · 12 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $459,200$449,900–$573,636 typical range
    Price per sq. ft.
    $239
    Sales
    20
    Paid in cash
    15.0%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $612,400
    Homes for sale
    40
    Median days on market
    7 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -9.5%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    2,221 sq. ft.