7,080

Homes in ZIP Code 20650

Section Image
    • /36

      Est $481,297

      Not Listed For Sale

      22605 Calvert St, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft
      • Built 2018
      22605 Calvert St, Leonardtown, MD 20650

      Last Sold Summary

      • 62 Days On Market

  • /36

    $93,500

    • Land
    • 4.11 Acres
    • $22,749 per Acre

    00 Saint Andrews Church Rd, Leonardtown, MD 20650

    Tucked away in Leonardtown in St. Mary's County, this 4.11 acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are encouraged to

    Casey Kennedy Whitetail Properties Real Estate

    00 Saint Andrews Church Rd, 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
    • /72

      Est $680,155

      Not Listed For Sale

      23748 Coventry Dr, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft
      • Built 2013
      23748 Coventry Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 6 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
  • /96

    $1,300,000

    Sold Nov 13, 2025

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft
    • Built 2020

    Last Sold Summary

    • $221/SF
    • 63 Days On Market

    Current Estimated Value $1,219,870

    Last Listing Agent Jimmy Hayden RE/MAX One

    23155 Greenstone Dr, 3, Leonardtown, MD 20650
    • /71

      Est $697,736

      Not Listed For Sale

      23287 Crestmar Ln, Leonardtown, MD 20650

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft
      • Built 2019
      23287 Crestmar Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 26 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
  • /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
    • /28

      Est $538,995

      Not Listed For Sale

      22301 Bayside Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft
      • Built 2012
      22301 Bayside Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 63 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
  • /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
    • /69

      Est $642,602

      Not Listed For Sale

      23567 Pine Bluff Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,736 Sq Ft
      • Built 2013
      23567 Pine Bluff Way, Leonardtown, MD 20650

      Last Sold Summary

      • 14 Days On Market

  • /12

    $454,900

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

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 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

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, 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
    • /30

      Est $774,580

      Not Listed For Sale

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft
      • Built 2021
      40630 Breton Oaks Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 80 Days On Market

  • /47

    $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
  • /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
    • /44

      Est $441,068

      Not Listed For Sale

      23380 Marview Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft
      • Built 2018
      23380 Marview Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 31 Days On Market

  • /2

    $715,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    22405 Hood Ln, Leonardtown, MD 20650

    Jaymie Lewis O'Brien Realty ERA Powered

    22405 Hood Ln, 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
    • /50

      Est $627,916

      Not Listed For Sale

      41442 Dauber Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,558 Sq Ft
      • Built 2013
      41442 Dauber Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /10

    $1,999,999

    $500K PRICE DROP Under Contract
    • 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
  • /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
    • /87

      Est $734,608

      Not Listed For Sale

      41408 W Citation St, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft
      • Built 2013
      41408 W Citation St, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /2

    $539,900

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Coming Soon in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access, Leonardtown Square, restaurants,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, 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
    • /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

  • /2

    $665,000

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft

    41531 Kalitan Ln, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    41531 Kalitan Ln, 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
    • /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

  • /44

    $449,900

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

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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

    Laura Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, 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
    • /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

  • /2

    $645,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    41462 Culpepper 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
    • /32

      Est $507,422

      Not Listed For Sale

      23822 Hollywood Rd, Hollywood, MD 20636

      • 3 Beds
      • 3 Baths
      • 2,461 Sq Ft
      • Built 2024
      23822 Hollywood Rd, Hollywood, MD 20636

      Last Sold Summary

      • 35 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
    • /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

Showing Results 41 - 80, Page 2 of 18

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