6,757

Leonardtown, MD Homes

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    • /64

      Est $475,966 Not Listed For Sale

      42705 Redgate Farm Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 2,243 Sq Ft
      • Built 1995
      42705 Redgate Farm Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $210/SF
      • 36 Days On Market

      Last Sold Price $470,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /2

    $365,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,644 Sq Ft

    44731 Blake Creek Rd, Leonardtown, MD 20650

    Welcome to 44731 Blake Creek Road in the sought-after Leonardtown. This beautifully updated single-story rambler sits on over an acre of private land, offering the best of Southern Maryland country living with easy access to everything you need. Step inside to find a home that has been thoughtfully refreshed and updated for today's buyer. With 1,644 square feet of single-level living, this

    Sarah Mulford-Martin EXP Realty, LLC

    44731 Blake Creek Rd, Leonardtown, MD 20650
  • /82

    $610,000 Sold Nov 21, 2025

    21745 Pinehurst Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft
    • Built 1991

    Last Sold Summary

    • $213/SF
    • 3 Days On Market

    Current Estimated Value $619,103

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21745 Pinehurst Ct, Leonardtown, MD 20650
    • /9

      Est $508,278 Not Listed For Sale

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,149 Sq Ft
      • Built 1996
      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 7% Above List Price
      • $221/SF
      • 1 Day On Market

      Last Sold Price $475,000

      Last Listing Agent Conor Loughran Century 21 New Millennium

  • /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
  • /5

    $664,900 Sold Mar 20, 2026

    41515 Risen Star Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,136 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Above List Price
    • $161/SF
    • 0 Days On Market

    Current Estimated Value $653,104

    Last Listing Agent Cynthia Crispell CENTURY 21 New Millennium

    41515 Risen Star Ln, Leonardtown, MD 20650
    • /43

      Est $422,819 Not Listed For Sale

      22292 White Oak Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 1978
      22292 White Oak Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3% Below List Price
      • $253/SF
      • 24 Days On Market

      Last Sold Price $435,000

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /2

    $800,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 3,122 Sq Ft

    21130 Someday Farm Ln, Leonardtown, MD 20650

    Welcome Home to Your Private Rural Retreat. Nestled on 11 serene, private acres and just steps from St. Mary's River State Park, this stunning 5-bedroom, 2.5-bath Cape Cod offers the perfect blend of country living and modern convenience, all within 15 minutes of Patuxent River Naval Air Station and the charming wharf and dining of Leonardtown. A long gravel driveway with freshly installed

    Sarah Mulford-Martin EXP Realty, LLC

    21130 Someday Farm Ln, Leonardtown, MD 20650
  • /37

    $355,000 Sold Oct 17, 2025

    23849 Point Lookout Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1980

    Last Sold Summary

    • $325/SF
    • 4 Days On Market

    Current Estimated Value $358,477

    Last Listing Agent Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
    • /81

      Est $696,101 Not Listed For Sale

      43164 Gum Spring Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,000 Sq Ft
      • Built 1999
      43164 Gum Spring Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 3% Below List Price
      • $238/SF
      • 3 Days On Market

      Last Sold Price $715,000

      Last Listing Agent Mike Hall Long & Foster

  • /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
  • /43

    $715,000 Sold Feb 20, 2026

    41832 Foxwell Point Ln, Leonardtown, MD 20650

    • 3 Beds
    • 4 Baths
    • 3,683 Sq Ft
    • Built 1991

    Last Sold Summary

    • $194/SF
    • 80 Days On Market

    Current Estimated Value $735,671

    Last Listing Agent Connie Fitzgerald RE/MAX One

    41832 Foxwell Point Ln, Leonardtown, MD 20650
    • /56

      Est $710,211 Not Listed For Sale

      40688 Clearfields Ct, Leonardtown, MD 20650

      • 4 Beds
      • 4.5 Baths
      • 3,524 Sq Ft
      • Built 2003
      40688 Clearfields Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $187/SF
      • 3 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Helen Mattingly Wernecke BHHS PenFed (actual)

  • /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
  • /30

    $519,900 Sold Feb 27, 2026

    20250 Hawks Way, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,557 Sq Ft
    • Built 2025

    Last Sold Summary

    • $334/SF
    • 11 Days On Market

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    20250 Hawks Way, Leonardtown, MD 20650
    • /68

      Est $974,864 Not Listed For Sale

      40741 Merlin Way, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 6,226 Sq Ft
      • Built 2003
      40741 Merlin Way, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $151/SF
      • 42 Days On Market

      Last Sold Price $940,000

      Last Listing Agent Cynthia Crispell Century 21 New Millennium

  • /33

    $360,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    22281 Nomoni St, Leonardtown, MD 20650

    Nice home in waterfront community. 3 bedrooms and 2 baths. New floors, new refrigerator, new dishwasher, freshly painted. This home is ready for its new owner. Enjoy community beach/water access for a small mfee each year! No HOA! This is only the beginning...move-in ready for you to start your home ownership dream here!

    Paul Fenton Coldwell Banker Premier

    22281 Nomoni St, Leonardtown, MD 20650
  • /50

    $610,000 Sold May 08, 2025

    41442 Dauber Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,558 Sq Ft
    • Built 2013

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $627,959

    Last Listing Agent Lesa Clark Redfin Corp

    41442 Dauber Way, Leonardtown, MD 20650
    • /51

      Est $459,069 Not Listed For Sale

      22152 Breton Woods Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,652 Sq Ft
      • Built 1987
      22152 Breton Woods Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Below List Price
      • $301/SF
      • 2 Days On Market

      Last Sold Price $497,646

      Last Listing Agent Melinda Brown EXP Realty, LLC

  • /58

    $399,900

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

    40736 Center 40 Cir, Leonardtown, MD 20650

    BACK ON MARKET. 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

    Kelly Padgett CENTURY 21 New Millennium

    40736 Center 40 Cir, Leonardtown, MD 20650
  • /26

    $460,000 Sold Oct 29, 2025

    41900 Nazareth Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,528 Sq Ft
    • Built 1999

    Last Sold Summary

    • $182/SF
    • 76 Days On Market

    Current Estimated Value $476,635

    Last Listing Agent Marizel Brewington RE/MAX One

    41900 Nazareth Ct, Leonardtown, MD 20650
    • /72

      Est $543,779 Not Listed For Sale

      23564 Gunnell Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,520 Sq Ft
      • Built 2003
      23564 Gunnell Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Below List Price
      • $158/SF
      • 2 Days On Market

      Last Sold Price $555,000

      Last Listing Agent Leah Molina Samson Properties

  • /2

    $750,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    20752 Penansey Ln, Leonardtown, MD 20650

    Multigenerationl suite is attached with a full kitchen, laundry room, living room, bedroom and full bathroom.

    Heather Foster RE/MAX One

    20752 Penansey Ln, Leonardtown, MD 20650
  • /73

    $520,000 Sold Sep 19, 2025

    21158 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,649 Sq Ft
    • Built 2001

    Last Sold Summary

    • $196/SF
    • 6 Days On Market

    Current Estimated Value $529,533

    Last Listing Agent Jarred Green Real Broker, LLC

    21158 Marigold St, Leonardtown, MD 20650
    • /6

      Est $678,080 Not Listed For Sale

      41985 White Point Beach Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,222 Sq Ft
      • Built 1944
      41985 White Point Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 18% Below List Price
      • $371/SF
      • 6 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Stephanie Smith Select Premium Properties, Inc

  • /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
  • /41

    $439,900 Sold Mar 16, 2026

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 85 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    • /28

      Est $336,291 Not Listed For Sale

      22340 Gore St, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,292 Sq Ft
      • Built 1964
      22340 Gore St, Leonardtown, MD 20650

      Last Sold Summary

      • 3% Above List Price
      • $252/SF
      • 76 Days On Market

      Last Sold Price $325,800

      Last Listing Agent Kimberly Bannister T&G Real Estate Advisors, Inc.

  • /48

    $450,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    41505 Margrove Cir, Leonardtown, MD 20650

    Welcome to this stunning end-unit townhome in the highly sought-after Clark’s Rest community. Built in the popular “Compton – Rear Kitchen” model, this home shows like new and delivers the ideal blend of style, space, and functionality. Step inside to a bright, open main level featuring hardwood flooring throughout, abundant natural light, and refined finishes including crown molding and

    Conor Loughran CENTURY 21 New Millennium

    41505 Margrove Cir, Leonardtown, MD 20650
  • /2

    $565,000 Sold Dec 05, 2025

    23261 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,575 Sq Ft
    • Built 2005

    Last Sold Summary

    • $158/SF
    • 15 Days On Market

    Current Estimated Value $577,506

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    23261 Jenifer Ct, Leonardtown, MD 20650
    • /37

      Est $603,082 Not Listed For Sale

      41625 Ferber Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,524 Sq Ft
      • Built 2005
      41625 Ferber Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $128/SF
      • 3 Days On Market

      Last Sold Price $579,900

      Last Listing Agent Jonnie Jamison J2 Real Estate

  • /3

    $779,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,745 Sq Ft

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Welcome to Breton Oaks—one of Leonardtown’s most sought-after communities—where this beautifully designed to-be-built home by Mednick Construction offers the perfect blend of modern farmhouse style and peaceful, wooded surroundings. Tucked away on a private, wooded lot on a quiet cul-de-sac, this thoughtfully crafted residence delivers timeless curb appeal paired with today’s most desirable

    Charlotte Long EXP Realty, LLC

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /33

    $570,000 Sold Oct 15, 2025

    23348 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,540 Sq Ft
    • Built 2022

    Last Sold Summary

    • $161/SF
    • 129 Days On Market

    Current Estimated Value $603,866

    Last Listing Agent Christi Turman-Rojas Fairfax Realty Premier

    23348 Lindsay Dr, Leonardtown, MD 20650
    • /67

      Est $560,419 Not Listed For Sale

      23626 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,916 Sq Ft
      • Built 2005
      23626 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $138/SF
      • 59 Days On Market

      Last Sold Price $539,000

      Last Listing Agent Dawn Wood O'Brien Realty

  • /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 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, 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
  • /35

    $449,900 Sold Apr 16, 2026

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650
    • /88

      Est $571,404 Not Listed For Sale

      23689 Jm Gough Ct, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,828 Sq Ft
      • Built 2005
      23689 Jm Gough Ct, Leonardtown, MD 20650

      Last Sold Summary

      • $149/SF
      • 1 Day On Market

      Last Sold Price $569,900

      Last Listing Agent Bill Oosterink Century 21 New Millennium

  • /45

    $569,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • /86

    $595,000 Sold Apr 14, 2026

    21749 Pinehurst Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,410 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Above List Price
    • $174/SF
    • 2 Days On Market

    Current Estimated Value $509,404

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21749 Pinehurst Ct, Leonardtown, MD 20650
    • /43

      Est $570,561 Not Listed For Sale

      21081 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft
      • Built 2002
      21081 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $168/SF
      • 3 Days On Market

      Last Sold Price $520,000

      Last Listing Agent Melissa Rodriguez RE/MAX

Showing Results 201 - 240, Page 6 of 18

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