6,720

Leonardtown, MD Homes

Section Image Section Image
    • /82

      Est $590,417

      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

      • 24 Days On Market

      Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

  • /3

    $175,000

    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    One of only two lots remaining! Breton Knolls is a 24-lot subdivision in Leonardtown with 1-7.5-acre lots. HOA of $300 annually with a $500 initial capital contribution.

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, 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 $662,810

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
    • /30

      Est $333,123

      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

      • 61 Days On Market

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /39

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23725 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersHerringbone Carolina Bead SidingMusket Brown ShuttersSedona Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorLVT in Bathrooms and Laundry RoomUpgraded Maple Kitchen CabinetsRoccoco Quartz CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23725 Dragonfly Ln, Leonardtown, MD 20650
  • /70

    $824,900

    Sold Jun 29, 2026

    39577 Potomac Ave, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Below List Price
    • $242/SF
    • 43 Days On Market

    Current Estimated Value $834,188

    Last Listing Agent Brooke Matthews RE/MAX One

    39577 Potomac Ave, Leonardtown, MD 20650
    • /42

      Est $663,756

      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

      • 2 Days On Market

      Last Listing Agent Jenny Norris EXP Realty, LLC

  • /90

    $699,999

    $30K PRICE DROP Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    VA LOAN MAY BE ASSUMABLE AT 4.375% BY A QUALIFIED BUYER, SUBJECT TO VA APPROVAL.Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • /48

    $515,000

    Sold Apr 29, 2026

    22547 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 57 Days On Market

    Current Estimated Value $514,161

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22547 Landing Way, Leonardtown, MD 20650
    • /82

      Est $688,932

      Not Listed For Sale

      44074 Medleys Neck Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 3,830 Sq Ft
      • Built 2006
      44074 Medleys Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

  • /31

    $614,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    Lot 3 - 42108 Wildflower Dr, Leonardtown, MD 20650

    New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing.The Fenwick offers a smart, comfortable layout with a spacious

    Laura Lee Hefley RE/MAX One

    Lot 3 - 42108 Wildflower Dr, 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 $494,980

    Last Listing Agent Sharon Cox Century 21 Redwood Realty

    41130 Cryer Ct, Leonardtown, MD 20650
    • /75

      Est $464,913

      Not Listed For Sale

      41925 Nazareth Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,512 Sq Ft
      • Built 2005
      41925 Nazareth Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Dawn Bell RE/MAX One

  • /15

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***Estimated Late 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

    Laura Lee Hefley RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • /2

    $435,000

    Sold Apr 20, 2026

    23369 Marview Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft
    • Built 2017

    Last Sold Summary

    • $188/SF
    • 38 Days On Market

    Current Estimated Value $436,305

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
    • /18

      Est $402,195

      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

      • 36 Days On Market

      Last Listing Agent Anne Davis CENTURY 21 New Millennium

  • /47

    $599,900

    $50K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,690 Sq Ft

    41444 Osborne Ln, Leonardtown, MD 20650

    Charming Home in Prime Leonardtown LocationThis inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops.Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650
  • /46

    $489,085

    Sold Aug 28, 2026

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

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

    Last Sold Summary

    • $158/SF
    • 7 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    • /55

      Est $556,232

      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

      • 5 Days On Market

      Last Listing Agent Mike Jordan CENTURY 21 New Millennium

  • /17

    $350,000

    • 5 Beds
    • 2 Baths
    • 1,552 Sq Ft

    23011 Newtowne Neck Rd, Leonardtown, MD 20650

    All forms of financing are available for this property. Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant

    Kelly Jackson Samson Properties

    23011 Newtowne Neck Rd, Leonardtown, MD 20650
  • /45

    $510,000

    Sold Dec 17, 2025

    41467 Osborne Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,827 Sq Ft
    • Built 2018

    Last Sold Summary

    • $180/SF
    • 13 Days On Market

    Current Estimated Value $524,021

    Last Listing Agent Susan Vogel Turtle Town Real Estate, LLC.

    41467 Osborne Ln, Leonardtown, MD 20650
    • /41

      Est $445,250

      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

      • 9 Days On Market

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • /42

    $483,400

    Sold Jun 05, 2026

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650

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

    Last Sold Summary

    • 1% Above List Price
    • $163/SF

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    • /72

      Est $578,211

      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

      • 5 Days On Market

      Last Listing Agent Kelly Padgett Century 21 Redwood Realty

  • /88

    $1,049,900

    Sold May 19, 2026

    40840 Greenwood Ln, Leonardtown, MD 20650

    • 9 Beds
    • 5 Baths
    • 6,476 Sq Ft
    • Built 2012

    Last Sold Summary

    • $162/SF
    • 6 Days On Market

    Current Estimated Value $1,038,836

    Last Listing Agent Romy Singh Samson Properties

    40840 Greenwood Ln, Leonardtown, MD 20650
    • /37

      Est $393,646

      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 Day On Market

      Last Listing Agent Paul Bell NOVA Brokers, LLC.

  • /2

    $2,500,000

    Sold Sep 15, 2026

    40111 Army Way, Leonardtown, MD 20650

    • 4 Beds
    • 7 Baths
    • 7,679 Sq Ft
    • Built 2004

    Last Sold Summary

    • $326/SF
    • 3 Days On Market

    Current Estimated Value $1,567,595

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    40111 Army Way, Leonardtown, MD 20650
    • /41

      Est $579,775

      Not Listed For Sale

      23635 Abraham Dr, Leonardtown, MD 20650

      • 6 Beds
      • 4 Baths
      • 3,272 Sq Ft
      • Built 2004
      23635 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

  • /2

    $325,000

    Sold Aug 14, 2026

    22332 Cedar St, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1958

    Last Sold Summary

    • 1% Below List Price
    • $325/SF
    • 10 Days On Market

    Current Estimated Value $310,324

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    22332 Cedar St, Leonardtown, MD 20650
    • /43

      Est $446,663

      Not Listed For Sale

      40905 Knight Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1980
      40905 Knight Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Rob Schou EXP Realty, LLC

  • /32

    $465,000

    Sold Jan 23, 2026

    43543 Bayberry Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft
    • Built 1991

    Last Sold Summary

    • $268/SF
    • 7 Days On Market

    Current Estimated Value $467,706

    Last Listing Agent Colin McHugh O'Brien Realty ERA Powered

    43543 Bayberry Ct, Leonardtown, MD 20650
    • /55

      Est $402,501

      Not Listed For Sale

      40905 Spring House Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1962
      40905 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Rob Schou EXP Realty, LLC

  • /45

    $639,000

    Sold Nov 17, 2025

    23534 Belmar Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,738 Sq Ft
    • Built 2008

    Last Sold Summary

    • $135/SF
    • 96 Days On Market

    Current Estimated Value $661,331

    Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
    • /80

      Est $648,384

      Not Listed For Sale

      23259 Jenifer Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,078 Sq Ft
      • Built 2005
      23259 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michael Rose Rory S. Coakley Realty, Inc.

  • /63

    $665,000

    Sold Jun 15, 2026

    23592 Belmar Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft
    • Built 2009

    Last Sold Summary

    • 2% Below List Price
    • $178/SF
    • 20 Days On Market

    Current Estimated Value $671,185

    Last Listing Agent Heather Foster RE/MAX One

    23592 Belmar Dr, Leonardtown, MD 20650
    • /71

      Est $1,217,141

      Not Listed For Sale

      21055 Breton Beach Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 3,052 Sq Ft
      • Built 2006
      21055 Breton Beach Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Robert Gauger EXP Realty, LLC

  • /40

    $469,900

    Sold Jan 27, 2026

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 73 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650
    • /113

      Est $667,952

      Not Listed For Sale

      23275 Jenifer Ct, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 6,311 Sq Ft
      • Built 2005
      23275 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /33

    $700,000

    Sold Apr 02, 2026

    21345 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,080 Sq Ft
    • Built 2012

    Last Sold Summary

    • $172/SF
    • 58 Days On Market

    Current Estimated Value $697,724

    Last Listing Agent Deanna Rothstein RE/MAX One

    21345 Fairwood Ct, Leonardtown, MD 20650
    • /51

      Est $634,848

      Not Listed For Sale

      22202 Hanover Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 3,261 Sq Ft
      • Built 2005
      22202 Hanover Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Danny Martin Keller Williams Flagship

Showing Results 281 - 320, Page 8 of 18

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