6,757

Leonardtown, MD Homes

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    • /60

      Est $757,333 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

      • 15% Below List Price
      • $282/SF
      • 10 Days On Market

      Last Sold Price $888,000

      Last Listing Agent Coley Reed Long & Foster

  • /75

    $669,900 Open Sun 12PM - 2:30PM

    • 3 Beds
    • 2.5 Baths
    • 3,098 Sq Ft

    41249 Brenda Ct, Leonardtown, MD 20650

    Meticulously cared for rambler, fully updated and move in ready, on nearly one private , partially wooded acre in the waterfront community of The Mulberries at Breton Bay. Brand new engineered hardwood floors plus fresh paint and brand new carpet in all three bedrooms. The kitchen has been updated with a sleek European elegance, white cabinets, granite countertops and stainless steel appliances.

    Robin Errington CENTURY 21 New Millennium

    41249 Brenda 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 $718,670

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /68

      Est $1,130,026 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

      • 3% Above List Price
      • $279/SF
      • 5 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Andy Schweigman Douglas Realty, LLC

  • /57

    $599,000 Pending

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

    23264 Lindsay Dr, Leonardtown, MD 20650

    PRICE IMPROVEMENT! **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot with extra large fenced backyard. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • /46

    $439,900 Sold Mar 31, 2026

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 74 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    • /45

      Est $248,861 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

      • 4% Below List Price
      • $339/SF
      • 19 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Lesa Clark Redfin Corp

  • /4

    $599,950 Under Contract

    • 1,691 Sq Ft

    22615 Washington St, Leonardtown, MD 20650

    Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts &

    Caitlin Vallandingham Infinitas Realty Group

    22615 Washington St, 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
    • /68

      Est $669,415 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

      • 1% Above List Price
      • $242/SF
      • 2 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /47

    $639,000

    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    This unique property has so much to offer and has been a great family home, however owners are moving and have found their next home. Well cared for 4 BR home has 2,116 sq. ft, and features an open floor plan. The kitchen has granite counters, maple cabinets, a custom-made bar/island and ceramic tile flooring, and is open to the dining area, with glass doors to the deck, and the Family Rm. The

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns 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 $1,028,318

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • /79

      Est $624,313 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

      • 5% Above List Price
      • $172/SF
      • 64 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Kimberly Scott Remax 100

  • /4

    $639,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,261 Sq Ft

    23621 Margrave Dr, Leonardtown, MD 20650

    Welcome to this beautifully maintained, single-owner Colonial in the highly sought-after Leonard’s Grant community. Blending classic charm with thoughtful upgrades, this home offers both comfort and functionality throughout. The main level features wood flooring in the living and dining areas, a private dining room, and a cozy fireplace. The spacious kitchen boasts stainless steel appliances,

    Lauren Garner EXP Realty, LLC

    23621 Margrave 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 $339,269

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • /92

      Est $1,100,806 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

      • 4% Below List Price
      • $341/SF
      • 5 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Andrew Shemeta Century 21 New Millennium

  • /56

    $635,000 Under Contract

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

    23590 Margrave Dr, Leonardtown, MD 20650

    Welcome home to the Patuxent QBH floor plan in sought-after Leonard's Grant Neighborhood, the epitome of community-centered living in Leonardtown, Maryland. Situated on a corner lot with extensive landscaping and a private fenced backyard, this home offers stunning curb appeal and a relaxed indoor-outdoor living with a large 18' x 18' composite screened deck and a concrete patio for gatherings.

    Darrin Carter RE/MAX One

    23590 Margrave Dr, 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 $548,438

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • /31

      Est $588,500 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

      • 15% Above List Price
      • $146/SF
      • 30 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Josh Yowell EXP Realty, LLC

  • /3

    $639,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,854 Sq Ft

    23073 Town Run Dr, Leonardtown, MD 20650

    ***Photos Coming Soon***Welcome home to 23073 Town Run Drive! Built in 2022, this beautifully maintained home in the highly sought-after neighborhood of The Meadows at Town Run in Leonardtown is truly a standout. Built by QBH, this desirable Ashland model offers thoughtfully designed living space with an open and inviting floor plan—perfect for both everyday living and entertaining. This home

    Laura Bernth RE/MAX One

    23073 Town Run Dr, 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 $505,211

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    41918 Sara Ann Ct, Leonardtown, MD 20650
    • /12

      Est $668,364 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

      • 5% Below List Price
      • $167/SF
      • 0 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Cynthia Ballard Century 21 New Millennium

  • /56

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,490 Sq Ft

    40003 Tippit Rd, Leonardtown, MD 20650

    If you've been looking for Leonardtown waterfront, look no further! This exceptional .83-acre waterfront retreat on deep, protected Combs Creek offers breathtaking, panoramic views stretching across Breton Bay to the Potomac River. A rare and versatile offering, 40003 Tippit Road features TWO beautifully appointed dwellings, blending historic charm with modern comfort in a truly serene setting.

    Charlotte Long EXP Realty, LLC

    40003 Tippit 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 $647,504

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • /37

      Est $383,149 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% Above List Price
      • $175/SF
      • 4 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Dawn Bell RE/MAX

  • /50

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    40810 Meadow Dr, Leonardtown, MD 20650

    Completely renovated and move-in ready, this stunning rambler in desirable Leonardtown is perfectly positioned near Breton Bay Golf Course and the scenic waters of Breton Bay. Every inch has been thoughtfully updated... brand new roof, windows, heat pump, water heater, washer & dryer, appliances, encapsulated crawl space... nothing to worry about for the years to come, offering a truly turnkey

    Cheryl Bare CENTURY 21 New Millennium

    40810 Meadow Dr, 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 $296,983

    Last Listing Agent Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
    • /65

      Est $834,944 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

      • 5% Below List Price
      • $181/SF
      • 4 Days On Market

      Last Sold Price $881,000

      Last Listing Agent MaryAnne Crewse O'Brien Realty

  • /3

    $335,000 Pending

    • 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
  • /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 $646,707

    Last Listing Agent Laura Bernth RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • /4

      Est $78,500 Not Listed For Sale

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • 482 Days On Market

      Last Sold Price $75,000

      Last Listing Agent Kelly Loveless BHHS PenFed (actual)

  • /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
  • /82

    $574,000 Sold Jul 24, 2025

    23075 Hollywood Rd, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft
    • Built 1942

    Last Sold Summary

    • $177/SF
    • 55 Days On Market

    Current Estimated Value $573,741

    Last Listing Agent Katy Galloway CENTURY 21 New Millennium

    23075 Hollywood Rd, Leonardtown, MD 20650
    • /23

      Est $328,403 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

      • $344/SF
      • 6 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Emily Gross EXP Realty, LLC

  • /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
  • /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 $625,355

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /70

      Est $653,329 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

      • 1% Above List Price
      • $200/SF
      • 9 Days On Market

      Last Sold Price $645,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /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
  • /87

    $475,203 Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $476,096

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • /87

      Est $625,315 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

      • $210/SF
      • 4 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

Showing Results 81 - 120, Page 3 of 18

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