71

Leonardtown, MD Homes for Sale

Section Image Section Image Section Image
  • 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
  • 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 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    /6

    $175,000

    • Land
    • 6.24 Acres
    • $28,045 per Acre

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650

    6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, 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
    /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
  • 23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    /85

    $629,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    CREDIT FOR REPAIRS!! 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

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • 43927 Lanedon Dr, Leonardtown, MD 20650
    43927 Lanedon Dr, Leonardtown, MD 20650
    43927 Lanedon Dr, Leonardtown, MD 20650
    /56

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    43927 Lanedon Dr, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY MONDAY AUGUST 10th at 10:00 AMOwned by the same family since the 1960s, this 3-bedroom, 2-bath rambler has been lovingly maintained and is ready for its next chapter. This one already has the space, setting, and major improvements to make the possibilities exciting. The larger updates have already been taken care of, including a newer roof, siding, windows, new

    Sarah Mulford-Martin EXP Realty, LLC

    43927 Lanedon Dr, Leonardtown, MD 20650
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /19

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, 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
  • 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
  • 25375 Loveville Rd, Leonardtown, MD 20650
    25375 Loveville Rd, Leonardtown, MD 20650
    25375 Loveville Rd, Leonardtown, MD 20650
    /94

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,388 Sq Ft

    25375 Loveville Rd, Leonardtown, MD 20650

    Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers

    Kandy Moore RMG Realty

    25375 Loveville Rd, 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
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /64

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • 40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    /17

    $750,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    40579 Port Place, Leonardtown, MD 20650

    Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40579 Port Place, Leonardtown, MD 20650
  • 24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    One of only two lots remaining! Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 to 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /75

    $645,000

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

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • 23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    /56

    $615,000

    Open Sat 12PM - 2PM
    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, 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

    Open Sat 1PM - 3PM
    • 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
  • 22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    /49

    $989,000

    $111K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,810 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 (almost 600 sq. ft.) where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled

    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
  • 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
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    /74

    $649,000

    $21K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home 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 room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • 41379 Margrove Cir, Leonardtown, MD 20650
    41379 Margrove Cir, Leonardtown, MD 20650
    41379 Margrove Cir, Leonardtown, MD 20650
    /78

    $459,900

    • 4 Beds
    • 3.5 Baths
    • 2,469 Sq Ft

    41379 Margrove Cir, Leonardtown, MD 20650

    IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf,

    Mark Frisco CENTURY 21 New Millennium

    41379 Margrove Cir, 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
  • 40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    /28

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • 23214 Dairy Barn Dr, Leonardtown, MD 20650
    23214 Dairy Barn Dr, Leonardtown, MD 20650
    23214 Dairy Barn Dr, Leonardtown, MD 20650
    /61

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room is ideal for a home office, library, study, or playroom. The dining room flows through the butler's pantry and adjoining walk-in pantry before

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $485,000

    $30K 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

    $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
  • 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
  • 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
  • 23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    /40

    $579,900

    Open Sat 12PM - 2PM $20K 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 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
  • 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

Showing Results 1 - 40, Page 1 of 2

Maryland St Marys County

Real Estate & Homes for Sale in Leonardtown, MD

Why Live in Leonardtown

Leonardtown, Maryland, is a rapidly growing community in Southern Maryland, with its population nearly doubling between 2010 and 2020. Located on a peninsula surrounded by the Potomac River, Patuxent River, and Chesapeake Bay, Leonardtown is home to around 19,000 residents. The town's appeal includes a revitalized downtown, water access, and proximity to Naval Air Station Patuxent River, the county's top employer. Leonardtown is approximately 60 miles south of Washington, D.C., making it a viable option for commuters. The town boasts above-average schools, including Leonardtown Elementary, Leonardtown Middle, Leonardtown High, and St. Mary's Ryken High. Housing in Leonardtown has seen significant development, with new subdivisions like Clark’s Rest featuring Colonial Revival-inspired homes and waterfront properties available in areas like Breton Bay. The town's historic downtown has been rejuvenated with new businesses, restaurants, and community-funded murals. Leonardtown is known for its freshly caught seafood, particularly at local restaurants such as T&Js Cove. The town earned the distinction of being the region’s first Arts & Entertainment District in 2013, with a thriving art scene and events like the annual Leonardtown Art Walk. The United States National Oyster Festival, held every October, is a major attraction, celebrating oysters with various activities and competitions. Outdoor recreation is abundant, with parks like Leonardtown Wharf Park and Newtowne Neck State Park offering boating, fishing, and hiking opportunities. Leonardtown is accessible via STS Transit and several state highways, with three major airports within 90 miles. Healthcare needs are met by MedStar St. Mary's Hospital.

Learn more about living in Leonardtown

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $593,097.
How many homes have sold over the last 12 months in Leonardtown, MD?
196 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, 20609 and 20659.
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 6.66%, your estimated principal and interest payment would be $2,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $121K 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 $538,750, down 2% year-over-year. Homes in Leonardtown sell in 43 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$538,750
Median Single Family Sale Price
$599,450
Median Townhouse Sale Price
$454,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$192
Number of Homes for Sale
43
Last 12 months Home Sales
196
Months of Supply
2.60
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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