7,069

Homes in ZIP Code 20650

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  • /35

    $449,900 Sold Apr 16, 2026

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650
    • /28

      Est $336,291 Not Listed For Sale

      22340 Gore St, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,292 Sq Ft
      • Built 1964
      22340 Gore St, Leonardtown, MD 20650

      Last Sold Summary

      • 3% Above List Price
      • $252/SF
      • 76 Days On Market
      • Last Sold Price $325,800
      • Mar 28, 2024

      Last Listing Agent Kimberly Bannister T&G Real Estate Advisors, Inc.

  • /40

    $489,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650

    ***Under Contract***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 the

    Laura Bernth RE/MAX One

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
  • /86

    $595,000 Sold Apr 14, 2026

    21749 Pinehurst Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,410 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Above List Price
    • $174/SF
    • 2 Days On Market

    Current Estimated Value $509,404

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21749 Pinehurst Ct, Leonardtown, MD 20650
    • /37

      Est $612,716 Not Listed For Sale

      41625 Ferber Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,524 Sq Ft
      • Built 2005
      41625 Ferber Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $128/SF
      • 3 Days On Market
      • Last Sold Price $579,900
      • May 14, 2024

      Last Listing Agent Jonnie Jamison J2 Real Estate

  • /33

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    22281 Nomoni St, Leonardtown, MD 20650

    Nice home in waterfront community. 3 bedrooms and 2 baths. New floors, new refrigerator, new dishwasher, freshly painted. This home is ready for its new owner. Enjoy community beach/water access for a small mfee each year! No HOA! This is only the beginning...move-in ready for you to start your home ownership dream here!

    Paul Fenton Coldwell Banker Premier

    22281 Nomoni St, Leonardtown, MD 20650
  • /82

    $675,000 Sold Aug 14, 2025

    44074 Medleys Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,830 Sq Ft
    • Built 2006

    Last Sold Summary

    • $176/SF
    • 3 Days On Market

    Current Estimated Value $684,923

    Last Listing Agent Cynthia Ballard CENTURY 21 New Millennium

    44074 Medleys Neck Rd, Leonardtown, MD 20650
    • /67

      Est $560,419 Not Listed For Sale

      23626 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,916 Sq Ft
      • Built 2005
      23626 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $138/SF
      • 59 Days On Market
      • Last Sold Price $539,000
      • Sep 25, 2023

      Last Listing Agent Dawn Wood O'Brien Realty

  • /2

    $750,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    20752 Penansey Ln, Leonardtown, MD 20650

    Multigenerationl suite is attached with a full kitchen, laundry room, living room, bedroom and full bathroom.

    Heather Foster RE/MAX One

    20752 Penansey Ln, Leonardtown, MD 20650
  • /41

    $572,000 Sold Jun 09, 2025

    23635 Abraham Dr, Leonardtown, MD 20650

    • 6 Beds
    • 4 Baths
    • 3,272 Sq Ft
    • Built 2004

    Last Sold Summary

    • $175/SF
    • 2 Days On Market

    Current Estimated Value $576,874

    Last Listing Agent Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • /88

      Est $571,404 Not Listed For Sale

      23689 Jm Gough Ct, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,828 Sq Ft
      • Built 2005
      23689 Jm Gough Ct, Leonardtown, MD 20650

      Last Sold Summary

      • $149/SF
      • 1 Day On Market
      • Last Sold Price $569,900
      • May 10, 2024

      Last Listing Agent Bill Oosterink Century 21 New Millennium

  • /6

    $24,900

    • Land
    • 7,840 Sq Ft
    • $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
  • /2

    $800,000 Sold May 05, 2026

    40737 Bobwhite Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $147/SF
    • 23 Days On Market

    Current Estimated Value $802,552

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
    • /43

      Est $574,438 Not Listed For Sale

      21081 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft
      • Built 2002
      21081 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $168/SF
      • 3 Days On Market
      • Last Sold Price $520,000
      • Aug 31, 2023

      Last Listing Agent Melissa Rodriguez RE/MAX

  • /48

    $435,000

    • 3 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    41505 Margrove Cir, Leonardtown, MD 20650

    Welcome to this stunning end-unit townhome in the highly sought-after Clark’s Rest community. Built in the popular “Compton – Rear Kitchen” model, this home shows like new and delivers the ideal blend of style, space, and functionality. Step inside to a bright, open main level featuring hardwood flooring throughout, abundant natural light, and refined finishes including crown molding and

    Conor Loughran CENTURY 21 New Millennium

    41505 Margrove Cir, Leonardtown, MD 20650
  • /34

    $625,000 Sold Sep 30, 2025

    23246 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft
    • Built 2017

    Last Sold Summary

    • $161/SF
    • 55 Days On Market

    Current Estimated Value $647,655

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
    • /82

      Est $552,816 Not Listed For Sale

      22030 Cartwright Rd, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft
      • Built 2005
      22030 Cartwright Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $220/SF
      • 24 Days On Market
      • Last Sold Price $545,000
      • Apr 29, 2024

      Last Listing Agent Bill Oosterink Century 21 New Millennium

  • /3

    $779,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,745 Sq Ft

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Welcome to Breton Oaks—one of Leonardtown’s most sought-after communities—where this beautifully designed to-be-built home by Mednick Construction offers the perfect blend of modern farmhouse style and peaceful, wooded surroundings. Tucked away on a private, wooded lot on a quiet cul-de-sac, this thoughtfully crafted residence delivers timeless curb appeal paired with today’s most desirable

    Charlotte Long EXP Realty, LLC

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /43

    $459,900 Sold Dec 02, 2025

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft
    • Built 2025

    Last Sold Summary

    • $155/SF
    • 29 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    • /50

      Est $445,247 Not Listed For Sale

      21807 Potomac View Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,019 Sq Ft
      • Built 1965
      21807 Potomac View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Below List Price
      • $225/SF
      • 4 Days On Market
      • Last Sold Price $455,000
      • Jun 13, 2024

      Last Listing Agent Kelly Padgett Century 21 Redwood Realty

  • /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 22323 Saint Clements Ave, Leonardtown, MD 20650

    $300,000 Sold Oct 15, 2025

    22323 Saint Clements Ave, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $250/SF
    • 0 Days On Market

    Current Estimated Value $295,038

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
    • /30

      Est $317,350 Not Listed For Sale

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 1991
      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Above List Price
      • $231/SF
      • 61 Days On Market
      • Last Sold Price $310,000
      • Apr 19, 2024

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /45

    $569,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • /48

    $360,000 Sold Sep 26, 2025

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,884 Sq Ft
    • Built 1974

    Last Sold Summary

    • $191/SF
    • 35 Days On Market

    Current Estimated Value $372,966

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
    • /42

      Est $637,390 Not Listed For Sale

      20708 Waterside Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft
      • Built 1925
      20708 Waterside Dr, Leonardtown, MD 20650

      Last Sold Summary

      • $346/SF
      • 2 Days On Market
      • Last Sold Price $635,000
      • Oct 16, 2024

      Last Listing Agent Jenny Norris EXP Realty, LLC

  • /34

    $98,900

    • Land
    • 4.11 Acres
    • $24,063 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Mary’s 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 conditions; buyers

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • /79

    $639,000 Sold Feb 02, 2026

    41430 Challedon Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 12 Days On Market

    Current Estimated Value $640,822

    Last Listing Agent Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
    • /57

      Est $521,472 Not Listed For Sale

      41898 Jenkins Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,689 Sq Ft
      • Built 2005
      41898 Jenkins Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $131/SF
      • 1 Day On Market
      • Last Sold Price $485,000
      • Jul 05, 2023

      Last Listing Agent Sharon Cox Century 21 New Millennium

  • /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • /45

    $340,000 Sold Apr 15, 2026

    23311 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $315,720

    Last Listing Agent JW Abney RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
    • /40

      Est $636,698 Not Listed For Sale

      23258 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 5 Baths
      • 5,100 Sq Ft
      • Built 2005
      23258 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 13% Above List Price
      • $111/SF
      • 4 Days On Market
      • Last Sold Price $564,000
      • Jul 10, 2023

      Last Listing Agent Conor Loughran Century 21 New Millennium

  • /78

    $550,000 Under Contract

    • 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 Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • /29

    $440,000 Sold Apr 24, 2026

    22224 Monterey Place, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,176 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $202/SF
    • 9 Days On Market

    Current Estimated Value $457,933

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    22224 Monterey Place, Leonardtown, MD 20650
    • /18

      Est $389,229 Not Listed For Sale

      40443 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,604 Sq Ft
      • Built 1994
      40443 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $148/SF
      • 36 Days On Market
      • Last Sold Price $385,000
      • Dec 11, 2024

      Last Listing Agent Anne Davis Century 21 New Millennium

  • /25

    $285,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,101 Sq Ft

    41810 Eastwick Ln Unit 2301, Leonardtown, MD 20650

    Pristine top-floor condo in the heart of Leonardtown available for immediate occupancy! Enjoy the best of small town living with an easy walk to the square for outdoor dining, live music, and year-round festivals. Just minutes away, the wharf and waterfront park offer the perfect setting for relaxation and recreation.Inside, this thoughtfully designed home features exceptional storage

    Patrick Dugan O'Brien Realty ERA Powered

    41810 Eastwick Ln Unit 2301, Leonardtown, MD 20650
  • /2

    $971,725 Sold Sep 24, 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 764 Days On Market

    Current Estimated Value $806,000

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
    • /55

      Est $557,839 Not Listed For Sale

      41935 Green Hills Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1998
      41935 Green Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 11% Below List Price
      • $357/SF
      • 5 Days On Market
      • Last Sold Price $629,999
      • May 24, 2024

      Last Listing Agent Mike Jordan Century 21 New Millennium

  • /41

    $479,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650

    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 functionality and style. The

    Laura Bernth RE/MAX One

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
  • /30

    $645,000 Sold Oct 15, 2025

    41430 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft
    • Built 2011

    Last Sold Summary

    • $165/SF
    • 26 Days On Market

    Current Estimated Value $659,464

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650

Showing Results 241 - 280, Page 7 of 18

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