6,749

Leonardtown, MD Homes

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    • /90

      Est $725,322 Not Listed For Sale

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 1999
      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $185/SF
      • 19 Days On Market

      Last Sold Price $695,000

      Last Listing Agent Lisa Riggleman RE/MAX

  • /2

    $149,900

    • Land
    • 1.44 Acres
    • $104,097 per Acre

    20265 Hawks Way, Leonardtown, MD 20650

    Prime 1.44-Acre Buildable Lot in Leonardtown, MD Welcome to 20265 Hawks Way, a fantastic opportunity to build your dream home on a spacious 1.44-acre parcel on a quiet street. This generous lot offers a blank canvas — cleared and ready for construction — surrounded by other new construction homes that bring a sense of neighborhood and modern living while maintaining a peaceful, rural feel.

    Mark Frisco CENTURY 21 New Millennium

    20265 Hawks Way, Leonardtown, MD 20650
  • /2

    $825,000 Sold Jul 31, 2025

    40738 Bobwhite Ln, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 4,648 Sq Ft
    • Built 2000

    Last Sold Summary

    • $177/SF
    • 14 Days On Market

    Current Estimated Value $823,498

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
    • /55

      Est $550,913 Not Listed For Sale

      23285 Joanne Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 2008
      23285 Joanne Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 22% Above List Price
      • $177/SF
      • 65 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Karen Alford-Brooks Century 21 New Millennium

  • /2

    $1,740,000 Under Contract

    • Land
    • 3.85 Acres
    • $451,948 per Acre

    25845 Point Lookout Rd, Leonardtown, MD 20650

    This listing is 3.85 acres of a total 6-acre commercial property in Leonardtown, Maryland. Don't miss the chance to invest in this thriving and picturesque community. Whether you're looking to create a retail haven, upscale office space, or a dining destination, this property has all the ingredients for success. With its size and location near Patuxent Naval Air Station, this property is a blank

    Anne Davis CENTURY 21 Commercial New Millennium

    25845 Point Lookout Rd, Leonardtown, MD 20650
  • /76

    $460,000 Sold Jun 12, 2025

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,524 Sq Ft
    • Built 1969

    Last Sold Summary

    • $182/SF
    • 61 Days On Market

    Current Estimated Value $473,242

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    • /43

      Est $524,809 Not Listed For Sale

      21108 Arbor Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,412 Sq Ft
      • Built 1991
      21108 Arbor Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $207/SF
      • 5 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Cheryl Bare Century 21 New Millennium

  • /40

    $489,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650

    ***Under Contract***New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the

    Laura Bernth RE/MAX One

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
  • /82

    $701,650 Sold Sep 11, 2025

    22064 Daffodil Ct, Leonardtown, MD 20650

    • 6 Beds
    • 4.5 Baths
    • 5,012 Sq Ft
    • Built 2022

    Last Sold Summary

    • $140/SF
    • 43 Days On Market

    Current Estimated Value $706,423

    Last Listing Agent Laura Bernth RE/MAX One

    22064 Daffodil Ct, Leonardtown, MD 20650
    • /39

      Est $663,894 Not Listed For Sale

      21136 Catnip Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 2002
      21136 Catnip Way, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $167/SF
      • 51 Days On Market

      Last Sold Price $624,999

      Last Listing Agent Kaitlyn Boas Infinitas Realty Group

  • /58

    $425,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,829 Sq Ft

    40736 Center 40 Cir, Leonardtown, MD 20650

    Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space to relax and

    Kelly Padgett CENTURY 21 New Millennium

    40736 Center 40 Cir, Leonardtown, MD 20650
  • /55

    $464,900 Sold Oct 07, 2025

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft
    • Built 2025

    Last Sold Summary

    • $157/SF
    • 54 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    • /19

      Est $361,238 Not Listed For Sale

      43950 Blake Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1995
      43950 Blake Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 17% Above List Price
      • $220/SF
      • 2 Days On Market

      Last Sold Price $310,000

      Last Listing Agent Karen Alford-Brooks Century 21 New Millennium

  • /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • /31

    $480,000 Sold Nov 24, 2025

    40534 Miss Ettas Way, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 82 Days On Market

    Current Estimated Value $488,951

    Last Listing Agent Connie Fitzgerald RE/MAX One

    40534 Miss Ettas Way, Leonardtown, MD 20650
    • /59

      Est $449,917 Not Listed For Sale

      40781 Center 40 Cir, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft
      • Built 1967
      40781 Center 40 Cir, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $216/SF
      • 18 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • /58

    $405,000 Sold Feb 25, 2026

    19137 Lake Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,308 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Above List Price
    • $310/SF

    Current Estimated Value $395,633

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    19137 Lake Dr, Leonardtown, MD 20650
    • /60

      Est $552,955 Not Listed For Sale

      42055 Starlight Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,288 Sq Ft
      • Built 2004
      42055 Starlight Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 24% Above List Price
      • $194/SF
      • 6 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Iris McCollam EXP Realty, LLC

  • /10

    $205,000

    • Land
    • 5 Acres
    • $41,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • /37

    $540,000 Sold Apr 30, 2025

    40222 Breton Beach Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1976

    Last Sold Summary

    • $417/SF
    • 207 Days On Market

    Current Estimated Value $546,788

    Last Listing Agent Jake Grier Baldus Real Estate, Inc.

    40222 Breton Beach Rd, Leonardtown, MD 20650
    • /39

      Est $670,587 Not Listed For Sale

      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 5,488 Sq Ft
      • Built 1999
      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 22% Above List Price
      • $100/SF
      • 32 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Jonathan Powell Real Broker, LLC

  • /80

    $730,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • /113

    $638,000 Sold Aug 12, 2025

    23275 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 6,311 Sq Ft
    • Built 2005

    Last Sold Summary

    • $101/SF
    • 86 Days On Market

    Current Estimated Value $656,609

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • /57

      Est $449,121 Not Listed For Sale

      22106 Society Hill Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft
      • Built 1977
      22106 Society Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Above List Price
      • $227/SF
      • 23 Days On Market

      Last Sold Price $412,500

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /46

    $489,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650

    Lot 112 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend

    Laura Bernth RE/MAX One

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
  • /27

    $375,000 Sold Mar 07, 2025

    22395 Gore St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1982

    Last Sold Summary

    • $258/SF
    • 53 Days On Market

    Current Estimated Value $376,559

    Last Listing Agent Billy Rabbitt The Southside Group Real Estate

    22395 Gore St, Leonardtown, MD 20650
    • /53

      Est $648,682 Not Listed For Sale

      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,564 Sq Ft
      • Built 1996
      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $173/SF
      • 1 Day On Market

      Last Sold Price $615,000

      Last Listing Agent Cynthia Crispell Century 21 New Millennium

  • /69

    $674,900

    • 4 Beds
    • 3.5 Baths
    • 3,243 Sq Ft

    44545 Brewer Ln, Leonardtown, MD 20650

    This beautiful custom rambler sits on over 2.5 peaceful acres, offering plenty of privacy and space. A welcoming circular driveway and a covered front porch greet you as you arrive, setting a relaxed tone right from the start.Inside, you’ll find thoughtful details throughout: 6-inch custom trim, wide 36-inch doorways, lots of natural light, and 9-foot ceilings that give the home an open,

    Tracey Summers CENTURY 21 New Millennium

    44545 Brewer Ln, Leonardtown, MD 20650
  • /60

    $625,000 Sold Nov 26, 2025

    43107 Gum Spring Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft
    • Built 1993

    Last Sold Summary

    • $228/SF
    • 11 Days On Market

    Current Estimated Value $635,045

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • /31

      Est $428,484 Not Listed For Sale

      40862 Spring House Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 2,055 Sq Ft
      • Built 1962
      40862 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 14% Above List Price
      • $182/SF
      • 9 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Brian Mayer Real Broker, LLC

  • /30

    $525,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    41635 Ferber Ct, Leonardtown, MD 20650

    Perfect Leonardtown Location near sought after schools and county services! Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and

    Alvin Frazier Home Towne Real Estate

    41635 Ferber Ct, Leonardtown, MD 20650
  • /39

    $469,900 Sold Dec 02, 2025

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    • /46

      Est $923,308 Not Listed For Sale

      40472 Port Place, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,828 Sq Ft
      • Built 1972
      40472 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $309/SF
      • 31 Days On Market

      Last Sold Price $875,000

      Last Listing Agent Sean Escobar O'Brien Realty

  • /60

    $599,000 Sold Sep 18, 2025

    23650 Rocky Ridge Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,914 Sq Ft
    • Built 1993

    Last Sold Summary

    • $153/SF
    • 20 Days On Market

    Current Estimated Value $592,195

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • /22

      Est $431,476 Not Listed For Sale

      42454 Wilderness Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft
      • Built 1994
      42454 Wilderness Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12% Above List Price
      • $277/SF
      • 12 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Jimmy Hayden RE/MAX

  • /4

    $163,500 Sold Nov 20, 2025

    21983 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1960

    Last Sold Summary

    • $143/SF
    • 37 Days On Market

    Current Estimated Value $192,947

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650
    • /48

      Est $436,148 Not Listed For Sale

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,692 Sq Ft
      • Built 1961
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $110/SF
      • 1 Day On Market

      Last Sold Price $405,000

      Last Listing Agent Teresa Dove Remax 100

  • /51

    $415,000 Sold Jun 09, 2025

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft
    • Built 1994

    Last Sold Summary

    • $308/SF
    • 48 Days On Market

    Current Estimated Value $407,028

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • /83

      Est $545,658 Not Listed For Sale

      41936 Kentucky Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,115 Sq Ft
      • Built 2002
      41936 Kentucky Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 7% Above List Price
      • $124/SF
      • 6 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Jessica Raley Century 21 New Millennium

Showing Results 161 - 200, Page 5 of 18

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