6,749

Leonardtown, MD Homes

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  • /68

    $624,900

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, 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 $553,546

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • /25

      Est $292,722 Not Listed For Sale

      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 2008
      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $264/SF
      • 5 Days On Market

      Last Sold Price $279,000

      Last Listing Agent Kelly Niland Kevin Turner

  • /45

    $564,900 Pending

    • 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
  • /2

    $959,600 Sold Aug 13, 2025

    40557 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF

    Current Estimated Value $935,656

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
    • /56

      Est $712,039 Not Listed For Sale

      21147 Catnip Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft
      • Built 2002
      21147 Catnip Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $164/SF

      Last Sold Price $705,000

      Last Listing Agent MaryAnne Crewse O'Brien Realty

  • /68

    $590,000

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees, plenty of open

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • /43

    $710,000 Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $708,018

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /80

      Est $708,687 Not Listed For Sale

      41503 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 5,065 Sq Ft
      • Built 2008
      41503 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $132/SF
      • 15 Days On Market

      Last Sold Price $670,000

      Last Listing Agent John Gatton Century 21 New Millennium

  • /61

    $635,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    43018 Bluejay Ln, Leonardtown, MD 20650

    ANOTHER PRICE REDUCTION from the highly motivated sellers of this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown! Don't miss this opportunity to own this gorgeous home on the best corner lot in the neighborhood. The weather will be warming up soon and you can enjoy gathering with family and friends in the spacious fenced in yard and fire pit. Walk to the playground

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • /88

    $1,052,000 Sold Feb 25, 2026

    22164 Miller Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Above List Price
    • $390/SF
    • 7 Days On Market

    Current Estimated Value $859,668

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • /29

      Est $581,773 Not Listed For Sale

      41650 Marie Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,808 Sq Ft
      • Built 2007
      41650 Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $198/SF
      • 2 Days On Market

      Last Sold Price $556,000

      Last Listing Agent Deanna Rothstein RE/MAX

  • /85

    $569,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,308 Sq Ft

    41536 Fairwood Ct, Leonardtown, MD 20650

    Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage includes

    Teresa Klopfer RE/MAX Realty Group

    41536 Fairwood Ct, Leonardtown, MD 20650
  • /41

    $458,550 Sold Feb 26, 2026

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 78 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    • /38

      Est $506,982 Not Listed For Sale

      40772 Magee Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,258 Sq Ft
      • Built 1973
      40772 Magee Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 13% Above List Price
      • $199/SF
      • 23 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Becky King Kevin Turner

  • /3

    $335,000 Coming Soon

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

    39725 Lady Baltimore Ave, Leonardtown, MD 20650

    This estate sale presents a rare opportunity to own three combined lots, offering added potential. A new roof was installed in August of last year, and the home features upgraded vinyl windows.This charming brick residence is much larger than it appears, offering a spacious layout designed for comfortable one-level living. The attached two-car garage provides ample room not only for parking,

    Jessica Raley CENTURY 21 New Millennium

    39725 Lady Baltimore Ave, Leonardtown, MD 20650
  • /3

    $1,225,000 Sold Mar 31, 2025

    19710 Tower Hill Rd, Leonardtown, MD 20650

    • 5 Beds
    • 6.5 Baths
    • 5,690 Sq Ft
    • Built 1984

    Last Sold Summary

    • $215/SF

    Current Estimated Value $1,229,296

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    19710 Tower Hill Rd, Leonardtown, MD 20650
    • /78

      Est $713,304 Not Listed For Sale

      21715 Pebble Beach Ct, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 4,437 Sq Ft
      • Built 1994
      21715 Pebble Beach Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $146/SF
      • 16 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Lucy Barbour Century 21 New Millennium

  • /6

    $175,000

    • Land
    • 6.24 Acres
    • $28,045 per Acre

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650

    6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
  • /27

    $460,000 Sold Mar 14, 2025

    41952 Loker Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,084 Sq Ft
    • Built 2006

    Last Sold Summary

    • $221/SF
    • 15 Days On Market

    Current Estimated Value $482,038

    Last Listing Agent Diane Fenwick RE/MAX One

    41952 Loker Ct, Leonardtown, MD 20650
    • /60

      Est $817,000 Not Listed For Sale

      39653 Potomac Ave, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,150 Sq Ft
      • Built 1988
      39653 Potomac Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Below List Price
      • $282/SF
      • 10 Days On Market

      Last Sold Price $888,000

      Last Listing Agent Coley Reed Long & Foster

  • /10

    $1,999,999

    • 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
  • /9

    $340,000 Sold Feb 20, 2026

    22820 Duke St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1947

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 0 Days On Market

    Current Estimated Value $305,170

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • /68

      Est $1,210,354 Not Listed For Sale

      40139 Combs Creek Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,944 Sq Ft
      • Built 1995
      40139 Combs Creek Way, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $279/SF
      • 5 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Andy Schweigman Douglas Realty, LLC

  • /87

    $475,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft

    20697 Chingville Rd, Leonardtown, MD 20650

    Charming three (3) bedroom, two (2) bathroom Cape Cod in Leonardtown with a detached three (3) car garage and workshop. Conveniently located 15 min from NAS PAX, shopping, and restaurants. Kitchen was recently updated to honor the original design while providing additional storage and modern amenities. Other home features include quartz countertops, new carpet, fresh paint throughout, updated

    Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
  • /27

    $515,000 Sold Aug 15, 2025

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $203/SF
    • 10 Days On Market

    Current Estimated Value $528,559

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • /45

      Est $259,484 Not Listed For Sale

      22321 Leonard St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1930
      22321 Leonard St, Leonardtown, MD 20650

      Last Sold Summary

      • $339/SF
      • 19 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Lesa Clark Redfin Corp

  • /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • /33

    $505,000 Sold Jun 02, 2025

    41918 Sara Ann Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,392 Sq Ft
    • Built 2005

    Last Sold Summary

    • $149/SF
    • 12 Days On Market

    Current Estimated Value $511,064

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    41918 Sara Ann Ct, Leonardtown, MD 20650
    • /68

      Est $674,373 Not Listed For Sale

      42990 Baywood Place, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft
      • Built 2009
      42990 Baywood Place, Leonardtown, MD 20650

      Last Sold Summary

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

      Last Sold Price $660,000

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /3

    $175,000

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

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 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
  • /75

    $640,000 Sold Dec 01, 2025

    22216 Hanover Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 4,206 Sq Ft
    • Built 2005

    Last Sold Summary

    • $152/SF
    • 1 Day On Market

    Current Estimated Value $634,956

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • /79

      Est $630,848 Not Listed For Sale

      24606 Pin Cushion Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,466 Sq Ft
      • Built 1987
      24606 Pin Cushion Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $172/SF
      • 64 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Kimberly Scott Remax 100

  • /45

    $449,900 New Construction

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

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 100 Madison D1: *** Mid March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. 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

    Laura Bernth RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
  • /23

    $295,000 Sold May 14, 2025

    20235 Big Oak Ln, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,036 Sq Ft
    • Built 1934

    Last Sold Summary

    • $285/SF
    • 4 Days On Market

    Current Estimated Value $295,517

    Last Listing Agent Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
    • /92

      Est $1,150,170 Not Listed For Sale

      40539 Port Place, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 3,371 Sq Ft
      • Built 1986
      40539 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • $341/SF
      • 5 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Andrew Shemeta Century 21 New Millennium

  • /55

    $437,000

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

    41516 Marwood Cir, Leonardtown, MD 20650

    Professional photos coming soon. Welcome home to Marwood Circle in the desirable Clark's Rest Neighborhood of Leonardtown. This nearly new townhome built in 2020 has over 2400 square feet of living space and is in move in condition. Nice open concept on the main level includes an updated kitchen with granite countertops and island, stainless appliances and pantry, large family room, separate

    Cynthia Ballard CENTURY 21 New Millennium

    41516 Marwood Cir, Leonardtown, MD 20650
  • /53

    $645,900 Sold Feb 26, 2026

    23581 Gallent Fox Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft
    • Built 2009

    Last Sold Summary

    • $173/SF
    • 42 Days On Market

    Current Estimated Value $646,086

    Last Listing Agent Laura Bernth RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • /31

      Est $601,061 Not Listed For Sale

      21084 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft
      • Built 2003
      21084 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 18% Above List Price
      • $146/SF
      • 30 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Josh Yowell EXP Realty, LLC

  • /42

    $479,900 Pending

    • 4 Beds
    • 3.5 Baths

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

    ***UNDER CONTRACT***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 at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of

    Laura Bernth RE/MAX One

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

Showing Results 81 - 120, Page 3 of 18

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