6,757

Leonardtown, MD Homes

Section Image
  • 40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, 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 $463,729

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    • 40862 Spring House Ln, Leonardtown, MD 20650
      40862 Spring House Ln, Leonardtown, MD 20650
      40862 Spring House Ln, Leonardtown, MD 20650
      /31

      Est $392,265 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

      • 5% Above List Price
      • $182/SF
      • 9 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Brian Mayer Real Broker, LLC

  • 40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    /28

    $149,900

    • Land
    • 2.28 Acres
    • $65,746 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • 22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, 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 $724,956

    Last Listing Agent Laura Bernth RE/MAX One

    22064 Daffodil Ct, Leonardtown, MD 20650
    • 40472 Port Place, Leonardtown, MD 20650
      40472 Port Place, Leonardtown, MD 20650
      40472 Port Place, Leonardtown, MD 20650
      /46

      Est $845,946 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

      • 3% Below List Price
      • $309/SF
      • 31 Days On Market

      Last Sold Price $875,000

      Last Listing Agent Sean Escobar O'Brien Realty

  • 40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    /101

    $809,900 Pending

    • 5,454 Sq Ft

    40737 Bobwhite Ln, Leonardtown, MD 20650

    Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful

    Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate 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 $188,760

    Last Listing Agent Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
    • 42454 Wilderness Rd, Leonardtown, MD 20650
      42454 Wilderness Rd, Leonardtown, MD 20650
      42454 Wilderness Rd, Leonardtown, MD 20650
      /22

      Est $398,035 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

      • 3% Above List Price
      • $277/SF
      • 12 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Jimmy Hayden RE/MAX

  • 41389 Holiday Ct, Leonardtown, MD 20650
    41389 Holiday Ct, Leonardtown, MD 20650
    41389 Holiday Ct, Leonardtown, MD 20650
    /77

    $715,000

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft

    41389 Holiday Ct, Leonardtown, MD 20650

    Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonard’s Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level,

    Laura Bernth RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
  • Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 - 23682 Dragonfly Ln, 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 Bernth RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    • 42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      /48

      Est $415,697 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

      • 3% Above List Price
      • $110/SF
      • 1 Day On Market

      Last Sold Price $405,000

      Last Listing Agent Teresa Dove Remax 100

  • 22224 Monterey Place, Leonardtown, MD 20650
    22224 Monterey Place, Leonardtown, MD 20650
    22224 Monterey Place, Leonardtown, MD 20650
    /29

    $459,900 Pending

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

    22224 Monterey Place, Leonardtown, MD 20650

    Welcome to this beautifully maintained contemporary home in the sought-after Society Hill section of Breton Bay, offering privacy, space, and timeless character on a generous .60-acre lot. From the moment you step inside, you’re greeted by soaring two-story ceilings in the great room, highlighted by rich hardwood floors and a striking stone gas fireplace that creates a warm and inviting focal

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    22224 Monterey Place, Leonardtown, MD 20650
  • 40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas 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 $483,045

    Last Listing Agent Connie Fitzgerald RE/MAX One

    40534 Miss Ettas Way, Leonardtown, MD 20650
    • 41936 Kentucky Ct, Leonardtown, MD 20650
      41936 Kentucky Ct, Leonardtown, MD 20650
      41936 Kentucky Ct, Leonardtown, MD 20650
      /83

      Est $541,265 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% Above List Price
      • $124/SF
      • 6 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Jessica Raley Century 21 New Millennium

  • 39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, Leonardtown, MD 20650
    /70

    $839,900

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft

    39577 Potomac Ave, Leonardtown, MD 20650

    There are waterfront homes—and then there are waterfront escapes with million-dollar views. Perched on an elevated lot overlooking St. Clements Bay, this uniquely charming brick mid-century modern home captures breathtaking panoramic water vistas from nearly every room. Whether you’re seeking a peaceful weekend retreat or a spectacular year-round residence, this property delivers serene coastal

    Brooke Matthews RE/MAX One

    39577 Potomac Ave, Leonardtown, MD 20650
  • 19137 Lake Dr, Leonardtown, MD 20650
    19137 Lake Dr, Leonardtown, MD 20650
    19137 Lake Dr, 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 $398,755

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    19137 Lake Dr, Leonardtown, MD 20650
    • 20370 Chingville Rd, Leonardtown, MD 20650
      20370 Chingville Rd, Leonardtown, MD 20650
      20370 Chingville Rd, Leonardtown, MD 20650
      /54

      Est $593,905 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

      • 13% Above List Price
      • $148/SF
      • 20 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Christina Reed RE/MAX

  • 0 Cedar Lane Rd, Leonardtown, MD 20650
    0 Cedar Lane Rd, Leonardtown, MD 20650
    0 Cedar Lane Rd, Leonardtown, MD 20650
    /17

    $3,800,000 Pending

    • Land
    • 52.18 Acres
    • $72,825 per Acre

    0 Cedar Lane Rd, Leonardtown, MD 20650

    This property offers the perfect blend of rural charm and convenient access to urban amenities. With the potential for annexation into the town of Leonardtown, there are exciting development possibilities on the horizon. Don't miss this unique opportunity!

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • 40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    /37

    $540,000 Sold Apr 30, 2025

    40222 Breton Beach Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1976

    Last Sold Summary

    • $417/SF
    • 207 Days On Market

    Current Estimated Value $551,856

    Last Listing Agent Jake Grier Baldus Real Estate, Inc.

    40222 Breton Beach Rd, Leonardtown, MD 20650
    • 22425 Archer St, Leonardtown, MD 20650
      22425 Archer St, Leonardtown, MD 20650
      22425 Archer St, Leonardtown, MD 20650
      /61

      Est $695,919 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

      • 3% Below List Price
      • $384/SF
      • 4 Days On Market

      Last Sold Price $720,000

      Last Listing Agent Kimberly Scott Remax 100

  • 23369 Marview Ct, Leonardtown, MD 20650
    23369 Marview Ct, Leonardtown, MD 20650
    23369 Marview Ct, Leonardtown, MD 20650
    /58

    $435,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft

    23369 Marview Ct, Leonardtown, MD 20650

    Beautiful Clark’s Rest townhome offering three finished levels, a two-car garage, and over 2,300 square feet of living space. The main level features hardwood floors, a gourmet kitchen with granite countertops and 42-inch cabinetry, a separate formal dining space, and a large family room—ideal for both everyday living and entertaining.The fully finished lower level includes a spacious

    Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
  • 23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, 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 $675,674

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • 23571 Gunnell Dr, Leonardtown, MD 20650
      23571 Gunnell Dr, Leonardtown, MD 20650
      23571 Gunnell Dr, Leonardtown, MD 20650
      /35

      Est $527,796 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

      • 3% Below List Price
      • $206/SF
      • 35 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Alicia Guinn RE/MAX

  • Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    /46

    $489,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 132 TO BE BUILT 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 Bernth RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
  • 22745 Duke St, Leonardtown, MD 20650
    22745 Duke St, Leonardtown, MD 20650
    22745 Duke St, 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 $259,863

    Last Listing Agent Jimmy Hayden RE/MAX One

    22745 Duke St, Leonardtown, MD 20650
    • 40457 Breton View Dr, Leonardtown, MD 20650
      40457 Breton View Dr, Leonardtown, MD 20650
      40457 Breton View Dr, Leonardtown, MD 20650
      /58

      Est $408,698 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

      • 2% Below List Price
      • $183/SF
      • 9 Days On Market

      Last Sold Price $417,500

      Last Listing Agent Anissa Hutchins Century 21 New Millennium

  • Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    /42

    $479,900 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 Bernth RE/MAX One

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
  • 43107 Gum Spring Dr, Leonardtown, MD 20650
    43107 Gum Spring Dr, Leonardtown, MD 20650
    43107 Gum Spring Dr, 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 $634,434

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • 23577 Abraham Dr, Leonardtown, MD 20650
      23577 Abraham Dr, Leonardtown, MD 20650
      23577 Abraham Dr, Leonardtown, MD 20650
      /47

      Est $590,158 Not Listed For Sale

      23577 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,929 Sq Ft
      • Built 2003
      23577 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Above List Price
      • $110/SF
      • 1 Day On Market

      Last Sold Price $542,500

      Last Listing Agent Chris Norris Residential Plus Real Estate Services

  • 40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    /88

    $1,049,900 Under Contract

    • 9 Beds
    • 5 Baths
    • 6,476 Sq Ft

    40840 Greenwood Ln, Leonardtown, MD 20650

    From the moment you enter over 6000+ sqft of finished home , it's clear this home has been enhanced well beyond the typical. High-quality finishes, updated systems, and carefully selected improvements are evident throughout, creating a move-in-ready experience that today's buyers will immediately appreciate. This meticulously maintained home features luxury living on 2.10 acres, offering the

    Romy Singh Samson Properties

    40840 Greenwood Ln, Leonardtown, MD 20650
  • Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    /39

    $469,900 Sold Dec 02, 2025

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    • 22909 Cedar Lane Rd, Leonardtown, MD 20650
      22909 Cedar Lane Rd, Leonardtown, MD 20650
      22909 Cedar Lane Rd, Leonardtown, MD 20650
      /77

      Est $491,706 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

      • $215/SF
      • 3 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Jessica Raley Century 21 New Millennium

  • 41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    /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
  • 23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    /60

    $599,000 Sold Sep 18, 2025

    23650 Rocky Ridge Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,914 Sq Ft
    • Built 1993

    Last Sold Summary

    • $153/SF
    • 20 Days On Market

    Current Estimated Value $604,000

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • 23244 Jenifer Ct, Leonardtown, MD 20650
      23244 Jenifer Ct, Leonardtown, MD 20650
      23244 Jenifer Ct, Leonardtown, MD 20650
      /48

      Est $561,495 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

      • 2% Above List Price
      • $164/SF
      • 24 Days On Market

      Last Sold Price $552,000

      Last Listing Agent Tracy Zhang Taylor Properties

  • 0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    /30

    $1,750,000

    • 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
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /4

    $163,500 Sold Nov 20, 2025

    21983 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1960

    Last Sold Summary

    • $143/SF
    • 37 Days On Market

    Current Estimated Value $194,035

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650
    • 40427 Breton View Dr, Leonardtown, MD 20650
      40427 Breton View Dr, Leonardtown, MD 20650
      40427 Breton View Dr, Leonardtown, MD 20650
      /86

      Est $416,718 Not Listed For Sale

      40427 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 4.5 Baths
      • 2,676 Sq Ft
      • Built 1994
      40427 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $148/SF
      • 0 Days On Market

      Last Sold Price $395,000

      Last Listing Agent Beverly Drewery Century 21 New Millennium

  • 23592 Belmar Dr, Leonardtown, MD 20650
    23592 Belmar Dr, Leonardtown, MD 20650
    23592 Belmar Dr, Leonardtown, MD 20650
    /63

    $680,000

    • 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
  • 39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    /51

    $415,000 Sold Jun 09, 2025

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft
    • Built 1994

    Last Sold Summary

    • $308/SF
    • 48 Days On Market

    Current Estimated Value $409,613

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

Showing Results 161 - 200, Page 5 of 18

Maryland St Marys County Leonardtown

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group