6,772

Leonardtown, MD Homes

Section Image
    • /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

  • /42

    $479,900

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

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT*** Unit 137 Oakley D1New 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 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

    Laura Hefley RE/MAX One

    Lot 137- 23667 Weeping Willow Way, 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
    • /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

  • /70

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • /76

    $460,000

    Sold Jun 12, 2025

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,524 Sq Ft
    • Built 1969

    Last Sold Summary

    • $182/SF
    • 61 Days On Market

    Current Estimated Value $474,416

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, 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

  • /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
  • /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
    • /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

  • /63

    $680,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft

    23592 Belmar Dr, Leonardtown, MD 20650

    Photos to come.QBH Belmont model with a beautiful Sunroom.

    Heather Foster RE/MAX One

    23592 Belmar Dr, 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
    • /37

      Est $547,356

      Not Listed For Sale

      40222 Breton Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 1,296 Sq Ft
      • Built 1976
      40222 Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 207 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
  • /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
    • /48

      Est $439,912

      Not Listed For Sale

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,692 Sq Ft
      • Built 1961
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /2

    $524,900

    Coming Soon
    • 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

    $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
    • /83

      Est $564,509

      Not Listed For Sale

      41936 Kentucky Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,115 Sq Ft
      • Built 2002
      41936 Kentucky Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 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
  • /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
    • /54

      Est $608,179

      Not Listed For Sale

      20370 Chingville Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,538 Sq Ft
      • Built 2007
      20370 Chingville Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 20 Days On Market

  • /43

    $559,900

    Coming Soon
    • 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
  • /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
    • /61

      Est $726,920

      Not Listed For Sale

      22425 Archer St, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft
      • Built 1973
      22425 Archer St, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /95

    $739,500

    $70K PRICE INCREASE Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    21390 Little Saint Annes Ln, Leonardtown, MD 20650

    Country Living at it's best!!! NO HOA in a minor subdivision of only 7 houses within a couples of miles of downtown Leonardtown. Two primary suites or one in-law ADA approved apartment on main level, includes gas fireplace in living area, pocket doors, walk in shower, coffee bar with small refrigerator, three season porch and direct access to laundry facilities/garage w/ADA approved ramp. Year

    Jan Barnes CENTURY 21 New Millennium

    21390 Little Saint Annes Ln, 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
    • /35

      Est $558,896

      Not Listed For Sale

      23571 Gunnell Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,652 Sq Ft
      • Built 2005
      23571 Gunnell Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 35 Days On Market

  • /96

    $800,000

    Pending
    • 5 Beds
    • 2.5 Baths
    • 3,122 Sq Ft

    21130 Someday Farm Ln, Leonardtown, MD 20650

    MULTIPLE OFFERS RECEIVED! ALL OFFER DUE BY MONDAY MAY 4th at NOONWelcome Home to Your Private Rural Retreat. Nestled on 11 serene, private acres and just steps from St. Mary's River State Park, this stunning 5-bedroom, 2.5-bath Cape Cod offers the perfect blend of country living and modern convenience, all within 15 minutes of Patuxent River Naval Air Station and the charming wharf and dining

    Sarah Mulford-Martin EXP Realty, LLC

    21130 Someday Farm 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
    • /58

      Est $414,080

      Not Listed For Sale

      40457 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,286 Sq Ft
      • Built 1995
      40457 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 9 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
  • /4

    $285,500

    Sold Mar 17, 2026

    22745 Duke St, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 868 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $329/SF
    • 0 Days On Market

    Current Estimated Value $285,343

    Last Listing Agent Jimmy Hayden RE/MAX One

    22745 Duke St, Leonardtown, MD 20650
    • /77

      Est $512,403

      Not Listed For Sale

      22909 Cedar Lane Rd, Leonardtown, MD 20650

      • 5 Beds
      • 2 Baths
      • 2,275 Sq Ft
      • Built 1963
      22909 Cedar Lane Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /33

    $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
  • /81

    $565,000

    Sold Jun 01, 2026

    21767 Potomac View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 4,384 Sq Ft
    • Built 1977

    Last Sold Summary

    • 2% Above List Price
    • $129/SF
    • 9 Days On Market

    Current Estimated Value $551,060

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    21767 Potomac View Dr, Leonardtown, MD 20650
    • /56

      Est $401,569

      Not Listed For Sale

      20161 Tower Hill Rd, Leonardtown, MD 20650

      • 2 Beds
      • 2 Baths
      • 1,661 Sq Ft
      • Built 1990
      20161 Tower Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /40

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 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
  • /60

    $625,000

    Sold Nov 26, 2025

    43107 Gum Spring Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft
    • Built 1993

    Last Sold Summary

    • $228/SF
    • 11 Days On Market

    Current Estimated Value $623,432

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • /48

      Est $596,424

      Not Listed For Sale

      23244 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,357 Sq Ft
      • Built 2004
      23244 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

Showing Results 161 - 200, Page 5 of 18

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