6,772

Leonardtown, MD Homes

Section Image
    • /10

      Est $277,061

      Not Listed For Sale

      22765 Duke St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft
      • Built 1949
      22765 Duke St, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /34

    $449,900

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

    Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650

    ****PENDING*** Homesite # 158 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 one-car garage and an entry-level flex space that includes built-in cubbies

    Laura Hefley RE/MAX One

    Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650
  • /18

    $570,000

    Sold Apr 16, 2026

    43641 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $261/SF
    • 0 Days On Market

    Current Estimated Value $574,258

    Last Listing Agent Jimmy Hayden RE/MAX One

    43641 Redmond Rd, Leonardtown, MD 20650
    • /20

      Est $376,739

      Not Listed For Sale

      28845 Point Lookout Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft
      • Built 1969
      28845 Point Lookout Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

  • /64

    $635,000

    Under Contract
    • 5 Beds
    • 3 Baths
    • 3,030 Sq Ft

    41585 Austin Ct, Leonardtown, MD 20650

    Welcome to the completely unforgettable curb appeal of this home situated in the only culdesac of custom homes in the Estates at Singletree! Loved and beautifully maintained from the start by its current owners, they have personally curated, creative florals that surround this Southern Living traditional build, all the way to the perimeters of the property which provide abundant blueberries,

    Drema Ballengee-grunst EXP Realty, LLC

    41585 Austin Ct, Leonardtown, MD 20650
  • /3

    $310,000

    Sold Apr 17, 2026

    39725 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $164/SF
    • 4 Days On Market

    Current Estimated Value $342,984

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    39725 Lady Baltimore Ave, Leonardtown, MD 20650
    • /76

      Est $577,305

      Not Listed For Sale

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft
      • Built 1987
      19661 Hickory Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 8 Days On Market

  • /19

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***Estimated Late October Delivery****To Be Built*** Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • /64

    $865,000

    Sold May 28, 2026

    40171 Little Woods Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,586 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Below List Price
    • $334/SF
    • 6 Days On Market

    Current Estimated Value $867,015

    Last Listing Agent Barbara Blades CENTURY 21 New Millennium

    40171 Little Woods Ln, Leonardtown, MD 20650
    • /79

      Est $684,864

      Not Listed For Sale

      18822 McKays Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft
      • Built 1998
      18822 McKays Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

  • /36

    $98,900

    $6K PRICE DROP
    • Land
    • 4.11 Acres
    • $24,063 per Acre

    000 Saint Andrews Church Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!! Located in Leonardtown in St. Marys County, this 4.11 acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable

    Casey Kennedy Whitetail Properties Real Estate

    000 Saint Andrews Church Rd, Leonardtown, MD 20650
  • /54

    $510,000

    Sold Dec 22, 2025

    41535 Singletree Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 2002

    Last Sold Summary

    • $225/SF
    • 44 Days On Market

    Current Estimated Value $513,659

    Last Listing Agent Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
    • /39

      Est $611,281

      Not Listed For Sale

      41419 Whimsical Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft
      • Built 2010
      41419 Whimsical Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 49 Days On Market

  • /91

    $715,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,367 Sq Ft

    41395 Omaha Ct, Leonardtown, MD 20650

    With a great layout, tons of living space, popular location, well-ranked schools, community amenities, and a corner, fenced, cul-de-sac lot, this Leonard's Grant "Frederick" model has it all! A 2' rear bump out gives this 5-bedroom, 3.5 bath Colonial more than 4,300 sq. ft of comfortable living space. Wave hi to the neighbors from the welcoming front porch, and then enter the soaring two-story

    Andrew Shemeta CENTURY 21 New Millennium

    41395 Omaha Ct, Leonardtown, MD 20650
  • /48

    $447,400

    Sold Oct 09, 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft
    • Built 2025

    Last Sold Summary

    • $175/SF
    • 58 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    • /76

      Est $652,811

      Not Listed For Sale

      41474 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft
      • Built 2010
      41474 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /50

    $459,900

    Under Contract
    • 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
  • /71

    $599,900

    Sold Jun 25, 2025

    42261 Bird Haven Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 2002

    Last Sold Summary

    • $186/SF
    • 18 Days On Market

    Current Estimated Value $598,322

    Last Listing Agent Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
    • /4

      Est $646,875

      Not Listed For Sale

      41443 Whimsical Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,400 Sq Ft
      • Built 2010
      41443 Whimsical Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • /46

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650

    ***PENDING********* Lot 151 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland 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 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Hefley RE/MAX One

    Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650
  • /2

    $400,000

    Sold Aug 18, 2025

    22190 Bull Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1987

    Last Sold Summary

    • $290/SF

    Current Estimated Value $399,748

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    22190 Bull Rd, Leonardtown, MD 20650
    • /10

      Est $663,751

      Not Listed For Sale

      23598 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,758 Sq Ft
      • Built 2010
      23598 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 16 Days On Market

  • /75

    $574,900

    • 5 Beds
    • 3.5 Baths
    • 4,300 Sq Ft

    41482 Pensive St, Leonardtown, MD 20650

    Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are

    Mark Frisco CENTURY 21 New Millennium

    41482 Pensive St, Leonardtown, MD 20650
  • /30

    $479,900

    Sold May 29, 2026

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    • /74

      Est $628,364

      Not Listed For Sale

      23546 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2009
      23546 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

  • /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
  • /16

    $281,650

    Sold Sep 30, 2025

    43658 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft
    • Built 1959

    Last Sold Summary

    • $136/SF
    • 12 Days On Market

    Current Estimated Value $319,335

    Last Listing Agent Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
    • /25

      Est $290,117

      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 Days On Market

  • /47

    $395,000

    Under Contract
    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    ***TEMP OFF WHILE REVIEWING OFFERS***Welcome home! If you need space to spread out, this unique and cozy home on a quiet half-acre lot is just what you've been looking for. Two separate living areas means enjoying movies and gaming in one room while you enjoy peace in the other. This one-of-a-kind floor plan maximizes every square foot, and surprisingly roomier than it appears! With 5

    Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
  • /49

    $447,400

    Sold Dec 11, 2025

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    • /56

      Est $654,257

      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

  • /46

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT********* Lot 117 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland 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 3095 sq ft home offers generous living areas, abundant natural

    Laura Hefley RE/MAX One

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
  • /55

    $430,000

    Sold Dec 01, 2025

    22592 Quiet Ln, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1991

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $431,660

    Last Listing Agent Paul Bell NOVA Brokers, LLC.

    22592 Quiet Ln, Leonardtown, MD 20650
    • /80

      Est $696,846

      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

      • 15 Days On Market

  • /10

    $1,999,999

    $500K PRICE DROP
    • 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
  • /6

    $320,500

    Sold Jun 13, 2025

    44662 Blake Creek Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 5 Days On Market

    Current Estimated Value $321,644

    Last Listing Agent Ruth Mudd RE/MAX One

    44662 Blake Creek Rd, Leonardtown, MD 20650
    • /29

      Est $576,972

      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

      • 2 Days On Market

  • /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
  • /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 $554,005

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • /38

      Est $491,624

      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

      • 23 Days On Market

Showing Results 41 - 80, Page 2 of 18

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