6,736

Leonardtown, MD Homes

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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
  • 20670 Bloombury Ln, Leonardtown, MD 20650
    20670 Bloombury Ln, Leonardtown, MD 20650
    20670 Bloombury Ln, Leonardtown, MD 20650
    /18

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft
    • House for Rent

    20670 Bloombury Ln, Leonardtown, MD 20650

    Secluded home in Leonardtown area. Wrap around porch, garage, and plenty of area to spread out. 3 bedrooms on upper level one bedroom or office on main level. Unfinished basement and garage. Lots of outside room to roam and explore nature.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 234-0617

    20670 Bloombury Ln, Leonardtown, MD 20650
  • 20483 White Point Rd, Leonardtown, MD 20650
    20483 White Point Rd, Leonardtown, MD 20650
    20483 White Point Rd, Leonardtown, MD 20650
    /22

    $300,000 Sold May 20, 2025

    20483 White Point Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1953

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $311,624

    Last Listing Agent Theresa Shoptaw Keller Williams Realty

    20483 White Point Rd, Leonardtown, MD 20650
    • 41541 Fairwood Ct, Leonardtown, MD 20650
      41541 Fairwood Ct, Leonardtown, MD 20650
      41541 Fairwood Ct, Leonardtown, MD 20650
      /44

      Est $656,568 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,080 Sq Ft

      41541 Fairwood Ct, Leonardtown, MD 20650

      41541 Fairwood Ct, 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 Under Contract

    • 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
  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    /32

    $2,175 - $2,575 per month

    The Hamptons at Leonardtown

    2 - 3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • 20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    /117

    $725,000 Sold Apr 17, 2025

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    • 5 Beds
    • 5 Baths
    • 5,862 Sq Ft
    • Built 1997

    Last Sold Summary

    • $124/SF
    • 19 Days On Market

    Current Estimated Value $753,434

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    • 22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      /36

      Est $468,943 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft

      22605 Calvert St, Leonardtown, MD 20650

      22605 Calvert St, 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
  • 42271 Bird Haven Dr, Leonardtown, MD 20650
    42271 Bird Haven Dr, Leonardtown, MD 20650
    42271 Bird Haven Dr, Leonardtown, MD 20650
    /51

    $2,995 per month

    • 5 Beds
    • 3.5 Baths
    • 3,448 Sq Ft
    • House for Rent

    42271 Bird Haven Dr, Leonardtown, MD 20650

    Gorgeous 5 Bedroom 3.5 Bathroom Colonial w/ 3500sqft of Finished Living Space, a 2 Car Garage, & a pool! Solar Panels are a nice touch that will help keep the utility bills low! Home is situated in a well kept community within the Leonardtown High School District. Driving up you notice the charming curb appeal & cozy front porch! Entering into the foyer you will find a formal living room & dining

    Mark Frisco CENTURY 21 New Millennium

    42271 Bird Haven Dr, Leonardtown, MD 20650
  • 44195 Jessica Ln, Leonardtown, MD 20650
    44195 Jessica Ln, Leonardtown, MD 20650
    44195 Jessica Ln, Leonardtown, MD 20650
    /49

    $591,000 Sold May 22, 2025

    44195 Jessica Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,918 Sq Ft
    • Built 1998

    Last Sold Summary

    • $203/SF
    • 5 Days On Market

    Current Estimated Value $586,284

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    44195 Jessica Ln, Leonardtown, MD 20650
    • 23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      /72

      Est $680,959 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft

      23748 Coventry Dr, Leonardtown, MD 20650

      23748 Coventry Dr, 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 Under Contract

    • 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 One

    (227) 230-5161

    21925 Budds Creek Rd, Leonardtown, MD 20650
  • 22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    /6

    $1,650 - $1,950 per month

    Seymour Apartments

    1 - 2 Beds

    22645 Washington St, Leonardtown, MD 20650

    Introducing Seymour Apartments, in the heart of Historic Downtown Leonardtown! Come live in town just up the hill from the Warf while being steps away from the shops and restaurants on the square. Apartments in the Seymour Apartment building. Access to unit is from a common stairwell with private entrance. Units have new ductless heat pumps, parking for two cars and access to a large side

    22645 Washington St, Leonardtown, MD 20650
  • 22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    /86

    $633,000 Sold Sep 19, 2025

    22272 Orchard Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft
    • Built 2004

    Last Sold Summary

    • $169/SF
    • 1 Day On Market

    Current Estimated Value $634,249

    Last Listing Agent Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
    • 23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      /71

      Est $701,177 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft

      23287 Crestmar Ln, Leonardtown, MD 20650

      23287 Crestmar Ln, 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
  • 44868 Blake Creek Rd Unit 4, Leonardtown, MD 20650
    44868 Blake Creek Rd Unit 4, Leonardtown, MD 20650
    44868 Blake Creek Rd Unit 4, Leonardtown, MD 20650
    /8

    $1,350 per month

    • 2 Beds
    • 1 Bath
    • 1,028 Sq Ft
    • Townhouse for Rent

    44868 Blake Creek Rd Unit 4, Leonardtown, MD 20650

    Small duplex apartment with Living Room, laundry room, eat-in kitchen, one bath and two bedrooms. Max one occupants. No pets allowed. Still waiting on a few repairs, but available for occupancy.Looking for good credit and background check. Off street parking. Total of four apartments in two building with two units per building. Freshly painted and new carpets. Waiting to paint front of unit

    Jan Barnes CENTURY 21 New Millennium

    44868 Blake Creek Rd Unit 4, Leonardtown, MD 20650
  • 22355 White Oak Rd, Leonardtown, MD 20650
    22355 White Oak Rd, Leonardtown, MD 20650
    /2

    $470,000 Sold Feb 11, 2025

    22355 White Oak Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,028 Sq Ft
    • Built 1978

    Last Sold Summary

    • $232/SF

    Current Estimated Value $478,470

    Last Listing Agent Donna Thomas O'Brien Realty ERA Powered

    22355 White Oak Rd, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $523,097 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft

      22301 Bayside Rd, Leonardtown, MD 20650

      22301 Bayside Rd, Leonardtown, MD 20650
  • 19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    /13

    $130,000 Under Contract

    • Land
    • 5.09 Acres
    • $25,540 per Acre

    19921 Tower Hill Rd, Leonardtown, MD 20650

    Water access on this 5+ acre lot in sought after Leonardtown buildable, wooded, and perc'd lot. Build your dream home or purchase for access for kayaking. Covenants and Restrictions for neighborhood.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 888-6903

    19921 Tower Hill Rd, Leonardtown, MD 20650
  • 43859 Bardmore Way, Leonardtown, MD 20650
    43859 Bardmore Way, Leonardtown, MD 20650
    43859 Bardmore Way, Leonardtown, MD 20650
    /11

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    43859 Bardmore Way, Leonardtown, MD 20650

    Property Id: 2200997This well-maintained 3-bedroom, 2-bath single-story home offers comfortable and convenient living in a quiet setting. Featuring a clean, neutral exterior with classic shutters and a welcoming front entrance, the home boasts great curb appeal.Inside, you'll find a practical layout with freshly painted rooms throughout, three bedrooms, and two fully remodeled

    43859 Bardmore Way, Leonardtown, MD 20650
  • 21717 Meadow Ct, Leonardtown, MD 20650
    21717 Meadow Ct, Leonardtown, MD 20650
    21717 Meadow Ct, Leonardtown, MD 20650
    /41

    $449,900 Sold Mar 14, 2025

    21717 Meadow Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,488 Sq Ft
    • Built 1981

    Last Sold Summary

    • $302/SF
    • 9 Days On Market

    Current Estimated Value $437,381

    Last Listing Agent Carol Kalmus-Choporis CENTURY 21 New Millennium

    21717 Meadow Ct, Leonardtown, MD 20650
    • 23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      /69

      Est $648,414 Not Listed For Sale

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

      23567 Pine Bluff Way, Leonardtown, MD 20650

      23567 Pine Bluff Way, 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
    /46

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***READY-NOW Builder 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 105 Madison D2: Photos Coming Soon 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

    Laura Bernth RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
  • 22802 Lawrence Ave, Leonardtown, MD 20650
    22802 Lawrence Ave, Leonardtown, MD 20650
    22802 Lawrence Ave, Leonardtown, MD 20650
    /28

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,080 Sq Ft
    • House for Rent

    22802 Lawrence Ave, Leonardtown, MD 20650

    Experience elevated living in this never-before-lived-in residence just steps from charming Leonardtown Square. This thoughtfully crafted home showcases designer-selected finishes, premium appliances, and modern conveniences that set a new standard for local rentals. Step inside to an open, light-filled layout designed for both style and function. The kitchen features high-end stainless steel

    Michelle Camaioni RE/MAX One

    22802 Lawrence Ave, Leonardtown, MD 20650
  • 40744 Fawns Rest Way, Leonardtown, MD 20650
    40744 Fawns Rest Way, Leonardtown, MD 20650
    40744 Fawns Rest Way, Leonardtown, MD 20650
    /21

    $731,084 Sold Dec 04, 2025

    40744 Fawns Rest Way, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,313 Sq Ft
    • Built 2025

    Last Sold Summary

    • $221/SF
    • 0 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    40744 Fawns Rest Way, Leonardtown, MD 20650
    • 40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      /30

      Est $791,495 Not Listed For Sale

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

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      40630 Breton Oaks 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 Pending

    • 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
  • 41599 Church St, Leonardtown, MD 20650
    41599 Church St, Leonardtown, MD 20650
    41599 Church St, Leonardtown, MD 20650
    /22

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,080 Sq Ft
    • House for Rent

    41599 Church St, Leonardtown, MD 20650

    Experience elevated living in this never-before-lived-in residence just steps from charming Leonardtown Square. This thoughtfully crafted home showcases designer-selected finishes, premium appliances, and modern conveniences that set a new standard for local rentals. Step inside to an open, light-filled layout designed for both style and function. The kitchen features high-end stainless steel

    Michelle Camaioni RE/MAX One

    41599 Church St, Leonardtown, MD 20650
  • 43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    /74

    $475,000 Sold Jul 15, 2025

    43985 Main Way Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1973

    Last Sold Summary

    • $198/SF
    • 1 Day On Market

    Current Estimated Value $479,550

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
    • 23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      /44

      Est $444,409 Not Listed For Sale

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

      23380 Marview Ct, Leonardtown, MD 20650

      23380 Marview Ct, 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
  • 41577 Church St, Leonardtown, MD 20650
    41577 Church St, Leonardtown, MD 20650
    41577 Church St, Leonardtown, MD 20650
    /25

    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 909 Sq Ft
    • House for Rent

    41577 Church St, Leonardtown, MD 20650

    Experience elevated living in this never-before-lived-in residence just steps from charming Leonardtown Square. This thoughtfully crafted home showcases designer-selected finishes, premium appliances, and modern conveniences that set a new standard for local rentals. Step inside to an open, light-filled layout designed for both style and function. The kitchen features high-end stainless steel

    Michelle Camaioni RE/MAX One

    41577 Church St, Leonardtown, MD 20650
  • 22539 Landing Way, Leonardtown, MD 20650
    22539 Landing Way, Leonardtown, MD 20650
    22539 Landing Way, Leonardtown, MD 20650
    /32

    $518,500 Sold Dec 05, 2025

    22539 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • $188/SF
    • 12 Days On Market

    Last Listing Agent Trish Brow EXP Realty, LLC

    22539 Landing Way, Leonardtown, MD 20650
    • 40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      /70

      Est $777,784 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,320 Sq Ft

      40840 Greenwood Ln, Leonardtown, MD 20650

      40840 Greenwood Ln, Leonardtown, MD 20650
  • 21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    /90

    $565,000 Under Contract

    • 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
  • 41573 Church St, Leonardtown, MD 20650
    41573 Church St, Leonardtown, MD 20650
    41573 Church St, Leonardtown, MD 20650
    /27

    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 909 Sq Ft
    • House for Rent

    41573 Church St, Leonardtown, MD 20650

    Experience elevated living in this never-before-lived-in residence just steps from charming Leonardtown Square. This thoughtfully crafted home showcases designer-selected finishes, premium appliances, and modern conveniences that set a new standard for local rentals. Step inside to an open, light-filled layout designed for both style and function. The kitchen features high-end stainless steel

    Michelle Camaioni RE/MAX One

    41573 Church St, Leonardtown, MD 20650
  • 41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    /79

    $639,000 Sold Oct 30, 2025

    41474 Charismatic Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft
    • Built 2015

    Last Sold Summary

    • $175/SF
    • 57 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
    • 41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      /87

      Est $745,172 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft

      41408 W Citation St, Leonardtown, MD 20650

      41408 W Citation St, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 18

Maryland St Marys County Leonardtown

Real Estate & Homes

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 39 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 $540,000, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$449,900
Average Price Per Sq Ft
$192
Number of Homes for Sale
22
Last 12 months Home Sales
159
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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