19

Leonardtown, MD Homes for Sale under $500,000

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  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    20798 Waterside Dr, 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
  • 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 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 Open Fri 11AM - 4PM
    • 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
  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, 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
  • 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
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    Buyers, come take a look. The estate just dropped the price by $20,000 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

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • 42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    /15

    $384,900

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns 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
  • 22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    /29

    $329,900

    • 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 new 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

    Carol Kalmus-Choporis Century 21 Redwood Realty

    22332 Cedar St, 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
  • 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
  • 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
  • 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
    /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
  • 23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    /36

    $429,000

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

    23898 Speith Rd, Leonardtown, MD 20650

    **Seller offering $10,000 in Closing Help** 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

    Jimmy Hayden RE/MAX One

    23898 Speith Rd, 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
  • 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
Maryland St Marys County

Real Estate & Homes in Leonardtown, MD under $500,000

Home Prices in Leonardtown, MD

The median home sale price in Leonardtown, MD is $545,000, down 1% year-over-year. Homes in Leonardtown sell in 41 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$191
Number of Homes for Sale
33
Last 12 months Home Sales
197
Months of Supply
2.00
Median List Price
$555,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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