1,798

Chesapeake City, MD Homes

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  • 19 Tower Rd, Chesapeake City, MD 21915
    19 Tower Rd, Chesapeake City, MD 21915
    19 Tower Rd, Chesapeake City, MD 21915
    /31

    $920,000

    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    19 Tower Rd, Chesapeake City, MD 21915

    Waterfront Home on the Elk River!Experience breathtaking views as ships from around the world glide by from your own backyard. This spacious and versatile home features 4+ bedrooms and 3 full baths, offering incredible potential to customize and make it your own. The main level boasts 2 bedrooms, a welcoming great room with a cozy fireplace, a dining area, and an eat-in kitchen—perfect for

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 498-8122

    19 Tower Rd, Chesapeake City, MD 21915
  • 302 3rd St, Chesapeake City, MD 21915
    302 3rd St, Chesapeake City, MD 21915
    302 3rd St, Chesapeake City, MD 21915
    /9

    $1,100 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Townhouse for Rent

    302 3rd St, Chesapeake City, MD 21915

    Welcome to Chesapeake City! This is a two bedroom, one bath home located on Third Street. Enter into a private living room and kitchen. Second floor features a spacious master bedroom and bathroom. The second bedroom is a loft style room located on the third floor. Washer and dryer is included. Rear yard and plenty of parking out front. Water, sewer and trash is $98.00 per month and due with the

    Jessica Stiner RE/MAX Edge

    302 3rd St, Chesapeake City, MD 21915
  • 339 Cecil St, Chesapeake City, MD 21915
    339 Cecil St, Chesapeake City, MD 21915
    339 Cecil St, Chesapeake City, MD 21915
    /24

    $335,000 Sold Sep 25, 2025

    339 Cecil St, Chesapeake City, MD 21915

    • 3 Beds
    • 1.5 Baths
    • 1,380 Sq Ft
    • Built 1919

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Last Listing Agent Terry Mulkins Patterson-Schwartz-Newark

    339 Cecil St, Chesapeake City, MD 21915
    • 208 George St, Chesapeake City, MD 21915
      208 George St, Chesapeake City, MD 21915
      208 George St, Chesapeake City, MD 21915
      /44

      Est $310,026 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,656 Sq Ft

      208 George St, Chesapeake City, MD 21915

      208 George St, Chesapeake City, MD 21915
  • 330 Cecil St, Chesapeake City, MD 21915
    330 Cecil St, Chesapeake City, MD 21915
    330 Cecil St, Chesapeake City, MD 21915
    /35

    $619,000

    • 3 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    330 Cecil St, Chesapeake City, MD 21915

    On the North side of the Canal, imagine sipping your morning coffee on the expansive front and back decks of this custom-built home. Located within walking distance of the highly desirable C & D Canal waterfront trail, this home offers access to one of Maryland's most scenic and walkable spots- perfect for biking, jogging, or a leisurely stroll. Walk to dinner at the beloved Schaeffer's Canal

    Anne Peoples Patterson-Schwartz Real Estate

    330 Cecil St, Chesapeake City, MD 21915
  • 366 Cayots Corner Rd, Chesapeake City, MD 21915
    366 Cayots Corner Rd, Chesapeake City, MD 21915
    366 Cayots Corner Rd, Chesapeake City, MD 21915
    /9

    $85,000 Sold Jan 17, 2025

    366 Cayots Corner Rd, Chesapeake City, MD 21915

    • Land
    • 2.9 Acres
    • $29,310 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Jason Zang RE/MAX Chesapeake

    366 Cayots Corner Rd, Chesapeake City, MD 21915
    • 87 Forest Ln, Chesapeake City, MD 21915
      87 Forest Ln, Chesapeake City, MD 21915
      87 Forest Ln, Chesapeake City, MD 21915
      /24

      Est $494,811 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,011 Sq Ft

      87 Forest Ln, Chesapeake City, MD 21915

      87 Forest Ln, Chesapeake City, MD 21915
  • 22 North Rd, Chesapeake City, MD 21915
    22 North Rd, Chesapeake City, MD 21915
    22 North Rd, Chesapeake City, MD 21915
    /16

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    22 North Rd, Chesapeake City, MD 21915

    There’s no place like home in this 3-bedroom, 2-bath ranch nestled in the water-oriented community of Harbour North! A welcoming covered front porch sets the tone as you enter into a bright, open floor plan featuring vaulted ceilings, skylights, laminate plank flooring, and an abundance of natural light. The living room flows seamlessly into the dining area, where glass sliders lead to a rear

    Kristin Lewis Integrity Real Estate

    22 North Rd, Chesapeake City, MD 21915
  • 346 Cecil St, Chesapeake City, MD 21915
    346 Cecil St, Chesapeake City, MD 21915
    346 Cecil St, Chesapeake City, MD 21915
    /40

    $285,000 Sold Aug 12, 2025

    346 Cecil St, Chesapeake City, MD 21915

    • 2 Beds
    • 1 Bath
    • 1,076 Sq Ft
    • Built 1900

    Last Sold Summary

    • $265/SF
    • 4 Days On Market

    Current Estimated Value $277,680

    Last Listing Agent Wanda Jackson RE/MAX Chesapeake

    346 Cecil St, Chesapeake City, MD 21915
    • 35 Sunnyside Dr, Chesapeake City, MD 21915
      35 Sunnyside Dr, Chesapeake City, MD 21915
      35 Sunnyside Dr, Chesapeake City, MD 21915
      /30

      Est $381,562 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft

      35 Sunnyside Dr, Chesapeake City, MD 21915

      35 Sunnyside Dr, Chesapeake City, MD 21915
  • 943 Cayots Corner Rd, Chesapeake City, MD 21915
    943 Cayots Corner Rd, Chesapeake City, MD 21915
    943 Cayots Corner Rd, Chesapeake City, MD 21915
    /33

    $124,999

    • 3 Beds
    • 1 Bath
    • 1,431 Sq Ft

    943 Cayots Corner Rd, Chesapeake City, MD 21915

    needs work sold as is

    Keith Brooks Thurston Wyatt Real Estate, LLC

    943 Cayots Corner Rd, Chesapeake City, MD 21915
  • 203 Charles St, Chesapeake City, MD 21915
    203 Charles St, Chesapeake City, MD 21915
    203 Charles St, Chesapeake City, MD 21915
    /9

    $136,000 Sold May 02, 2025

    203 Charles St, Chesapeake City, MD 21915

    • Land
    • 0.05 Acre
    • $2,720,000 per Acre

    Last Sold Summary

    • 144 Days On Market

    Last Listing Agent Amber Durand Patterson-Schwartz Real Estate

    203 Charles St, Chesapeake City, MD 21915
    • 89 Forest Ln, Chesapeake City, MD 21915
      89 Forest Ln, Chesapeake City, MD 21915
      89 Forest Ln, Chesapeake City, MD 21915
      /33

      Est $472,555 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,680 Sq Ft

      89 Forest Ln, Chesapeake City, MD 21915

      89 Forest Ln, Chesapeake City, MD 21915
  • 210 Bohemia Ave, Chesapeake City, MD 21915
    210 Bohemia Ave, Chesapeake City, MD 21915
    210 Bohemia Ave, Chesapeake City, MD 21915
    /42

    $460,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,856 Sq Ft

    210 Bohemia Ave, Chesapeake City, MD 21915

    Tatman- Smithers House, built in 1856 and set in the heart of Chesapeake City’s beloved Historic District, 210 Bohemia Ave is the kind of home that doesn’t just tell a story — it invites you to live one. Nestled on one of the largest lots along Main Street and just a short stroll to the waterfront, local boutiques, and award-winning restaurants, this residence blends timeless architecture with

    Jules Burchett Foraker Realty Co.

    210 Bohemia Ave, Chesapeake City, MD 21915
  • 170 Canal Rd, Chesapeake City, MD 21915
    170 Canal Rd, Chesapeake City, MD 21915
    170 Canal Rd, Chesapeake City, MD 21915
    /9

    $70,000 Sold Feb 28, 2025

    170 Canal Rd, Chesapeake City, MD 21915

    • Land
    • 0.52 Acre
    • $134,615 per Acre

    Last Sold Summary

    • 92 Days On Market

    Last Listing Agent Mrs. Brittany Fox RE/MAX Chesapeake

    170 Canal Rd, Chesapeake City, MD 21915
    • 1360 Town Point Rd, Chesapeake City, MD 21915
      1360 Town Point Rd, Chesapeake City, MD 21915
      1360 Town Point Rd, Chesapeake City, MD 21915
      /50

      Est $3,185,547 Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 6,718 Sq Ft

      1360 Town Point Rd, Chesapeake City, MD 21915

      1360 Town Point Rd, Chesapeake City, MD 21915
  • 420 Biddle St, Chesapeake City, MD 21915
    420 Biddle St, Chesapeake City, MD 21915
    420 Biddle St, Chesapeake City, MD 21915
    /31

    $448,900

    • 2 Beds
    • 2.5 Baths
    • 1,973 Sq Ft

    420 Biddle St, Chesapeake City, MD 21915

    Modernized Waterfront Living on the C&D Canal – Chesapeake City, MD This beautifully revitalized waterfront home on the C&D Canal offers a stunning transformation from dark and dated to bright, open, and timeless. Thoughtfully renovated throughout, every space reflects quality upgrades, cohesive design, and an effortless coastal style. Upon entering the main living area, you’re immediately drawn

    Michele Burch Patterson-Schwartz-Middletown

    420 Biddle St, Chesapeake City, MD 21915
  • 329 Biddle St, Chesapeake City, MD 21915
    329 Biddle St, Chesapeake City, MD 21915
    329 Biddle St, Chesapeake City, MD 21915
    /18

    $140,000 Sold Oct 17, 2025

    329 Biddle St, Chesapeake City, MD 21915

    • 3 Beds
    • 1.5 Baths
    • 1,090 Sq Ft
    • Built 1931

    Last Sold Summary

    • $128/SF
    • 20 Days On Market

    Last Listing Agent Norman Wehner Real-Trust-Associates, LLC.

    329 Biddle St, Chesapeake City, MD 21915
    • 960 Cayots Corner Rd, Chesapeake City, MD 21915
      960 Cayots Corner Rd, Chesapeake City, MD 21915
      960 Cayots Corner Rd, Chesapeake City, MD 21915
      /131

      Est $2,498,029 Not Listed For Sale

      • 5 Beds
      • 7.5 Baths
      • 8,436 Sq Ft

      960 Cayots Corner Rd, Chesapeake City, MD 21915

      960 Cayots Corner Rd, Chesapeake City, MD 21915
  • 321 Cecil St, Chesapeake City, MD 21915
    321 Cecil St, Chesapeake City, MD 21915
    321 Cecil St, Chesapeake City, MD 21915
    /29

    $324,500

    • 3 Beds
    • 1.5 Baths
    • 3,792 Sq Ft

    321 Cecil St, Chesapeake City, MD 21915

    Welcome to this charming Colonial Traditional style home in Chesapeake City, MD! This delightful property features 3 bedrooms and 1.1 bathrooms spread across 2 levels/stories. Stay cool in the summer with ductless/Mini split cooling, while staying warm in the winter with ceiling, programmable thermostat, wall unit, and zoned heating options. The interior boasts a plethora of desirable features

    Peggy Sheehan Patterson-Schwartz-Middletown

    321 Cecil St, Chesapeake City, MD 21915
  • 3192 Augustine Herman Hwy, Chesapeake City, MD 21915
    3192 Augustine Herman Hwy, Chesapeake City, MD 21915
    3192 Augustine Herman Hwy, Chesapeake City, MD 21915
    /53

    $1,400,000 Sold Nov 03, 2025

    3192 Augustine Herman Hwy, Chesapeake City, MD 21915

    • 4 Beds
    • 2 Baths
    • 2,761 Sq Ft
    • Built 1973

    Last Sold Summary

    • $507/SF
    • 25 Days On Market

    Last Listing Agent David Landon Patterson-Schwartz-Newark

    3192 Augustine Herman Hwy, Chesapeake City, MD 21915
    • 192 Hollywood Beach Rd, Chesapeake City, MD 21915
      192 Hollywood Beach Rd, Chesapeake City, MD 21915
      192 Hollywood Beach Rd, Chesapeake City, MD 21915
      /45

      Est $714,927 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,661 Sq Ft

      192 Hollywood Beach Rd, Chesapeake City, MD 21915

      192 Hollywood Beach Rd, Chesapeake City, MD 21915
  • 300 Bohemia Ave, Chesapeake City, MD 21915
    300 Bohemia Ave, Chesapeake City, MD 21915
    300 Bohemia Ave, Chesapeake City, MD 21915
    /117

    $1,489,000

    • 9 Beds
    • 10 Baths
    • 7,044 Sq Ft

    300 Bohemia Ave, Chesapeake City, MD 21915

    PRICE ADJUSTMENT!!Step Back in Time at the Blue Max InnWelcome to the Blue Max Inn, a charming and historic Bed & Breakfast nestled in the heart of Chesapeake City, Maryland. This beautiful Victorian Inn offers a unique blend of old-world elegance and modern comforts, making it a beloved retreat in Chesapeake City which is along the Chesapeake and Delaware Canal.Operating under the

    Joseph A Zang III RE/MAX Chesapeake

    300 Bohemia Ave, Chesapeake City, MD 21915
  • 2619 Augustine Herman Hwy, Chesapeake City, MD 21915
    2619 Augustine Herman Hwy, Chesapeake City, MD 21915
    2619 Augustine Herman Hwy, Chesapeake City, MD 21915
    /16

    $300,000 Sold Feb 07, 2025

    2619 Augustine Herman Hwy, Chesapeake City, MD 21915

    • 3 Beds
    • 1 Bath
    • 1,754 Sq Ft
    • Built 1951

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $315,217

    Last Listing Agent Kristin Lewis Integrity Real Estate

    2619 Augustine Herman Hwy, Chesapeake City, MD 21915
    • 1367 Randalia Rd, Chesapeake City, MD 21915
      1367 Randalia Rd, Chesapeake City, MD 21915
      1367 Randalia Rd, Chesapeake City, MD 21915
      /61

      Est $2,884,056 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 4,512 Sq Ft

      1367 Randalia Rd, Chesapeake City, MD 21915

      1367 Randalia Rd, Chesapeake City, MD 21915
  • 534 Biddle St, Chesapeake City, MD 21915
    534 Biddle St, Chesapeake City, MD 21915
    534 Biddle St, Chesapeake City, MD 21915
    /36

    $330,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    534 Biddle St, Chesapeake City, MD 21915

    Enjoy this million dollar view of the historic C&D Canal at an affordable price! Located in Historic Chesapeake City, near shopping and dining. Just down the street from the well known Schaefer's Canal House Restaurant. This 2 Bedroom, 1 bath home features a large deck, opening to a flower garden and patio, overlooking the canal. This home is 2 doors down from the entrance to the C&D Canal

    Norman Wehner Real-Trust-Associates, LLC.

    534 Biddle St, Chesapeake City, MD 21915
  • 00 Nicholas Loop, Chesapeake City, MD 21915
    00 Nicholas Loop, Chesapeake City, MD 21915
    00 Nicholas Loop, Chesapeake City, MD 21915
    /16

    $275,000 Sold Jul 10, 2025

    00 Nicholas Loop, Chesapeake City, MD 21915

    • Land
    • 2.13 Acres
    • $129,108 per Acre

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Daniel Billig A.J. Billig & Company

    00 Nicholas Loop, Chesapeake City, MD 21915
    • 142 Two Rivers Rd, Chesapeake City, MD 21915
      142 Two Rivers Rd, Chesapeake City, MD 21915
      142 Two Rivers Rd, Chesapeake City, MD 21915
      /58

      Est $827,287 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,305 Sq Ft

      142 Two Rivers Rd, Chesapeake City, MD 21915

      142 Two Rivers Rd, Chesapeake City, MD 21915
  • 15 Buddy Blvd, Chesapeake City, MD 21915
    15 Buddy Blvd, Chesapeake City, MD 21915
    15 Buddy Blvd, Chesapeake City, MD 21915
    /10

    $116,900

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    15 Buddy Blvd, Chesapeake City, MD 21915

    NEW home coming SOON! Located in Chesapeake Estates, take a tour on this brand NEW 3 bed 2 bath single family home! Featuring open concept floor plans, kitchen appliance packages, driveways, and spacious yards to BBQ and garden in. Our community amenities include on-site management and 24-hour emergency maintenance. *Must complete a community application and be approved for residency. Lot rent is

    Celine Geigel Arx Housing, LLC

    15 Buddy Blvd, Chesapeake City, MD 21915
  • 58 Woodside Dr, Chesapeake City, MD 21915
    58 Woodside Dr, Chesapeake City, MD 21915
    58 Woodside Dr, Chesapeake City, MD 21915
    /36

    $415,000 Sold Jun 30, 2025

    58 Woodside Dr, Chesapeake City, MD 21915

    • 3 Beds
    • 2 Baths
    • 2,308 Sq Ft
    • Built 2001

    Last Sold Summary

    • $180/SF
    • 3 Days On Market

    Current Estimated Value $408,587

    Last Listing Agent Annie Barker Integrity Real Estate

    58 Woodside Dr, Chesapeake City, MD 21915
    • 801 N Saint Augustine Rd, Chesapeake City, MD 21915
      801 N Saint Augustine Rd, Chesapeake City, MD 21915
      801 N Saint Augustine Rd, Chesapeake City, MD 21915
      /37

      Est $2,094,465 Not Listed For Sale

      • 10 Beds
      • 8 Baths
      • 8,790 Sq Ft

      801 N Saint Augustine Rd, Chesapeake City, MD 21915

      801 N Saint Augustine Rd, Chesapeake City, MD 21915
  • 00 Maryland 342, Chesapeake City, MD 21915
    00 Maryland 342, Chesapeake City, MD 21915
    00 Maryland 342, Chesapeake City, MD 21915
    /19

    $1,100,000 Pending

    • Land
    • 15.3 Acres
    • $71,895 per Acre

    00 Maryland 342, Chesapeake City, MD 21915

    Chesapeake Village is a potential residential development situated off of St Augustine Road in Chesapeake City. The Land has 15 acres with two potential access points off of Saint Augustine Road. Concept plans have included 60 Villas with rear-loading garages or 52 Units with 28 Townhomes & 24 Single-family Homes. This prime development site is adjacent to the historic District of Chesapeake

    Amber Durand Patterson-Schwartz Real Estate

    00 Maryland 342, Chesapeake City, MD 21915
  • 324 Cayots Corner Rd, Chesapeake City, MD 21915
    324 Cayots Corner Rd, Chesapeake City, MD 21915
    324 Cayots Corner Rd, Chesapeake City, MD 21915
    /38

    $240,000 Sold May 07, 2025

    324 Cayots Corner Rd, Chesapeake City, MD 21915

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1920

    Last Sold Summary

    • $306/SF
    • 21 Days On Market

    Current Estimated Value $242,739

    Last Listing Agent Natasha Lasek AB & Co Realtors, Inc.

    324 Cayots Corner Rd, Chesapeake City, MD 21915
    • 324 Hemphill St, Chesapeake City, MD 21915
      324 Hemphill St, Chesapeake City, MD 21915
      324 Hemphill St, Chesapeake City, MD 21915
      /24

      Est $322,437 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,217 Sq Ft

      324 Hemphill St, Chesapeake City, MD 21915

      324 Hemphill St, Chesapeake City, MD 21915
  • 280 Hollywood Beach Rd, Chesapeake City, MD 21915
    280 Hollywood Beach Rd, Chesapeake City, MD 21915
    280 Hollywood Beach Rd, Chesapeake City, MD 21915
    /46

    $1,000,000 Under Contract

    • 6 Beds
    • 5.5 Baths
    • 3,757 Sq Ft

    280 Hollywood Beach Rd, Chesapeake City, MD 21915

    Best of everything on the water. Build you own dock or ask about the possible deep water community boat slips. Community boat ramp. You will own a private sandy beach 100 feet wide off your deck. No better views anywhere. Total of five bedrooms and three full baths. Finished en suite above garage with separate entrance and full bath. Oversized garage with full garage doors on both ends. Beautiful

    Rodman Mullins Sterling Real Estate LLC

    280 Hollywood Beach Rd, Chesapeake City, MD 21915
  • 340 Cayots Corner Rd, Chesapeake City, MD 21915
    340 Cayots Corner Rd, Chesapeake City, MD 21915
    340 Cayots Corner Rd, Chesapeake City, MD 21915
    /32

    $200,000 Sold Jun 13, 2025

    340 Cayots Corner Rd, Chesapeake City, MD 21915

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1960

    Last Sold Summary

    • $208/SF
    • 60 Days On Market

    Current Estimated Value $211,746

    Last Listing Agent Lois Alberti Alberti Realty, LLC

    340 Cayots Corner Rd, Chesapeake City, MD 21915
    • 107 George St, Chesapeake City, MD 21915
      107 George St, Chesapeake City, MD 21915
      107 George St, Chesapeake City, MD 21915
      /45

      Est $539,365 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,500 Sq Ft

      107 George St, Chesapeake City, MD 21915

      107 George St, Chesapeake City, MD 21915
  • 1455 Cayots Corner Rd, Chesapeake City, MD 21915
    1455 Cayots Corner Rd, Chesapeake City, MD 21915
    1455 Cayots Corner Rd, Chesapeake City, MD 21915
    /141

    $19,900,000

    • 4 Beds
    • 5 Baths

    1455 Cayots Corner Rd, Chesapeake City, MD 21915

    Rarely... does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is

    George Hobbs Monument Sotheby's International Realty

    1455 Cayots Corner Rd, Chesapeake City, MD 21915
  • 410 George St, Chesapeake City, MD 21915
    410 George St, Chesapeake City, MD 21915
    410 George St, Chesapeake City, MD 21915
    /30

    $300,000 Sold Jul 18, 2025

    410 George St, Chesapeake City, MD 21915

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1885

    Last Sold Summary

    • $206/SF
    • 3 Days On Market

    Current Estimated Value $304,750

    Last Listing Agent Jim Lacey RE/MAX Associates - Newark

    410 George St, Chesapeake City, MD 21915
    • 316 Bohemia Ave, Chesapeake City, MD 21915
      316 Bohemia Ave, Chesapeake City, MD 21915
      316 Bohemia Ave, Chesapeake City, MD 21915
      /55

      Est $433,502 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,545 Sq Ft

      316 Bohemia Ave, Chesapeake City, MD 21915

      316 Bohemia Ave, Chesapeake City, MD 21915

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