6,772

Leonardtown, MD Homes

Section Image
  • /3

    $175,000

    $50K PRICE DROP
    • 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
  • /2

    $959,600

    Sold Aug 13, 2025

    40557 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF

    Current Estimated Value $934,282

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
    • /60

      Est $768,667

      Not Listed For Sale

      39653 Potomac Ave, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,150 Sq Ft
      • Built 1988
      39653 Potomac Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 10 Days On Market

  • /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 Hefley RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • /43

    $710,000

    Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $721,048

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /68

      Est $1,209,577

      Not Listed For Sale

      40139 Combs Creek Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,944 Sq Ft
      • Built 1995
      40139 Combs Creek Way, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /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 the

    Laura Hefley RE/MAX One

    Lot 138 - 23671 Dragonfly Ln, 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 Hefley RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    • /45

      Est $260,710

      Not Listed For Sale

      22321 Leonard St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1930
      22321 Leonard St, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

  • /41

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT***Oakley D1 End Unit at Meadows at Town Run II 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 in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of

    Laura Hefley RE/MAX One

    Lot 113 - 23696 Weeping Willow Way, 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 Hefley RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    • /68

      Est $680,022

      Not Listed For Sale

      42990 Baywood Place, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft
      • Built 2009
      42990 Baywood Place, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /54

    $485,000

    Open Sat 10AM - 12PM Under Contract
    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft

    21807 Potomac View Dr, Leonardtown, MD 20650

    Welcome home to the sought after community of Breton Bay in Leonardtown, where thoughtful updates, flexible living space, and an unbeatable location come together beautifully. This property offers the rare opportunity to enjoy all that Breton Bay has to offer, while still benefiting from no HOA restrictions. For a minimal optional annual fee, residents can enjoy private beach access at two

    Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View 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 Hefley RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    • /79

      Est $650,640

      Not Listed For Sale

      24606 Pin Cushion Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,466 Sq Ft
      • Built 1987
      24606 Pin Cushion Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 64 Days On Market

  • /79

    $669,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 3,098 Sq Ft

    41249 Brenda Ct, Leonardtown, MD 20650

    Meticulously cared for rambler, fully updated and move in ready, on nearly one private , partially wooded acre in the waterfront community of The Mulberries at Breton Bay. Brand new engineered hardwood floors plus fresh paint and brand new carpet in all three bedrooms. The kitchen has been updated with a sleek European elegance, white cabinets, granite countertops and stainless steel appliances.

    Robin Errington CENTURY 21 New Millennium

    41249 Brenda Ct, 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 $1,027,170

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • /92

      Est $1,162,817

      Not Listed For Sale

      40539 Port Place, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 3,371 Sq Ft
      • Built 1986
      40539 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /2

    $435,000

    • Land
    • 23.44 Acres
    • $18,558 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    23 acres with ability to build at least two homes

    Samara Dinnius JPAR Real Estate Professionals

    0 Whirlwind 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 $335,513

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • /31

      Est $596,402

      Not Listed For Sale

      21084 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft
      • Built 2003
      21084 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 30 Days On Market

  • /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
  • /27

    $515,000

    Sold Aug 15, 2025

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $203/SF
    • 10 Days On Market

    Current Estimated Value $543,005

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • /12

      Est $698,705

      Not Listed For Sale

      23569 Belmar Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,181 Sq Ft
      • Built 2008
      23569 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • /89

    $599,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    40704 Chance Way, Leonardtown, MD 20650

    Beautiful 4 bedroom, 2 1/2 bathroom colonial located in Leonardtown. Just mins from downtown Leonardtown amenities, shopping, restaurants, schools and more. This home has hardwood floors throughout. Spacious formal living and dining rooms. Kitchen with lots of cabinets and island with seating. Breakfast area and sliding doors that open to the back yard and patio. Family room w/gas fireplace off

    Kelly Padgett Century 21 Redwood Realty

    40704 Chance Way, 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 $643,261

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • /37

      Est $400,424

      Not Listed For Sale

      23005 Abell St, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 2,109 Sq Ft
      • Built 1955
      23005 Abell St, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /33

    $428,799

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft

    41600 Miss Bessie Dr, Leonardtown, MD 20650

    Brick-front one-level rambler featuring 3 bedrooms, 2 full bathrooms, and over 1,900 finished square feet. A welcoming covered front porch leads to an open and spacious interior with hardwood flooring throughout the foyer, hallway, living room, and formal dining room. The living room features a gas fireplace, while the dining room offers cathedral ceilings and Palladian windows for abundant

    Mike Mason Long & Foster Real Estate, Inc.

    41600 Miss Bessie Dr, Leonardtown, MD 20650
  • /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 $644,187

    Last Listing Agent Laura Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • /65

      Est $878,239

      Not Listed For Sale

      22265 Orchard Ct, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 4,873 Sq Ft
      • Built 2005
      22265 Orchard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /57

    $599,000

    Pending
    • 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
  • /82

    $574,000

    Sold Jul 24, 2025

    23075 Hollywood Rd, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft
    • Built 1942

    Last Sold Summary

    • $177/SF
    • 55 Days On Market

    Current Estimated Value $570,745

    Last Listing Agent Katy Galloway Century 21 Redwood Realty

    23075 Hollywood Rd, Leonardtown, MD 20650
    • /4

      Est $80,500

      Not Listed For Sale

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      40435 Old Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 482 Days On Market

  • /4

    $725,000

    Coming Soon
    • 5 Beds
    • 2 Baths
    • 2,834 Sq Ft

    41655 Church St, Leonardtown, MD 20650

    Built in 1875, this substantial 2,800 sq ft residence offers a rare opportunity to own a large historic home in highly desirable Leonardtown. Featuring 5 bedrooms and 2 bathrooms, the property showcases classic architecture with a formal living room and dining room, and enduring period details. Original features include a beautiful antique stamped tin ceiling and two fireplaces, adding

    Chris Norris Topside Realty

    41655 Church St, Leonardtown, MD 20650
  • /69

    $622,500

    Sold Jul 21, 2025

    21143 Catnip Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 16 Days On Market

    Current Estimated Value $621,545

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /23

      Est $334,583

      Not Listed For Sale

      23028 Hopton Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1988
      23028 Hopton Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /31

    $379,900

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been thoughtfully updated with a brand new roof, new windows, new

    Natalya Ford RE/MAX One

    21983 Point Lookout 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 $472,124

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • /70

      Est $683,842

      Not Listed For Sale

      21380 Fairwood Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft
      • Built 2008
      21380 Fairwood Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

  • /16

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650

    ***PENDING***** ***Late August Delivery*** Homesite 130 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that

    Laura Hefley RE/MAX One

    Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650

Showing Results 81 - 120, Page 3 of 18

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