7,080

Homes in ZIP Code 20650

Section Image
  • /69

    $622,500

    Sold Jul 21, 2025

    21143 Catnip Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 16 Days On Market

    Current Estimated Value $621,545

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /68

      Est $680,022

      Not Listed For Sale

      42990 Baywood Place, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft
      • Built 2009
      42990 Baywood Place, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /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
  • /87

    $475,203

    Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $472,124

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • /79

      Est $650,640

      Not Listed For Sale

      24606 Pin Cushion Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,466 Sq Ft
      • Built 1987
      24606 Pin Cushion Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 64 Days On Market

  • /10

    $399,900

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

    42249 Saint Johns Rd, Leonardtown, MD 20650

    The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, 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
    • /92

      Est $1,162,817

      Not Listed For Sale

      40539 Port Place, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 3,371 Sq Ft
      • Built 1986
      40539 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /43

    $449,900

    New Construction
    • 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
  • /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
    • /31

      Est $596,402

      Not Listed For Sale

      21084 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft
      • Built 2003
      21084 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 30 Days On Market

  • /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
  • /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
    • /12

      Est $698,705

      Not Listed For Sale

      23569 Belmar Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,181 Sq Ft
      • Built 2008
      23569 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • /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
  • /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
    • /37

      Est $400,424

      Not Listed For Sale

      23005 Abell St, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 2,109 Sq Ft
      • Built 1955
      23005 Abell St, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /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
  • /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
    • /65

      Est $878,239

      Not Listed For Sale

      22265 Orchard Ct, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 4,873 Sq Ft
      • Built 2005
      22265 Orchard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /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
  • /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
    • /4

      Est $80,500

      Not Listed For Sale

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 482 Days On Market

  • /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
  • /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
    • /23

      Est $334,583

      Not Listed For Sale

      23028 Hopton Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1988
      23028 Hopton Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /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
  • /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
    • /70

      Est $683,842

      Not Listed For Sale

      21380 Fairwood Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft
      • Built 2008
      21380 Fairwood Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /70

    $399,000

    Under Contract
    • 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
  • /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
    • /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

  • /31

    $599,500

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial offers nearly 3,000 square feet of comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, 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

Showing Results 121 - 160, Page 4 of 18

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