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Homes for Sale in 20650

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  • /33

    $699,900

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

    21345 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21345 Fairwood Court! Back active after brief weather -related pause. Showings now available. 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

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 230-5835

    21345 Fairwood Ct, Leonardtown, MD 20650
  • /2

    $25,000

    • Land
    • 0.25 Acre
    • $100,000 per Acre

    0 Sunset Dr, 2, Valley Lee, MD 20650

    Mills Point Perfection! Looking for a lot in a water access community? Take a look at this flat, mostly cleared lot in desirable Mills Point in Southern Maryland. Buyer to perform all due diligence.

    Agent Photo

    Stephanie Rivers

    The Southside Group Real Estate

    (227) 234-0672

    0 Sunset Dr, 2, Valley Lee, 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
  • /18

    $589,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft

    43641 Redmond Rd, Leonardtown, MD 20650

    This great 8+ acre property with scenic pasture views. Solid 4 bedroom rambler on full basement. So many possibilities.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 231-3115

    43641 Redmond Rd, Leonardtown, MD 20650
  • /48

    $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) 230-5778

    22547 Landing Way, Leonardtown, MD 20650
  • /68

    $779,900

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

    22393 Saint Clements Ave, Leonardtown, MD 20650

    Experience refined waterfront living in this completely renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this residence has been thoughtfully reimagined from top to bottom with extensive structural, electrical, and plumbing upgrades, blending modern luxury with effortless coastal charm. Situated on a waterfront lot, the property offers its own private L-shaped

    Ralph Harvey ListWithFreedom.com

    22393 Saint Clements Ave, 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
  • /5

    $659,900 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,136 Sq Ft

    41515 Risen Star Ln, Leonardtown, MD 20650

    Welcome to the perfect blend of elegance, comfort, and location—this gorgeous Leonard's Grant home truly has it all and shows like a model. Meticulously maintained and move-in ready, this home offers 5 full bedrooms and 3.5 baths with a thoughtfully designed floor plan with plenty of room at 3,824 sq ft of finished space. The gourmet kitchen features a wall oven, gas cooktop, gorgeous cabinetry,

    Cynthia Crispell CENTURY 21 New Millennium

    41515 Risen Star Ln, Leonardtown, MD 20650
  • /35

    $809,900 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft

    40737 Bobwhite Ln, Leonardtown, MD 20650

    Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful

    Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
  • /68

    $624,900

    • 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
  • /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
  • /61

    $640,000

    • 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
  • /6

    $175,000

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

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

    6+ lot zoned RPD in a prime location with 600 +/- ft of road frontage with 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 Materials and

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
  • /49

    $595,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /2

    $315,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft

    22175 Bayside Rd, Leonardtown, MD 20650

    The perfect location for a starter home, Located in Leonardtown MD! This two bedroom and two bathroom open floor plan, single-level rambler is conveniently just a short drive to restaurants, fast food locations, Port Of Leonardtown Winery, Newtowne Neck State Park for the water views and just a short walk next door to check your mail. A few great features about the home include a modern black

    Darrin Carter RE/MAX One

    22175 Bayside Rd, Leonardtown, MD 20650
  • /13

    $189,000

    • 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
  • /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
  • /41

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, READY- NOW Incentive, 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. Unit 104 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit,

    Laura Bernth RE/MAX One

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
  • /58

    $435,000

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft

    23369 Marview Ct, Leonardtown, MD 20650

    Beautiful Clark’s Rest townhome offering three finished levels, a two-car garage, and over 2,300 square feet of living space. The main level features hardwood floors, a gourmet kitchen with granite countertops and 42-inch cabinetry, a separate formal dining space, and a large family room—ideal for both everyday living and entertaining.The fully finished lower level includes a spacious

    Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, 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
  • /30

    $1,750,000

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

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

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • /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
  • /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
  • /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
  • /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
  • /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
  • /30

    $555,000

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

    41635 Ferber Ct, Leonardtown, MD 20650

    PRICE IMPROVEMENT! 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

    Alvin Frazier Home Towne Real Estate

    41635 Ferber Ct, Leonardtown, MD 20650
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