6,993

Homes in ZIP Code 20650

Section Image Section Image
    • /43

      Est $581,220

      Not Listed For Sale

      21081 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft
      • Built 2002
      21081 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Melissa Rodriguez RE/MAX One

  • /56

    $738,997

    $36K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,097 Sq Ft

    22393 Saint Clements Ave, Leonardtown, MD 20650

    Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space.Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively

    Alyson Anderson Allfirst Realty, Inc.

    22393 Saint Clements Ave, Leonardtown, MD 20650
  • /79

    $639,000

    Sold Feb 02, 2026

    41430 Challedon Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 12 Days On Market

    Current Estimated Value $647,974

    Last Listing Agent Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
    • /82

      Est $590,417

      Not Listed For Sale

      22030 Cartwright Rd, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft
      • Built 2005
      22030 Cartwright Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

  • /72

    $609,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,701 Sq Ft

    42102 Wildflower Dr, Leonardtown, MD 20650

    New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow.The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s

    Laura Lee Hefley RE/MAX One

    42102 Wildflower Dr, Leonardtown, MD 20650
  • /45

    $340,000

    Sold Apr 15, 2026

    23311 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $341,755

    Last Listing Agent JW Abney CENTURY 21 New Millennium

    23311 Point Lookout Rd, Leonardtown, MD 20650
    • /30

      Est $333,123

      Not Listed For Sale

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 1991
      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /2

    $290,000

    $10K PRICE DROP
    • Land
    • 15 Acres
    • $19,333 per Acre

    42700 Moll Dyer Rd, Leonardtown, MD 20650

    Discover a prime 15-acre parcel of land, offering a unique investment opportunity with significant potential returns. This property features a serene backdrop of trees and wooded areas, providing a tranquil setting while ensuring privacy. The sloping terrain enhances the natural beauty and could be ideal for various development projects, from residential homes to recreational retreats. The wooded

    Paul Fenton Coldwell Banker Premier

    42700 Moll Dyer Rd, Leonardtown, MD 20650
  • /77

    $728,000

    Sold May 22, 2026

    41389 Holiday Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Above List Price
    • $166/SF
    • 0 Days On Market

    Current Estimated Value $723,197

    Last Listing Agent Laura Lee Hefley RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
    • /42

      Est $663,756

      Not Listed For Sale

      20708 Waterside Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft
      • Built 1925
      20708 Waterside Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jenny Norris EXP Realty, LLC

  • /4

    $450,000

    Coming Soon Sep 30
    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft

    20410 Chingville Rd, Leonardtown, MD 20650

    This well-maintained 2004 ranch-style home offers 2,604 square feet of functional living space on a private, non-HOA 2-acre lot. The interior features four spacious bedrooms, three full bathrooms, and an open-concept layout that seamlessly connects the main living and dining areas. A fully finished basement provides flexible additional square footage ideal for a home office, media room, or gym.

    Billy Rabbitt The Southside Group Real Estate

    20410 Chingville Rd, Leonardtown, MD 20650
  • /29

    $440,000

    Sold Apr 24, 2026

    22224 Monterey Place, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,176 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $202/SF
    • 9 Days On Market

    Current Estimated Value $442,267

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    22224 Monterey Place, Leonardtown, MD 20650
    • /82

      Est $688,932

      Not Listed For Sale

      44074 Medleys Neck Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 3,830 Sq Ft
      • Built 2006
      44074 Medleys Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

  • /67

    $799,900

    Under Contract
    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • /2

    $971,725

    Sold Sep 24, 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 764 Days On Market

    Current Estimated Value $735,000

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
    • /75

      Est $464,913

      Not Listed For Sale

      41925 Nazareth Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,512 Sq Ft
      • Built 2005
      41925 Nazareth Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Dawn Bell RE/MAX One

  • /3

    $175,000

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

    22501 Bull Rd, Leonardtown, MD 20650

    One of only two lots remaining! Breton Knolls is a 24-lot subdivision in Leonardtown with 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
  • /30

    $645,000

    Sold Oct 15, 2025

    41430 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft
    • Built 2011

    Last Sold Summary

    • $165/SF
    • 26 Days On Market

    Current Estimated Value $662,810

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
    • /18

      Est $402,195

      Not Listed For Sale

      40443 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,604 Sq Ft
      • Built 1994
      40443 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Anne Davis CENTURY 21 New Millennium

  • /39

    $449,900

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

    23725 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersHerringbone Carolina Bead SidingMusket Brown ShuttersSedona Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorLVT in Bathrooms and Laundry RoomUpgraded Maple Kitchen CabinetsRoccoco Quartz CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23725 Dragonfly Ln, Leonardtown, MD 20650
  • /70

    $824,900

    Sold Jun 29, 2026

    39577 Potomac Ave, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Below List Price
    • $242/SF
    • 43 Days On Market

    Current Estimated Value $834,188

    Last Listing Agent Brooke Matthews RE/MAX One

    39577 Potomac Ave, Leonardtown, MD 20650
    • /55

      Est $556,232

      Not Listed For Sale

      41935 Green Hills Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1998
      41935 Green Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Mike Jordan CENTURY 21 New Millennium

  • /90

    $715,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    VA LOAN MAY BE ASSUMABLE AT 4.375% BY A QUALIFIED BUYER, SUBJECT TO VA APPROVAL.Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • /48

    $515,000

    Sold Apr 29, 2026

    22547 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 57 Days On Market

    Current Estimated Value $514,161

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22547 Landing Way, Leonardtown, MD 20650
    • /41

      Est $445,250

      Not Listed For Sale

      21717 Meadow Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft
      • Built 1981
      21717 Meadow Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • /31

    $614,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42108 Wildflower Dr, Leonardtown, MD 20650

    New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing.The Fenwick offers a smart, comfortable layout with a spacious

    Laura Lee Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • /15

    $485,000

    Sold Nov 14, 2025

    41130 Cryer Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1955

    Last Sold Summary

    • $326/SF
    • 115 Days On Market

    Current Estimated Value $494,980

    Last Listing Agent Sharon Cox Century 21 Redwood Realty

    41130 Cryer Ct, Leonardtown, MD 20650
    • /72

      Est $578,211

      Not Listed For Sale

      23638 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,352 Sq Ft
      • Built 2005
      23638 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kelly Padgett Century 21 Redwood Realty

  • /47

    $599,900

    $50K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,690 Sq Ft

    41444 Osborne Ln, Leonardtown, MD 20650

    Charming Home in Prime Leonardtown LocationThis inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops.Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650
  • /2

    $435,000

    Sold Apr 20, 2026

    23369 Marview Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft
    • Built 2017

    Last Sold Summary

    • $188/SF
    • 38 Days On Market

    Current Estimated Value $436,305

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
    • /37

      Est $393,646

      Not Listed For Sale

      39862 Big Pine Trail, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 1,656 Sq Ft
      • Built 2002
      39862 Big Pine Trail, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Paul Bell NOVA Brokers, LLC.

  • /17

    $350,000

    • 5 Beds
    • 2 Baths
    • 1,552 Sq Ft

    23011 Newtowne Neck Rd, Leonardtown, MD 20650

    Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage,

    Kelly Jackson Samson Properties

    23011 Newtowne Neck Rd, Leonardtown, MD 20650
  • /46

    $489,085

    Sold Aug 28, 2026

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

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

    Last Sold Summary

    • $158/SF
    • 7 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    • /41

      Est $579,775

      Not Listed For Sale

      23635 Abraham Dr, Leonardtown, MD 20650

      • 6 Beds
      • 4 Baths
      • 3,272 Sq Ft
      • Built 2004
      23635 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

  • /45

    $510,000

    Sold Dec 17, 2025

    41467 Osborne Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,827 Sq Ft
    • Built 2018

    Last Sold Summary

    • $180/SF
    • 13 Days On Market

    Current Estimated Value $524,021

    Last Listing Agent Susan Vogel Turtle Town Real Estate, LLC.

    41467 Osborne Ln, Leonardtown, MD 20650
    • /43

      Est $446,663

      Not Listed For Sale

      40905 Knight Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1980
      40905 Knight Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Rob Schou EXP Realty, LLC

  • /42

    $483,400

    Sold Jun 05, 2026

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Last Sold Summary

    • 1% Above List Price
    • $163/SF

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    • /28

      Est $398,849

      Not Listed For Sale

      39919 Lake Cecil Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,008 Sq Ft
      • Built 2004
      39919 Lake Cecil Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Sharyn Ahmad RE/MAX Realty Group

  • /88

    $1,049,900

    Sold May 19, 2026

    40840 Greenwood Ln, Leonardtown, MD 20650

    • 9 Beds
    • 5 Baths
    • 6,476 Sq Ft
    • Built 2012

    Last Sold Summary

    • $162/SF
    • 6 Days On Market

    Current Estimated Value $1,038,836

    Last Listing Agent Romy Singh Samson Properties

    40840 Greenwood Ln, Leonardtown, MD 20650
    • /55

      Est $402,501

      Not Listed For Sale

      40905 Spring House Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1962
      40905 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Rob Schou EXP Realty, LLC

Showing Results 281 - 320, Page 8 of 18

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