39

Leonardtown, MD Homes for Sale

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  • 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

    $689,900

    • 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
  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect 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

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (240) 376-2980

    20798 Waterside Dr, 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

    $825,000

    • 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
  • 21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    /31

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,527 Sq Ft

    21925 Budds Creek Rd, Leonardtown, MD 20650

    This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 230-5161

    21925 Budds Creek 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 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 105- 23689 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, 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

    Laura Bernth RE/MAX One

    Lot 105- 23689 Dragonfly 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
    /47

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 104- 23695 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, 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: PHOTOS COMING SOONWelcome to Meadows at Town

    Laura Bernth RE/MAX One

    Lot 104- 23695 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
    /49

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, 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!

    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
  • 41492 Charismatic Way, Leonardtown, MD 20650
    41492 Charismatic Way, Leonardtown, MD 20650
    41492 Charismatic Way, Leonardtown, MD 20650
    /49

    $639,900

    • 4 Beds
    • 3.5 Baths
    • 3,322 Sq Ft

    41492 Charismatic Way, Leonardtown, MD 20650

    Welcome home to 41492 Charismatic Way, the stunning Fenwick model by Quality Built Homes in the highly sought-after Leonard’s Grant community in Leonardtown! With 4 spacious bedrooms, 3.5 baths, and nearly 4,000 finished sq ft, this well-appointed home blends elevated design, thoughtful functionality, and timeless comfort in every detail. A welcoming foyer opens to formal living and dining rooms,

    Laura Bernth RE/MAX One

    41492 Charismatic Way, Leonardtown, MD 20650
  • 23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    /59

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    PRICE IMPROVEMENT! **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot with extra large fenced backyard. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • 43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    /66

    $655,000

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

    43018 Bluejay Ln, Leonardtown, MD 20650

    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 features a large

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, 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

    Located on a quiet, no-through street in the desirable Kingston Estates community of Leonardtown, this home sits atop a gentle hill with no other houses in sight, offering exceptional privacy. A classic southern-style front porch welcomes you with views of mature landscaping, including weeping willows. The extra-large driveway provides ample parking, including two additional spaces beyond the

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • 40171 Little Woods Ln, Leonardtown, MD 20650
    40171 Little Woods Ln, Leonardtown, MD 20650
    40171 Little Woods Ln, Leonardtown, MD 20650
    /64

    $859,000

    • 4 Beds
    • 2 Baths
    • 2,586 Sq Ft

    40171 Little Woods Ln, Leonardtown, MD 20650

    Waterfront Retreat with Spectacular SunsetsWaterfront Retreat with Spectacular Sunsets. Welcome to your dream waterfront retreat! This charming 4-bedroom, 2-bath home is perfectly situated on 2.1 quiet acres with no HOA, offering the peace and privacy you’ve been looking for. Step inside to find large windows that frame breathtaking water views and allow natural light to fill the spacious

    Barbara Blades CENTURY 21 New Millennium

    40171 Little Woods Ln, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    /65

    $614,900

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    Welcome to 22626 Chickadee Lane—an exceptional 4-bedroom, 3.5-bath home nestled on a serene 2-acre lot in the highly sought-after Avenmar neighborhood of Leonardtown. This elegant property offers the perfect blend of privacy, space, and convenience with an open-concept layout that is flooded with natural light and designed for comfortable living and entertaining. Inside, you'll find generously

    Matthew Burgan Infinitas Realty Group

    22626 Chickadee Ln, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $639,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, 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
  • 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
  • 40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    /36

    $859,900 New Construction

    • 4 Beds
    • 2.5 Baths

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxury living. As you step inside, you are greeted by an open layout that radiates warmth and spaciousness. The heart of the home, a two-story family room with fireplace, is bathed in natural light, creating an inviting atmosphere for entertaining and relaxation. Cook gourmet

    Michele Posey RE/MAX Realty Group

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • 41467 Osborne Ln, Leonardtown, MD 20650
    41467 Osborne Ln, Leonardtown, MD 20650
    41467 Osborne Ln, Leonardtown, MD 20650
    /45

    $538,900

    • 4 Beds
    • 3.5 Baths
    • 2,827 Sq Ft

    41467 Osborne Ln, Leonardtown, MD 20650

    Nestled in the highly sought-after Clark's Rest community, this exceptional home offers the perfect blend of convenience and charm. Hardwood floors in the entryway set the tone for the quality finishes throughout the home - including the spacious living room, dining room, and kitchen - featuring luxury vinyl plank flooring, combining durability and style. The kitchen stands out as a true

    Susan Vogel Turtle Town Real Estate, LLC.

    41467 Osborne 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
  • 42611 Wilderness Rd, Leonardtown, MD 20650
    42611 Wilderness Rd, Leonardtown, MD 20650
    42611 Wilderness Rd, Leonardtown, MD 20650
    /42

    $520,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    42611 Wilderness Rd, Leonardtown, MD 20650

    Classic Private Colonial offers the perfect blend of tranquility and convenience, nestled on a generous 1.25-acre lot that backs to mature trees for ultimate shade and privacy. Outdoor Living: Enjoy entertaining or quiet mornings on the large vinyl deck, overlooking a great yard. The circular paved driveway provides easy access and added convenience. The Home: Featuring a traditional layout, you

    Dawn Bell RE/MAX One

    42611 Wilderness Rd, 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
  • 21920 Newtowne Neck Rd, Leonardtown, MD 20650
    21920 Newtowne Neck Rd, Leonardtown, MD 20650
    21920 Newtowne Neck Rd, Leonardtown, MD 20650
    /57

    $520,000

    • 4 Beds
    • 2.5 Baths
    • 2,291 Sq Ft

    21920 Newtowne Neck Rd, Leonardtown, MD 20650

    Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,291 sq. ft. of comfortable living space, 4 bedrooms, and 2.5 bathrooms, perfectly situated on a .55-acre lot in Leonardtown. Inside, you’ll find a bright and spacious layout designed for both everyday living and entertaining. The heart of the home features an eat-in kitchen with stainless steel appliances, a

    Katherine Dean RE/MAX One

    21920 Newtowne Neck Rd, Leonardtown, MD 20650
  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /49

    $559,900

    • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    /3

    $180,000

    • Land
    • 1.87 Acres
    • $96,257 per Acre

    40533 Breton Knolls Ct, Leonardtown, MD 20650

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

    Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, 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
  • 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
  • lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650
    /39

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, 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: PHOTOS COMING SOON!!!!Welcome to Meadows at

    Laura Bernth RE/MAX One

    lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $489,900 Open Fri 1PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650

    *** HOME IN TIME FOR THE HOLIDAYS, Receive $20,000 in Builder Credit plus $12,500 in Closing Help OR $20,000 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. Offer valid for Homesite 103 only. Must use preferred lender and title to receive closing assistance.) New

    Laura Bernth RE/MAX One

    Lot 103-23701 Dragonfly Ln, 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 $598,924.
How many homes have sold over the last 12 months in Leonardtown, MD?
152 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 $542,500. If you put a 20% down payment of $108,500 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $2,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K a year to afford the median home price in Leonardtown.
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 $538,750, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$538,750
Median Single Family Sale Price
$586,925
Median Townhouse Sale Price
$448,650
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$196
Number of Homes for Sale
25
Last 12 months Home Sales
152
Months of Supply
2.00
Median List Price
$542,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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