6,817

Chestertown, MD Homes

Section Image
    • 10670 Tintah Rd, Chestertown, MD 21620
      10670 Tintah Rd, Chestertown, MD 21620
      10670 Tintah Rd, Chestertown, MD 21620
      /29

      Est $295,680

      Not Listed For Sale

      10670 Tintah Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      10670 Tintah Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Bronwyn Scott Samson Properties

  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    /74

    $459,000

    Sold Mar 27, 2026

    105 Pearl Creek Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,961 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Above List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $449,547

    Last Listing Agent Lona Todd Taylor Properties

    105 Pearl Creek Ln, Chestertown, MD 21620
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $330,322

      Not Listed For Sale

      23399 Cloquet Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2004
      23399 Cloquet Rd, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
  • 109 Cedar St, Chestertown, MD 21620
    109 Cedar St, Chestertown, MD 21620
    /2

    $318,000

    Sold Aug 14, 2026

    109 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,397 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Below List Price
    • $228/SF
    • 4 Days On Market

    Current Estimated Value $326,807

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    109 Cedar St, Chestertown, MD 21620
    • 305 Washington Ave, Chestertown, MD 21620
      305 Washington Ave, Chestertown, MD 21620
      305 Washington Ave, Chestertown, MD 21620
      /28

      Est $573,144

      Not Listed For Sale

      305 Washington Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,476 Sq Ft
      • Built 1930
      305 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • 23741 L Rd, Chestertown, MD 21620
    23741 L Rd, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /45

    $545,000

    Sold Apr 30, 2026

    206 S Water St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,008 Sq Ft
    • Built 1900

    Last Sold Summary

    • 7% Below List Price
    • $271/SF
    • 40 Days On Market

    Current Estimated Value $546,490

    Last Listing Agent Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $343,440

      Not Listed For Sale

      203 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1963
      203 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Alex Modaressi RE/MAX Distinctive Real Estate, Inc.

  • 896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    /34

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

    A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • 24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    /29

    $264,900

    Sold Oct 30, 2025

    24415 Chestertown Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft
    • Built 1962

    Last Sold Summary

    • $239/SF
    • 23 Days On Market

    Current Estimated Value $268,838

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • 316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      /27

      Est $276,684

      Not Listed For Sale

      316 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1966
      316 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • 124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    /23

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis

    Beth Green Doug Ashley Realtors, LLC

    124 Wilton Rd, Chestertown, MD 21620
  • 302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    /70

    $550,000

    Sold Dec 05, 2025

    302 Rosin Dr, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 3,877 Sq Ft
    • Built 1996

    Last Sold Summary

    • $142/SF
    • 5 Days On Market

    Current Estimated Value $554,137

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    302 Rosin Dr, Chestertown, MD 21620
    • 508 Cannon St, Chestertown, MD 21620
      508 Cannon St, Chestertown, MD 21620
      508 Cannon St, Chestertown, MD 21620
      /20

      Est $386,029

      Not Listed For Sale

      508 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1921
      508 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Deborah Dawkins Coldwell Banker Realty

  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    $23K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $535,000

    Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Current Estimated Value $533,048

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • 21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      /13

      Est $239,988

      Not Listed For Sale

      21286 Maine Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 2001
      21286 Maine Ave, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Kristie Midash L. C. Parker Real Estate

  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $314,000

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
  • 10594 Millbrook Dr, Chestertown, MD 21620
    10594 Millbrook Dr, Chestertown, MD 21620
    10594 Millbrook Dr, Chestertown, MD 21620
    /14

    $329,000

    Sold May 27, 2026

    10594 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 2020

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $332,240

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    10594 Millbrook Dr, Chestertown, MD 21620
    • 619 Cannon St, Chestertown, MD 21620
      619 Cannon St, Chestertown, MD 21620
      619 Cannon St, Chestertown, MD 21620
      /9

      Est $195,633

      Not Listed For Sale

      619 Cannon St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 882 Sq Ft
      • Built 1983
      619 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $260,000

    Sold Feb 18, 2026

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1954

    Last Sold Summary

    • $230/SF
    • 170 Days On Market

    Current Estimated Value $263,245

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
    • 545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      /28

      Est $295,100

      Not Listed For Sale

      545 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft
      • Built 1900
      545 High St, Chestertown, MD 21620

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • 107 Oak Leaf Dr, Chestertown, MD 21620
    107 Oak Leaf Dr, Chestertown, MD 21620
    107 Oak Leaf Dr, Chestertown, MD 21620
    /13

    $295,000

    Sold Mar 31, 2026

    107 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2004

    Last Sold Summary

    • $152/SF
    • 8 Days On Market

    Current Estimated Value $294,601

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
    • 9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      /47

      Est $325,580

      Not Listed For Sale

      9041 S Bayview Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 2009
      9041 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Gregory Osborn Long & Foster Real Estate, Inc.

  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    /14

    $85,000

    Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Current Estimated Value $150,628

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • 10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      /31

      Est $302,872

      Not Listed For Sale

      10640 Watonga Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,196 Sq Ft
      • Built 1995
      10640 Watonga Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    Sold Jun 05, 2026

    21125 Iowa Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1962

    Last Sold Summary

    • $263/SF
    • 54 Days On Market

    Current Estimated Value $335,728

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21125 Iowa Ave, Chestertown, MD 21620
    • 217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      /37

      Est $568,633

      Not Listed For Sale

      217 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft
      • Built 2003
      217 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    /67

    $2,100,000

    Sold Feb 02, 2026

    10121 Fairlee Rd, Chestertown, MD 21620

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft
    • Built 1858

    Last Sold Summary

    • $424/SF
    • 58 Days On Market

    Current Estimated Value $1,955,265

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
    • 111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      /44

      Est $431,134

      Not Listed For Sale

      111 Manor Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2007
      111 Manor Ave, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    /46

    $365,000

    Sold Apr 17, 2026

    148 E Step Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $261/SF
    • 16 Days On Market

    Current Estimated Value $366,025

    Last Listing Agent Norman Lee III Anne Arundel Properties, Inc.

    148 E Step Rd, Chestertown, MD 21620
    • 631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      /9

      Est $226,476

      Not Listed For Sale

      631 High St, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,234 Sq Ft
      • Built 1917
      631 High St, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

  • 6 Byford Ct, Chestertown, MD 21620
    6 Byford Ct, Chestertown, MD 21620
    /2

    $749,500

    Sold Apr 13, 2026

    6 Byford Ct, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1978

    Last Sold Summary

    • $239/SF
    • 0 Days On Market

    Current Estimated Value $759,903

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6 Byford Ct, Chestertown, MD 21620
    • 207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      /44

      Est $634,100

      Not Listed For Sale

      207 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1900
      207 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 372 Days On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    /35

    $438,000

    Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $445,934

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
    • 7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      /13

      Est $778,134

      Not Listed For Sale

      7694 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,322 Sq Ft
      • Built 1966
      7694 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    /36

    $730,000

    Sold Sep 01, 2026

    210 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $267/SF
    • 7 Days On Market

    Current Estimated Value $734,046

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    210 N Queen St, Chestertown, MD 21620
    • 10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      /50

      Est $1,342,796

      Not Listed For Sale

      10705 Tilden Ln, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,345 Sq Ft
      • Built 1943
      10705 Tilden Ln, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Glenn Sutton TTR Sotheby's International Realty

Showing Results 361 - 400, Page 10 of 18

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