6,772

Leonardtown, MD Homes

Section Image
  • 21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    /39

    $720,000

    Sold May 11, 2026

    21335 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,533 Sq Ft
    • Built 2011

    Last Sold Summary

    • 1% Above List Price
    • $159/SF
    • 3 Days On Market

    Current Estimated Value $713,000

    Last Listing Agent Deanna Rothstein RE/MAX One

    21335 Fairwood Ct, Leonardtown, MD 20650
    • 43610 Deer Run Ct, Leonardtown, MD 20650
      43610 Deer Run Ct, Leonardtown, MD 20650
      43610 Deer Run Ct, Leonardtown, MD 20650
      /87

      Est $651,719

      Not Listed For Sale

      43610 Deer Run Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,980 Sq Ft
      • Built 1997
      43610 Deer Run Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

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

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 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
  • 23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $469,900

    Sold Sep 18, 2025

    23664 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • 21120 Someday Farm Ln, Leonardtown, MD 20650
      21120 Someday Farm Ln, Leonardtown, MD 20650
      21120 Someday Farm Ln, Leonardtown, MD 20650
      /42

      Est $595,624

      Not Listed For Sale

      21120 Someday Farm Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft
      • Built 1990
      21120 Someday Farm Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • 43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    /72

    $605,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    This 5 BR, 3 full BA, 2 half BA home offers nearly 3,000 square feet of comfortable living, but what truly sets it apart is everything beyond the main house. Step outside to your own backyard oasis featuring an in-ground saltwater pool, gazebo, and expansive entertaining space—perfect for summer gatherings or quiet evenings under the stars.Need room to grow, work, or host? The 28x40 detached

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • 41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    /50

    $537,500

    Sold Sep 05, 2025

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft
    • Built 2019

    Last Sold Summary

    • $200/SF
    • 67 Days On Market

    Current Estimated Value $543,157

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    • 20440 Chingville Rd, Leonardtown, MD 20650
      20440 Chingville Rd, Leonardtown, MD 20650
      20440 Chingville Rd, Leonardtown, MD 20650
      /34

      Est $366,441

      Not Listed For Sale

      20440 Chingville Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 1969
      20440 Chingville Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

  • 23642 Hansel Ct, Leonardtown, MD 20650
    23642 Hansel Ct, Leonardtown, MD 20650
    23642 Hansel Ct, Leonardtown, MD 20650
    /79

    $649,900

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,726 Sq Ft

    23642 Hansel Ct, Leonardtown, MD 20650

    Welcome Home! This beautifully maintained home in Leonard's Grant backs up to trees, a rainwater pond and lots of wildlife! Enjoy watching the deer, bunnies and squirrels in the privacy of your fenced in back yard and large deck. The home features 4 spacious bedrooms, 3.5 baths, a finished basement, new (2022) luxury vinyl plank flooring throughout all levels, new energy efficient sliders (2022),

    Diane Fenwick RE/MAX One

    23642 Hansel Ct, Leonardtown, MD 20650
  • Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $447,400

    Sold Dec 16, 2025

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2025

    Last Sold Summary

    • $172/SF
    • 90 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    • 41464 Helen Marie Ct, Leonardtown, MD 20650
      41464 Helen Marie Ct, Leonardtown, MD 20650
      41464 Helen Marie Ct, Leonardtown, MD 20650
      /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

  • 42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    /10

    $399,900

    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    Charming and beautifully updated brick rancher located in the heart of Leonardtown! This single-level home offers 3 bedrooms and 1.5 bathrooms, making it ideal for easy, comfortable living. Recently remodeled, the property features fresh updates throughout, blending classic charm with modern touches. Enjoy a spacious, level lot perfect for outdoor entertaining, gardening, or simply relaxing. The

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, Leonardtown, MD 20650
  • 23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    /47

    $660,000

    Sold Jul 14, 2025

    23278 Applewood Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 4,306 Sq Ft
    • Built 2022

    Last Sold Summary

    • $153/SF
    • 10 Days On Market

    Current Estimated Value $671,600

    Last Listing Agent Jonathan Benya EXP Realty, LLC

    23278 Applewood Ln, Leonardtown, MD 20650
    • 20746 Deer Wood Park Dr, Leonardtown, MD 20650
      20746 Deer Wood Park Dr, Leonardtown, MD 20650
      20746 Deer Wood Park Dr, 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

  • Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    /43

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

    BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's Preferred Lender and Title. ****Available Now***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 2,604 sq ft of beautifully finished living space. This interior unit

    Laura Hefley RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
  • 23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    /76

    $580,000

    Sold Mar 23, 2026

    23593 Mitchell Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2004

    Last Sold Summary

    • $197/SF
    • 15 Days On Market

    Current Estimated Value $578,473

    Last Listing Agent Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
    • 23285 Joanne Dr, Leonardtown, MD 20650
      23285 Joanne Dr, Leonardtown, MD 20650
      23285 Joanne Dr, 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

  • Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650
    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650
    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650
    /18

    $449,900

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

    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650

    ****PENDING***** ***End of August Delivery**** ***Builder Incentive $12,500 in Closing Help with the use of both Preferred Lender & Title*** Homesite #129 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

    Laura Hefley RE/MAX One

    Lot 129 - 23715 Weeping Willow Way, Leonardtown, MD 20650
  • 44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    /97

    $640,000

    Sold Jun 29, 2025

    44114 Woodmont Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1999

    Last Sold Summary

    • $176/SF
    • 10 Days On Market

    Current Estimated Value $647,763

    Last Listing Agent Lori Jean Buongiovanni (Hethmon) EXP Realty, LLC

    44114 Woodmont Dr, Leonardtown, MD 20650
    • 40449 Breton View Dr, Leonardtown, MD 20650
      40449 Breton View Dr, Leonardtown, MD 20650
      40449 Breton View Dr, 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

  • 41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, Leonardtown, MD 20650
  • 42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    /42

    $906,500

    Sold Jul 18, 2025

    42239 Riverwinds Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft
    • Built 1980

    Last Sold Summary

    • $418/SF
    • 3 Days On Market

    Current Estimated Value $917,851

    Last Listing Agent Connie Fitzgerald RE/MAX One

    42239 Riverwinds Dr, Leonardtown, MD 20650
    • 21108 Arbor Ct, Leonardtown, MD 20650
      21108 Arbor Ct, Leonardtown, MD 20650
      21108 Arbor Ct, 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

  • 42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    /57

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, Leonardtown, MD 20650
  • Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    /45

    $449,900

    Sold May 29, 2026

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $175/SF
    • 36 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    • 21136 Catnip Way, Leonardtown, MD 20650
      21136 Catnip Way, Leonardtown, MD 20650
      21136 Catnip Way, 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

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

    $839,900

    Under Contract
    • 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
  • 41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    /105

    $690,000

    Sold Mar 31, 2026

    41438 Silver Charm Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft
    • Built 2010

    Last Sold Summary

    • $165/SF
    • 5 Days On Market

    Current Estimated Value $688,979

    Last Listing Agent Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
    • 43950 Blake Creek Rd, Leonardtown, MD 20650
      43950 Blake Creek Rd, Leonardtown, MD 20650
      43950 Blake Creek Rd, 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

  • 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 Redwood Realty

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • 20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    /56

    $549,000

    Sold Oct 30, 2025

    20919 Ridge Path Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft
    • Built 1992

    Last Sold Summary

    • $158/SF
    • 69 Days On Market

    Current Estimated Value $584,164

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
    • 40781 Center 40 Cir, Leonardtown, MD 20650
      40781 Center 40 Cir, Leonardtown, MD 20650
      40781 Center 40 Cir, 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

  • 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

    New Construction 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 Hefley RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
  • 23207 Moakley St, Leonardtown, MD 20650
    23207 Moakley St, Leonardtown, MD 20650
    23207 Moakley St, Leonardtown, MD 20650
    /60

    $530,000

    Sold Jun 02, 2026

    23207 Moakley St, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft
    • Built 1996

    Last Sold Summary

    • 2% Above List Price
    • $275/SF
    • 5 Days On Market

    Current Estimated Value $517,741

    Last Listing Agent Heather Foster RE/MAX One

    23207 Moakley St, Leonardtown, MD 20650
    • 21885 Newtowne Neck Rd, Leonardtown, MD 20650
      21885 Newtowne Neck Rd, Leonardtown, MD 20650
      21885 Newtowne Neck Rd, 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

  • 22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    /4

    $599,950

    Under Contract
    • 1,691 Sq Ft

    22615 Washington St, Leonardtown, MD 20650

    Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts &

    Caitlin Vallandingham Infinitas Realty Group

    22615 Washington St, Leonardtown, MD 20650
  • 22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck 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
    • 22106 Society Hill Rd, Leonardtown, MD 20650
      22106 Society Hill Rd, Leonardtown, MD 20650
      22106 Society Hill Rd, 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

  • Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
    /30

    $479,900

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

    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650

    *** PENDING *** Homesite 159 Oakley D1 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 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 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
  • 40738 Bobwhite Ln, Leonardtown, MD 20650
    40738 Bobwhite 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

Showing Results 121 - 160, Page 4 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