6,758

Leonardtown, MD Homes

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  • 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
  • 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 $308,745

    Last Listing Agent Theresa Shoptaw CENTURY 21 New Millennium

    20483 White Point Rd, Leonardtown, MD 20650
    • 19710 Tower Hill Rd, Leonardtown, MD 20650
      19710 Tower Hill Rd, Leonardtown, MD 20650
      19710 Tower Hill Rd, Leonardtown, MD 20650
      /3

      Est $1,274,015 Not Listed For Sale

      19710 Tower Hill Rd, Leonardtown, MD 20650

      • 5 Beds
      • 6.5 Baths
      • 5,690 Sq Ft
      • Built 1984
      19710 Tower Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $215/SF

      Last Sold Price $1,225,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • 21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    /39

    $715,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,533 Sq Ft

    21335 Fairwood Ct, Leonardtown, MD 20650

    **Multiple offers received. Highest and best offers due by 12:00 PM tomorrow, 4/8. Seller is limiting additional showings—please contact listing agent for availability. Welcome to Leonardtown Farms—where space, comfort, and thoughtful upgrades come together in one beautiful home.This spacious Pinehurst 3 model offers over 4,300 square feet of living space with 5 bedrooms and 3.5 bathrooms,

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 240-6165

    21335 Fairwood Ct, Leonardtown, MD 20650
  • 41855 Meynard Ct, Leonardtown, MD 20650
    41855 Meynard Ct, Leonardtown, MD 20650
    41855 Meynard Ct, Leonardtown, MD 20650
    /15

    $3,100 per month

    • 4 Beds
    • 3.5 Baths
    • 3,528 Sq Ft
    • House for Rent

    41855 Meynard Ct, Leonardtown, MD 20650

    GOOD CREDIT A MUST - MINIMAL SCORE OF 700 REQUIRED BY OWNER, if your client is interested please have them fill out the rent spree application. All adults-anyone over the age of 18 must be on the lease and fill out an application with credit check. Beautiful, spacious 4 bedroom 3.5 bath home for rent in desirable Leonardtown neighborhood. Two car finished garage, basement and back deck are just a

    Agent Photo

    Edward Tully

    RE/MAX One

    (227) 240-8880

    41855 Meynard Ct, 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 $756,396

    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 $450,030 Not Listed For Sale

      22605 Calvert St, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft
      • Built 2018
      22605 Calvert St, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $175/SF
      • 62 Days On Market

      Last Sold Price $410,000

      Last Listing Agent kyle Antel BHHS PenFed (actual)

  • 22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    /48

    $515,000 Under Contract

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

    22547 Landing Way, Leonardtown, MD 20650

    Experience life in a charming waterfront community where every day feels like a getaway. Enjoy kayaking, paddleboarding, and a variety of outdoor activities right at your doorstep. Start your mornings with yoga on the wharf or take a short stroll to the square for weekend concerts and local events. Located in the heart of Leonardtown, this home offers not only convenience but a vibrant lifestyle

    Agent Photo

    Trish Brow

    EXP Realty, LLC

    (227) 230-5778

    22547 Landing Way, Leonardtown, MD 20650
  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    /32

    $2,225 - $2,400 per month

    The Hamptons at Leonardtown

    2 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
  • 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 $596,465

    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 $669,412 Not Listed For Sale

      23748 Coventry Dr, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft
      • Built 2013
      23748 Coventry Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $156/SF
      • 6 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Patrick Deighan Century 21 New Millennium

  • 18866 Russell Rd, Leonardtown, MD 20650
    18866 Russell Rd, Leonardtown, MD 20650
    18866 Russell Rd, Leonardtown, MD 20650
    /3

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    18866 Russell Rd, Leonardtown, MD 20650

    ***Rare Waterfront Opportunity*** Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD, a truly exceptional waterfront property offering a private, peaceful setting on a premium lot with stunning views of the water. Currently a 3-bedroom, 1.5-bath home, this property presents the perfect opportunity to reimagine, renovate, or rebuild into your dream waterfront retreat. Surrounded by natural

    Agent Photo

    Shelly Hibbert

    KW Metro Center

    (227) 997-7054

    18866 Russell Rd, Leonardtown, MD 20650
  • 41470 Margrove Cir, Leonardtown, MD 20650
    41470 Margrove Cir, Leonardtown, MD 20650
    41470 Margrove Cir, Leonardtown, MD 20650
    /24

    $2,975 per month

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft
    • Townhouse for Rent

    41470 Margrove Cir, Leonardtown, MD 20650

    Location is key.... Not just in Leonardtown, but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Townhome living. Clarks Rest residents enjoy a range of community amenities, including the community pool, a baby/toddler pool, sports courts (basketball and tennis), a beautiful

    Wayne & Christine Floyd RE/MAX Realty Group

    41470 Margrove Cir, 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 $647,113

    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 $694,148 Not Listed For Sale

      23287 Crestmar Ln, Leonardtown, MD 20650

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft
      • Built 2019
      23287 Crestmar Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $155/SF
      • 26 Days On Market

      Last Sold Price $659,000

      Last Listing Agent Marizel Brewington RE/MAX

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

    $500,000

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

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (227) 230-6008

    20798 Waterside Dr, Leonardtown, MD 20650
  • 23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
    /54

    $2,695 per month

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    23581 Belmar Dr, Leonardtown, MD 20650

    Recently Renovated Cabin on Over 2 Acres in Leonardtown! 3 Spacious Bedrooms; 2 Full Baths; Fully Renovated Kitchen with New Cabinets, Countertops, Appliances; New Flooring! See it Today! Walking Distance to Duke Elementary and Minutes to Leonardtown Middle School and Leonardtown High School! Close to Leonardtown Square, Shopping, Restaurants, Schools, and More! Application fee is $65 per adult

    Erika Yowell EXP Realty, LLC

    23581 Belmar Dr, 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
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $516,299 Not Listed For Sale

      22301 Bayside Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft
      • Built 2012
      22301 Bayside Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Above List Price
      • $201/SF
      • 63 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Chad Istvan EXP Realty, LLC

  • 40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    /2

    $679,900 Coming Soon

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

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Experience waterfront living at its best with this beautifully maintained 2-bedroom, 2.5-bath home with a loft, perfectly positioned along the Potomac River just minutes from historic Leonardtown. Whether you’re looking for a full-time residence or a relaxing getaway, this property delivers the ideal blend of comfort, functionality, and breathtaking views. Designed for those who truly enjoy life

    Agent Photo

    Billy Rabbitt

    The Southside Group Real Estate

    (227) 239-0461

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • 41386 Margrove Cir, Leonardtown, MD 20650
    41386 Margrove Cir, Leonardtown, MD 20650
    41386 Margrove Cir, Leonardtown, MD 20650
    /38

    $3,200 per month

    • 4 Beds
    • 3.5 Baths
    • 3,195 Sq Ft
    • Townhouse for Rent

    41386 Margrove Cir, Leonardtown, MD 20650

    Discover modern living in this 4-bedroom, 3.5-bath end-unit townhome located in the highly desirable Clark's Rest community. This spacious rental boasts an abundance of natural light, an attached garage, and a fully finished basement for all your living and storage needs. The large balcony off the kitchen is perfect for enjoying your morning coffee or entertaining guests. Pet-friendly on a

    Matthew Burgan Infinitas Realty Group

    41386 Margrove Cir, 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 $483,898

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, 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 $612,993 Not Listed For Sale

      23567 Pine Bluff Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,736 Sq Ft
      • Built 2013
      23567 Pine Bluff Way, Leonardtown, MD 20650

      Last Sold Summary

      • $163/SF
      • 14 Days On Market

      Last Sold Price $610,000

      Last Listing Agent Kimberly Scott Remax 100

  • 40295 Busy Corner Rd, Leonardtown, MD 20650
    40295 Busy Corner Rd, Leonardtown, MD 20650
    /2

    $439,900 Coming Soon

    • 4 Beds
    • 3 Baths
    • 1,624 Sq Ft

    40295 Busy Corner Rd, Leonardtown, MD 20650

    One level living at its best. No HOA. Two Primary suites.

    Agent Photo

    Kelly Niland

    Home Towne Real Estate

    (227) 997-7373

    40295 Busy Corner Rd, Leonardtown, MD 20650
  • 42464 Fairgrounds Rd, Leonardtown, MD 20650
    42464 Fairgrounds Rd, Leonardtown, MD 20650
    42464 Fairgrounds Rd, Leonardtown, MD 20650
    /33

    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft
    • House for Rent

    42464 Fairgrounds Rd, Leonardtown, MD 20650

    This great home offers hardwood floors, toasty warm oil heat, a circle drive and a level lot. Landlord has several requirements including a firm no pet policy. Please ask your tenant's agent to read the private agent remarks.

    Karen Gioia RE/MAX One

    42464 Fairgrounds Rd, 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

    Current Estimated Value $522,394

    Last Listing Agent Trish Brow EXP Realty, LLC

    22539 Landing 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 $771,624 Not Listed For Sale

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft
      • Built 2021
      40630 Breton Oaks Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 3% Above List Price
      • $201/SF
      • 80 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Helen Mattingly Wernecke BHHS PenFed (actual)

  • Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    /45

    $449,900 Open Fri 11AM - 3:45PM

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

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

    ***June Delivery*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town

    Laura Bernth RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • 20503 Chestnut Ridge Dr, Leonardtown, MD 20650
    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
    /36

    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • House for Rent

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650

    Effective 4/6/2026: Owner will consider Pets as follows: 1 dog 75lbs or less, applicant must have at least 700 credit score, continuous Employment history greater than 5 years, No late payments of rents in the last 5 years and Gross monthly income of at $8,400 or higher only 2 incomes will be considered for gross monthly income. Monthly RENT AT $2,750.00. Nestled in the serene enclave of Chestnut

    Jay Camp Coldwell Banker Premier

    20503 Chestnut Ridge Dr, 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

    Current Estimated Value $652,257

    Last Listing Agent Laura Bernth RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
    • 23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      /44

      Est $422,209 Not Listed For Sale

      23380 Marview Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft
      • Built 2018
      23380 Marview Ct, Leonardtown, MD 20650

      Last Sold Summary

      • $183/SF
      • 31 Days On Market

      Last Sold Price $422,000

      Last Listing Agent Diana Washabaugh Century 21 New Millennium

  • 20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    /65

    $1,450,000 Under Contract

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft

    20045 Tower Hill Rd, Leonardtown, MD 20650

    Set quietly within 12 picturesque acres overlooking a peaceful creek, Tower Hill Retreat offers an extraordinary opportunity to experience refined country living in a natural setting. This impressive estate features 5 bedrooms (with potential for a sixth) and 5 full and 2 half bathrooms in a thoughtfully designed and exceptionally versatile floor plan. Rich hardwood and tile flooring extend

    Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
  • 40865 Spring House Ln, Leonardtown, MD 20650
    40865 Spring House Ln, Leonardtown, MD 20650
    40865 Spring House Ln, Leonardtown, MD 20650
    /33

    $2,595 per month

    • 3 Beds
    • 2.5 Baths
    • 1,736 Sq Ft
    • House for Rent

    40865 Spring House Ln, Leonardtown, MD 20650

    Enjoy the community of Breton Bay in this 3BR 2.5FB home with two car garage. On the main level of the home are the open living and dining room areas, kitchen, 2 bedrooms and hall full bath as well as the Primary bedroom and Primary bath. On the lower level is the family room with fireplace, half bath, laundry area and access to the two car front loading garage with storage area. Outside living

    Joycelyn Clark-Young CENTURY 21 New Millennium

    40865 Spring House Ln, Leonardtown, MD 20650
  • 21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    /90

    $575,000 Sold Mar 05, 2026

    21060 Woodmere Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $187/SF
    • 18 Days On Market

    Current Estimated Value $567,820

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, 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 $705,730 Not Listed For Sale

      41408 W Citation St, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft
      • Built 2013
      41408 W Citation St, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Below List Price
      • $149/SF
      • 3 Days On Market

      Last Sold Price $740,000

      Last Listing Agent Heather Foster RE/MAX

  • 23282 Lindsay Dr, Leonardtown, MD 20650
    23282 Lindsay Dr, Leonardtown, MD 20650
    23282 Lindsay Dr, Leonardtown, MD 20650
    /55

    $590,000

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

    23282 Lindsay Dr, Leonardtown, MD 20650

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

    Nichelle Jeter Samson Properties

    23282 Lindsay Dr, Leonardtown, MD 20650
  • 18937 McKays Cove Ln, Leonardtown, MD 20650
    18937 McKays Cove Ln, Leonardtown, MD 20650
    18937 McKays Cove Ln, Leonardtown, MD 20650
    /37

    $2,100 per month

    • 3 Beds
    • 1.5 Baths
    • 1,583 Sq Ft
    • House for Rent

    18937 McKays Cove Ln, Leonardtown, MD 20650

    Welcome to this charming water-access rambler! This inviting 3-bedroom, 1.5-bath home offers comfortable single-level living in a peaceful coastal setting.Inside, you’ll find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinet space, perfect for everyday living and entertaining. The functional open floor plan provides bright living areas, well-sized

    Erika Yowell EXP Realty, LLC

    18937 McKays Cove Ln, Leonardtown, MD 20650
  • 43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    /59

    $600,000 Sold Oct 01, 2025

    43571 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 1993

    Last Sold Summary

    • $204/SF
    • 22 Days On Market

    Current Estimated Value $615,299

    Last Listing Agent Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
    • 22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      /10

      Est $264,997 Not Listed For Sale

      22765 Duke St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft
      • Built 1949
      22765 Duke St, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Above List Price
      • $302/SF
      • 6 Days On Market

      Last Sold Price $259,950

      Last Listing Agent Ronald Watson Flag Real Estate Inc.

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 47 days on the market compared to the national average of 56 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $542,500, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$542,500
Median Single Family Sale Price
$590,000
Median Townhouse Sale Price
$449,900
Average Price Per Sq Ft
$199
Number of Homes for Sale
32
Last 12 months Home Sales
170
Months of Supply
2.30
Median List Price
$547,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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