6,740

Leonardtown, MD Homes

Section Image Section Image
  • Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
    /41

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650

    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 light, and the perfect blend of functionality and style. The

    Laura Lee Hefley RE/MAX One

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, 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
    • 23638 Abraham Dr, Leonardtown, MD 20650
      23638 Abraham Dr, Leonardtown, MD 20650
      23638 Abraham Dr, 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

  • 20750 Deer Wood Park Dr, Leonardtown, MD 20650
    20750 Deer Wood Park Dr, Leonardtown, MD 20650
    20750 Deer Wood Park Dr, Leonardtown, MD 20650
    /107

    $674,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,381 Sq Ft

    20750 Deer Wood Park Dr, Leonardtown, MD 20650

    Nestled in the serene community of Chestnut Hills of Leonardtown, this charming Colonial-style home offers a perfect blend of comfort and privacy. With 4 spacious bedrooms and 3.5 bathrooms, this residence spans an impressive 3,381 square feet, providing ample space for both relaxation and entertaining. Step inside to discover a warm and inviting interior. The open floor plan seamlessly connects

    Cynthia Ballard Century 21 Redwood Realty

    20750 Deer Wood Park Dr, Leonardtown, MD 20650
  • 23311 Point Lookout Rd, Leonardtown, MD 20650
    23311 Point Lookout Rd, Leonardtown, MD 20650
    23311 Point Lookout Rd, 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 RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
    • 39862 Big Pine Trail, Leonardtown, MD 20650
      39862 Big Pine Trail, Leonardtown, MD 20650
      39862 Big Pine Trail, 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.

  • 0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    /37

    $93,500

    • Land
    • 4.11 Acres
    • $22,749 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Nestled in the countryside of Leonardtown in St. Mary's County, this 4.11± acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 41389 Holiday Ct, Leonardtown, MD 20650
    41389 Holiday Ct, Leonardtown, MD 20650
    41389 Holiday Ct, 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
    • 41805 Meynard Ct, Leonardtown, MD 20650
      41805 Meynard Ct, Leonardtown, MD 20650
      41805 Meynard Ct, Leonardtown, MD 20650
      /37

      Est $497,769

      Not Listed For Sale

      41805 Meynard Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,715 Sq Ft
      • Built 2005
      41805 Meynard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Luke Pahel The Southside Group Real Estate

  • 42700 Moll Dyer Rd, Leonardtown, MD 20650
    42700 Moll Dyer Rd, Leonardtown, MD 20650
    /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
  • 22224 Monterey Place, Leonardtown, MD 20650
    22224 Monterey Place, Leonardtown, MD 20650
    22224 Monterey Place, 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
    • 23635 Abraham Dr, Leonardtown, MD 20650
      23635 Abraham Dr, Leonardtown, MD 20650
      23635 Abraham Dr, 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

  • 39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    /67

    $799,900

    • 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
  • 40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, 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
    • 40905 Knight Rd, Leonardtown, MD 20650
      40905 Knight Rd, Leonardtown, MD 20650
      40905 Knight Rd, 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

  • Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    /43

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    ***Available Now*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town

    Laura Lee Hefley RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, 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
    • 39919 Lake Cecil Ln, Leonardtown, MD 20650
      39919 Lake Cecil Ln, Leonardtown, MD 20650
      39919 Lake Cecil Ln, 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

  • 22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    /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
  • 39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, 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
    • 40905 Spring House Ln, Leonardtown, MD 20650
      40905 Spring House Ln, Leonardtown, MD 20650
      40905 Spring House 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

  • 23725 Dragonfly Ln, Leonardtown, MD 20650
    23725 Dragonfly Ln, Leonardtown, MD 20650
    23725 Dragonfly Ln, Leonardtown, MD 20650
    /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
  • 22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, 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
    • 23259 Jenifer Ct, Leonardtown, MD 20650
      23259 Jenifer Ct, Leonardtown, MD 20650
      23259 Jenifer Ct, Leonardtown, MD 20650
      /80

      Est $648,384

      Not Listed For Sale

      23259 Jenifer Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,078 Sq Ft
      • Built 2005
      23259 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michael Rose Rory S. Coakley Realty, Inc.

  • 23628 Belmar Dr, Leonardtown, MD 20650
    23628 Belmar Dr, Leonardtown, MD 20650
    23628 Belmar Dr, Leonardtown, MD 20650
    /90

    $730,000

    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    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 effortless entertaining.Inside, stunning Tigerwood floors flow throughout much of

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • 41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, 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
    • 22202 Hanover Dr, Leonardtown, MD 20650
      22202 Hanover Dr, Leonardtown, MD 20650
      22202 Hanover Dr, Leonardtown, MD 20650
      /51

      Est $634,848

      Not Listed For Sale

      22202 Hanover Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 3,261 Sq Ft
      • Built 2005
      22202 Hanover Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Danny Martin Keller Williams Flagship

  • 25010 Meadowlark Ct, Leonardtown, MD 20650
    25010 Meadowlark Ct, Leonardtown, MD 20650
    25010 Meadowlark Ct, Leonardtown, MD 20650
    /57

    $650,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,961 Sq Ft

    25010 Meadowlark Ct, Leonardtown, MD 20650

    Welcome home to this beautifully maintained rambler that is truly move-in ready! From the moment you step inside, you’ll appreciate the bright, airy feel, neutral colors, and pride of ownership throughout.The open floor plan features a gorgeous gourmet kitchen with plenty of space to gather, plus a massive pantry that provides incredible storage. The thoughtfully designed split-bedroom layout

    Heather Foster RE/MAX One

    25010 Meadowlark Ct, Leonardtown, MD 20650
  • 23369 Marview Ct, Leonardtown, MD 20650
    23369 Marview Ct, 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
    • 18808 McKays Beach Rd, Leonardtown, MD 20650
      18808 McKays Beach Rd, Leonardtown, MD 20650
      18808 McKays Beach Rd, Leonardtown, MD 20650
      /7

      Est $334,387

      Not Listed For Sale

      18808 McKays Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1955
      18808 McKays Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • 42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    /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 family

    Laura Lee Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • 41467 Osborne Ln, Leonardtown, MD 20650
    41467 Osborne Ln, Leonardtown, MD 20650
    41467 Osborne Ln, Leonardtown, MD 20650
    /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
    • 22113 Philip Dr, Leonardtown, MD 20650
      22113 Philip Dr, Leonardtown, MD 20650
      22113 Philip Dr, Leonardtown, MD 20650
      /85

      Est $650,100

      Not Listed For Sale

      22113 Philip Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,295 Sq Ft
      • Built 1990
      22113 Philip Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

  • Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    /15

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***Estimated Late November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 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

    Laura Lee Hefley RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    /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
    • 42023 Starlight Dr, Leonardtown, MD 20650
      42023 Starlight Dr, Leonardtown, MD 20650
      42023 Starlight Dr, Leonardtown, MD 20650
      /73

      Est $605,426

      Not Listed For Sale

      42023 Starlight Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,326 Sq Ft
      • Built 2004
      42023 Starlight Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Jessica Raley CENTURY 21 New Millennium

  • 41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    /47

    $599,900

    $50K PRICE DROP
    • 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 room

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650
  • 40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    /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
    • 41918 Sara Ann Ct, Leonardtown, MD 20650
      41918 Sara Ann Ct, Leonardtown, MD 20650
      41918 Sara Ann Ct, Leonardtown, MD 20650
      /33

      Est $509,755

      Not Listed For Sale

      41918 Sara Ann Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,392 Sq Ft
      • Built 2005
      41918 Sara Ann Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Tracey Summers CENTURY 21 New Millennium

  • 0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    /35

    $840,000

    • Land
    • 10.2 Acres
    • $82,353 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650

Showing Results 281 - 320, Page 8 of 18

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