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Newest Homes for Sale in Leonardtown, MD

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  • 23592 Belmar Dr, Leonardtown, MD 20650
    23592 Belmar Dr, Leonardtown, MD 20650
    23592 Belmar Dr, Leonardtown, MD 20650
    /63

    $680,000

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft

    23592 Belmar Dr, Leonardtown, MD 20650

    Photos to come.QBH Belmont model with a beautiful Sunroom.

    Heather Foster RE/MAX One

    23592 Belmar Dr, Leonardtown, MD 20650
  • 23207 Moakley St, Leonardtown, MD 20650
    23207 Moakley St, Leonardtown, MD 20650
    /2

    $520,000

    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft

    23207 Moakley St, Leonardtown, MD 20650

    Professional photos coming! Charming home located in Leonardtown, offering the perfect combination of privacy and convenience. Situated on a flat 1-acre lot with no HOA, this property gives you space to spread out while still being just minutes from shopping, dining, and everything Leonardtown has to offer.Inside, you’ll find wood floors throughout the entire first level and a bright white

    Heather Foster RE/MAX One

    23207 Moakley St, Leonardtown, MD 20650
  • 40810 Meadow Dr, Leonardtown, MD 20650
    40810 Meadow Dr, Leonardtown, MD 20650
    40810 Meadow Dr, Leonardtown, MD 20650
    /50

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    40810 Meadow Dr, Leonardtown, MD 20650

    Completely renovated and move-in ready, this stunning rambler in desirable Leonardtown is perfectly positioned near Breton Bay Golf Course and the scenic waters of Breton Bay. Every inch has been thoughtfully updated... brand new roof, windows, heat pump, water heater, washer & dryer, appliances, encapsulated crawl space... nothing to worry about for the years to come, offering a truly turnkey

    Cheryl Bare CENTURY 21 New Millennium

    40810 Meadow Dr, Leonardtown, MD 20650
  • 40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    /78

    $550,000

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • 43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    43430 Browns Ln, Leonardtown, MD 20650
    /43

    $649,000

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

    43430 Browns Ln, Leonardtown, MD 20650

    This unique property has so much to offer and has been a great family home, however owners are moving and have found their next home. Well cared for 4 BR home has 2,116 sq. ft, and features an open floor plan. The kitchen has granite counters, maple cabinets, a custom-made bar/island and ceramic tile flooring, and is open to the dining area, with glass doors to the deck, and the Family Rm. The

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • 41505 Margrove Cir, Leonardtown, MD 20650
    41505 Margrove Cir, Leonardtown, MD 20650
    41505 Margrove Cir, Leonardtown, MD 20650
    /48

    $435,000

    • 3 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    41505 Margrove Cir, Leonardtown, MD 20650

    Welcome to this stunning end-unit townhome in the highly sought-after Clark’s Rest community. Built in the popular “Compton – Rear Kitchen” model, this home shows like new and delivers the ideal blend of style, space, and functionality. Step inside to a bright, open main level featuring hardwood flooring throughout, abundant natural light, and refined finishes including crown molding and

    Conor Loughran CENTURY 21 New Millennium

    41505 Margrove Cir, Leonardtown, MD 20650
  • 41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    /74

    $680,000

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    41488 Pensive St, Leonardtown, MD 20650

    Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard’s Grant, offering a spacious layout and thoughtful design throughout. As you enter the home, you’re welcomed by hardwood floors, a grand entryway, and a beautiful staircase that creates an inviting first impression.To the right, French doors open to a large room that works well as a home office or additional

    Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
  • 23073 Town Run Dr, Leonardtown, MD 20650
    23073 Town Run Dr, Leonardtown, MD 20650
    23073 Town Run Dr, Leonardtown, MD 20650
    /3

    $639,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,854 Sq Ft

    23073 Town Run Dr, Leonardtown, MD 20650

    ***Photos Coming Soon***Welcome home to 23073 Town Run Drive! Built in 2022, this beautifully maintained home in the highly sought-after neighborhood of The Meadows at Town Run in Leonardtown is truly a standout. Built by QBH, this desirable Ashland model offers thoughtfully designed living space with an open and inviting floor plan—perfect for both everyday living and entertaining. This home

    Laura Bernth RE/MAX One

    23073 Town Run Dr, Leonardtown, MD 20650
  • 40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    40840 Greenwood Ln, Leonardtown, MD 20650
    /88

    $1,049,900

    • 9 Beds
    • 5 Baths
    • 6,476 Sq Ft

    40840 Greenwood Ln, Leonardtown, MD 20650

    From the moment you enter over 6000+ sqft of finished home , it's clear this home has been enhanced well beyond the typical. High-quality finishes, updated systems, and carefully selected improvements are evident throughout, creating a move-in-ready experience that today's buyers will immediately appreciate. This meticulously maintained home features luxury living on 2.10 acres, offering the

    Romy Singh Samson Properties

    40840 Greenwood Ln, 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
    /35

    $449,900 New Construction

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

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

    Homesite #111 Madison D3: ****May Delivery***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 features an oversized one-car garage and an entry-level flex space that includes built-in cubbies

    Laura Bernth RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
  • 39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, Leonardtown, MD 20650
    39577 Potomac Ave, Leonardtown, MD 20650
    /70

    $839,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft

    39577 Potomac Ave, Leonardtown, MD 20650

    Brooke Matthews RE/MAX One

    39577 Potomac Ave, 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
    /46

    $489,900 New Construction

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

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***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 Leonardtown, Maryland.

    Laura Bernth RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    /41

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

    **TO BE BUILT**** Homesite 141 - Oakley D1 End Unit ***October Delivery**** ***Choose your color scheme from of our available options** 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous

    Laura Bernth RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • 41389 Holiday Ct, Leonardtown, MD 20650
    41389 Holiday Ct, Leonardtown, MD 20650
    /2

    $715,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft

    41389 Holiday Ct, Leonardtown, MD 20650

    Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonard’s Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level,

    Laura Bernth RE/MAX One

    41389 Holiday Ct, 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
  • 40003 Tippit Rd, Leonardtown, MD 20650
    40003 Tippit Rd, Leonardtown, MD 20650
    40003 Tippit Rd, Leonardtown, MD 20650
    /56

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,490 Sq Ft

    40003 Tippit Rd, Leonardtown, MD 20650

    If you've been looking for Leonardtown waterfront, look no further! This exceptional .83-acre waterfront retreat on deep, protected Combs Creek offers breathtaking, panoramic views stretching across Breton Bay to the Potomac River. A rare and versatile offering, 40003 Tippit Road features TWO beautifully appointed dwellings, blending historic charm with modern comfort in a truly serene setting.

    Charlotte Long EXP Realty, LLC

    40003 Tippit Rd, Leonardtown, MD 20650
  • 22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    /40

    $464,900

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft

    22343 Newtowne Neck Rd, Leonardtown, MD 20650

    MOVE-IN READY!! Welcome to this beautifully maintained 4-bedroom, 2-bath rambler situated on a 1-acre lot in Leonardtown, Maryland. Offering the ease of one-level living and a functional, flowing floor plan, this home combines space, comfort, and practicality in a peaceful Southern Maryland setting. Step inside to find a spacious living room with gleaming floors and abundant natural light. The

    Mark Frisco CENTURY 21 New Millennium

    22343 Newtowne Neck Rd, Leonardtown, MD 20650
  • 23282 Lindsay Dr, Leonardtown, MD 20650
    23282 Lindsay Dr, Leonardtown, MD 20650
    23282 Lindsay Dr, Leonardtown, MD 20650
    /55

    $590,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,123 Sq Ft

    23282 Lindsay Dr, Leonardtown, MD 20650

    Located in the highly sought-after Clark’s Rest community, known for its amenities and walkable access to downtown Leonardtown, this well-maintained three-level home offers the perfect blend of comfort, space, and functionality. The main level features a thoughtfully designed layout beginning with a separate formal dining room just off the foyer. Toward the rear of the home, the kitchen flows

    Nichelle Jeter Samson Properties

    23282 Lindsay Dr, Leonardtown, MD 20650
  • 22281 Nomoni St, Leonardtown, MD 20650
    22281 Nomoni St, Leonardtown, MD 20650
    22281 Nomoni St, Leonardtown, MD 20650
    /33

    $360,000

    • 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
  • 23621 Margrave Dr, Leonardtown, MD 20650
    23621 Margrave Dr, Leonardtown, MD 20650
    23621 Margrave Dr, Leonardtown, MD 20650
    /4

    $639,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,261 Sq Ft

    23621 Margrave Dr, Leonardtown, MD 20650

    Welcome to this beautifully maintained, single-owner Colonial in the highly sought-after Leonard’s Grant community. Blending classic charm with thoughtful upgrades, this home offers both comfort and functionality throughout. The main level features wood flooring in the living and dining areas, a private dining room, and a cozy fireplace. The spacious kitchen boasts stainless steel appliances,

    Lauren Garner EXP Realty, LLC

    23621 Margrave Dr, Leonardtown, MD 20650
  • Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    /45

    $449,900 New Construction

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

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 110 Madison D1: *** May Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. 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 features an

    Laura Bernth RE/MAX One

    Lot 110 - 23678 Weeping Willow Way, 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
    /45

    $449,900 New Construction

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

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

    ***Mid-May Delivery*** 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

    Laura Bernth 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
  • 22394 White Oak Rd, Leonardtown, MD 20650
    22394 White Oak Rd, Leonardtown, MD 20650
    22394 White Oak Rd, Leonardtown, MD 20650
    /32

    $495,000

    • 4 Beds
    • 3 Baths
    • 2,507 Sq Ft

    22394 White Oak Rd, Leonardtown, MD 20650

    Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for

    Barbara Stellway KW Metro Center

    22394 White Oak Rd, Leonardtown, MD 20650
  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $500,000

    • 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

    • 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

    $104,900

    • Land
    • 4.11 Acres
    • $25,523 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
  • 41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    /63

    $620,000

    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    Price Improvement! This adjustment creates a fantastic opportunity for buyers to own a well-maintained home — one of the largest in the subdivision. Schedule your showing today before it’s gone. Welcome home! 41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a POND just

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /28

    $579,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, 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
    /35

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #99 Madison D3: ****ALMOST READY FOR SPRING DELIVERY***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 features an oversized one-car garage and an entry-level flex space that

    Laura Bernth RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    /34

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #101 Madison D3: ***ALMOST READY FOR MARCH DELIVERY***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 features an oversized one-car garage and an entry-level flex space that

    Laura Bernth RE/MAX One

    Lot 101 - 23713 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
  • 22393 Saint Clements Ave, Leonardtown, MD 20650
    22393 Saint Clements Ave, Leonardtown, MD 20650
    22393 Saint Clements Ave, Leonardtown, MD 20650
    /62

    $788,900

    • 4 Beds
    • 4 Baths
    • 2,097 Sq Ft

    22393 Saint Clements Ave, Leonardtown, MD 20650

    **BRAND NEW ROOF!** Experience refined waterfront living in this fully renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this home has been thoughtfully reimagined with extensive structural, electrical, and plumbing upgrades—blending modern finishes with relaxed coastal charm. Set on a waterfront lot, the property features a private L-shaped pier (approx. 7’ water

    Ralph Harvey ListWithFreedom.com

    22393 Saint Clements Ave, Leonardtown, MD 20650
  • 40736 Center 40 Cir, Leonardtown, MD 20650
    40736 Center 40 Cir, Leonardtown, MD 20650
    40736 Center 40 Cir, Leonardtown, MD 20650
    /58

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,829 Sq Ft

    40736 Center 40 Cir, Leonardtown, MD 20650

    BACK ON MARKET. Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space

    Kelly Padgett CENTURY 21 New Millennium

    40736 Center 40 Cir, 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

    $149,900

    • Land
    • 2.28 Acres
    • $65,746 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

    $205,000

    • Land
    • 5 Acres
    • $41,000 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
    • 0.18 Acre
    • $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

Showing Results 1 - 40, Page 1 of 2

Maryland St Marys County Leonardtown

Newest Listings for Sale in Leonardtown, MD

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $606,864.
How many homes have sold over the last 12 months in Leonardtown, MD?
166 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, 20609 and 20606.
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 $547,500. If you put a 20% down payment of $109,500 and had a 30-year fixed mortgage with an interest rate of 6.37%, 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 47 days on the market compared to the national average of 55 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $538,750, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$538,750
Median Single Family Sale Price
$599,450
Median Townhouse Sale Price
$449,900
Average Price Per Sq Ft
$197
Number of Homes for Sale
30
Last 12 months Home Sales
166
Months of Supply
2.20
Median List Price
$547,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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