Leonardtown, MD Homes for Sale

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  /10

  $190,000

  • Land
  • 5 Acres
  • $38,000 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 seeking

  Bill Oosterink CENTURY 21 New Millennium

  43488 Medleys Neck Rd, Leonardtown, MD 20650
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  /55

  $749,000

  $26K 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
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  /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 suite

  Laura Hefley RE/MAX One

  42102 Wildflower Dr, Leonardtown, MD 20650
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  /7

  $454,900

  New Construction $5K PRICE INCREASE

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

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

  ***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level

  Laura Hefley RE/MAX One

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
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  $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
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  /2

  $300,000

  • Land
  • 15 Acres
  • $20,000 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
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  /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
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  /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
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  /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 Hefley RE/MAX One

  42108 Wildflower Dr, Leonardtown, MD 20650
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  /43

  $575,000

  • 3 Beds
  • 3.5 Baths
  • 3,422 Sq Ft

  22503 Sparrow Ct, Leonardtown, MD 20650

  If you’re seeking a peaceful place with the ease of popping out to every convenience Leonardtown has to offer within a couple of minutes, without sacrificing being tucked away on a serene and sizeable landscape, this former custom builder’s home offers the perfect setting to settle into before summer ends. Sparrow Court is situated beautifully surrounded by just enough woods to offer both shade

  Melinda Brown EXP Realty, LLC

  22503 Sparrow Ct, Leonardtown, MD 20650
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  /47

  $624,900

  $25K 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
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  /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

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