30

Leonardtown, MD Homes for Sale under $600,000

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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
    /21

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ALMOST READY***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

    Laura Lee Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 40717 Lake and Breton View Dr, Leonardtown, MD 20650
    40717 Lake and Breton View Dr, Leonardtown, MD 20650
    40717 Lake and Breton View Dr, Leonardtown, MD 20650
    /60

    $435,000

    • 4 Beds
    • 2.5 Baths
    • 2,624 Sq Ft

    40717 Lake and Breton View Dr, Leonardtown, MD 20650

    Breton Bay/Society Hill! Steps away and within view of the golf course. Desirable location within a sought after school zone. This community has water access to Breton Bay via community association (voluntary dues, No HOA). Affordability within a desirable location is hard to find so here's your change. This 2 story colonial style home has a large addition off the back of the home that features a

    Farrah Fuchs Redfin Corp

    40717 Lake and Breton View Dr, Leonardtown, MD 20650
  • 23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 Dragonfly Ln, Leonardtown, MD 20650
    /41

    $449,900

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

    23684 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersNatural Clay 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 Shower

    Quality Built Homes Builder
    23684 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
    /13

    $454,900

    New Construction Open Thu 11:30AM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    **** 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 townhome offering 2,571 sq ft of beautifully finished living space. This interior unit

    Laura Lee Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • 23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, Leonardtown, MD 20650
    /40

    $449,900

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

    23672 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSandstone Beige Carolina Bead SidingMusket Brown ShuttersBronze 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 CabinetsWhite Ice Granite CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23672 Weeping Willow Way, Leonardtown, MD 20650
  • Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
    /42

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

    ***** October Delivery *********** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #139 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.

    Laura Lee Hefley RE/MAX One

    Lot 139 - 23665 Dragonfly 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

    $524,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, 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
  • 22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    /45

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, 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

    $374,900

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. 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

    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
  • 41888 Jenkins Ct, Leonardtown, MD 20650
    41888 Jenkins Ct, Leonardtown, MD 20650
    41888 Jenkins Ct, Leonardtown, MD 20650
    /41

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne & Christine Floyd RE/MAX Realty Group

    41888 Jenkins Ct, Leonardtown, MD 20650
  • 41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    /70

    $389,000

    $10K PRICE DROP
    • 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
  • 23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    /40

    $559,900

    $40K PRICE DROP
    • 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 living space on a beautifully maintained 0.51-acre lot, combining comfortable everyday living with plenty of room to grow.Step inside to a bright, inviting interior featuring new carpet and luxury vinyl plank flooring, giving the home a fresh, move-in-ready feel.

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • 23679 Weeping Willow Way, Leonardtown, MD 20650
    23679 Weeping Willow Way, Leonardtown, MD 20650
    23679 Weeping Willow Way, Leonardtown, MD 20650
    /41

    $449,900

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

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay 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 Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    /42

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

    *** November Delivery ******Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #143 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.

    Laura Lee Hefley RE/MAX One

    Lot 143 - 23641 Dragonfly Ln, 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

    $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
  • 23714 Weeping Willow Way, Leonardtown, MD 20650
    23714 Weeping Willow Way, Leonardtown, MD 20650
    23714 Weeping Willow Way, Leonardtown, MD 20650
    /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
  • 41524 Fairwood Ct, Leonardtown, MD 20650
    41524 Fairwood Ct, Leonardtown, MD 20650
    41524 Fairwood Ct, Leonardtown, MD 20650
    /28

    $600,000

    • 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
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /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
  • 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
  • Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    /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
  • 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
  • 23011 Newtowne Neck Rd, Leonardtown, MD 20650
    23011 Newtowne Neck Rd, Leonardtown, MD 20650
    23011 Newtowne Neck Rd, Leonardtown, MD 20650
    /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
Maryland St Marys County

Real Estate & Homes in Leonardtown, MD under $600,000

Home Prices in Leonardtown, MD

The median home sale price in Leonardtown, MD is $532,500, down 2% year-over-year. Homes in Leonardtown sell in 44 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$532,500
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
55
Last 12 months Home Sales
198
Months of Supply
3.30
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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