50

Newest Homes for Sale in Leonardtown, MD

Section Image
  • 40582 Port Place, Leonardtown, MD 20650
    40582 Port Place, Leonardtown, MD 20650
    40582 Port Place, Leonardtown, MD 20650
    /46

    $439,900

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft

    40582 Port Place, Leonardtown, MD 20650

    Located in the highly sought-after Society Hill community, this home offers close proximity to the water with a partial view of Breton Bay. Just one street from the members-only beach access, you'll enjoy exclusive community amenities including a picnic pavilion, fishing pier, and playground—perfect for embracing the waterfront lifestyle. The home was extensively remodeled in 2008 with quality

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40582 Port Place, Leonardtown, MD 20650
  • 40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    /29

    $359,777

    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft

    40743 Magee Dr, Leonardtown, MD 20650

    Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished

    Liam Coonahan Real of Pennsylvania

    40743 Magee Dr, Leonardtown, MD 20650
  • 41400 Real Quiet Dr, Leonardtown, MD 20650
    41400 Real Quiet Dr, Leonardtown, MD 20650
    41400 Real Quiet Dr, Leonardtown, MD 20650
    /4

    $769,000

    Coming Soon
    • 6 Beds
    • 4 Baths
    • 5,569 Sq Ft

    41400 Real Quiet Dr, Leonardtown, MD 20650

    Welcome to your peaceful sanctuary at 41400 Real Quiet Drive! This exceptional property perfectly blends interior comfort with an extraordinary outdoor living experience. The highlight of this home is a $40,000 outdoor transformation featuring an expansive, premium patio designed for ultimate entertaining and a fully enclosed black aluminum fence. Inside, you will find a bright, open-concept

    James Dick Long & Foster Real Estate, Inc.

    41400 Real Quiet Dr, Leonardtown, MD 20650
  • 23628 Belmar Dr, Leonardtown, MD 20650
    23628 Belmar Dr, Leonardtown, MD 20650
    /2

    $730,000

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

    23628 Belmar Dr, Leonardtown, MD 20650

    PROFESSIONAL PHOTOS COMING!

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • 41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    /47

    $649,900

    • 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
  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • 42970 Heritage Dr, Leonardtown, MD 20650
    42970 Heritage Dr, Leonardtown, MD 20650
    42970 Heritage Dr, Leonardtown, MD 20650
    /94

    $829,900

    • 5 Beds
    • 4.5 Baths
    • 5,082 Sq Ft

    42970 Heritage Dr, Leonardtown, MD 20650

    Welcome home to this stunning luxury residence in the sought-after Leonardtown Farms neighborhood, offering over 5000 finished square feet! Built and impeccably maintained by its original owners, this home feels brand new; not a detail has been overlooked. A detailed record of every upgrade and maintenance item from 2012 through 2026 is available, giving buyers complete peace of mind and a clear

    Sarah Mulford-Martin EXP Realty, LLC

    42970 Heritage Dr, Leonardtown, MD 20650
  • 22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    /12

    $329,900

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    22332 Cedar St, Leonardtown, MD 20650

    Quaint All-Brick Rambler in a Water-Oriented Community This well-built, all-brick rambler offers timeless charm and solid construction. Features include a gas furnace, central air conditioning, and hardwood floors beneath the carpeting. The interior has been freshly painted and includes a bright eat-in kitchen. Oversized two car garage with large workshop area & pull down stairs to attic storage.

    Carol Kalmus-Choporis Century 21 Redwood Realty

    22332 Cedar St, Leonardtown, MD 20650
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $515,000

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

    40659 Klear Ct, Leonardtown, MD 20650

    This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and 2 full baths and the laundry room on the upper level. The main level

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • 42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    /45

    $619,900

    New Construction
    • 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 is

    Laura Hefley RE/MAX One

    42096 Wildflower Dr, Leonardtown, MD 20650
  • 23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    /85

    $649,000

    Open Sun 1PM - 3PM $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • 18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    /16

    $465,000

    • 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
  • 42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    /33

    $629,900

    New Construction
    • 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 inviting

    Laura Hefley RE/MAX One

    42084 Wildflower Dr, Leonardtown, MD 20650
  • 42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    /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
  • 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 Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
    Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
    Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
    /4

    $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
  • 23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    /37

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    23898 Speith Rd, Leonardtown, MD 20650

    Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless appliances, sought after barn type door bedroom

    Jimmy Hayden RE/MAX One

    23898 Speith Rd, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /49

    $20,000,000

    • 3 Baths
    • 5,120 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    LUXURY PROPERTY AUCTION: 28 July-12 August. Accepting starting bids through 27 July. Listed for $20M. Earn an incentive by 27 July. 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 so

    Wesley Mitchell Concierge Auctions, LLC

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    /74

    $670,000

    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this well-maintained Belmont model in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • 40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    /89

    $1,700,000

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

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • 22405 Hood Ln, Leonardtown, MD 20650
    22405 Hood Ln, Leonardtown, MD 20650
    22405 Hood Ln, Leonardtown, MD 20650
    /73

    $715,000

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    22405 Hood Ln, Leonardtown, MD 20650

    **Professional photography was delayed due to weather and will be uploaded as soon as possible** Welcome to 22405 Hood Lane - a custom home nestled on 11 acres. Built in 2024, you get all the benefits of new construction, without the wait and hassle of building. The drive along Hood Lane feels so private and serene, it is easy to forget that you are just minutes from both Downtown Leonardtown and

    Jaymie Lewis O'Brien Realty ERA Powered

    22405 Hood Ln, Leonardtown, MD 20650
  • 22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    /49

    $1,100,000

    • 5 Beds
    • 5 Baths
    • 5,410 Sq Ft

    22856 White Swan Way, Leonardtown, MD 20650

    This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light

    Barbara Stellway KW Metro Center

    22856 White Swan Way, Leonardtown, MD 20650
  • 0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, Leonardtown, MD 20650
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /2

    $645,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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 features an oversized

    Laura Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
  • Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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 features an oversized

    Laura Hefley RE/MAX One

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
  • 23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    /37

    $599,500

    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial offers nearly 3,000 square feet of comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • 22393 Saint Clements Ave, Leonardtown, MD 20650
    22393 Saint Clements Ave, Leonardtown, MD 20650
    22393 Saint Clements Ave, Leonardtown, MD 20650
    /55

    $774,900

    • 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 stunning bay views, the light-filled interior offers an open-concept layout that seamlessly blends comfortable everyday living with exceptional entertaining space. Featuring 4 bedrooms, 2 full baths, and 2 half baths, this home showcases modern finishes, coastal

    Alyson Anderson Allfirst Realty, Inc.

    22393 Saint Clements Ave, Leonardtown, MD 20650
  • 00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, Leonardtown, MD 20650
    /36

    $93,500

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

    00 Saint Andrews Church Rd, Leonardtown, MD 20650

    Tucked away in 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 encouraged to

    Casey Kennedy Whitetail Properties Real Estate

    00 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
    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
  • 42700 Moll Dyer Rd, Leonardtown, MD 20650
    42700 Moll Dyer Rd, Leonardtown, MD 20650
    /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
  • Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    /12

    $454,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    /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
  • 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
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /30

    $369,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been

    Natalya Ford RE/MAX One

    21983 Point Lookout Rd, Leonardtown, MD 20650
  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    /19

    $449,900

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

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***Estimated Late October Delivery****Under Construction*** 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 Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    /57

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, Leonardtown, MD 20650
  • 41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, Leonardtown, MD 20650
  • 41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    /70

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    /43

    $449,900

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

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

    BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's Preferred Lender and Title. ****Available Now***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 2,604 sq ft of beautifully finished living space. This interior unit

    Laura Hefley RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 2

Maryland St Marys County Leonardtown

Newest Listings for Sale in Leonardtown, MD

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $596,895.
How many homes have sold over the last 12 months in Leonardtown, MD?
195 homes have sold in Leonardtown, MD over the last 12 months.
What is the average household income in Leonardtown, MD?
The average household income in Leonardtown, MD is $140K.
Is Leonardtown, MD a safe city?
In general, the safest neighborhoods in Leonardtown, MD with lower crime scores are Callaway, Saint George Island and Piney Point.
What are the most popular zip codes in Leonardtown, MD?
The most popular zip codes in Leonardtown, MD include 20650, 20636, 20619, 20659 and 20609.
What are the most popular neighborhoods in Leonardtown, MD?
The most popular neighborhoods in Leonardtown, MD with the most homes for sale are Callaway, Saint George Island and Piney Point.
How much do you need to make to afford a house in Leonardtown?
The median home price in Leonardtown is $550,000. If you put a 20% down payment of $110,000 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $2,780 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $119K a year to afford the median home price in Leonardtown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Leonardtown is $140K.
How are the schools in Leonardtown, MD?
Leonardtown, MD has highly rated public and private schools. Some of the best schools in Leonardtown based on Niche Grades are St. Mary's Ryken High School, Captain Walter Francis Duke Elementary School and Leonardtown Middle School. The neighborhoods in Leonardtown with the highest rated schools are Callaway, Saint George Island and Piney Point. Browse all the schools in Leonardtown, MD to learn more.

Home Prices in Leonardtown, MD

The median home sale price in Leonardtown, MD is $540,000, down 3% year-over-year. Homes in Leonardtown sell in 43 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$599,000
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$192
Number of Homes for Sale
31
Last 12 months Home Sales
195
Months of Supply
1.90
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group