7,080

Homes in ZIP Code 20650

Section Image
    • /39

      Est $473,482

      Not Listed For Sale

      41464 Helen Marie Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft
      • Built 1995
      41464 Helen Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 60 Days On Market

  • /30

    $1,750,000

    $115K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

    Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • /40

    $450,000

    Sold May 15, 2026

    22343 Newtowne Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $213/SF
    • 21 Days On Market

    Current Estimated Value $467,096

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    • /90

      Est $695,271

      Not Listed For Sale

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 1999
      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

  • /16

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650

    *****PENDING****** Homesite 154 Oakley D1 TO BE Built Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. Photos shown are representative and intended to illustrate a similar finished townhouse. New Construction – 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

    Laura Hefley RE/MAX One

    Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650
  • /2

    $825,000

    Sold Jul 31, 2025

    40738 Bobwhite Ln, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 4,648 Sq Ft
    • Built 2000

    Last Sold Summary

    • $177/SF
    • 14 Days On Market

    Current Estimated Value $826,162

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
    • /55

      Est $543,558

      Not Listed For Sale

      23285 Joanne Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 2008
      23285 Joanne Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 65 Days On Market

  • /64

    $524,900

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,260 Sq Ft

    41992 Loker Ct, Leonardtown, MD 20650

    Classic Elegance in the Heart of Sought-After Leonardtown! Nestled at the end of a quiet cul-de-sac in the desirable Academy Hills community, this stunning 5-bedroom, 3.5-bath Colonial offers nearly 4,000 square feet of beautifully finished living space surrounded by peaceful wooded views and open pastureland. Step outside to enjoy the private, fenced backyard featuring split-rail fencing, a

    Matthew Burgan Infinitas Realty Group

    41992 Loker Ct, Leonardtown, MD 20650
  • /55

    $440,000

    Sold May 14, 2026

    41516 Marwood Cir, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Above List Price
    • $183/SF
    • 25 Days On Market

    Current Estimated Value $437,190

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    41516 Marwood Cir, Leonardtown, MD 20650
    • /29

      Est $414,452

      Not Listed For Sale

      40449 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,288 Sq Ft
      • Built 1995
      40449 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

  • /2

    $149,900

    • Land
    • 1.44 Acres
    • $104,097 per Acre

    20265 Hawks Way, Leonardtown, MD 20650

    Prime 1.44-Acre Buildable Lot in Leonardtown, MD Welcome to 20265 Hawks Way, a fantastic opportunity to build your dream home on a spacious 1.44-acre parcel on a quiet street. This generous lot offers a blank canvas — cleared and ready for construction — surrounded by other new construction homes that bring a sense of neighborhood and modern living while maintaining a peaceful, rural feel.

    Mark Frisco CENTURY 21 New Millennium

    20265 Hawks Way, Leonardtown, MD 20650
  • /48

    $479,900

    Sold Jun 17, 2026

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

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650
    • /43

      Est $528,367

      Not Listed For Sale

      21108 Arbor Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,412 Sq Ft
      • Built 1991
      21108 Arbor Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /43

    $559,900

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,688 Sq Ft

    23008 Hopton Ln, Leonardtown, MD 20650

    This property represents the definition of "Pride of Ownership" and their move is bittersweet. To have everything they have built here is remarkable and you could be the lucky one to obtain this property. Everything has been taken care of like it was purchased yesterday, books and invoices for most included, with comfort and convenience in mind. From the blacktop driveway, manicured lawn, to the

    Jimmy Hayden RE/MAX One

    23008 Hopton Ln, Leonardtown, MD 20650
  • /25

    $315,000

    Sold May 28, 2026

    22175 Bayside Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Built 1967

    Last Sold Summary

    • $264/SF
    • 55 Days On Market

    Current Estimated Value $314,341

    Last Listing Agent Darrin Carter RE/MAX One

    22175 Bayside Rd, Leonardtown, MD 20650
    • /39

      Est $642,497

      Not Listed For Sale

      21136 Catnip Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 2002
      21136 Catnip Way, Leonardtown, MD 20650

      Last Sold Summary

      • 51 Days On Market

  • /2

    $1,740,000

    Under Contract
    • Land
    • 3.85 Acres
    • $451,948 per Acre

    25845 Point Lookout Rd, Leonardtown, MD 20650

    This listing is 3.85 acres of a total 6-acre commercial property in Leonardtown, Maryland. Don't miss the chance to invest in this thriving and picturesque community. Whether you're looking to create a retail haven, upscale office space, or a dining destination, this property has all the ingredients for success. With its size and location near Patuxent Naval Air Station, this property is a blank

    Anne Davis CENTURY 21 Commercial New Millennium

    25845 Point Lookout Rd, Leonardtown, MD 20650
  • /82

    $701,650

    Sold Sep 11, 2025

    22064 Daffodil Ct, Leonardtown, MD 20650

    • 6 Beds
    • 4.5 Baths
    • 5,012 Sq Ft
    • Built 2022

    Last Sold Summary

    • $140/SF
    • 43 Days On Market

    Current Estimated Value $722,494

    Last Listing Agent Laura Hefley RE/MAX One

    22064 Daffodil Ct, Leonardtown, MD 20650
    • /19

      Est $354,545

      Not Listed For Sale

      43950 Blake Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1995
      43950 Blake Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /76

    $599,900

    Pending
    • 5 Beds
    • 3.5 Baths
    • 3,384 Sq Ft

    21822 Riviera Ct, Leonardtown, MD 20650

    Welcome to 21822 Riviera Court ... where classic Breton Bay charm meets thoughtful modern updates. Set on nearly half an acre of beautifully landscaped grounds, this 5-bedroom, 3.5-bath Colonial offers the space, warmth, and lifestyle buyers are looking for. From the moment you arrive, the curb appeal, mature trees, irrigation system, and inviting front entry set the tone. Inside, you’ll love the

    Laura Hefley RE/MAX One

    21822 Riviera Ct, Leonardtown, MD 20650
  • /79

    $669,900

    Sold Jun 18, 2026

    41249 Brenda Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 3,098 Sq Ft
    • Built 1987

    Last Sold Summary

    • $216/SF
    • 27 Days On Market

    Current Estimated Value $667,124

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    41249 Brenda Ct, Leonardtown, MD 20650
    • /59

      Est $443,379

      Not Listed For Sale

      40781 Center 40 Cir, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft
      • Built 1967
      40781 Center 40 Cir, Leonardtown, MD 20650

      Last Sold Summary

      • 18 Days On Market

  • /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
  • /13

    $150,000

    Sold Apr 03, 2026

    20959 Redgate Ln, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft
    • Built 1961

    Last Sold Summary

    • $146/SF
    • 209 Days On Market

    Current Estimated Value $212,823

    Last Listing Agent Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
    • /39

      Est $690,356

      Not Listed For Sale

      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 5,488 Sq Ft
      • Built 1999
      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 32 Days On Market

  • /42

    $355,000

    $5K PRICE DROP
    • 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
  • /55

    $464,900

    Sold Oct 07, 2025

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $157/SF
    • 54 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    • /57

      Est $439,248

      Not Listed For Sale

      22106 Society Hill Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft
      • Built 1977
      22106 Society Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 23 Days On Market

  • /55

    $310,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    41704 Courthouse Dr, Leonardtown, MD 20650

    Charming Townhome in the Heart of Downtown Leonardtown!Enjoy the best of Leonardtown living in this beautifully maintained townhome located just steps from local restaurants, shops, cafés, bars, and the scenic Leonardtown Wharf. This home offers the perfect combination of convenience, comfort, and small-town charm.Step inside to a welcoming lower-level recreation room featuring a full

    Heather Foster RE/MAX One

    41704 Courthouse Dr, Leonardtown, MD 20650
  • /31

    $480,000

    Sold Nov 24, 2025

    40534 Miss Ettas Way, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 82 Days On Market

    Current Estimated Value $483,513

    Last Listing Agent Connie Fitzgerald RE/MAX One

    40534 Miss Ettas Way, Leonardtown, MD 20650
    • /53

      Est $634,814

      Not Listed For Sale

      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,564 Sq Ft
      • Built 1996
      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /40

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's preferred lender and title co*** (special is for this Homesite #99 Madison D3 only). ***Available NOW*** Homesite #99 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

    Laura Hefley RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • /58

    $405,000

    Sold Feb 25, 2026

    19137 Lake Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,308 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Above List Price
    • $310/SF

    Current Estimated Value $402,148

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    19137 Lake Dr, Leonardtown, MD 20650
    • /31

      Est $420,740

      Not Listed For Sale

      40862 Spring House Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 2,055 Sq Ft
      • Built 1962
      40862 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

  • /57

    $653,000

    $3K PRICE INCREASE Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,340 Sq Ft

    42032 Starlight Dr, Leonardtown, MD 20650

    Welcome to 42032 Starlight Drive in Leonardtown, MD, a spacious and beautifully updated home offering comfort, flexibility, and thoughtful upgrades throughout. This beautiful property backs to woods, providing a peaceful and private setting to enjoy year-round. Inside, fresh new paint throughout, new carpet upstairs, and new vinyl plank flooring in the basement give the home a clean,

    Bill Oosterink CENTURY 21 New Millennium

    42032 Starlight Dr, Leonardtown, MD 20650
  • /82

    $727,360

    Sold May 14, 2026

    43500 Deer Run Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,972 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Above List Price
    • $245/SF
    • 4 Days On Market

    Current Estimated Value $682,169

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    43500 Deer Run Ct, Leonardtown, MD 20650
    • /46

      Est $935,268

      Not Listed For Sale

      40472 Port Place, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,828 Sq Ft
      • Built 1972
      40472 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 31 Days On Market

  • /3

    $779,000

    New Construction 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
  • /113

    $638,000

    Sold Aug 12, 2025

    23275 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 6,311 Sq Ft
    • Built 2005

    Last Sold Summary

    • $101/SF
    • 86 Days On Market

    Current Estimated Value $671,410

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • /22

      Est $417,547

      Not Listed For Sale

      42454 Wilderness Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft
      • Built 1994
      42454 Wilderness Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

Showing Results 161 - 200, Page 5 of 18

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