6,717

Leonardtown, MD Homes

Section Image
    • 40435 Breton View Dr, Leonardtown, MD 20650
      40435 Breton View Dr, Leonardtown, MD 20650
      40435 Breton View Dr, Leonardtown, MD 20650
      /61

      Est $401,758 Not Listed For Sale

      • 2 Beds
      • 3.5 Baths
      • 2,286 Sq Ft

      40435 Breton View Dr, Leonardtown, MD 20650

      40435 Breton View Dr, Leonardtown, MD 20650
  • 41470 Garrett Ct, Leonardtown, MD 20650
    41470 Garrett Ct, Leonardtown, MD 20650
    41470 Garrett Ct, Leonardtown, MD 20650
    /31

    $589,000 Sold Dec 13, 2024

    • 3,439 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2001

    41470 Garrett Ct, Leonardtown, MD 20650

    This spacious Cape Cod, nestled at the end of a quiet cul-de-sac, offers the perfect blend of privacy and convenience. Boasting over 3,400 square feet of living space, this home features 4 generous bedrooms and 3 full bathrooms. Two main floor primary bedrooms! Enjoy the serene views as this property as it backs to trees on both the rear and side, providing a tranquil setting with no HOA.

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    41470 Garrett Ct, Leonardtown, MD 20650
    • 22373 Bretmar Dr, Leonardtown, MD 20650
      22373 Bretmar Dr, Leonardtown, MD 20650
      22373 Bretmar Dr, Leonardtown, MD 20650
      /76

      Est $591,024 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,410 Sq Ft

      22373 Bretmar Dr, Leonardtown, MD 20650

      22373 Bretmar Dr, Leonardtown, MD 20650
  • 40443 Breton View Dr, Leonardtown, MD 20650
    40443 Breton View Dr, Leonardtown, MD 20650
    40443 Breton View Dr, Leonardtown, MD 20650
    /18

    $385,000 Sold Dec 11, 2024

    • 2,604 Sq Ft
    • $148/SF
    • 36 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1994

    40443 Breton View Dr, Leonardtown, MD 20650

    Why settle for a typical subdivision when you can enjoy the beauty and lifestyle of Breton Bay? With its proximity to Breton Bay Country Club—offering pool, tennis, and golf amenities—and historic Leonardtown for dining, shopping, and events, this townhome is the perfect blend of convenience and coastal living. The 3-level, three-bedroom, 3.5 bath townhome features beautiful luxury vinyl plank

    Anne Davis CENTURY 21 New Millennium

    40443 Breton View Dr, Leonardtown, MD 20650
    • 42403 Riverwinds Dr, Leonardtown, MD 20650
      42403 Riverwinds Dr, Leonardtown, MD 20650
      42403 Riverwinds Dr, Leonardtown, MD 20650
      /81

      Est $746,708 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,079 Sq Ft

      42403 Riverwinds Dr, Leonardtown, MD 20650

      42403 Riverwinds Dr, Leonardtown, MD 20650
  • 40435 Old Breton Beach Rd, Leonardtown, MD 20650
    40435 Old Breton Beach Rd, Leonardtown, MD 20650
    40435 Old Breton Beach Rd, Leonardtown, MD 20650
    /4

    $75,000 Sold Dec 09, 2024

    • Land
    • 1.16 Acres
    • $64,655 per Acre
    • 482 Days On Market

    40435 Old Breton Beach Rd, Leonardtown, MD 20650

    IMPROVED PRICE!!!!! Motivated seller, bring your offer!!!!!!Spectacular views of the Potomac River! Recreational waterfront property for sale. Lots included in price are: 500-34, 33 and 32. Parcel 263 across the road also conveys. This property is listed for recreational use, it is non-buildable. There was a dock at one time and it is likely a new one can be built.

    Kelly Loveless Berkshire Hathaway HomeServices PenFed Realty

    40435 Old Breton Beach Rd, Leonardtown, MD 20650
    • 20488 Deer Wood Park Dr, Leonardtown, MD 20650
      20488 Deer Wood Park Dr, Leonardtown, MD 20650
      20488 Deer Wood Park Dr, Leonardtown, MD 20650
      /28

      Est $639,390 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,774 Sq Ft

      20488 Deer Wood Park Dr, Leonardtown, MD 20650

      20488 Deer Wood Park Dr, Leonardtown, MD 20650
  • 43610 Deer Run Ct, Leonardtown, MD 20650
    43610 Deer Run Ct, Leonardtown, MD 20650
    43610 Deer Run Ct, Leonardtown, MD 20650
    /87

    $625,000 Sold Dec 06, 2024

    • 2,980 Sq Ft
    • $210/SF
    • 4 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1997

    43610 Deer Run Ct, Leonardtown, MD 20650

    Wonderful brick front colonial home sitting on over 6.5 acres in Chestnut Hills. This home has been recently updated with fresh paint, new carpet, beautiful solid surface countertops and tiled backsplash along with refreshed baths and is ready for its new owners to call home. Main level has formal living and dining areas with hardwood floors, a generously sized kitchen with SS appliances,

    Jennifer Goddard CENTURY 21 New Millennium

    43610 Deer Run Ct, Leonardtown, MD 20650
    • 43560 Ridge Ct, Leonardtown, MD 20650
      43560 Ridge Ct, Leonardtown, MD 20650
      43560 Ridge Ct, Leonardtown, MD 20650
      /80

      Est $650,802 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,702 Sq Ft

      43560 Ridge Ct, Leonardtown, MD 20650

      43560 Ridge Ct, Leonardtown, MD 20650
  • 21726 Lake Cir, Leonardtown, MD 20650
    21726 Lake Cir, Leonardtown, MD 20650
    21726 Lake Cir, Leonardtown, MD 20650
    /45

    $365,000 Sold Dec 06, 2024

    • 1,956 Sq Ft
    • $187/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1980

    21726 Lake Cir, Leonardtown, MD 20650

    MULTIPLE OFFERS RECEIVED - OFFER DEADLINE 11/14 4PM Looking for an affordable home in a great location? This split foyer in Breton Bay is calling your name! This property is perfect for those looking to put their own touch on their home and offers tons of space with 4 bedrooms and 3 full bathrooms as well as a bonus room downstairs that could be used as an extra bedroom, playroom, storage

    Amanda Littleford Infinitas Realty Group

    21726 Lake Cir, Leonardtown, MD 20650
    • 20510 Deer Wood Park Dr, Leonardtown, MD 20650
      20510 Deer Wood Park Dr, Leonardtown, MD 20650
      20510 Deer Wood Park Dr, Leonardtown, MD 20650
      /57

      Est $625,769 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,436 Sq Ft

      20510 Deer Wood Park Dr, Leonardtown, MD 20650

      20510 Deer Wood Park Dr, Leonardtown, MD 20650
  • 22135 Cartwright Rd, Leonardtown, MD 20650
    22135 Cartwright Rd, Leonardtown, MD 20650
    22135 Cartwright Rd, Leonardtown, MD 20650
    /30

    $445,000 Sold Dec 06, 2024

    • 1,836 Sq Ft
    • $242/SF
    • 115 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1991

    22135 Cartwright Rd, Leonardtown, MD 20650

    New & Updated!! New Roof and Gutters!! Bring your ideas and discover the allure of this custom-built gem situated in a serene locale of Leonardtown, a stone's throw from the vibrant St. Mary's fairgrounds and the bustling heart of the community. This distinguished home spans 1,836 square feet, offering 3 bedrooms, 2 full bathrooms, and a convenient half bath. The residence is a testament to

    adrian abramson The Southside Group Real Estate

    22135 Cartwright Rd, Leonardtown, MD 20650
    • 41510 Reins Ct, Leonardtown, MD 20650
      41510 Reins Ct, Leonardtown, MD 20650
      41510 Reins Ct, Leonardtown, MD 20650
      /59

      Est $530,075 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,732 Sq Ft

      41510 Reins Ct, Leonardtown, MD 20650

      41510 Reins Ct, Leonardtown, MD 20650
  • 22876 White Swan Way, Leonardtown, MD 20650
    22876 White Swan Way, Leonardtown, MD 20650
    22876 White Swan Way, Leonardtown, MD 20650
    /49

    $708,750 Sold Dec 05, 2024

    • 4,984 Sq Ft
    • $142/SF
    • 56 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    22876 White Swan Way, Leonardtown, MD 20650

    Welcome to your new home in the Avenmar neighborhood of Breton Bay where there is something for everyone, including your fur babies! This amazing QBH Willow model boasts a beautiful brick front Colonial with a sideload 2 car garage that sits on 3.6 acres off of a private road at the end of a cul de sac. The first floor has hardwood and ceramic tile flooring, featuring a bedroom and full bathroom.

    Ross Simone RE/MAX Realty Group

    22876 White Swan Way, Leonardtown, MD 20650
    • 41575 Coach Ct, Leonardtown, MD 20650
      41575 Coach Ct, Leonardtown, MD 20650
      41575 Coach Ct, Leonardtown, MD 20650
      /31

      Est $603,263 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,514 Sq Ft

      41575 Coach Ct, Leonardtown, MD 20650

      41575 Coach Ct, Leonardtown, MD 20650
  • 43035 Bluejay Ln, Leonardtown, MD 20650
    43035 Bluejay Ln, Leonardtown, MD 20650
    43035 Bluejay Ln, Leonardtown, MD 20650
    /81

    $620,000 Sold Dec 05, 2024

    • 2,614 Sq Ft
    • $237/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2021

    43035 Bluejay Ln, Leonardtown, MD 20650

    Welcome to this beautiful 4-bedroom, 2.5 bath Montross Model, built by Quality Built Homes, Inc. in 2021, offering over 2,600 sq ft of luxurious living space that shows like new! This meticulously maintained home features luxury vinyl plank (LVP) flooring throughout, with upgraded tile in the bathrooms—there’s no carpet anywhere in the house!The chef's kitchen is a masterpiece, showcasing

    Laura Bernth RE/MAX One

    43035 Bluejay Ln, Leonardtown, MD 20650
    • 23960 R G Way, Leonardtown, MD 20650
      23960 R G Way, Leonardtown, MD 20650
      23960 R G Way, Leonardtown, MD 20650
      /56

      Est $679,141 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,788 Sq Ft

      23960 R G Way, Leonardtown, MD 20650

      23960 R G Way, Leonardtown, MD 20650
  • 24749 Trailside Ln, Leonardtown, MD 20650
    24749 Trailside Ln, Leonardtown, MD 20650
    24749 Trailside Ln, Leonardtown, MD 20650
    /4

    $180,000 Sold Dec 03, 2024

    • Land
    • 1.3 Acres
    • $138,462 per Acre
    • 818 Days On Market

    24749 Trailside Ln, Leonardtown, MD 20650

    Price reduction! Only 5 lots left! 24 lot subdivision in Leonardtown! 1-7.5 acre lots! Perced, recorded and ready to go! Buy a lot and sit on it, buy a lot and use one of our preferred builders or bring your own builder. HOA - $300 annual, $500 initial capital contribution

    Patricia Nicely JPAR Real Estate Professionals

    24749 Trailside Ln, Leonardtown, MD 20650
    • 43210 Oakway Ct, Leonardtown, MD 20650
      43210 Oakway Ct, Leonardtown, MD 20650
      43210 Oakway Ct, Leonardtown, MD 20650
      /66

      Est $563,466 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,517 Sq Ft

      43210 Oakway Ct, Leonardtown, MD 20650

      43210 Oakway Ct, Leonardtown, MD 20650
  • 40738 Bobwhite Ln, Leonardtown, MD 20650
    40738 Bobwhite Ln, Leonardtown, MD 20650
    /2

    $825,000 Sold Jul 31, 2025

    • 4,648 Sq Ft
    • $177/SF
    • 14 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2000

    40738 Bobwhite Ln, Leonardtown, MD 20650

    Welcome to this extraordinary 5,242 sq. ft. estate, perfectly nestled on 3.52 acres of beautifully landscaped grounds in the prestigious Avenmar community. Privately situated at the end of a tranquil cul-de-sac, this five-bedroom, four-bathroom home is a masterclass in luxury, craftsmanship, and timeless design.From the moment you arrive, the expansive private driveway and lush, mature

    Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
    • 42601 Wilderness Rd, Leonardtown, MD 20650
      42601 Wilderness Rd, Leonardtown, MD 20650
      42601 Wilderness Rd, Leonardtown, MD 20650
      /50

      Est $447,813 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,181 Sq Ft

      42601 Wilderness Rd, Leonardtown, MD 20650

      42601 Wilderness Rd, Leonardtown, MD 20650
  • 24554 Pin Cushion Rd, Leonardtown, MD 20650
    24554 Pin Cushion Rd, Leonardtown, MD 20650
    /2

    $366,000 Sold Jul 02, 2025

    • 1,856 Sq Ft
    • $197/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    24554 Pin Cushion Rd, Leonardtown, MD 20650

    OPEN HOUSE Cancelled due to multiple offers in hand. All offers considered until noon on June 19th. a Welcome to your next adventure! This almost all brick rambler sits on 1.26 acres with NO HOA — giving you the freedom to live how you want. Inside, you’ll find 3 bedrooms, 2 full baths, and a private primary suite ready to be your personal retreat. Outside, enjoy a detached carport, a storage

    Connie Fitzgerald RE/MAX One

    24554 Pin Cushion Rd, Leonardtown, MD 20650
    • 20815 Chestnut Ridge Dr, Leonardtown, MD 20650
      20815 Chestnut Ridge Dr, Leonardtown, MD 20650
      20815 Chestnut Ridge Dr, Leonardtown, MD 20650
      /50

      Est $475,284 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft

      20815 Chestnut Ridge Dr, Leonardtown, MD 20650

      20815 Chestnut Ridge Dr, Leonardtown, MD 20650
  • 23617 Belmar Dr, Leonardtown, MD 20650
    23617 Belmar Dr, Leonardtown, MD 20650
    /2

    $615,000 Sold May 27, 2025

    • 2,870 Sq Ft
    • $214/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2011

    23617 Belmar Dr, Leonardtown, MD 20650

    Welcome to this beautifully maintained Colonial home, perfectly situated on a lovely lot! Featuring 5 bedrooms and 3.5 baths, this open and airy home boasts fresh, light-colored paint throughout, creating a bright and inviting atmosphere.The heart of the home is the gourmet kitchen, complete with granite countertops, a gas stovetop, and a huge pantry—perfect for cooking and

    Heather Foster RE/MAX One

    23617 Belmar Dr, Leonardtown, MD 20650
    • 43536 Bayberry Ct, Leonardtown, MD 20650
      43536 Bayberry Ct, Leonardtown, MD 20650
      43536 Bayberry Ct, Leonardtown, MD 20650
      /38

      Est $532,655 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,980 Sq Ft

      43536 Bayberry Ct, Leonardtown, MD 20650

      43536 Bayberry Ct, Leonardtown, MD 20650
  • 22805 Lawrence Ave, Leonardtown, MD 20650
    22805 Lawrence Ave, Leonardtown, MD 20650
    /2

    $295,000 Sold Mar 11, 2025

    • 1,606 Sq Ft
    • $184/SF
    • 0 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1945

    22805 Lawrence Ave, Leonardtown, MD 20650

    Everything you can ask for is in quick walking distance of this classic home. Just a two minute walk to downtown Leonardtown. Walk to restaurants, shopping, post office, bank, & entertainment. Unwind on your recently re-screened porch, or by your fireplace. Oil burning furnace is less than five years old. Roof is new, too! Shed is less than two years old. Extra large laundry room. There

    John Gatton CENTURY 21 New Millennium

    22805 Lawrence Ave, Leonardtown, MD 20650
    • 40613 Oakmont Ct, Leonardtown, MD 20650
      40613 Oakmont Ct, Leonardtown, MD 20650
      40613 Oakmont Ct, Leonardtown, MD 20650
      /67

      Est $579,295 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,507 Sq Ft

      40613 Oakmont Ct, Leonardtown, MD 20650

      40613 Oakmont Ct, Leonardtown, MD 20650
  • 23245 Jenifer Ct, Leonardtown, MD 20650
    23245 Jenifer Ct, Leonardtown, MD 20650
    /2

    $584,850 Sold Feb 04, 2025

    • 3,841 Sq Ft
    • $152/SF
    • 71 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2004

    23245 Jenifer Ct, Leonardtown, MD 20650

    Beautiful 4 bedroom home in the convenient and established Single Tree neighborhood feels like your “forever home” the minute you walk in the front door! This house makes a statement with the large 2 story foyer with cathedral window and chandelier. The spacious main floor has it all! A great room featuring gas fireplace is open to the large kitchen with bar seating at island and separate dining

    Thomas Hennerty NetRealtyNow.com, LLC

    23245 Jenifer Ct, Leonardtown, MD 20650
    • 21818 Hazeltine Ct, Leonardtown, MD 20650
      21818 Hazeltine Ct, Leonardtown, MD 20650
      21818 Hazeltine Ct, Leonardtown, MD 20650
      /33

      Est $576,362 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,800 Sq Ft

      21818 Hazeltine Ct, Leonardtown, MD 20650

      21818 Hazeltine Ct, Leonardtown, MD 20650
  • 20958 Camp Cosoma Rd, Leonardtown, MD 20650
    20958 Camp Cosoma Rd, Leonardtown, MD 20650
    /2

    $354,900 Sold Dec 16, 2024

    • 1,508 Sq Ft
    • $235/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    20958 Camp Cosoma Rd, Leonardtown, MD 20650

    **Charming Rambler in Leonardtown, MD**Discover this inviting 3-bedroom, 2-bath rambler set on a spacious one-acre lot in Leonardtown. With a well-designed layout, this home offers a comfortable living space that's perfect for relaxing or entertaining guests. The detached one-car garage provides added convenience and storage options.Situated just a short drive from PAX River Navy

    Mike Melius The Southside Group Real Estate

    20958 Camp Cosoma Rd, Leonardtown, MD 20650
    • 21821 Rosebank Ct, Leonardtown, MD 20650
      21821 Rosebank Ct, Leonardtown, MD 20650
      21821 Rosebank Ct, Leonardtown, MD 20650
      /105

      Est $882,035 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,200 Sq Ft

      21821 Rosebank Ct, Leonardtown, MD 20650

      21821 Rosebank Ct, Leonardtown, MD 20650
  • 23641 Belmar Dr, Leonardtown, MD 20650
    23641 Belmar Dr, Leonardtown, MD 20650
    23641 Belmar Dr, Leonardtown, MD 20650
    /42

    $630,000 Sold Jul 10, 2025

    • 3,236 Sq Ft
    • $195/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2012

    23641 Belmar Dr, Leonardtown, MD 20650

    Heather Foster RE/MAX One

    23641 Belmar Dr, Leonardtown, MD 20650
    • 21829 Rosebank Ct, Leonardtown, MD 20650
      21829 Rosebank Ct, Leonardtown, MD 20650
      21829 Rosebank Ct, Leonardtown, MD 20650
      /56

      Est $880,264 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,428 Sq Ft

      21829 Rosebank Ct, Leonardtown, MD 20650

      21829 Rosebank Ct, Leonardtown, MD 20650
  • 40557 Breton Knolls Ct, Leonardtown, MD 20650
    40557 Breton Knolls Ct, Leonardtown, MD 20650
    /2

    $959,600 Sold Aug 13, 2025

    • 3,400 Sq Ft
    • $282/SF
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    40557 Breton Knolls Ct, Leonardtown, MD 20650

    Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
    • 22644 Quiet Ln, Leonardtown, MD 20650
      22644 Quiet Ln, Leonardtown, MD 20650
      22644 Quiet Ln, Leonardtown, MD 20650
      /8

      Est $389,097 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,712 Sq Ft

      22644 Quiet Ln, Leonardtown, MD 20650

      22644 Quiet Ln, Leonardtown, MD 20650
    • 41390 Philip Ln, Leonardtown, MD 20650
      41390 Philip Ln, Leonardtown, MD 20650
      41390 Philip Ln, Leonardtown, MD 20650
      /61

      Est $958,435 Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 5,846 Sq Ft

      41390 Philip Ln, Leonardtown, MD 20650

      41390 Philip Ln, Leonardtown, MD 20650
    • 42820 Lytle Ln, Leonardtown, MD 20650
      42820 Lytle Ln, Leonardtown, MD 20650
      42820 Lytle Ln, Leonardtown, MD 20650
      /42

      Est $382,973 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,872 Sq Ft

      42820 Lytle Ln, Leonardtown, MD 20650

      42820 Lytle Ln, Leonardtown, MD 20650
    • 21545 Breton View Ct, Leonardtown, MD 20650
      21545 Breton View Ct, Leonardtown, MD 20650
      21545 Breton View Ct, Leonardtown, MD 20650
      /98

      Est $1,121,873 Not Listed For Sale

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

      21545 Breton View Ct, Leonardtown, MD 20650

      21545 Breton View Ct, Leonardtown, MD 20650
    • 41740 Eldon Ct, Leonardtown, MD 20650
      41740 Eldon Ct, Leonardtown, MD 20650
      41740 Eldon Ct, Leonardtown, MD 20650
      /50

      Est $500,762 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,791 Sq Ft

      41740 Eldon Ct, Leonardtown, MD 20650

      41740 Eldon Ct, Leonardtown, MD 20650
    • 22325 White Oak Rd, Leonardtown, MD 20650
      22325 White Oak Rd, Leonardtown, MD 20650
      22325 White Oak Rd, Leonardtown, MD 20650
      /79

      Est $649,389 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,975 Sq Ft

      22325 White Oak Rd, Leonardtown, MD 20650

      22325 White Oak Rd, Leonardtown, MD 20650

Showing Results 401 - 440, Page 11 of 18

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