6,720

Leonardtown, MD Homes

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  • /44

    $449,900

    Sold Aug 24, 2026

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

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

    Last Sold Summary

    • $176/SF
    • 41 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    • /29

      Est $572,993

      Not Listed For Sale

      41650 Marie Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,808 Sq Ft
      • Built 2007
      41650 Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Deanna Rothstein RE/MAX One

  • /43

    $629,900

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    23444 Lindsay Dr, Leonardtown, MD 20650

    Discover a luxurious lifestyle in this stunning 2023 Colonial home nestled in the desirable Clark's Rest community. This exquisite residence boasts four spacious bedrooms and three and a half elegantly appointed bathrooms, perfect for both relaxation and entertaining. There are two unfinished bedrooms in the basement, so potentially it can be 6 bedrooms house. The heart of the home features

    Natalya Ford RE/MAX One

    23444 Lindsay 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 $581,397

    Last Listing Agent Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
    • /60

      Est $810,000

      Not Listed For Sale

      39653 Potomac Ave, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,150 Sq Ft
      • Built 1988
      39653 Potomac Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Coley Reed Long & Foster Real Estate, Inc.

  • /58

    $624,990

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    40611 Merion Ct, Leonardtown, MD 20650

    Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The

    Kalee Kelly Infinitas Realty Group

    40611 Merion Ct, Leonardtown, MD 20650
  • /3

    $175,000

    Sold Sep 09, 2026

    24645 Springhill Ln, Leonardtown, MD 20650

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $267,500

    Last Listing Agent Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
    • /68

      Est $1,212,833

      Not Listed For Sale

      40139 Combs Creek Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,944 Sq Ft
      • Built 1995
      40139 Combs Creek Way, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Andy Schweigman Douglas Realty, LLC

  • /74

    $649,000

    $21K PRICE DROP Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, 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 Lee Hefley RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    • /45

      Est $260,711

      Not Listed For Sale

      22321 Leonard St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1930
      22321 Leonard St, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Lesa Clark Redfin Corp

  • /78

    $460,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,469 Sq Ft

    41379 Margrove Cir, Leonardtown, MD 20650

    IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf,

    Mark Frisco CENTURY 21 New Millennium

    41379 Margrove Cir, 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 $692,074

    Last Listing Agent Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
    • /68

      Est $694,828

      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

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /28

    $99,000

    Pending
    • 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
  • /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 $592,969

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
    • /79

      Est $652,477

      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

      Last Listing Agent Kimberly Scott Century 21 Redwood Realty

  • /44

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Located in the sought-after Clark's Rest community, this home features Marrick’s Kensington floor plan with a covered front entry and separate sitting porch. Inside, the two-story foyer opens to a formal dining room and versatile office, library, or playroom. The kitchen features a large center island, granite countertops, gas cooktop, double wall ovens, abundant cabinetry, butler’s pantry, and

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn 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 $525,145

    Last Listing Agent Heather Foster RE/MAX One

    23207 Moakley St, Leonardtown, MD 20650
    • /92

      Est $1,137,328

      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

      Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

  • /15

    $374,900

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. 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

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns 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 $450,589

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    • /88

      Est $690,323

      Not Listed For Sale

      23558 Belmar Dr, Leonardtown, MD 20650

      • 6 Beds
      • 3.5 Baths
      • 4,267 Sq Ft
      • Built 2008
      23558 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      Last Listing Agent Heather Foster RE/MAX One

  • /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
  • /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 $441,163

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    41516 Marwood Cir, Leonardtown, MD 20650
    • /31

      Est $595,777

      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

      Last Listing Agent Josh Yowell EXP Realty, LLC

  • /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 Lee Hefley RE/MAX One

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650
    • /12

      Est $706,125

      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

      Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

  • /57

    $659,000

    $41K PRICE DROP Under Contract
    • 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
  • /54

    $485,000

    Sold Jul 02, 2026

    21807 Potomac View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft
    • Built 1965

    Last Sold Summary

    • $240/SF
    • 2 Days On Market

    Current Estimated Value $483,031

    Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View Dr, Leonardtown, MD 20650
    • /37

      Est $395,400

      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

      Last Listing Agent Dawn Bell RE/MAX One

  • /10

    $175,000

    • Land
    • 5 Acres
    • $35,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location.The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck 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 $314,435

    Last Listing Agent Darrin Carter RE/MAX One

    22175 Bayside Rd, Leonardtown, MD 20650
    • /65

      Est $891,629

      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

      Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

  • /41

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne Floyd RE/MAX One

    41888 Jenkins Ct, Leonardtown, MD 20650
  • /48

    $989,000

    Sold Sep 03, 2026

    22856 White Swan Way, Leonardtown, MD 20650

    • 5 Beds
    • 5 Baths
    • 5,810 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $170/SF
    • 43 Days On Market

    Current Estimated Value $1,021,904

    Last Listing Agent Barbara Stellway KW Metro Center

    22856 White Swan Way, Leonardtown, MD 20650
    • /4

      Est $104,000

      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

      Last Listing Agent Kelly Loveless Berkshire Hathaway HomeServices PenFed Realty

  • /53

    $609,900

    Open Sat 2PM - 4PM $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,736 Sq Ft

    23354 Lindsay Dr, Leonardtown, MD 20650

    Welcome to this stunning rambler in the highly sought-after community of Clark's Rest! Thoughtfully designed with 9' ceilings, quartz countertops, designer finishes, and upgrades throughout, this home offers the perfect blend of style, comfort, and functionality.The main level features three spacious bedrooms and two full bathrooms, including a beautiful owner's suite with dual vanities. The

    Dorothy Bistransin Redfin Corp

    23354 Lindsay Dr, 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 $660,752

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    41249 Brenda Ct, Leonardtown, MD 20650

Showing Results 121 - 160, Page 4 of 18

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