6,720

Leonardtown, MD Homes

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  • /41

    $449,900

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

    23684 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersNatural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe Shower

    Quality Built Homes Builder
    23684 Dragonfly Ln, Leonardtown, MD 20650
  • /2

    $3,800 Per Month

    • 5 Beds
    • 5 Baths
    • 4,873 Sq Ft
    • House for Rent

    41402 Omaha Ct, Leonardtown, MD 20650

    Welcome home to 41402 Omaha Court! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Owner will maintain the trees. Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the Kitchen where you

    Derek Eisenberg Continental Real Estate Group

    41402 Omaha Ct, Leonardtown, MD 20650
  • /57

    $799,000

    Sold Aug 14, 2026

    41400 Real Quiet Dr, Leonardtown, MD 20650

    • 6 Beds
    • 4 Baths
    • 5,569 Sq Ft
    • Built 2013

    Last Sold Summary

    • 4% Above List Price
    • $143/SF
    • 2 Days On Market

    Current Estimated Value $771,883

    Last Listing Agent James Dick Long & Foster Real Estate, Inc.

    41400 Real Quiet Dr, Leonardtown, MD 20650
    • /36

      Est $461,637

      Not Listed For Sale

      22605 Calvert St, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft
      • Built 2018
      22605 Calvert St, Leonardtown, MD 20650

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent kyle Antel Berkshire Hathaway HomeServices PenFed Realty

  • /13

    $454,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    **** December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting!Homesite 157 Madison D1: 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

    Laura Lee Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • /18

    $570,000

    Sold Apr 16, 2026

    43641 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $261/SF
    • 0 Days On Market

    Current Estimated Value $571,870

    Last Listing Agent Jimmy Hayden RE/MAX One

    43641 Redmond Rd, Leonardtown, MD 20650
    • /28

      Est $544,401

      Not Listed For Sale

      22301 Bayside Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft
      • Built 2012
      22301 Bayside Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Chad Istvan EXP Realty, LLC

  • /30

    $1,450,000

    • Land
    • 70.61 Acres
    • $20,535 per Acre

    43175 N Megan Ln, Leonardtown, MD 20650

    Discover 89± acres of prime real estate offering unparalleled privacy just minutes from Leonardtown, California, Solomons Island, and Naval Air Station Patuxent River. Zoned RPD (Rural Preservation District) with agricultural use, this expansive TWO-PARCEL listing presents many possibilities. Rebuild on an existing foundation overlooking scenic rolling fields, design a custom private estate,

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    43175 N Megan Ln, Leonardtown, MD 20650
  • /3

    $310,000

    Sold Apr 17, 2026

    39725 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $164/SF
    • 4 Days On Market

    Current Estimated Value $361,918

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    39725 Lady Baltimore Ave, Leonardtown, MD 20650
    • /69

      Est $652,792

      Not Listed For Sale

      23567 Pine Bluff Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,736 Sq Ft
      • Built 2013
      23567 Pine Bluff Way, Leonardtown, MD 20650

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kimberly Scott Century 21 Redwood Realty

  • /64

    $865,000

    Sold May 28, 2026

    40171 Little Woods Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,586 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Below List Price
    • $334/SF
    • 6 Days On Market

    Current Estimated Value $858,663

    Last Listing Agent Barbara Blades CENTURY 21 New Millennium

    40171 Little Woods Ln, Leonardtown, MD 20650
    • /30

      Est $785,085

      Not Listed For Sale

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft
      • Built 2021
      40630 Breton Oaks Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

  • /74

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • /54

    $510,000

    Sold Dec 22, 2025

    41535 Singletree Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 2002

    Last Sold Summary

    • $225/SF
    • 44 Days On Market

    Current Estimated Value $518,609

    Last Listing Agent Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
    • /44

      Est $440,544

      Not Listed For Sale

      23380 Marview Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft
      • Built 2018
      23380 Marview Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

  • /29

    $359,777

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft

    40743 Magee Dr, Leonardtown, MD 20650

    Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished

    Liam Coonahan Real of Pennsylvania

    40743 Magee Dr, Leonardtown, MD 20650
  • /56

    $387,000

    Sold Sep 04, 2026

    43927 Lanedon Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $209/SF
    • 7 Days On Market

    Current Estimated Value $353,188

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    43927 Lanedon Dr, Leonardtown, MD 20650
    • /39

      Est $637,594

      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

      • 51 Days On Market

      Last Listing Agent Kaitlyn Boas Infinitas Realty Group

  • /40

    $449,900

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

    23672 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSandstone Beige Carolina Bead SidingMusket Brown ShuttersBronze Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsWhite Ice Granite CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23672 Weeping Willow Way, Leonardtown, MD 20650
  • /48

    $447,400

    Sold Oct 09, 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft
    • Built 2025

    Last Sold Summary

    • $175/SF
    • 58 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    • /50

      Est $639,210

      Not Listed For Sale

      41442 Dauber Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,558 Sq Ft
      • Built 2013
      41442 Dauber Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Lesa Clark Redfin Corp

  • /42

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

    ***** October Delivery *********** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #139 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space.

    Laura Lee Hefley RE/MAX One

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
  • /30

    $479,900

    Sold May 29, 2026

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    • /58

      Est $704,404

      Not Listed For Sale

      23687 Coventry Dr, Leonardtown, MD 20650

      • 6 Beds
      • 4.5 Baths
      • 4,650 Sq Ft
      • Built 2012
      23687 Coventry Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Lesa Clark Redfin Corp

  • /43

    $424,900

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    41517 Margrove Cir, Leonardtown, MD 20650

    Welcome to 41517 Margrove Cir, a beautifully maintained 3-bedroom, 3.5-bath townhome nestled in the highly desirable Clark's Rest community. This spacious and stylish home offers a perfect blend of comfort, convenience, and community living.Inside, you’ll find a bright and open floor plan with generous living spaces, modern finishes, and meticulous upkeep throughout. Each bedroom provides

    Matthew Burgan Infinitas Realty Group

    41517 Margrove Cir, Leonardtown, MD 20650
  • /16

    $281,650

    Sold Sep 30, 2025

    43658 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft
    • Built 1959

    Last Sold Summary

    • $136/SF
    • 12 Days On Market

    Current Estimated Value $320,501

    Last Listing Agent Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
    • /42

      Est $522,892

      Not Listed For Sale

      22542 Landing Way, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,752 Sq Ft
      • Built 2005
      22542 Landing Way, Leonardtown, MD 20650

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Trish Brow O'Brien Realty ERA Powered

  • /94

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,388 Sq Ft

    25375 Loveville Rd, Leonardtown, MD 20650

    Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2017, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers

    Kandy Moore RMG Realty

    25375 Loveville Rd, Leonardtown, MD 20650
  • /49

    $447,400

    Sold Dec 11, 2025

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    • /87

      Est $752,151

      Not Listed For Sale

      41408 W Citation St, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft
      • Built 2013
      41408 W Citation St, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /10

    $1,999,999

    $500K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • /55

    $430,000

    Sold Dec 01, 2025

    22592 Quiet Ln, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1991

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $429,289

    Last Listing Agent Paul Bell NOVA Brokers, LLC.

    22592 Quiet Ln, Leonardtown, MD 20650
    • /10

      Est $271,668

      Not Listed For Sale

      22765 Duke St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft
      • Built 1949
      22765 Duke St, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Ronald Watson Flag Real Estate Inc.

  • /77

    $524,900

    $15K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /42

    $555,000

    Sold Sep 26, 2025

    21137 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,382 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 6 Days On Market

    Current Estimated Value $563,622

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • /20

      Est $372,598

      Not Listed For Sale

      28845 Point Lookout Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft
      • Built 1969
      28845 Point Lookout Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Beverly Moody RE/MAX Realty Group

  • /60

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 3,314 Sq Ft

    22157 Monterey Place, Leonardtown, MD 20650

    Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining.At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer

    Tracey Summers CENTURY 21 New Millennium

    22157 Monterey Place, Leonardtown, MD 20650
  • /2

    $400,000

    Sold Jun 15, 2026

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Above List Price
    • $184/SF
    • 7 Days On Market

    Current Estimated Value $403,646

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    • /42

      Est $637,412

      Not Listed For Sale

      23641 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,236 Sq Ft
      • Built 2012
      23641 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

Showing Results 41 - 80, Page 2 of 18

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