6,736

Leonardtown, MD Homes

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    • /4

      Est $164,000 Not Listed For Sale

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      40435 Old Breton Beach Rd, Leonardtown, MD 20650
  • /2

    $225,000

    • Land
    • 7.5 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • /109

    $655,000 Sold Feb 21, 2025

    40721 Merlin Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,469 Sq Ft
    • Built 2002

    Last Sold Summary

    • $265/SF
    • 110 Days On Market

    Current Estimated Value $665,899

    Last Listing Agent Ron Leonard Leonard Realty, Inc.

    40721 Merlin Way, Leonardtown, MD 20650
    • /50

      Est $303,355 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft

      22204 Nomoni St, Leonardtown, MD 20650

      22204 Nomoni St, Leonardtown, MD 20650
  • /7

    $720,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,650 Sq Ft

    41810 Chelsey Faye Ln, Leonardtown, MD 20650

    Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other

    Jessica Ascenzo JPAR Real Estate Professionals

    41810 Chelsey Faye Ln, Leonardtown, MD 20650
  • /69

    $622,500 Sold Jul 21, 2025

    21143 Catnip Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 16 Days On Market

    Current Estimated Value $618,500

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /23

      Est $339,045 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      23028 Hopton Ln, Leonardtown, MD 20650

      23028 Hopton Ln, Leonardtown, MD 20650
  • /40

    $489,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650

    *** INCENTIVE, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. (Builder to honor promotional pricing for contracts that close by 12/31/25. Offer valid for Homesite 103 only. Must use preferred lender and title to receive closing assistance.) New Construction – Cumberland

    Laura Bernth RE/MAX One

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650
  • /53

    $605,000 Sold May 16, 2025

    41403 Heritage Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft
    • Built 2016

    Last Sold Summary

    • $181/SF
    • 6 Days On Market

    Current Estimated Value $603,213

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    41403 Heritage Ln, Leonardtown, MD 20650
    • /76

      Est $674,647 Not Listed For Sale

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

      41488 Pensive St, Leonardtown, MD 20650

      41488 Pensive St, Leonardtown, MD 20650
  • /45

    $564,900

    • 4 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650

    Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acres. Quality construction throughout from the sunroom to the kitchen remodel you will see the workmanship!Once inside you will feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious

    Tracey Summers CENTURY 21 New Millennium

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /42

    $740,000 Sold Feb 03, 2025

    41041 Knight Rd, Leonardtown, MD 20650

    • 6 Beds
    • 5 Baths
    • 5,716 Sq Ft
    • Built 2006

    Last Sold Summary

    • $129/SF
    • 13 Days On Market

    Current Estimated Value $768,404

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    41041 Knight Rd, Leonardtown, MD 20650
    • /70

      Est $697,821 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft

      21380 Fairwood Ct, Leonardtown, MD 20650

      21380 Fairwood Ct, Leonardtown, MD 20650
  • /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
  • /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 Bernth RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • /87

      Est $647,406 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,980 Sq Ft

      43610 Deer Run Ct, Leonardtown, MD 20650

      43610 Deer Run Ct, Leonardtown, MD 20650
  • /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
  • /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 $544,284

    Last Listing Agent Delaney Burgess RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    • /44

      Est $471,024 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,204 Sq Ft

      22480 Sparrow Ct, Leonardtown, MD 20650

      22480 Sparrow Ct, Leonardtown, MD 20650
  • /18

    $200,000 Pending

    • Land
    • 3.53 Acres
    • $56,657 per Acre

    0 Kiskadee Ln, Leonardtown, MD 20650

    The LAST BUILDING SITE in Avenmar! You won't want to miss this opportunity to purchase the last builder developed parcel in one of Leonardtown's most sought after communities! With over 3.5 wooded acres, this property offers a flat, private, wooded setting like no other. Community features pier, boat ramp, stables, pool, community center and so much more! Contact us for more info, or to set up a

    Pattee McInerney Scott McInerney RE/MAX One

    0 Kiskadee Ln, Leonardtown, MD 20650
  • /95

    $605,000 Sold Mar 14, 2025

    22395 Hood Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,120 Sq Ft
    • Built 2011

    Last Sold Summary

    • $194/SF
    • 42 Days On Market

    Current Estimated Value $626,518

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    22395 Hood Ln, Leonardtown, MD 20650
    • /42

      Est $602,031 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft

      21120 Someday Farm Ln, Leonardtown, MD 20650

      21120 Someday Farm Ln, Leonardtown, MD 20650
  • /50

    $539,900

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    42043 Starlight Dr, Leonardtown, MD 20650

    Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has a bright and cheery interior with four spacious bedrooms on the upper level. Generous closets. Convenient upper level laundry. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen sink to grow fresh herbs. A front sitting room makes for a

    Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, 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 Bernth RE/MAX One

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    • /34

      Est $397,929 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      20440 Chingville Rd, Leonardtown, MD 20650

      20440 Chingville Rd, Leonardtown, MD 20650
  • /57

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,829 Sq Ft

    40736 Center 40 Cir, Leonardtown, MD 20650

    Charming Split Level home on just over 1/2 in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space to relax and enjoy a

    Kelly Padgett CENTURY 21 New Millennium

    40736 Center 40 Cir, Leonardtown, MD 20650
  • /47

    $660,000 Sold Jul 14, 2025

    23278 Applewood Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 4,306 Sq Ft
    • Built 2022

    Last Sold Summary

    • $153/SF
    • 10 Days On Market

    Current Estimated Value $663,958

    Last Listing Agent Jonathan Benya EXP Realty, LLC

    23278 Applewood Ln, Leonardtown, MD 20650
    • /39

      Est $491,697 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft

      41464 Helen Marie Ct, Leonardtown, MD 20650

      41464 Helen Marie Ct, Leonardtown, MD 20650
  • /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • /97

    $640,000 Sold Jun 29, 2025

    44114 Woodmont Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1999

    Last Sold Summary

    • $176/SF
    • 10 Days On Market

    Current Estimated Value $640,626

    Last Listing Agent Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
    • /90

      Est $716,076 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      20746 Deer Wood Park Dr, Leonardtown, MD 20650
  • /59

    $495,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    21738 Pinehurst Ct, Leonardtown, MD 20650

    A rare opportunity for golf course living! Welcome home to this beautifully appointed colonial, perfectly situated on the 6th hole of the Breton Bay Golf Course. Featuring granite countertops, some new appliances, fresh paint, and more, this home is move-in ready. The upper level offers three spacious bedrooms, with a fourth bedroom located in the finished basement—ideal for guests or a home

    Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    21738 Pinehurst Ct, Leonardtown, MD 20650
  • /42

    $906,500 Sold Jul 18, 2025

    42239 Riverwinds Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft
    • Built 1980

    Last Sold Summary

    • $418/SF
    • 3 Days On Market

    Current Estimated Value $897,463

    Last Listing Agent Connie Fitzgerald RE/MAX One

    42239 Riverwinds Dr, Leonardtown, MD 20650
    • /55

      Est $542,376 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft

      23285 Joanne Dr, Leonardtown, MD 20650

      23285 Joanne Dr, Leonardtown, MD 20650
  • /65

    $699,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,372 Sq Ft

    42975 Baywood Place, Leonardtown, MD 20650

    Stunning Dunleigh model by Marrick Homes, tucked away at the end of a quiet cul-de-sac on over 1 full acre in desirable Leonardtown Farm! Offering nearly 3,400 sq ft of finished living space, this beautifully maintained 4BR/2.5BA home features a spacious, gourmet kitchen with large center island, upgraded cabinets and granite countertops, and stainless steel appliances – perfect for entertaining.

    Erika Yowell EXP Realty, LLC

    42975 Baywood Place, Leonardtown, MD 20650
  • /10

    $660,000 Sold May 15, 2025

    23598 Belmar Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,758 Sq Ft
    • Built 2010

    Last Sold Summary

    • $176/SF
    • 16 Days On Market

    Current Estimated Value $663,255

    Last Listing Agent Heather Foster RE/MAX One

    23598 Belmar Dr, Leonardtown, MD 20650
    • /50

      Est $699,209 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,540 Sq Ft

      39994 Ben Morgan Rd, Leonardtown, MD 20650

      39994 Ben Morgan Rd, Leonardtown, MD 20650
  • /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, 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

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
    • /43

      Est $532,048 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,412 Sq Ft

      21108 Arbor Ct, Leonardtown, MD 20650

      21108 Arbor Ct, Leonardtown, MD 20650

Showing Results 121 - 160, Page 4 of 18

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