6,740

Leonardtown, MD Homes

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  • /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 $626,335

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • /58

      Est $417,709

      Not Listed For Sale

      40457 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,286 Sq Ft
      • Built 1995
      40457 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Anissa Hutchins CENTURY 21 New Millennium

  • /3

    $155,000

    • Land
    • 19,166 Sq Ft
    • $352,273 per Acre

    41650 Miss Bessie Dr, Leonardtown, MD 20650

    Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

    Jan Barnes CENTURY 21 New Millennium

    41650 Miss Bessie Dr, Leonardtown, MD 20650
  • /57

    $600,000

    Sold Jun 10, 2026

    23264 Lindsay Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft
    • Built 2020

    Last Sold Summary

    • $212/SF
    • 39 Days On Market

    Current Estimated Value $594,470

    Last Listing Agent Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
    • /77

      Est $517,303

      Not Listed For Sale

      22909 Cedar Lane Rd, Leonardtown, MD 20650

      • 5 Beds
      • 2 Baths
      • 2,275 Sq Ft
      • Built 1963
      22909 Cedar Lane Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jessica Raley CENTURY 21 New Millennium

  • /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 Lee Hefley RE/MAX One

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    • /56

      Est $408,159

      Not Listed For Sale

      20161 Tower Hill Rd, Leonardtown, MD 20650

      • 2 Beds
      • 2 Baths
      • 1,661 Sq Ft
      • Built 1990
      20161 Tower Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Trish Wallmark RE/MAX One

  • /16

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650

    *****PENDING****** Homesite 154 Oakley D1 TO BE Built Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. Photos shown are representative and intended to illustrate a similar finished townhouse. New Construction – 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

    Laura Lee Hefley RE/MAX One

    Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650
  • /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 $604,289

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • /48

      Est $588,205

      Not Listed For Sale

      23244 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,357 Sq Ft
      • Built 2004
      23244 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Tracy Zhang Taylor Properties

  • /48

    $610,000

    Sold Jul 13, 2026

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft
    • Built 2016

    Last Sold Summary

    • 5% Below List Price
    • $164/SF
    • 86 Days On Market

    Current Estimated Value $618,284

    Last Listing Agent Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    • /86

      Est $423,476

      Not Listed For Sale

      40427 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 4.5 Baths
      • 2,676 Sq Ft
      • Built 1994
      40427 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Beverly Drewery CENTURY 21 New Millennium

  • /33

    $629,900

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

    42084 Wildflower Dr, Leonardtown, MD 20650

    To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start. This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an inviting

    Laura Lee Hefley RE/MAX One

    42084 Wildflower Dr, 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 $622,168

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21745 Pinehurst Ct, Leonardtown, MD 20650
    • /64

      Est $492,286

      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

      • 36 Days On Market

      Last Listing Agent Jennifer Goddard 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 $665,581

    Last Listing Agent Cynthia Crispell Century 21 Redwood Realty

    41515 Risen Star Ln, Leonardtown, MD 20650
    • /9

      Est $531,026

      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

      • 1 Day On Market

      Last Listing Agent Conor Loughran CENTURY 21 New Millennium

  • /16

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    18800 McKays Beach Rd, Leonardtown, MD 20650

    This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one

    Chris Coughlan RE/MAX One

    18800 McKays Beach Rd, 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 $351,101

    Last Listing Agent Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
    • /43

      Est $438,680

      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

      • 24 Days On Market

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /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 $732,547

    Last Listing Agent Connie Fitzgerald RE/MAX One

    41832 Foxwell Point Ln, Leonardtown, MD 20650
    • /81

      Est $732,437

      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 Days On Market

      Last Listing Agent Mike Hall Long & Foster Real Estate, Inc.

  • /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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. This interior unit features an oversized

    Laura Lee Hefley RE/MAX One

    Lot 114 - 23702 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
    • /51

      Est $469,389

      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

      • 2 Days On Market

      Last Listing Agent Melinda Brown EXP Realty, LLC

  • /36

    $449,900

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

    23714 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSavannah Wicker 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

    Quality Built Homes Builder
    23714 Weeping Willow Way, 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 $475,626

    Last Listing Agent Marizel Brewington JPAR Real Estate Professionals

    41900 Nazareth Ct, Leonardtown, MD 20650
    • /72

      Est $579,002

      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 Days On Market

      Last Listing Agent Leah Molina Samson Properties

  • /94

    $829,900

    Under Contract
    • 5 Beds
    • 4.5 Baths
    • 5,082 Sq Ft

    42970 Heritage Dr, Leonardtown, MD 20650

    Welcome home to this stunning luxury residence in the sought-after Leonardtown Farms neighborhood, offering over 5000 finished square feet! Built and impeccably maintained by its original owners, this home feels brand new; not a detail has been overlooked. A detailed record of every upgrade and maintenance item from 2012 through 2026 is available, giving buyers complete peace of mind and a clear

    Sarah Mulford-Martin EXP Realty, LLC

    42970 Heritage Dr, 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 $522,165

    Last Listing Agent Jarred Green Real Broker, LLC

    21158 Marigold St, Leonardtown, MD 20650
    • /23

      Est $297,536

      Not Listed For Sale

      20235 Big Oak Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft
      • Built 1934
      20235 Big Oak Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jan Kleponis O'Brien Realty ERA Powered

  • /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 Lee Hefley RE/MAX One

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    • /6

      Est $750,177

      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

      • 6 Days On Market

      Last Listing Agent Stephanie Smith Select Premium Properties, Inc

  • /2

    $390,000

    • 5 Beds
    • 3 Baths
    • 1,080 Sq Ft

    23750 Hollywood Rd, Leonardtown, MD 20650

    Located on a private lot in Leonardtown, this 5 bedroom 3 full bathroom house has been updated and is ready for a new owner! Move right in and make it your own home. The upper level features an open kitchen with breakfast bar, formal dining & living rooms. There are 3 bedrooms and a full bathroom in the hallway. The primary bedroom has it's own bathroom. The lower level has 2 additional bedrooms

    Kelly Padgett Century 21 Redwood Realty

    23750 Hollywood Rd, 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 $581,192

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    23261 Jenifer Ct, Leonardtown, MD 20650

Showing Results 201 - 240, Page 6 of 18

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