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Leonardtown, MD Homes for Sale — Page 2 | Realty.com
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Homes for Sale in Leonardtown, MD

Homes for Sale in Leonardtown, MD

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22 of 46 Listings
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Homes for Sale in Leonardtown, MD

22 of 46 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 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

  2. 41888 Jenkins Ct — photoPrice Reduced41Active

    $535,000

    4 bd · 4 ba · 2,562 sqft

    41888 Jenkins Ct, Leonardtown, MD

    Wayne A Floyd · RE/MAX One

  3. 23011 Newtowne Neck Rd — photo17Active

    $350,000

    5 bd · 2 ba · 1,552 sqft

    23011 Newtowne Neck Rd, Leonardtown, MD

    Kelly A Jackson · Samson Properties

  4. 18937 Hodges Ln — photoPrice Reduced74Active

    $675,000

    3 bd · 2 ba · 1,834 sqft

    18937 Hodges Ln, Leonardtown, MD

    Ingrid H Butler · CENTURY 21 New Millennium

  5. 22010 Society Hill Rd — photoPrice Reduced45Active

    $560,000

    4 bd · 3 ba · 2,730 sqft

    22010 Society Hill Rd, Leonardtown, MD

    Fran Slade · Compass

  6. 23620 Gunnell Dr — photo56Active

    $615,000

    5 bd · 4 ba · 4,346 sqft

    23620 Gunnell Dr, Leonardtown, MD

    William T Mattingly · Coldwell Banker Premier

  7. Lot 5 - 42096 Wildflower Dr — photo45Active

    $619,900

    4 bd · 3 ba · 2,976 sqft

    Lot 5 - 42096 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  8. Lot 3 - 42108 Wildflower Dr — photo31Active

    $614,900

    4 bd · 3 ba · 3,072 sqft

    Lot 3 - 42108 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  9. Lot 4 - 42102 Wildflower Dr — photo72Active

    $609,900

    4 bd · 3 ba · 2,701 sqft

    Lot 4 - 42102 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  10. 41462 Culpepper Way — photoPrice Reduced75Active

    $599,999

    4 bd · 4 ba · 3,314 sqft

    41462 Culpepper Way, Leonardtown, MD

    Heather Leigh Foster · RE/MAX One

  11. 43954 Main Way Rd — photoPrice Reduced28Active

    $449,900

    3 bd · 3 ba · 1,691 sqft

    43954 Main Way Rd, Leonardtown, MD

    Daniel W Martin · Keller Williams Flagship

  12. 23636 Gunnell Dr — photoPrice Reduced40Active

    $529,900

    4 bd · 3 ba · 2,948 sqft

    23636 Gunnell Dr, Leonardtown, MD

    Marie Hankinson · EXP Realty, LLC

  13. 22393 Saint Clements Ave — photoPrice Reduced56Active

    $723,997

    4 bd · 4 ba · 2,097 sqft

    22393 Saint Clements Ave, Leonardtown, MD

    Alyson Anderson I · Allfirst Realty, Inc.

  14. Lot 7 - 42084 Wildflower Dr — photo33Active

    $629,900

    4 bd · 3 ba · 3,072 sqft

    Lot 7 - 42084 Wildflower Dr, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  15. Lot 154 - 23808 Wisteria Ln — photo45Active

    $485,900

    4 bd · 4 ba · 2,966 sqft

    Lot 154 - 23808 Wisteria Ln, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  16. Lot 156 - 23634 Dragonfly Ln — photo33Active

    $454,900

    4 bd · 4 ba · 2,554 sqft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  17. 41620 Church St — photoPrice Reduced70Active

    $389,000

    3 bd · 2 ba · 1,728 sqft

    41620 Church St, Leonardtown, MD

    Chanel Li · Evergreen Properties

  18. 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

  19. 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

  20. Lot 140 - 23659 Dragonfly Ln — photo42Active

    $454,900

    4 bd · 4 ba · 2,604 sqft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD

    Laura Lee Hefley · RE/MAX One

  21. 19700 Mulberry Fields Rd — photoPrice Reduced140Active

    $15,000,000

    6 bd · 5 ba · 5,500 sqft

    19700 Mulberry Fields Rd, Leonardtown, MD

    Kornelia Stuphan · Long & Foster Real Estate, Inc.

  22. Bayside Rd — photo30Active

    $1,750,000

    4 bd · 2 ba · 2,130 sqft

    Bayside Rd, Leonardtown, MD

    Larry J Haley · Haley Family Realty

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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Listing data & MLS disclosures

Bright MLS
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: 2026-10-30 16:11:31 UTC
  • Your local brokerage

    TO

    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

    October 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 10 sales · as of Oct 19, 2026

    Homes on the market · MLS, as of Oct 19, 2026–Oct 25, 2026

    Median list price
    $560,000
    Homes for sale
    43
    Median days on market
    30 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    2,244 sq. ft.

    Nearby areas

    ZIP codes

    • 20646 (114)
    • 20603 (104)
    • 20695 (99)
    • 20657 (93)
    • 20602 (69)
    • 20601 (64)
    • 20653 (50)
    • 20650 (46)

    Cities

    • Waldorf (237)
    • La Plata (114)
    • White Plains (99)
    • Lusby (93)
    • Lexington Park (50)
    • Mechanicsville (44)
    • Prince Frederick (42)
    • Huntingtown (41)