6,740

Leonardtown, MD Homes

Section Image
    • /12

      Est $706,125

      Not Listed For Sale

      23569 Belmar Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,181 Sq Ft
      • Built 2008
      23569 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

  • /49

    $989,000

    $111K PRICE DROP Under Contract
    • 5 Beds
    • 5 Baths
    • 5,810 Sq Ft

    22856 White Swan Way, Leonardtown, MD 20650

    This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch (almost 600 sq. ft.) where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled

    Barbara Stellway KW Metro Center

    22856 White Swan Way, Leonardtown, MD 20650
  • /48

    $469,900

    Sold Sep 18, 2025

    23664 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • /37

      Est $395,400

      Not Listed For Sale

      23005 Abell St, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 2,109 Sq Ft
      • Built 1955
      23005 Abell St, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Dawn Bell RE/MAX One

  • /7

    $772,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, Leonardtown, MD 20650
  • /50

    $537,500

    Sold Sep 05, 2025

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft
    • Built 2019

    Last Sold Summary

    • $200/SF
    • 67 Days On Market

    Current Estimated Value $542,698

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    • /65

      Est $891,629

      Not Listed For Sale

      22265 Orchard Ct, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 4,873 Sq Ft
      • Built 2005
      22265 Orchard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

  • /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, Leonardtown, MD 20650
  • /46

    $447,400

    Sold Dec 16, 2025

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2025

    Last Sold Summary

    • $172/SF
    • 90 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    • /4

      Est $105,000

      Not Listed For Sale

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 482 Days On Market

      Last Listing Agent Kelly Loveless Berkshire Hathaway HomeServices PenFed Realty

  • /89

    $1,590,000

    $110K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year.Perfectly positioned to capture breathtaking water views, this exceptional property offers a

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • /83

    $660,000

    Sold Jul 14, 2026

    41531 Kalitan Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $185/SF
    • 4 Days On Market

    Current Estimated Value $662,993

    Last Listing Agent Heather Foster RE/MAX One

    41531 Kalitan Ln, Leonardtown, MD 20650
    • /23

      Est $335,260

      Not Listed For Sale

      23028 Hopton Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1988
      23028 Hopton Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Emily Gross EXP Realty, LLC

  • /74

    $649,000

    $21K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • /76

    $580,000

    Sold Mar 23, 2026

    23593 Mitchell Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2004

    Last Sold Summary

    • $197/SF
    • 15 Days On Market

    Current Estimated Value $581,397

    Last Listing Agent Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
    • /70

      Est $687,581

      Not Listed For Sale

      21380 Fairwood Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft
      • Built 2008
      21380 Fairwood Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /78

    $460,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,469 Sq Ft

    41379 Margrove Cir, Leonardtown, MD 20650

    IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf,

    Mark Frisco CENTURY 21 New Millennium

    41379 Margrove Cir, Leonardtown, MD 20650
  • /45

    $449,900

    Sold May 29, 2026

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $175/SF
    • 36 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    • /87

      Est $659,121

      Not Listed For Sale

      43610 Deer Run Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,980 Sq Ft
      • Built 1997
      43610 Deer Run Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /30

    $369,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been

    Natalya Ford RE/MAX One

    21983 Point Lookout Rd, Leonardtown, MD 20650
  • /105

    $690,000

    Sold Mar 31, 2026

    41438 Silver Charm Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft
    • Built 2010

    Last Sold Summary

    • $165/SF
    • 5 Days On Market

    Current Estimated Value $692,074

    Last Listing Agent Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
    • /42

      Est $610,484

      Not Listed For Sale

      21120 Someday Farm Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft
      • Built 1990
      21120 Someday Farm Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Christiana Keefer EXP Realty, LLC

  • /16

    $449,900

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

    Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650

    ***PENDING***** ***Late August Delivery*** Homesite 130 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 features an oversized one-car garage and an entry-level flex space that

    Laura Lee Hefley RE/MAX One

    Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650
  • /56

    $549,000

    Sold Oct 30, 2025

    20919 Ridge Path Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft
    • Built 1992

    Last Sold Summary

    • $158/SF
    • 69 Days On Market

    Current Estimated Value $592,969

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
    • /34

      Est $364,233

      Not Listed For Sale

      20440 Chingville Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 1969
      20440 Chingville Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Michelle Camaioni RE/MAX One

  • /28

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • /60

    $530,000

    Sold Jun 02, 2026

    23207 Moakley St, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft
    • Built 1996

    Last Sold Summary

    • 2% Above List Price
    • $275/SF
    • 5 Days On Market

    Current Estimated Value $525,145

    Last Listing Agent Heather Foster RE/MAX One

    23207 Moakley St, Leonardtown, MD 20650
    • /39

      Est $493,644

      Not Listed For Sale

      41464 Helen Marie Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft
      • Built 1995
      41464 Helen Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Josh Wilson RE/MAX One

  • /61

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    *** VA LOAN ASSUMPTION OPPORTUNITY: Seller’s existing VA loan carries a 3.5% interest rate and may be assumable by a qualified buyer, subject to lender/servicer approval and applicable VA requirements. *** Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • /40

    $450,000

    Sold May 15, 2026

    22343 Newtowne Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $213/SF
    • 21 Days On Market

    Current Estimated Value $450,589

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    • /90

      Est $703,173

      Not Listed For Sale

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 1999
      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Lisa Riggleman RE/MAX One

  • /54

    $485,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    Buyers, come take a look. The estate just dropped the price by $20,000 This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • /55

    $440,000

    Sold May 14, 2026

    41516 Marwood Cir, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Above List Price
    • $183/SF
    • 25 Days On Market

    Current Estimated Value $439,460

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    41516 Marwood Cir, Leonardtown, MD 20650
    • /29

      Est $415,757

      Not Listed For Sale

      40449 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,288 Sq Ft
      • Built 1995
      40449 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Edward Tully RE/MAX One

  • /15

    $374,900

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, Leonardtown, MD 20650
  • /48

    $479,900

    Sold Jun 17, 2026

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650
    • /43

      Est $534,725

      Not Listed For Sale

      21108 Arbor Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,412 Sq Ft
      • Built 1991
      21108 Arbor Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Cheryl Bare CENTURY 21 New Millennium

  • /18

    $449,900

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

    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650

    ****PENDING***** ***End of August Delivery**** ***Builder Incentive $12,500 in Closing Help with the use of both Preferred Lender & Title*** Homesite #129 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

    Laura Lee Hefley RE/MAX One

    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650
  • /54

    $485,000

    Sold Jul 02, 2026

    21807 Potomac View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft
    • Built 1965

    Last Sold Summary

    • $240/SF
    • 2 Days On Market

    Current Estimated Value $483,031

    Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View 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

Showing Results 121 - 160, Page 4 of 18

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