7,035

Homes in ZIP Code 20650

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  • /90

    $565,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft

    21060 Woodmere Dr, Leonardtown, MD 20650

    Nestled on a beautifully maintained 1 acre lot, this 5 bedroom, 3.5 bathroom home is conveniently located in Leonardtown's Wilderness Run community. A welcoming foyer leads to a formal dining room and a charming country style kitchen which opens to a spacious family room. The kitchen features space for a table, a large pantry, stainless steel appliances, granite countertops, and direct access to

    Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, Leonardtown, MD 20650
  • /50

    $2,800 per month

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft
    • House for Rent

    40905 Spring House Ln, Leonardtown, MD 20650

    Welcome to 40905 Spring House Ln, Leonardtown, MD 20650. This beautifully renovated, modern country themed home offers comfort, charm, and convenience in one of Southern Maryland’s most desirable communities. This cozy, retreat has been thoughtfully updated with warm rustic accents and contemporary finishes, creating an inviting atmosphere that instantly feels like home. Bright open spaces,

    Michael Hunter Real Broker, LLC

    40905 Spring House Ln, Leonardtown, MD 20650
  • /59

    $600,000 Sold Oct 01, 2025

    43571 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 1993

    Last Sold Summary

    • $204/SF
    • 22 Days On Market

    Current Estimated Value $602,884

    Last Listing Agent Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
    • /70

      Est $777,784 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,320 Sq Ft

      40840 Greenwood Ln, Leonardtown, MD 20650

      40840 Greenwood Ln, Leonardtown, MD 20650
  • /49

    $610,000

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • /49

    $2,650 per month

    • 3 Beds
    • 3 Baths
    • 2,331 Sq Ft
    • House for Rent

    22397 Armstrong Dr, Leonardtown, MD 20650

    **Now Accepting Housing Vouchers** Just 7 minutes from the Leonardtown Square & Wharf, St. Mary's Hospital. 10 minutes from the beaches & trails of Newtowne Neck State Park. Armstrong Drive is located in the charming Breton Bay community. This delightful split-level home offers a perfect blend of comfort and convenience. Students are served by Benjamin Banneker Elementary School and Leonardtown

    Jonathan Powell Real Broker, LLC

    22397 Armstrong Dr, Leonardtown, MD 20650
  • /61

    $440,000 Sold Jun 16, 2025

    23445 Grovewood Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • Built 2022

    Last Sold Summary

    • $185/SF
    • 46 Days On Market

    Current Estimated Value $444,902

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
    • /87

      Est $745,172 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft

      41408 W Citation St, Leonardtown, MD 20650

      41408 W Citation St, Leonardtown, MD 20650
  • /39

    $479,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT********* 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 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
  • /42

    $5,000 per month

    • 6 Beds
    • 5 Baths
    • 5,278 Sq Ft
    • House for Rent

    43840 Tarrywyle Way, Leonardtown, MD 20650

    Tatiana Bell Quasar Property Management And Real Estate LLC

    43840 Tarrywyle Way, Leonardtown, MD 20650
  • /96

    $1,300,000 Sold Nov 13, 2025

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft
    • Built 2020

    Last Sold Summary

    • $221/SF
    • 63 Days On Market

    Last Listing Agent Jimmy Hayden RE/MAX One

    23155 Greenstone Dr, 3, Leonardtown, MD 20650
    • /10

      Est $273,827 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft

      22765 Duke St, Leonardtown, MD 20650

      22765 Duke St, Leonardtown, MD 20650
  • /41

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***READY-NOW Builder Incentive, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Unit 106 Madison D3: Welcome to Meadows at Town Run....Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a

    Laura Bernth RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
  • /9

    $740,500 Sold Mar 27, 2025

    43012 Bluejay Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,440 Sq Ft
    • Built 2021

    Last Sold Summary

    • $215/SF
    • 0 Days On Market

    Current Estimated Value $747,558

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    43012 Bluejay Ln, Leonardtown, MD 20650
    • /76

      Est $739,775 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,785 Sq Ft

      20102 Whippoorwill Ln, Leonardtown, MD 20650

      20102 Whippoorwill Ln, Leonardtown, MD 20650
  • /53

    $645,900 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft

    23581 Gallent Fox Way, Leonardtown, MD 20650

    Welcome to 23581 Gallent Fox Way, a beautifully maintained and thoughtfully upgraded home nestled in the heart of highly desirable Leonard’s Grant. Situated in one of Leonardtown’s most sought-after communities, this 4-bedroom, 3.5-bath 3,933 sq ft residence combines comfort, convenience, and a true sense of community living. Perfectly positioned directly across from the community pool and

    Laura Bernth RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
  • /12

    $135,000 Sold May 09, 2025

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    • Land
    • 4.8 Acres
    • $28,125 per Acre

    Last Sold Summary

    • 76 Days On Market

    Current Estimated Value $135,535

    Last Listing Agent Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
    • /20

      Est $381,626 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft

      28845 Point Lookout Rd, Leonardtown, MD 20650

      28845 Point Lookout Rd, Leonardtown, MD 20650
  • /10

    $1,999,999

    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • /28

    $305,000 Sold Feb 28, 2025

    40315 Wathen Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1971

    Last Sold Summary

    • $293/SF
    • 1 Day On Market

    Current Estimated Value $308,993

    Last Listing Agent Brian Mayer Real Broker, LLC

    40315 Wathen Rd, Leonardtown, MD 20650
    • /76

      Est $572,593 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      19661 Hickory Hills Ln, Leonardtown, MD 20650
  • /87

    $475,000 Pending

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

    20697 Chingville Rd, Leonardtown, MD 20650

    Charming three (3) bedroom, two (2) bathroom Cape Cod in Leonardtown with a detached three (3) car garage and workshop. Conveniently located 15 min from NAS PAX, shopping, and restaurants. Kitchen was recently updated to honor the original design while providing additional storage and modern amenities. Other home features include quartz countertops, new carpet, fresh paint throughout, updated

    Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
  • /67

    $691,000 Sold May 09, 2025

    21620 Coves End Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,541 Sq Ft
    • Built 2001

    Last Sold Summary

    • $195/SF
    • 33 Days On Market

    Current Estimated Value $699,773

    Last Listing Agent Hannah Cole Real Broker, LLC

    21620 Coves End Ct, Leonardtown, MD 20650
    • /79

      Est $691,738 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft

      18822 McKays Beach Rd, Leonardtown, MD 20650

      18822 McKays Beach Rd, Leonardtown, MD 20650
  • /71

    $580,000 Coming Soon

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

    23593 Mitchell Dr, Leonardtown, MD 20650

    Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof is only 5 years old, new paint throughout and a new BEAUTIFUL patio!!Key Features:

    Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
  • /54

    $510,000 Sold Dec 22, 2025

    41535 Singletree Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 2002

    Last Sold Summary

    • $225/SF
    • 44 Days On Market

    Last Listing Agent Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
    • /39

      Est $631,435 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft

      41419 Whimsical Ct, Leonardtown, MD 20650

      41419 Whimsical Ct, Leonardtown, MD 20650
  • /3

    $175,000

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

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • /48

    $447,400 Sold Oct 09, 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft
    • Built 2025

    Last Sold Summary

    • $175/SF
    • 58 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    • /76

      Est $663,122 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft

      41474 Affirmed Way, Leonardtown, MD 20650

      41474 Affirmed Way, Leonardtown, MD 20650
  • /3

    $175,000

    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • /71

    $599,900 Sold Jun 25, 2025

    42261 Bird Haven Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 2002

    Last Sold Summary

    • $186/SF
    • 18 Days On Market

    Current Estimated Value $594,727

    Last Listing Agent Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
    • /74

      Est $638,252 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft

      23546 Belmar Dr, Leonardtown, MD 20650

      23546 Belmar Dr, Leonardtown, MD 20650
  • /38

    $487,400 Pending

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

    Lot 138- 23671 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT*** 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 the

    Laura Bernth RE/MAX One

    Lot 138- 23671 Dragonfly Ln, Leonardtown, MD 20650
  • /2

    $385,000 Sold Jun 12, 2025

    28590 Point Lookout Rd, Loveville, MD 20656

    • 4 Beds
    • 1.5 Baths
    • 1,816 Sq Ft
    • Built 1963

    Last Sold Summary

    • $212/SF
    • 0 Days On Market

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    28590 Point Lookout Rd, Loveville, MD 20656
    • /60

      Est $682,982 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,660 Sq Ft

      41429 Challedon Way, Leonardtown, MD 20650

      41429 Challedon Way, Leonardtown, MD 20650
  • /29

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • /2

    $400,000 Sold Aug 18, 2025

    22190 Bull Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1987

    Last Sold Summary

    • $290/SF

    Current Estimated Value $400,599

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    22190 Bull Rd, Leonardtown, MD 20650
    • /25

      Est $291,990 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft

      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650
  • /13

    $199,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC. This

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650

Showing Results 41 - 80, Page 2 of 18

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