6,757

Leonardtown, MD Homes

Section Image
  • 0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    /34

    $98,900

    • Land
    • 4.11 Acres
    • $24,063 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Mary’s County, this 4.11± acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable conditions; buyers

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 44074 Medleys Neck Rd, Leonardtown, MD 20650
    44074 Medleys Neck Rd, Leonardtown, MD 20650
    44074 Medleys Neck Rd, Leonardtown, MD 20650
    /82

    $675,000 Sold Aug 14, 2025

    44074 Medleys Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,830 Sq Ft
    • Built 2006

    Last Sold Summary

    • $176/SF
    • 3 Days On Market

    Current Estimated Value $684,923

    Last Listing Agent Cynthia Ballard CENTURY 21 New Millennium

    44074 Medleys Neck Rd, Leonardtown, MD 20650
    • 22030 Cartwright Rd, Leonardtown, MD 20650
      22030 Cartwright Rd, Leonardtown, MD 20650
      22030 Cartwright Rd, Leonardtown, MD 20650
      /82

      Est $552,816 Not Listed For Sale

      22030 Cartwright Rd, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft
      • Built 2005
      22030 Cartwright Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $220/SF
      • 24 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Bill Oosterink Century 21 New Millennium

  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 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
  • 23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    /41

    $572,000 Sold Jun 09, 2025

    23635 Abraham Dr, Leonardtown, MD 20650

    • 6 Beds
    • 4 Baths
    • 3,272 Sq Ft
    • Built 2004

    Last Sold Summary

    • $175/SF
    • 2 Days On Market

    Current Estimated Value $576,874

    Last Listing Agent Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • 21807 Potomac View Dr, Leonardtown, MD 20650
      21807 Potomac View Dr, Leonardtown, MD 20650
      21807 Potomac View Dr, Leonardtown, MD 20650
      /50

      Est $445,247 Not Listed For Sale

      21807 Potomac View Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,019 Sq Ft
      • Built 1965
      21807 Potomac View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Below List Price
      • $225/SF
      • 4 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Kelly Padgett Century 21 New Millennium

  • 23299 Jenifer Ct, Leonardtown, MD 20650
    23299 Jenifer Ct, Leonardtown, MD 20650
    23299 Jenifer Ct, Leonardtown, MD 20650
    /57

    $550,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,482 Sq Ft

    23299 Jenifer Ct, Leonardtown, MD 20650

    Beautiful 5BR, 3BA home with over 3,100 sq ft above grade tucked away on a peaceful 1⁄2-acre flag lot backing to trees in the heart of Leonardtown. Inside you’ll find hardwood flooring, spacious living areas, and a warm, inviting family room perfect for everyday living or entertaining. The kitchen features granite countertops, stainless steel appliances, and plenty of workspace. The main level

    Conor Loughran CENTURY 21 New Millennium

    23299 Jenifer Ct, Leonardtown, MD 20650
  • 23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    /34

    $625,000 Sold Sep 30, 2025

    23246 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft
    • Built 2017

    Last Sold Summary

    • $161/SF
    • 55 Days On Market

    Current Estimated Value $647,655

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
    • 39790 Lady Baltimore Ave, Leonardtown, MD 20650
      39790 Lady Baltimore Ave, Leonardtown, MD 20650
      39790 Lady Baltimore Ave, Leonardtown, MD 20650
      /30

      Est $317,350 Not Listed For Sale

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 1991
      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Above List Price
      • $231/SF
      • 61 Days On Market

      Last Sold Price $310,000

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • 40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    /78

    $550,000

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    /43

    $459,900 Sold Dec 02, 2025

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $155/SF
    • 29 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    • 20708 Waterside Dr, Leonardtown, MD 20650
      20708 Waterside Dr, Leonardtown, MD 20650
      20708 Waterside Dr, Leonardtown, MD 20650
      /42

      Est $628,235 Not Listed For Sale

      20708 Waterside Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft
      • Built 1925
      20708 Waterside Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Below List Price
      • $346/SF
      • 2 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Jenny Norris EXP Realty, LLC

  • Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    /41

    $479,900 Pending

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

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650

    Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley 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 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The

    Laura Bernth RE/MAX One

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
  • 22323 Saint Clements Ave, Leonardtown, MD 20650

    $300,000 Sold Oct 15, 2025

    22323 Saint Clements Ave, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $250/SF
    • 0 Days On Market

    Current Estimated Value $295,038

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
    • 41898 Jenkins Ct, Leonardtown, MD 20650
      41898 Jenkins Ct, Leonardtown, MD 20650
      41898 Jenkins Ct, Leonardtown, MD 20650
      /57

      Est $521,472 Not Listed For Sale

      41898 Jenkins Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,689 Sq Ft
      • Built 2005
      41898 Jenkins Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $131/SF
      • 1 Day On Market

      Last Sold Price $485,000

      Last Listing Agent Sharon Cox Century 21 New Millennium

  • Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    /45

    $449,900 Open Sun 11AM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 110 Madison D1: *** May Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an

    Laura Bernth RE/MAX One

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
  • 40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, Leonardtown, MD 20650
    /48

    $360,000 Sold Sep 26, 2025

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,884 Sq Ft
    • Built 1974

    Last Sold Summary

    • $191/SF
    • 35 Days On Market

    Current Estimated Value $372,966

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
    • 22318 Armstrong Dr, Leonardtown, MD 20650
      22318 Armstrong Dr, Leonardtown, MD 20650
      22318 Armstrong Dr, Leonardtown, MD 20650
      /21

      Est $476,180 Not Listed For Sale

      22318 Armstrong Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 2005
      22318 Armstrong Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Above List Price
      • $208/SF
      • 6 Days On Market

      Last Sold Price $434,900

      Last Listing Agent Joyce Sandidge Residential Plus Real Estate Services

  • 23324 Lindsay Dr, Leonardtown, MD 20650
    23324 Lindsay Dr, Leonardtown, MD 20650
    23324 Lindsay Dr, Leonardtown, MD 20650
    /64

    $679,900 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,168 Sq Ft

    23324 Lindsay Dr, Leonardtown, MD 20650

    ELEGANCE IN LEONARDTOWN! Welcome to Leonardtown living at its finest, where thoughtful design, elevated finishes, and everyday functionality come together in a home that truly stands out. This 5 bedroom, 3.5 bath 4168sqft residence immediately sets the tone with a light-filled, open-concept layout that feels both expansive and inviting. The main level flows effortlessly starting with a large open

    Mark Frisco CENTURY 21 New Millennium

    23324 Lindsay Dr, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $639,000 Sold Feb 02, 2026

    41430 Challedon Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 12 Days On Market

    Current Estimated Value $639,295

    Last Listing Agent Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
    • 23258 Jenifer Ct, Leonardtown, MD 20650
      23258 Jenifer Ct, Leonardtown, MD 20650
      23258 Jenifer Ct, Leonardtown, MD 20650
      /40

      Est $629,032 Not Listed For Sale

      23258 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 5 Baths
      • 5,100 Sq Ft
      • Built 2005
      23258 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 12% Above List Price
      • $111/SF
      • 4 Days On Market

      Last Sold Price $564,000

      Last Listing Agent Conor Loughran Century 21 New Millennium

  • 43552 Bayberry Ct, Leonardtown, MD 20650
    43552 Bayberry Ct, Leonardtown, MD 20650
    43552 Bayberry Ct, Leonardtown, MD 20650
    /32

    $579,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,428 Sq Ft

    43552 Bayberry Ct, Leonardtown, MD 20650

    Nestled on 2.2 private acres in Chestnut Ridge, this beautiful 4-bedroom home offers space, comfort, and functionality for modern living. The home features generously sized bedrooms and a thoughtfully designed layout perfect for both everyday life and entertaining. The main level includes a spacious kitchen and family room combination—ideal for gatherings—complete with a cozy brick gas fireplace

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    43552 Bayberry Ct, Leonardtown, MD 20650
  • 23311 Point Lookout Rd, Leonardtown, MD 20650
    23311 Point Lookout Rd, Leonardtown, MD 20650
    23311 Point Lookout Rd, Leonardtown, MD 20650
    /45

    $340,000 Sold Apr 15, 2026

    23311 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $315,720

    Last Listing Agent JW Abney RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
    • 22676 Chickadee Ln, Leonardtown, MD 20650
      22676 Chickadee Ln, Leonardtown, MD 20650
      22676 Chickadee Ln, Leonardtown, MD 20650
      /104

      Est $743,549 Not Listed For Sale

      22676 Chickadee Ln, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,804 Sq Ft
      • Built 2001
      22676 Chickadee Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 12% Above List Price
      • $138/SF
      • 13 Days On Market

      Last Sold Price $665,000

      Last Listing Agent Melanie Humphrey JPAR Real Estate Professionals

  • 41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    /74

    $680,000

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    41488 Pensive St, Leonardtown, MD 20650

    Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard’s Grant, offering a spacious layout and thoughtful design throughout. As you enter the home, you’re welcomed by hardwood floors, a grand entryway, and a beautiful staircase that creates an inviting first impression.To the right, French doors open to a large room that works well as a home office or additional

    Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
  • 40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, Leonardtown, MD 20650
    /2

    $971,725 Sold Sep 24, 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 764 Days On Market

    Current Estimated Value $806,000

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
    • 40443 Breton View Dr, Leonardtown, MD 20650
      40443 Breton View Dr, Leonardtown, MD 20650
      40443 Breton View Dr, Leonardtown, MD 20650
      /18

      Est $389,229 Not Listed For Sale

      40443 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,604 Sq Ft
      • Built 1994
      40443 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $148/SF
      • 36 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Anne Davis Century 21 New Millennium

  • 41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    /85

    $569,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,308 Sq Ft

    41536 Fairwood Ct, Leonardtown, MD 20650

    Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage includes

    Teresa Klopfer RE/MAX Realty Group

    41536 Fairwood Ct, Leonardtown, MD 20650
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    /30

    $645,000 Sold Oct 15, 2025

    41430 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft
    • Built 2011

    Last Sold Summary

    • $165/SF
    • 26 Days On Market

    Current Estimated Value $660,354

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
    • 41935 Green Hills Ln, Leonardtown, MD 20650
      41935 Green Hills Ln, Leonardtown, MD 20650
      41935 Green Hills Ln, Leonardtown, MD 20650
      /55

      Est $543,502 Not Listed For Sale

      41935 Green Hills Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1998
      41935 Green Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 14% Below List Price
      • $357/SF
      • 5 Days On Market

      Last Sold Price $629,999

      Last Listing Agent Mike Jordan Century 21 New Millennium

  • Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $489,900 New Construction

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

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 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.

    Laura Bernth RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • 22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    /56

    $500,000 Sold May 09, 2025

    22158 Monterey Place, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1975

    Last Sold Summary

    • $281/SF
    • 4 Days On Market

    Current Estimated Value $504,503

    Last Listing Agent C. Brandon Harrington PAX Real Estate

    22158 Monterey Place, Leonardtown, MD 20650
    • 21717 Meadow Ct, Leonardtown, MD 20650
      21717 Meadow Ct, Leonardtown, MD 20650
      21717 Meadow Ct, Leonardtown, MD 20650
      /41

      Est $448,011 Not Listed For Sale

      21717 Meadow Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft
      • Built 1981
      21717 Meadow Ct, Leonardtown, MD 20650

      Last Sold Summary

      • $302/SF
      • 9 Days On Market

      Last Sold Price $449,900

      Last Listing Agent Carol Kalmus-Choporis Century 21 New Millennium

  • 0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    /35

    $840,000

    • Land
    • 10.2 Acres
    • $82,353 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • 41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    /54

    $531,000 Sold Jul 18, 2025

    41699 Courthouse Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 2,420 Sq Ft
    • Built 2012

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $527,872

    Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
    • 23638 Abraham Dr, Leonardtown, MD 20650
      23638 Abraham Dr, Leonardtown, MD 20650
      23638 Abraham Dr, Leonardtown, MD 20650
      /72

      Est $547,353 Not Listed For Sale

      23638 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,352 Sq Ft
      • Built 2005
      23638 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Below List Price
      • $167/SF
      • 5 Days On Market

      Last Sold Price $560,000

      Last Listing Agent Kelly Padgett Century 21 New Millennium

  • 20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    /56

    $395,000 Sold Jun 02, 2025

    20161 Tower Hill Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,661 Sq Ft
    • Built 1990

    Last Sold Summary

    • $238/SF
    • 2 Days On Market

    Current Estimated Value $405,285

    Last Listing Agent Trish Wallmark RE/MAX One

    20161 Tower Hill Rd, Leonardtown, MD 20650
    • 39862 Big Pine Trail, Leonardtown, MD 20650
      39862 Big Pine Trail, Leonardtown, MD 20650
      39862 Big Pine Trail, Leonardtown, MD 20650
      /37

      Est $380,109 Not Listed For Sale

      39862 Big Pine Trail, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 1,656 Sq Ft
      • Built 2002
      39862 Big Pine Trail, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Below List Price
      • $232/SF
      • 1 Day On Market

      Last Sold Price $385,000

      Last Listing Agent Paul Bell NOVA Brokers, LLC.

  • 41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    /15

    $485,000 Sold Nov 14, 2025

    41130 Cryer Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1955

    Last Sold Summary

    • $326/SF
    • 115 Days On Market

    Current Estimated Value $511,947

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, Leonardtown, MD 20650
    • 23219 Jenifer Ct, Leonardtown, MD 20650
      23219 Jenifer Ct, Leonardtown, MD 20650
      23219 Jenifer Ct, Leonardtown, MD 20650
      /27

      Est $582,802 Not Listed For Sale

      23219 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft
      • Built 2005
      23219 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $171/SF
      • 0 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Laura Holley O'Brien Realty

Showing Results 241 - 280, Page 7 of 18

Maryland St Marys County Leonardtown

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