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Newest Homes for Sale in Leonardtown, MD

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  • 21807 Potomac View Dr, Leonardtown, MD 20650
    21807 Potomac View Dr, Leonardtown, MD 20650
    21807 Potomac View Dr, Leonardtown, MD 20650
    /54

    $485,000

    Open Sat 10AM - 12PM Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft

    21807 Potomac View Dr, Leonardtown, MD 20650

    Welcome home to the sought after community of Breton Bay in Leonardtown, where thoughtful updates, flexible living space, and an unbeatable location come together beautifully. This property offers the rare opportunity to enjoy all that Breton Bay has to offer, while still benefiting from no HOA restrictions. For a minimal optional annual fee, residents can enjoy private beach access at two

    Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View Dr, Leonardtown, MD 20650
  • 41986 Satchel Paige Way, Hollywood, MD 20636
    41986 Satchel Paige Way, Hollywood, MD 20636
    41986 Satchel Paige Way, Hollywood, MD 20636
    /34

    $259,900

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    41986 Satchel Paige Way, Hollywood, MD 20636

    Looking for an affordable, move-in ready home in Southern Maryland? This beautifully updated end-unit townhouse in Hollywood offers the perfect blend of comfort, convenience, and value.Freshly updated with new paint and durable LVP flooring throughout, the home feels clean, modern, and truly turnkey. Major improvements like a newer HVAC system and roof provide peace of mind, while thoughtful

    Sophie Seltzer CENTURY 21 New Millennium

    41986 Satchel Paige Way, Hollywood, MD 20636
  • 0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    /2

    $435,000

    • Land
    • 23.44 Acres
    • $18,558 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    23 acres with ability to build at least two homes

    Samara Dinnius JPAR Real Estate Professionals

    0 Whirlwind Rd, Leonardtown, MD 20650
  • 39944 Lady Baltimore Ave, Leonardtown, MD 20650
    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    /47

    $395,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    Welcome home! If you need space to spread out, this unique and cozy home on a quiet half-acre lot is just what you've been looking for. Two separate living areas means enjoying movies and gaming in one room while you enjoy peace in the other. This one-of-a-kind floor plan maximizes every square foot, and surprisingly roomier than it appears! With 5 bedrooms, 2 full and 1half bathrooms, there is

    Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
  • 41992 Loker Ct, Leonardtown, MD 20650
    41992 Loker Ct, Leonardtown, MD 20650
    /2

    $524,900

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,260 Sq Ft

    41992 Loker Ct, Leonardtown, MD 20650

    Classic Elegance in the Heart of Sought-After Leonardtown! Nestled at the end of a quiet cul-de-sac in the desirable Academy Hills community, this stunning 5-bedroom, 3.5-bath Colonial offers nearly 4,000 square feet of beautifully finished living space surrounded by peaceful wooded views and open pastureland. Step outside to enjoy the private, fenced backyard featuring split-rail fencing, a

    Matthew Burgan Infinitas Realty Group

    41992 Loker Ct, 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

    $449,900

    New Construction
    • 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
  • 43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    /72

    $605,000

    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    This 5 BR, 3 full BA, 2 half BA home offers nearly 3,000 square feet of comfortable living, but what truly sets it apart is everything beyond the main house. Step outside to your own backyard oasis featuring an in-ground saltwater pool, gazebo, and expansive entertaining space—perfect for summer gatherings or quiet evenings under the stars.Need room to grow, work, or host? The 28x40 detached

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • 22381 Cedar St, Leonardtown, MD 20650
    22381 Cedar St, Leonardtown, MD 20650
    22381 Cedar St, Leonardtown, MD 20650
    /27

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    22381 Cedar St, Leonardtown, MD 20650

    New pictures added! Back on the market due to buyer financing issues-no fault of the seller. Welcome to 23281 Cedar St in Leonardtown — where thoughtful updates meet easy coastal living in the sought-after St. Clements Shores community.This home was fully refreshed in 2021, offering today’s buyers the perfect blend of modern finishes and established reliability. Inside, you’ll find luxury

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 888-9336

    22381 Cedar St, 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
  • 23642 Hansel Ct, Leonardtown, MD 20650
    23642 Hansel Ct, Leonardtown, MD 20650
    23642 Hansel Ct, Leonardtown, MD 20650
    /79

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 3,726 Sq Ft

    23642 Hansel Ct, Leonardtown, MD 20650

    Welcome Home! This beautifully maintained home in Leonard's Grant backs up to trees, a rainwater pond and lots of wildlife! Enjoy watching the deer, bunnies and squirrels in the privacy of your fenced in back yard and large deck. The home features 4 spacious bedrooms, 3.5 baths, a finished basement, new (2022) luxury vinyl plank flooring throughout all levels, new energy efficient sliders (2022),

    Diane Fenwick RE/MAX One

    23642 Hansel Ct, 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****To Be Built*** 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 full

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 23008 Hopton Ln, Leonardtown, MD 20650
    23008 Hopton Ln, Leonardtown, MD 20650
    23008 Hopton Ln, Leonardtown, MD 20650
    /43

    $559,900

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 2,688 Sq Ft

    23008 Hopton Ln, Leonardtown, MD 20650

    This property represents the definition of "Pride of Ownership" and their move is bittersweet. To have everything they have built here is remarkable and you could be the lucky one to obtain this property. Everything has been taken care of like it was purchased yesterday, books and invoices for most included, with comfort and convenience in mind. From the blacktop driveway, manicured lawn, to the

    Jimmy Hayden RE/MAX One

    23008 Hopton 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
  • Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
    /48

    $449,900

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

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650

    ***AVAILABLE NOW*** RECIEVE $12,500 in CLOSING HELP! (with use of Builder's Preferred Lender & Title) 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 one-car garage and

    Laura Hefley RE/MAX One

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
  • 42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    /10

    $399,900

    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    Charming and beautifully updated brick rancher located in the heart of Leonardtown! This single-level home offers 3 bedrooms and 1.5 bathrooms, making it ideal for easy, comfortable living. Recently remodeled, the property features fresh updates throughout, blending classic charm with modern touches. Enjoy a spacious, level lot perfect for outdoor entertaining, gardening, or simply relaxing. The

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, Leonardtown, MD 20650
  • 41482 Pensive St, Leonardtown, MD 20650
    41482 Pensive St, Leonardtown, MD 20650
    41482 Pensive St, Leonardtown, MD 20650
    /75

    $574,900

    • 5 Beds
    • 3.5 Baths
    • 4,300 Sq Ft

    41482 Pensive St, Leonardtown, MD 20650

    Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are

    Mark Frisco CENTURY 21 New Millennium

    41482 Pensive St, 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
  • 40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    /41

    $650,000

    $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Experience waterfront living at its best with this beautifully maintained 2-bedroom, 2.5-bath home with a loft, perfectly positioned along the Potomac River just minutes from historic Leonardtown. Whether you’re looking for a full-time residence or a relaxing getaway, this property delivers the ideal blend of comfort, functionality, and breathtaking views. Designed for those who truly enjoy life

    Agent Photo

    Billy Rabbitt

    The Southside Group Real Estate

    (227) 239-0461

    40461 Old Breton 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
  • 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 Open Thu 11AM - 4PM
    • 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
  • Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
    /15

    $489,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***Estimated Late November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of

    Laura Hefley RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • 18866 Russell Rd, Leonardtown, MD 20650
    18866 Russell Rd, Leonardtown, MD 20650
    18866 Russell Rd, Leonardtown, MD 20650
    /3

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    18866 Russell Rd, Leonardtown, MD 20650

    ***Rare Waterfront Opportunity*** Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD, a truly exceptional waterfront property offering a private, peaceful setting on a premium lot with stunning views of the water. Currently a 3-bedroom, 1.5-bath home, this property presents the perfect opportunity to reimagine, renovate, or rebuild into your dream waterfront retreat. Surrounded by natural

    Agent Photo

    Shelly Hibbert

    KW Metro Center

    (227) 997-7054

    18866 Russell Rd, Leonardtown, MD 20650
  • 22281 Nomoni St, Leonardtown, MD 20650
    22281 Nomoni St, Leonardtown, MD 20650
    22281 Nomoni St, Leonardtown, MD 20650
    /33

    $355,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    22281 Nomoni St, Leonardtown, MD 20650

    Nice home in waterfront community. 3 bedrooms and 2 baths. New floors, new refrigerator, new dishwasher, freshly painted. This home is ready for its new owner. Enjoy community beach/water access for a small mfee each year! No HOA! This is only the beginning...move-in ready for you to start your home ownership dream here!

    Paul Fenton Coldwell Banker Premier

    22281 Nomoni St, Leonardtown, MD 20650
  • Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    /50

    $449,900

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

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    ***Available Now*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage 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

    Laura Hefley RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • 0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    0 Ferny Hills Ln, Leonardtown, MD 20650
    /35

    $840,000

    • Land
    • 10.2 Acres
    • $82,353 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • 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

    (227) 230-6008

    20798 Waterside Dr, Leonardtown, MD 20650
  • 000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    /36

    $98,900

    $6K PRICE DROP
    • Land
    • 4.11 Acres
    • $24,063 per Acre

    000 Saint Andrews Church Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!! Located in Leonardtown in St. Marys County, this 4.11 acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable

    Casey Kennedy Whitetail Properties Real Estate

    000 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
    /34

    $98,900

    $6K PRICE DROP
    • Land
    • 4.11 Acres
    • $24,063 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Mary’s County, this 4.11± acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable conditions; buyers

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 41655 Church St, Leonardtown, MD 20650
    41655 Church St, Leonardtown, MD 20650
    41655 Church St, Leonardtown, MD 20650
    /4

    $725,000

    Coming Soon
    • 5 Beds
    • 2 Baths
    • 2,834 Sq Ft

    41655 Church St, Leonardtown, MD 20650

    Built in 1875, this substantial 2,800 sq ft residence offers a rare opportunity to own a large historic home in highly desirable Leonardtown. Featuring 5 bedrooms and 2 bathrooms, the property showcases classic architecture with a formal living room and dining room, and enduring period details. Original features include a beautiful antique stamped tin ceiling and two fireplaces, adding

    Chris Norris Topside Realty

    41655 Church St, Leonardtown, MD 20650
  • Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $449,900

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

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's preferred lender and title co*** (special is for this Homesite #99 Madison D3 only). ***Available NOW*** Homesite #99 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

    Laura Hefley RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, 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
  • 20265 Hawks Way, Leonardtown, MD 20650
    20265 Hawks Way, Leonardtown, MD 20650
    /2

    $149,900

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

    20265 Hawks Way, Leonardtown, MD 20650

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

    Mark Frisco CENTURY 21 New Millennium

    20265 Hawks Way, 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
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    /6

    $24,900

    • Land
    • 7,840 Sq Ft
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    /30

    $1,750,000

    $115K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

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

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • 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

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 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
  • 22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    /3

    $175,000

    $50K PRICE DROP
    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /10

    $1,999,999

    $500K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
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 $602,873.
How many homes have sold over the last 12 months in Leonardtown, MD?
184 homes have sold in Leonardtown, MD over the last 12 months.
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 $537,500. If you put a 20% down payment of $107,500 and had a 30-year fixed mortgage with an interest rate of 6.53%, your estimated principal and interest payment would be $2,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K a year to afford the median home price in Leonardtown. Learn how much home you can afford with our Home Affordability Calculator.
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 Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 45 days on the market compared to the national average of 58 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $541,250, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$541,250
Median Single Family Sale Price
$592,000
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$302,000
Average Price Per Sq Ft
$194
Number of Homes for Sale
24
Last 12 months Home Sales
184
Months of Supply
1.60
Median List Price
$537,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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