6,720

Leonardtown, MD Homes

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  • /2

    $549,000

    Coming Soon Oct 22
    • 4 Beds
    • 3.5 Baths
    • 3,006 Sq Ft

    23208 Clarks Rest Rd, Leonardtown, MD 20650

    LOCATION! LOCATION! LOCATION! Coming Soon. Full Pictures and Remarks to come closer to active date.

    Jimmy Hayden RE/MAX One

    23208 Clarks Rest Rd, Leonardtown, MD 20650
  • /46

    $439,900

    Sold Mar 31, 2026

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 74 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    • /31

      Est $584,235

      Not Listed For Sale

      42439 Dean Forest Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,519 Sq Ft
      • Built 2003
      42439 Dean Forest Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent DJ Brady EXP Realty, LLC

  • /73

    $750,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    40579 Port Place, Leonardtown, MD 20650

    Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft.Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40579 Port Place, Leonardtown, MD 20650
  • /40

    $485,900

    Sold Apr 28, 2026

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1% Above List Price

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    • /25

      Est $399,087

      Not Listed For Sale

      23888 Hollywood Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1972
      23888 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mark Frisco CENTURY 21 New Millennium

  • /75

    $624,900

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • /88

    $1,052,000

    Sold Feb 25, 2026

    22164 Miller Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Above List Price
    • $390/SF
    • 7 Days On Market

    Current Estimated Value $1,037,772

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • /140

      Not Listed For Sale

      41115 Paw Hollow Ln, Leonardtown, MD 20650

      • 4 Beds
      • 5.5 Baths
      • 6,116 Sq Ft
      • Built 1997
      41115 Paw Hollow Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /56

    $615,000

    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, Leonardtown, MD 20650
  • /41

    $458,550

    Sold Feb 26, 2026

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 78 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    • /54

      Est $534,694

      Not Listed For Sale

      41699 Courthouse Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 2,420 Sq Ft
      • Built 2012
      41699 Courthouse Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

  • /82

    $850,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,731 Sq Ft

    19445 Blake Farms Ln, Leonardtown, MD 20650

    Rare Waterfront Estate in Leonardtown! Nestled on 26.62 scenic acres, this charming Cape Cod farmhouse offers an unbeatable blend of pastoral beauty and waterfront living. Enjoy sweeping views of Blake Creek, extensive water frontage, and a private pier—perfect for kayaking, paddle boarding, crabbing, fishing, and peaceful small motor boating on this quiet tidal inlet.Inside, thoughtful

    Dawn Wood O'Brien Realty ERA Powered

    19445 Blake Farms Ln, Leonardtown, MD 20650
  • /47

    $489,900

    Sold Jun 30, 2026

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Last Sold Summary

    • $158/SF

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
    • /79

      Est $665,043

      Not Listed For Sale

      18822 McKays Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft
      • Built 1998
      18822 McKays Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Ron Leonard Leonard Realty, Inc.

  • /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • /9

    $340,000

    Sold Feb 20, 2026

    22820 Duke St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1947

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 0 Days On Market

    Current Estimated Value $334,270

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • /76

      Est $660,677

      Not Listed For Sale

      41474 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft
      • Built 2010
      41474 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /11

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

    **TO BE BUILT**** Homesite 141 - Oakley D1 End Unit ***October Delivery**** ***Choose your color scheme from of our available options** Photos shown are representative and intended to illustrate a similar finished townhouse. 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located

    Laura Lee Hefley RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • /75

    $640,000

    Sold Dec 01, 2025

    22216 Hanover Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 4,206 Sq Ft
    • Built 2005

    Last Sold Summary

    • $152/SF
    • 1 Day On Market

    Current Estimated Value $646,383

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • /4

      Est $655,080

      Not Listed For Sale

      41443 Whimsical Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,400 Sq Ft
      • Built 2010
      41443 Whimsical Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /38

    $487,400

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT***New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Lee Hefley RE/MAX One

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
  • /46

    $461,000

    Sold Aug 20, 2026

    40582 Port Place, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Above List Price
    • $210/SF
    • 2 Days On Market

    Current Estimated Value $401,160

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    40582 Port Place, Leonardtown, MD 20650
    • /10

      Est $668,359

      Not Listed For Sale

      23598 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,758 Sq Ft
      • Built 2010
      23598 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /53

    $645,900

    Sold Feb 26, 2026

    23581 Gallent Fox Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft
    • Built 2009

    Last Sold Summary

    • $173/SF
    • 42 Days On Market

    Current Estimated Value $647,141

    Last Listing Agent Laura Lee Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • /74

      Est $635,875

      Not Listed For Sale

      23546 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2009
      23546 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /45

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, Leonardtown, MD 20650
  • /87

    $475,203

    Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $478,611

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • /25

      Est $289,588

      Not Listed For Sale

      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 2008
      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kelly Niland Home Towne Real Estate

  • /77

    $675,000

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,953 Sq Ft

    44450 Schumann Way, Leonardtown, MD 20650

    Welcome to this beautiful custom-built home situated on over 4 acres, offering an incredible combination of space, privacy, and versatility. A welcoming covered front porch and mature landscaping create beautiful curb appeal and the perfect place to sit back and enjoy the peaceful surroundings. Inside, you’ll find a thoughtfully designed floor plan featuring a main-level primary suite, spacious

    Jesieryl Hartzer CENTURY 21 New Millennium

    44450 Schumann Way, Leonardtown, MD 20650
  • /39

    $720,000

    Sold May 11, 2026

    21335 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,533 Sq Ft
    • Built 2011

    Last Sold Summary

    • 1% Above List Price
    • $159/SF
    • 3 Days On Market

    Current Estimated Value $715,769

    Last Listing Agent Deanna Rothstein RE/MAX One

    21335 Fairwood Ct, Leonardtown, MD 20650
    • /82

      Est $574,165

      Not Listed For Sale

      23075 Hollywood Rd, Leonardtown, MD 20650

      • 5 Beds
      • 2.5 Baths
      • 3,238 Sq Ft
      • Built 1942
      23075 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Katy Galloway Century 21 Redwood Realty

  • /7

    $772,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, Leonardtown, MD 20650
  • /46

    $447,400

    Sold Dec 16, 2025

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2025

    Last Sold Summary

    • $172/SF
    • 90 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
    • /56

      Est $652,553

      Not Listed For Sale

      21147 Catnip Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft
      • Built 2002
      21147 Catnip Ct, Leonardtown, MD 20650

      Last Sold Summary

      Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

  • /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, Leonardtown, MD 20650
  • /83

    $660,000

    Sold Jul 14, 2026

    41531 Kalitan Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $185/SF
    • 4 Days On Market

    Current Estimated Value $662,993

    Last Listing Agent Heather Foster RE/MAX One

    41531 Kalitan Ln, Leonardtown, MD 20650
    • /80

      Est $703,036

      Not Listed For Sale

      41503 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 5,065 Sq Ft
      • Built 2008
      41503 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent John Gatton CENTURY 21 New Millennium

  • /89

    $1,590,000

    $110K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year.Perfectly positioned to capture breathtaking water views, this exceptional property offers a

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650

Showing Results 81 - 120, Page 3 of 18

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