37

Leonardtown, MD Homes for Sale

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  • 22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    /42

    $520,000

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft

    22547 Landing Way, Leonardtown, MD 20650

    Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the

    Agent Photo

    Trish Brow

    EXP Realty, LLC

    (227) 999-2906

    22547 Landing Way, Leonardtown, MD 20650
  • 41832 Foxwell Point Ln, Leonardtown, MD 20650
    41832 Foxwell Point Ln, Leonardtown, MD 20650
    41832 Foxwell Point Ln, Leonardtown, MD 20650
    /43

    $800,000

    • 3 Beds
    • 4 Baths
    • 3,683 Sq Ft

    41832 Foxwell Point Ln, Leonardtown, MD 20650

    Discover this stunning cedar siding contemporary waterfront home offering a perfect blend of comfort and character. Enjoy water access with a private shared dock, ideal for relaxing days on the water. Freshly painted throughout with brand-new flooring in basement and two bedrooms, this home shines inside and out.The sunroom features beautiful slate floors and peaceful views of the surrounding

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (227) 238-0627

    41832 Foxwell Point Ln, Leonardtown, MD 20650
  • 21345 Fairwood Ct, Leonardtown, MD 20650
    21345 Fairwood Ct, Leonardtown, MD 20650
    21345 Fairwood Ct, Leonardtown, MD 20650
    /33

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 4,080 Sq Ft

    21345 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this move-in-ready home in the desirable Leonardtown Farms community offers space, layout, and functionality. With 5 bedrooms on the upper level, 3.5 bathrooms, and generous living spaces on every level, there is room to grow, gather, and truly settle in. Beautiful landscaping welcomes you to the covered front

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 203-7895

    21345 Fairwood Ct, 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
    /61

    $679,900

    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike.Inside, you’ll find a

    Agent Photo

    Mileah Walker

    Real Broker, LLC

    (227) 240-6440

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    /44

    $449,900 Open Sun 12PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 105 Madison D2: Photos Coming Soon New Construction: Madison D2 at Meadows at Town

    Laura Bernth RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
    /35

    $449,900 Open Sun 12PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. (Must Settle In 2025!) Unit 95 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the

    Laura Bernth RE/MAX One

    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
  • 25895 Point Lookout Rd, Leonardtown, MD 20650
    25895 Point Lookout Rd, Leonardtown, MD 20650
    25895 Point Lookout Rd, Leonardtown, MD 20650
    /20

    $249,000

    • Land
    • 1 Acre
    • $249,000 per Acre

    25895 Point Lookout Rd, Leonardtown, MD 20650

    Position your business for success with this 1.00-acre commercial lot in Leonardtown, MD, zoned Commercial Highway (C-H). Located next to PNC Bank and across from a storage facility, this property boasts great visibility and easy access, making it ideal for a variety of commercial uses.Zoning allows for flexible development options such as: Retail and Business Establishments

    Krista Depenthal Lands2Love

    25895 Point Lookout Rd, Leonardtown, MD 20650
  • 21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    /90

    $565,000

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft

    21060 Woodmere Dr, Leonardtown, MD 20650

    Nestled on a beautifully maintained 1 acre lot, this 5 bedroom, 3.5 bathroom home is conveniently located in Leonardtown's Wilderness Run community. A welcoming foyer leads to a formal dining room and a charming country style kitchen which opens to a spacious family room. The kitchen features space for a table, a large pantry, stainless steel appliances, granite countertops, and direct access to

    Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, Leonardtown, MD 20650
  • 21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    /49

    $610,000

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 106 Madison D3: Welcome to Meadows at Town Run....Leonardtown’s Newest Townhome

    Laura Bernth RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
  • 23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    /53

    $645,900

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft

    23581 Gallent Fox Way, Leonardtown, MD 20650

    Welcome to 23581 Gallent Fox Way, a beautifully maintained and thoughtfully upgraded home nestled in the heart of highly desirable Leonard’s Grant. Situated in one of Leonardtown’s most sought-after communities, this 4-bedroom, 3.5-bath 3,933 sq ft residence combines comfort, convenience, and a true sense of community living. Perfectly positioned directly across from the community pool and

    Laura Bernth RE/MAX One

    23581 Gallent Fox Way, 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

    • 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
  • 23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    /71

    $580,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    23593 Mitchell Dr, Leonardtown, MD 20650

    Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof is only 5 years old, new paint throughout and a new BEAUTIFUL patio!!Key Features:

    Heather Foster RE/MAX One

    23593 Mitchell Dr, 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

    • 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
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    /13

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC. This

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /32

    $659,000

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

    18937 Hodges Ln, Leonardtown, MD 20650

    Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront, shared pier with boatlift, sunroom, 2-car attached garage, 1-car detached garage, 2-car carport. Gorgeous back yard, perfect for entertaining and spending those summer nights with friends and family. Get on your boat whenever the mood strikes you. This is the perfect home to

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • 40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    /27

    $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
  • Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, SETTLE in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 104 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome

    Laura Bernth RE/MAX One

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
  • 22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    /4

    $599,950

    • 1,691 Sq Ft

    22615 Washington St, Leonardtown, MD 20650

    Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts &

    Caitlin Vallandingham Infinitas Realty Group

    22615 Washington St, Leonardtown, MD 20650
  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /29

    $599,900 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
  • 40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    /68

    $650,000

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

    40855 Spring House Ln, Leonardtown, MD 20650

    Contemporary-style home offering exceptional flexibility as a single-family residence or an income-producing property with a private apartment. The freshly painted interior features 5 bedrooms and 3 full baths, including a 2BR/1BA apartment with its own entrance—ideal for multigenerational living, guests, or rental income. The main living level showcases hardwood floors, an open living/dining

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • 0 Wathen Rd, Leonardtown, MD 20650
    0 Wathen Rd, Leonardtown, MD 20650
    /2

    $225,000

    • Land
    • 7.5 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • 41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    /7

    $720,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,650 Sq Ft

    41810 Chelsey Faye Ln, Leonardtown, MD 20650

    Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other

    Jessica Ascenzo JPAR Real Estate Professionals

    41810 Chelsey Faye Ln, Leonardtown, MD 20650
  • 20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    /45

    $574,900

    • 4 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650

    Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acresStep inside and feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious separate dining room into a beautifully updated kitchen. Corian countertops, stainless steel appliances, and

    Tracey Summers CENTURY 21 New Millennium

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /49

    $539,900

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    42043 Starlight Dr, Leonardtown, MD 20650

    Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has all-new flooring and a freshly painted interior. A bright and cheery home with four spacious bedrooms on the upper level, with generous closets. Convenient laundry on this upper level. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen

    Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, 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
  • 42975 Baywood Place, Leonardtown, MD 20650
    42975 Baywood Place, Leonardtown, MD 20650
    42975 Baywood Place, Leonardtown, MD 20650
    /65

    $699,900

    • 4 Beds
    • 2.5 Baths
    • 3,372 Sq Ft

    42975 Baywood Place, Leonardtown, MD 20650

    Stunning Dunleigh model by Marrick Homes, tucked away at the end of a quiet cul-de-sac on over 1 full acre in desirable Leonardtown Farm! Offering nearly 3,400 sq ft of finished living space, this beautifully maintained 4BR/2.5BA home features a spacious, gourmet kitchen with large center island, upgraded cabinets and granite countertops, and stainless steel appliances – perfect for entertaining.

    Erika Yowell EXP Realty, LLC

    42975 Baywood Place, Leonardtown, MD 20650
  • 25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, 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 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is 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
  • 40624 Breton Oaks Ln, Leonardtown, MD 20650
    40624 Breton Oaks Ln, Leonardtown, MD 20650
    40624 Breton Oaks Ln, Leonardtown, MD 20650
    /6

    $159,900

    • Land
    • 1.49 Acres
    • $107,315 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks 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

    $215,000

    • Land
    • 5 Acres
    • $43,000 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
  • 43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    /66

    $645,900

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    43018 Bluejay Ln, Leonardtown, MD 20650

    Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • 0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    /6

    $5,000

    • Land
    • 0.14 Acre
    • $35,714 per Acre

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650

    Fully Available!Wonderful opportunity with a buyer that has vision. Nice lot to possibly build on. Call St Mary's county for details and confirm if suitable for your needs.

    Jan Kleponis O'Brien Realty ERA Powered

    0 Long Leaf Ln Unit MDSM2026514, 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
  • 44646 Medleys Neck Rd, Leonardtown, MD 20650
    44646 Medleys Neck Rd, Leonardtown, MD 20650
    /2

    $80,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    44646 Medleys Neck Rd, Leonardtown, MD 20650

    Presenting an opportunity for creative redevelopment: a level lot equipped with a septic system and a driveway easement, along with a trailer that has microbiological growth. The property will require the removal of the existing trailer, with the option to proceed with new construction or secure a trailer replacement. Qualified buyers looking to customize and reimagine the site are encouraged to

    Ron Lord Home Towne Real Estate

    44646 Medleys Neck Rd, Leonardtown, MD 20650
  • 41635 Ferber Ct, Leonardtown, MD 20650
    41635 Ferber Ct, Leonardtown, MD 20650
    /2

    $565,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    41635 Ferber Ct, Leonardtown, MD 20650

    Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room

    Alvin Frazier Home Towne Real Estate

    41635 Ferber Ct, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Real Estate & Homes for Sale in Leonardtown, MD

Why Live in Leonardtown

Leonardtown is a Southern Maryland community on the rise, with the population nearly doubling between 2010 and 2020. “It’s one of the fastest-growing municipalities in Maryland,” says Jimmy Hayden , a Leonardtown native and Realtor with Re/Max Realty Group. ...

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 $598,757.
How many homes have sold over the last 12 months in Leonardtown, MD?
165 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 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 $550,000. If you put a 20% down payment of $110,000 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $2,700 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K 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 38 days on the market compared to the national average of 53 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $537,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$537,500
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$449,900
Average Price Per Sq Ft
$192
Number of Homes for Sale
24
Last 12 months Home Sales
165
Months of Supply
1.70
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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