• Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Sell
    1. Home Valuation
  • Melissa Young Melissa Young
  • Sports
    1. Professional Athletes Relocation
    2. Athletes Coming To Philly
    3. Athletes Leaving Philly
  • About
    1. About Us
    2. Contact Us
    3. News
  • Market Snapshot
    • Register
    • Sign In
    Filters Reset
    1 Filter
    Price
    • Any
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • $ 800,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 1,000,000
    Beds
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Baths
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Reset
    0 Filters
    0 Filters Applied

    Days On Site
    Advanced
    Less Than
    Days
    Unit Level

    SqFt
    Switch to Acre
    Sqft
    Sqft
    Lot Size
    Switch to Acre
    Sqft
    Sqft
    Price per Sqft
    Monthly HOA Fee
    Year Built
    Stories
    Kitchens
    Acres
    Full Bathrooms
    Half Bathrooms
    Frontage
    Tax Amount
    Land Lease Fee
    Keyword
    Maintenance Fee
    Assessed Value

    Fireplace Number

    Parking Space
    Garage Space
    Carport Spaces

    Open House
    Has Picture
    New
    Hot
    Virtual Tour
    3D Tour
    Price Reduced
    Save Search (1)
    Save your search to get Alerts
    86 Properties
    Map

    86 Properties Available

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    The average price in the selected areas has remained stable. Learn more
    • 43985 MAIN WAY RD, Leonardtown, MD 20650
      4 Beds2 Baths2,400 SqFt
      1/74 74
      Pending

      $479,900

      43985 MAIN WAY RD, Leonardtown, MD 20650

      MLS# MDSM2025202

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 23264 LINDSAY DR, Leonardtown, MD 20650
      3 Beds2 Baths2,824 SqFt
      1/59 59
      Active

      $640,000

      23264 LINDSAY DR, Leonardtown, MD 20650

      MLS# MDSM2024888

      Listed by RE/MAX Realty Group

      Bright MLS (BMLS)
    • 21143 CATNIP CT, Leonardtown, MD 20650
      4 Beds3 Baths2,642 SqFt
      1/69 69
      Under Contract

      $635,000

      21143 CATNIP CT, Leonardtown, MD 20650

      MLS# MDSM2025046

      Listed by RE/MAX One

      Bright MLS (BMLS)
    • 23350 POTATO HILL FARM LN, Leonardtown, MD 20650
      5 Beds6 Baths6,508 SqFt
      1/64 64
      Under Contract

      $1,100,000

      23350 POTATO HILL FARM LN, Leonardtown, MD 20650

      MLS# MDSM2024800

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • 41412 DOCTORS CROSSING RD, Leonardtown, MD 20650
      4 Beds4 Baths2,686 SqFt
      1/50 50
      Under Contract

      $540,000

      41412 DOCTORS CROSSING RD, Leonardtown, MD 20650

      MLS# MDSM2024976

      Listed by RE/MAX United Real Estate

      Bright MLS (BMLS)
    • 41115 PAW PAW HOLLOW LN, Leonardtown, MD 20650
      4 Beds6 Baths6,116 SqFt
      1/140 140
      Active

      $775,000

      41115 PAW PAW HOLLOW LN, Leonardtown, MD 20650

      MLS# MDSM2025074

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 23278 APPLEWOOD LN, Leonardtown, MD 20650
      4 Beds4 Baths4,306 SqFt
      1/47 47
      Pending

      $650,000

      23278 APPLEWOOD LN, Leonardtown, MD 20650

      MLS# MDSM2025020

      Listed by EXP Realty, LLC

      Bright MLS (BMLS)
    • 23641 BELMAR DR, Leonardtown, MD 20650
      5 Beds4 Baths3,236 SqFt
      1/42 42
      Pending

      $630,000

      23641 BELMAR DR, Leonardtown, MD 20650

      MLS# MDSM2024660

      Listed by RE/MAX One

      Bright MLS (BMLS)
    • 21549 POINT LOOKOUT, Leonardtown, MD 20650
      5 Beds4 Baths3,153 SqFt
      1/43 43
      Under Contract

      $710,000

      21549 POINT LOOKOUT, Leonardtown, MD 20650

      MLS# MDSM2024990

      Listed by O'Brien Realty ERA Powered

      Bright MLS (BMLS)
    • 44646 MEDLEYS NECK RD, Leonardtown, MD 20650
      3 Beds1 Bath924 SqFt
      Price Dropped by $25K

      $99,999

      44646 MEDLEYS NECK RD, Leonardtown, MD 20650

      MLS# MDSM2024652

      Listed by Home Towne Real Estate

      Bright MLS (BMLS)
    • 23242 CLARKS REST RD, Leonardtown, MD 20650
      5 Beds4 Baths2,296 SqFt
      Coming Soon

      $599,000

      23242 CLARKS REST RD, Leonardtown, MD 20650

      MLS# MDSM2024822

      Listed by Infinitas Realty Group

      Bright MLS (BMLS)
    • 41505 KNIGHT RD, Leonardtown, MD 20650
      5 Beds8 Baths12,113 SqFt
      1/126 126
      Active

      $5,950,000

      41505 KNIGHT RD, Leonardtown, MD 20650

      MLS# MDSM2023270

      Listed by Engel & Volkers Annapolis

      Bright MLS (BMLS)
    • 40738 BOBWHITE LN, Leonardtown, MD 20650
      5 Beds4 Baths4,648 SqFt
      1/120 120
      Under Contract

      $843,000

      40738 BOBWHITE LN, Leonardtown, MD 20650

      MLS# MDSM2023806

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 22626 CHICKADEE LN, Leonardtown, MD 20650
      4 Beds4 Baths2,948 SqFt
      1/75 75
      Active

      $649,900

      22626 CHICKADEE LN, Leonardtown, MD 20650

      MLS# MDSM2024686

      Listed by JPAR Real Estate Professionals

      Bright MLS (BMLS)
    • 23433 GROVEWOOD CT, Leonardtown, MD 20650
      4 Beds4 Baths2,804 SqFt
      1/78 78
      Pending

      $519,000

      23433 GROVEWOOD CT, Leonardtown, MD 20650

      MLS# MDSM2023900

      Listed by RE/MAX Realty Group

      Bright MLS (BMLS)
    • 23075 HOLLYWOOD RD, Leonardtown, MD 20650
      5 Beds3 Baths3,238 SqFt
      1/82 82
      Under Contract

      $574,000

      23075 HOLLYWOOD RD, Leonardtown, MD 20650

      MLS# MDSM2023778

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 41430 WHIMSICAL CT, Leonardtown, MD 20650
      5 Beds4 Baths3,907 SqFt
      1/30 30
      Price Dropped by $15K

      $634,999

      41430 WHIMSICAL CT, Leonardtown, MD 20650

      MLS# MDSM2023560

      Listed by Realty Navigator

      Bright MLS (BMLS)
    • 23578 PINE BLUFF WAY, Leonardtown, MD 20650
      3 Beds4 Baths3,188 SqFt
      1/75 75
      Pending

      $585,000

      23578 PINE BLUFF WAY, Leonardtown, MD 20650

      MLS# MDSM2023102

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 23275 JENIFER CT, Leonardtown, MD 20650
      5 Beds5 Baths6,311 SqFt
      1/113 113
      Price Dropped by $9K

      $625,000

      23275 JENIFER CT, Leonardtown, MD 20650

      MLS# MDSM2023552

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 18937 HODGES LN, Leonardtown, MD 20650
      3 Beds2 Baths1,834 SqFt
      1/32 32
      Active

      $699,900

      18937 HODGES LN, Leonardtown, MD 20650

      MLS# MDSM2023654

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 41402 SILVER CHARM CT, Leonardtown, MD 20650
      5 Beds4 Baths4,046 SqFt
      1/93 93
      Active

      $655,000

      41402 SILVER CHARM CT, Leonardtown, MD 20650

      MLS# MDSM2023568

      Listed by CENTURY 21 New Millennium

      Bright MLS (BMLS)
    • 41572 BRIARWOOD CIR, Leonardtown, MD 20650
      5 Beds4 Baths2,850 SqFt
      1/80 80
      Pending

      $495,000

      41572 BRIARWOOD CIR, Leonardtown, MD 20650

      MLS# MDSM2023192

      Listed by RE/MAX Realty Group

      Bright MLS (BMLS)
    • 23558 BELMAR DR, Leonardtown, MD 20650
      6 Beds4 Baths4,267 SqFt
      3D
      Under Contract

      $685,000

      23558 BELMAR DR, Leonardtown, MD 20650

      MLS# MDSM2023238

      Listed by RE/MAX One

      Bright MLS (BMLS)
    • 21897 FAIRWAY DR, Leonardtown, MD 20650
      5 Beds3 Baths3,664 SqFt
      1/70 70
      Under Contract

      $624,900

      21897 FAIRWAY DR, Leonardtown, MD 20650

      MLS# MDSM2022878

      Listed by Infinitas Realty Group

      Bright MLS (BMLS)
    • 1
    • 2
    • 3
    • 4