Leonardtown, MD Homes for Sale

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  /30

  $1,750,000

  $115K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft

  0 Bayside Rd, Leonardtown, MD 20650

  Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The

  Bonnie Haley Haley Family Realty

  0 Bayside Rd, Leonardtown, MD 20650
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  /3

  $155,000

  • Land
  • 19,166 Sq Ft
  • $352,273 per Acre

  41650 Miss Bessie Dr, Leonardtown, MD 20650

  Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

  Jan Barnes CENTURY 21 New Millennium

  41650 Miss Bessie Dr, Leonardtown, MD 20650
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  $449,900

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,571 Sq Ft

  Madison D1 Plan at Meadows at Town Run II, Leonardtown, MD 20650

  Quality Built Homes Builder

  23731 Dragonfly Ln Unit 41509690, Leonardtown, MD 20650
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  $449,900

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  Madison D2 Plan at Meadows at Town Run II, Leonardtown, MD 20650

  Quality Built Homes Builder

  23731 Dragonfly Ln Unit 41509694, Leonardtown, MD 20650
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  $629,900

  New Construction Open Thu 1PM - 3PM

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

  42084 Wildflower Dr, Leonardtown, MD 20650

  To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start.This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an

  Laura Lee Hefley RE/MAX One

  42084 Wildflower Dr, Leonardtown, MD 20650
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  /2

  $149,900

  • Land
  • 1.44 Acres
  • $104,097 per Acre

  20265 Hawks Way, Leonardtown, MD 20650

  Prime 1.44-Acre Buildable Lot in Leonardtown, MDWelcome to 20265 Hawks Way, a fantastic opportunity to build your dream home on a spacious 1.44-acre parcel on a quiet street. This generous lot offers a blank canvas — cleared and ready for construction — surrounded by other new construction homes that bring a sense of neighborhood and modern living while maintaining a peaceful, rural

  Mark Frisco CENTURY 21 New Millennium

  20265 Hawks Way, Leonardtown, MD 20650
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  /16

  $350,000

  $115K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  18800 McKays Beach Rd, Leonardtown, MD 20650

  This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one

  Chris Coughlan RE/MAX One

  18800 McKays Beach Rd, Leonardtown, MD 20650
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  /36

  $449,900

  New Construction

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

  23714 Weeping Willow Way, Leonardtown, MD 20650

  Interior Elevation D3 with DormersSavannah Wicker Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe

  Quality Built Homes Builder

  23714 Weeping Willow Way, Leonardtown, MD 20650
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  $600,000

  Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,793 Sq Ft

  41524 Fairwood Ct, Leonardtown, MD 20650

  Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality.The thoughtful layout

  Billy Rabbitt The Southside Group Real Estate

  41524 Fairwood Ct, Leonardtown, MD 20650
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  /54

  $449,500

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  40659 Klear Ct, Leonardtown, MD 20650

  Discover a prime investment opportunity in the charming VILLAGES AT LEONARDTOWN! This 4-bedroom, 2.5-bath Colonial home, built in 2004, boasts 2,774 sq. ft. of potential. With a spacious unfinished basement featuring walkout stairs and rough bath plumbing, you have the perfect canvas to create additional living space or rental units, maximizing your return on investment. The property sits on a

  Christopher Blondin Baldus Real Estate, Inc.

  40659 Klear Ct, Leonardtown, MD 20650
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  $619,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  The Bell Plan at Meadows at Town Run - Single Family Homes, Leonardtown, MD 20650

  Quality Built Homes Builder

  23731 Dragonfly Ln Unit 41509729, Leonardtown, MD 20650
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  /45

  $619,900

  New Construction Open Thu 11:30AM - 3:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft

  42096 Wildflower Dr, Leonardtown, MD 20650

  Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space.This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level

  Laura Lee Hefley RE/MAX One

  42096 Wildflower Dr, Leonardtown, MD 20650
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  /13

  $399,000

  • Land
  • 10,890 Sq Ft
  • $1,596,000 per Acre

  Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650

  Build your dream home in one of Leonardtown's most desirable locations! Welcome to Parcel 323, Tract 2, a newly created homesite just moments from the heart of historic downtown Leonardtown. Perfectly positioned to take advantage of beautiful water views of Breton Bay, this exceptional parcel offers the opportunity to enjoy the best of small-town coastal living. Imagine strolling to Leonardtown's

  Charlotte Long EXP Realty, LLC

  Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
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  /10

  $299,000

  • Land
  • 5.8 Acres
  • $51,552 per Acre

  21365 Bogies Ln, Leonardtown, MD 20650

  Looking for land to build your dream home....well wait no more! This 5.8 acre parcel has been perc tested, recorded, surveyed and even has builder specs for a future home site and floor plans. You can also pick your own builder and get construction started on your new home. Property is currently registered and enrolled in an Agricultural program. Close to schools, shopping and area amenities.

  Kelly Padgett Century 21 Redwood Realty

  21365 Bogies Ln, Leonardtown, MD 20650
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  $15,000,000

  • 6 Beds
  • 4.5 Baths
  • 5,500 Sq Ft

  19700 Mulberry Fields Rd, Leonardtown, MD 20650

  OPEN HOUSES BY APPOINTMENT. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED!Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design

  Kornelia Stuphan Long & Foster Real Estate, Inc.

  19700 Mulberry Fields Rd, Leonardtown, MD 20650
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  $614,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,785 Sq Ft

  The Fenwick Plan at Meadows at Town Run - Single Family Homes, Leonardtown, MD 20650

  Quality Built Homes Builder

  23731 Dragonfly Ln Unit 41509703, Leonardtown, MD 20650
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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

  Bill Oosterink CENTURY 21 New Millennium

  43488 Medleys Neck Rd, Leonardtown, MD 20650
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  $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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  $609,900

  New Construction Open Thu 11:30AM - 3:30PM

  • 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
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  /9

  $454,900

  New Construction Open Thu 11:15AM - 3:30PM $5K PRICE INCREASE

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

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

  ****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 townhome offering 2,554 sq ft of beautifully finished living space. This interior unit

  Laura Lee Hefley RE/MAX One

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
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  /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
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  $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
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  /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
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  /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
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  /31

  $614,900

  New Construction Open Thu 11:30AM - 3:30PM

  • 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
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  /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

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