Leonardtown, MD Real Estate & Homes For Sale

47 homes

  • Grandhaven Plan in Clarks Rest, Leonardtown, MD 20650
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    NEW CONSTRUCTION
    $512,900+
    4bd
    3ba
    2,650 sqft
    Grandhaven Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 41625 Ferber Ct, Leonardtown, MD 20650
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    NEWOPEN SUN, 2-4PMCOMING SOON 4/260.28 ACRES
    $574,900
    4bd
    4ba
    4,524 sqft (on 0.28 acres)
    41625 Ferber Ct,
    Leonardtown, MD 20650
    J2 Real Estate
  • 22373 Bretmar Dr, Leonardtown, MD 20650
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    3.83 ACRES
    $565,000
    3bd
    3ba
    2,410 sqft (on 3.83 acres)
    22373 Bretmar Dr,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 21821 Rosebank Ct, Leonardtown, MD 20650
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    4.2 ACRES
    $975,000
    5bd
    4ba
    4,200 sqft (on 4.20 acres)
    21821 Rosebank Ct,
    Leonardtown, MD 20650
    Hawkins Real Estate Company
  • 43560 Ridge Ct, Leonardtown, MD 20650
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    5.71 ACRES
    $649,900
    4bd
    4ba
    3,702 sqft (on 5.71 acres)
    43560 Ridge Ct,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 18981 Little Pond Ln, Leonardtown, MD 20650
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    COMING SOON 5/1
    $419,900
    2bd
    2ba
    1,120 sqft
    18981 Little Pond Ln,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 40410 Wathen Rd, Leonardtown, MD 20650
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    4.93 ACRES
    $144,900
    40410 Wathen Rd,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 40428 Wathen Rd, Leonardtown, MD 20650
    6.06 ACRES
    $149,900
    40428 Wathen Rd,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 23005 Abell St, Leonardtown, MD 20650
    OPEN SUN, 1-3PMCOMING SOON 4/260.46 ACRES
    $365,000
    3bd
    2ba
    2,109 sqft (on 0.46 acres)
    23005 Abell St,
    Leonardtown, MD 20650
    RE/MAX One
  • 23276 Lindsay Dr, Leonardtown, MD 20650
    $599,500
    5bd
    4ba
    3,780 sqft
    23276 Lindsay Dr,
    Leonardtown, MD 20650
    RE/MAX One
  • 42705 Redgate Farm Ln, Leonardtown, MD 20650
    2.45 ACRES
    $499,900
    3bd
    3ba
    2,243 sqft (on 2.45 acres)
    42705 Redgate Farm Ln,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 40929 Falcon Way, Leonardtown, MD 20650
    OPEN SUN, 12-2PM3.42 ACRES
    $730,000
    3bd
    5ba
    3,712 sqft (on 3.42 acres)
    40929 Falcon Way,
    Leonardtown, MD 20650
    EXP Realty, LLC
  • 21933 Point Lookout Rd, Leonardtown, MD 20650
    COMING SOON 5/11.83 ACRES
    $325,000
    4bd
    2ba
    2,151 sqft (on 1.83 acres)
    21933 Point Lookout Rd,
    Leonardtown, MD 20650
    EXP Realty, LLC
  • 41584 Briarwood Cir, Leonardtown, MD 20650
    $480,000
    4bd
    4ba
    2,849 sqft
    41584 Briarwood Cir,
    Leonardtown, MD 20650
    JPAR Real Estate Professionals
  • Breton Plan in Clarks Rest, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $517,900+
    5bd
    3ba
    2,654 sqft
    Breton Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 41436 Whimsical Ct, Leonardtown, MD 20650
    $590,000
    5bd
    4ba
    3,209 sqft
    41436 Whimsical Ct,
    Leonardtown, MD 20650
    RE/MAX One
  • Pinehurst Plan in Clarks Rest, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $517,900+
    4bd
    3ba
    2,646 sqft
    Pinehurst Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 21885 Newtowne Neck Rd, Leonardtown, MD 20650
    0.49 ACRES
    $569,900
    5bd
    5ba
    5,488 sqft (on 0.49 acres)
    21885 Newtowne Neck Rd,
    Leonardtown, MD 20650
    EXP Realty, LLC
  • 42451 Saint Andrews Church Rd, Leonardtown, MD 20650
    58.58 ACRES
    $379,000
    42451 Saint Andrews Church Rd,
    Leonardtown, MD 20650
    JPAR Real Estate Professionals
  • St. Mary's Plan in Clarks Rest, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $475,900+
    4bd
    3ba
    2,259 sqft
    St. Mary's Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 23380 Marview Ct, Leonardtown, MD 20650
    $441,500
    3bd
    4ba
    2,306 sqft
    23380 Marview Ct,
    Leonardtown, MD 20650
    KW Metro Center
  • Patuxent Plan in Clarks Rest, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $512,900+
    3bd
    2ba
    1,864 sqft
    Patuxent Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 41541 Fairwood Ct, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $642,900
    4bd
    4ba
    3,080 sqft
    41541 Fairwood Ct,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 41505 Knight Rd, Leonardtown, MD 20650
    17.87 ACRES
    $6,500,000
    5bd
    8ba
    12,113 sqft (on 17.87 acres)
    41505 Knight Rd,
    Leonardtown, MD 20650
    Engel & Volkers Annapolis
  • 39645 Sweetpea Ln, Leonardtown, MD 20650
    3.56 ACRES
    $799,900
    39645 Sweetpea Ln,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • Elizabeth Plan in Clarks Rest, Leonardtown, MD 20650
    NEW CONSTRUCTION
    $502,900+
    4bd
    3ba
    2,031 sqft
    Elizabeth Plan in Clarks Rest,
    Leonardtown, MD 20650
  • 19936 Tower Hill Rd, Leonardtown, MD 20650
    6.33 ACRES
    $192,000
    19936 Tower Hill Rd,
    Leonardtown, MD 20650
    RE/MAX 100
  • 41815 Chelsey Faye Ln, Leonardtown, MD 20650
    NEW CONSTRUCTION0.84 ACRES
    $530,000
    3bd
    2ba
    1,627 sqft (on 0.84 acres)
    41815 Chelsey Faye Ln,
    Leonardtown, MD 20650
    JPAR Real Estate Professionals
  • 23673 J M Gough Ct, Leonardtown, MD 20650
    0.43 ACRES
    $659,000
    6bd
    6ba
    4,500 sqft (on 0.43 acres)
    23673 J M Gough Ct,
    Leonardtown, MD 20650
    CENTURY 21 New Millennium
  • 20230 Big Oak Ln, Leonardtown, MD 20650
    $280,000
    3bd
    2ba
    1,588 sqft
    20230 Big Oak Ln,
    Leonardtown, MD 20650
    Coldwell Banker Jay Lilly Real Estate
  • 20775 Deer Wood Park Dr, Leonardtown, MD 20650
    2.2 ACRES
    $729,900
    6bd
    5ba
    5,124 sqft (on 2.20 acres)
    20775 Deer Wood Park Dr,
    Leonardtown, MD 20650
    Coldwell Banker Jay Lilly Real Estate
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    490.17 ACRES
    $30,000,000
    6bd
    5ba
    13,458 sqft (on 490.17 acres)
    19700 Mulberry Fields Rd,
    Leonardtown, MD 20650
    Long & Foster Real Estate, Inc.
  • WATHEN Rd, Leonardtown, MD 20650
    7.5 ACRES
    $225,000
    WATHEN Rd,
    Leonardtown, MD 20650
    Amber & Company Real Estate
  • Maypole Rd, Leonardtown, MD 20650
    8 ACRES
    $200,000
    Maypole Rd,
    Leonardtown, MD 20650
    Home Towne Real Estate
  • 24308 Maypole Rd, Leonardtown, MD 20650
    5 ACRES
    $185,000
    24308 Maypole Rd,
    Leonardtown, MD 20650
    Home Towne Real Estate
  • 20945 Edna Marie Ln, Leonardtown, MD 20650
    75.09 ACRES
    $665,000
    20945 Edna Marie Ln,
    Leonardtown, MD 20650
    Cousino Realty
  • 40435 Old Breton Beach Rd, Leonardtown, MD 20650
    1.16 ACRES
    $149,000
    40435 Old Breton Beach Rd,
    Leonardtown, MD 20650
    Berkshire Hathaway HomeServices PenFed Realty
  • 19795 Tower Hill Rd, Leonardtown, MD 20650
    19.67 ACRES
    $949,000
    4bd
    4ba
    3,681 sqft (on 19.67 acres)
    19795 Tower Hill Rd,
    Leonardtown, MD 20650
    KW Metro Center
  • Long leaf Ln, Leonardtown, MD 20650
    $24,900
    Long leaf Ln,
    Leonardtown, MD 20650
    Residential Plus Real Estate Services
  • Maypole Rd, Leonardtown, MD 20650
    2 ACRES
    $125,000
    Maypole Rd,
    Leonardtown, MD 20650
    Leonard Realty, Inc.

Leonardtown, MD Real Estate Trends

Learn about the Leonardtown, MD housing market through trends and averages.

Affordability of Living in Leonardtown, MD

The median home value is $499,660
MonthMedian home value
April 2023$484k
May 2023$487k
June 2023$489k
July 2023$491k
August 2023$492k
September 2023$494k
October 2023$495k
November 2023$496k
December 2023$497k
January 2024$497k
February 2024$497k
March 2024$500k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Leonardtown, MD, by Home Size

Currently, there are 9 new listings and 47 homes for sale in Leonardtown.
Home SizeHome Value*
2 bedrooms (1 home)$314,939
3 bedrooms (8 homes)$419,019
4 bedrooms (12 homes)$551,079
*Home value over the past month

What Locals Say about Leonardtown

  • Vmagostinelli
    "It’s an amazing small town with entertainment and great restaurants within walking distance. Located on Breton Bay with great boating and fishing options. "
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  • Keith H.
    "Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
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  • Mybeachjeweler
    "I see many walking their dogs on a daily path around the neighborhood everybody has their dog on a leash and we wave"
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  • Keith H.
    "Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
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  • Stillask8in
    "This is a very small town. Most people commute 45 mins to the military base for work. Longest commute of my life. "
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  • Roy M.
    "Great schools in the Leonardtown area and lots of history as well. Many different food choices from Seafood Mexican AMERICAN Chinese and the olde town cafe. "
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  • Roy M.
    "Local town events and close to water access. Great food lots of shopping and small businesses Everyone is polite and friendly Great schools and local parks Volunteer rescue squad and fire departments and local hospital Local beach communities Golfing "
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  • Jennie C.
    "30 minutes from pax naval base, 40 min to Waldorf, 30-45 min from Calvert County. Some local buses available also."
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  • Unspecified
    "Easy, multiple routes to the Naval Air Station. From Leonardtown it is easy to get to all restaurants, shopping and entertainment."
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  • Unspecified
    "Perfect, close to the base and beautiful downtown Leonardtown. On the golf course with a few hundred yard walk to clubhouse (which has fantastic food and drinks), but most importantly, only a short walk to the Breton Bay Beach and playground which the children (and adults) love!"
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  • Destiny A. M.
    "I have two dogs myself and walk them all the time. I like they have side walks for my dogs to walk on but I don’t like that there isn’t a dog park anywhere around here. I feel they should add dog parks around here to make it better for dogs to get the excerise they need and want. "
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  • Destiny A. M.
    "Love leonardtown and love the area that I’m in. I love that everything is right here in the square and have so many nice people around me. Everyone in this area knows me and says hi even if they don’t know who you are. "
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