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141 Properties
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141 Properties Available

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The average price in the selected areas has remained stable. Learn more
  • 300 HILLTOP LN, Chestertown, MD 21620
    3 Beds3 Baths1,200 SqFt
    1/20 20
    Price Dropped by $15K

    $220,000

    300 HILLTOP LN, Chestertown, MD 21620

    MLS# MDKE2005004

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 105 HIGH ST, Chestertown, MD 21620
    5 Beds5 Baths3,243 SqFt
    1/52 52
    Active

    $1,395,500

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005002

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 110 PHILOSOPHERS TER, Chestertown, MD 21620
    2 Beds1 Bath896 SqFt
    1/22 22
    Under Contract

    $199,900

    110 PHILOSOPHERS TER, Chestertown, MD 21620

    MLS# MDKE2004982

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 128 EDMORE RD, Chestertown, MD 21620
    4 Beds2 Baths2,568 SqFt
    1/59 59
    Active

    $425,000

    128 EDMORE RD, Chestertown, MD 21620

    MLS# MDQA2012546

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
  • 314 DEVON DR, Chestertown, MD 21620
    4 Beds4 Baths3,420 SqFt
    1/45 45
    Under Contract

    $499,900

    314 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2004946

    Listed by The Parker Group

    Bright MLS (BMLS)
  • 226 S WATER ST, Chestertown, MD 21620
    3 Beds4 Baths3,782 Sqft Lot
    1/22 22
    Active

    $998,000

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2004940

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 118 TUXEDO RD, Chestertown, MD 21620
    3 Beds1 Bath1,056 SqFt
    1/26 26
    Active

    $274,000

    118 TUXEDO RD, Chestertown, MD 21620

    MLS# MDQA2012402

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 21217 TEXAS AVE, Chestertown, MD 21620
    2 Beds1 Bath912 SqFt
    1/16 16
    Price Dropped by $17K

    $232,000

    21217 TEXAS AVE, Chestertown, MD 21620

    MLS# MDKE2004902

    Listed by RE/MAX Leading Edge

    Bright MLS (BMLS)
  • 24576 LANGFORD RD, Chestertown, MD 21620
    3 Beds3 Baths4,023 SqFt
    1/52 52
    Price Dropped by $40K

    $845,000

    24576 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2004906

    Listed by Maryland Heritage Properties

    Bright MLS (BMLS)
  • 110 FLYING CLOUD COURT, Chestertown, MD 21620
    3 Beds3 Baths1,856 SqFt
    1/17 17
    Active

    $349,900

    110 FLYING CLOUD COURT, Chestertown, MD 21620

    MLS# MDKE2004850

    Listed by Berkshire Hathaway HomeServices Homesale Realty

    Bright MLS (BMLS)
  • 23620 LANDS END RD, Chestertown, MD 21620
    5 Beds8 Baths9,852 SqFt
    1/66 66
    Pending

    $5,500,000

    23620 LANDS END RD, Chestertown, MD 21620

    MLS# MDKE2004760

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 109 WILTON RD, Chestertown, MD 21620
    3 Beds2 Baths1,392 SqFt
    1/30 30
    Active

    $349,900

    109 WILTON RD, Chestertown, MD 21620

    MLS# MDQA2011782

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 107 DUTCHESS RD, Chestertown, MD 21620
    3 Beds2 Baths1,380 SqFt
    1/23 23
    Active

    $325,000

    107 DUTCHESS RD, Chestertown, MD 21620

    MLS# MDQA2011746

    Listed by The Hogans Agency

    Bright MLS (BMLS)
  • 11040 KYLIE LN, Chestertown, MD 21620
    4 Beds4 Baths3,684 SqFt
    1/66 66
    Price Dropped by $19K

    $679,000

    11040 KYLIE LN, Chestertown, MD 21620

    MLS# MDKE2004586

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 24543 CHESTERTOWN RD, Chestertown, MD 21620
    3 Beds2 Baths3,280 SqFt
    1/55 55
    Pending

    $475,000

    24543 CHESTERTOWN RD, Chestertown, MD 21620

    MLS# MDKE2004580

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
  • 26865 MALLARD RD, Chestertown, MD 21620
    4 Beds3 Baths3,355 SqFt
    1/49 49
    Under Contract

    $950,000

    26865 MALLARD RD, Chestertown, MD 21620

    MLS# MDKE2004550

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 23393 CACAWAY FARM LN, Chestertown, MD 21620
    3 Beds4 Baths4,446 SqFt
    1/44 44
    Price Dropped by $100K

    $1,350,000

    23393 CACAWAY FARM LN, Chestertown, MD 21620

    MLS# MDKE2004002

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 116 PINE CHIP RD, Chestertown, MD 21620
    3 Beds2 Baths2,767 SqFt
    1/35 35
    Active

    $515,000

    116 PINE CHIP RD, Chestertown, MD 21620

    MLS# MDQA2010882

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 117 N WATER ST #1A, Chestertown, MD 21620
    3 Beds3 Baths
    1/28 28
    Active

    $725,000

    117 N WATER ST #1A, Chestertown, MD 21620

    MLS# MDKE2004206

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 349 HIGH ST, Chestertown, MD 21620
    7 Beds4 Baths3,664 SqFt
    1/33 33
    Active

    $395,000

    349 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2004076

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 117 WATER ST N #2A, Chestertown, MD 21620
    2 Beds1 Bath787 SqFt
    1/28 28
    Active

    $399,000

    117 WATER ST N #2A, Chestertown, MD 21620

    MLS# MDKE2003742

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 117 N WATER ST N #3B, Chestertown, MD 21620
    1 Bed1 Bath652 SqFt
    1/24 24
    Price Dropped by $48K

    $299,900

    117 N WATER ST N #3B, Chestertown, MD 21620

    MLS# MDKE2003722

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 228 S WATER ST, Chestertown, MD 21620
    3 Beds4 Baths2,592 Sqft Lot
    1/23 23
    Price Dropped by $52K

    $898,000

    228 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2001612

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 209 RIVER RD, Chestertown, MD 21620
    1.01 Acres
    1/3 3
    Pending

    $135,000

    209 RIVER RD, Chestertown, MD 21620

    MLS# MDQA2013730

    Listed by Select Land & Homes, LLC

    Bright MLS (BMLS)
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Aligned + Real Transparent (2)
      Home
      PORTFOLIO
      Home Search
      1. Browse Homes
      2. Falls Church
      3. Tysons Corner
      4. McLean Chase
      5. Great Falls
      6. Vienna
      7. Aldie Heights
      8. South Riding
      9. Broadlands
      10. Lansdowne
      11. Brambleton
      12. Hamilton
      13. Purcellville
      14. Clifton Crest
      15. Oakton
      16. Centerville
      17. Chantilly
      18. Fairfax City
      19. Herndon
      20. Sterling
      21. Reston
      Home Valuation
      NEIGHBORHOODS
      Real Estate Statistics
      1. Loudoun County
      2. Fairfax County
      Contact Us
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      Partner Lender
Real Broker LLC

Aligned Real Estate Group

+1(703) 966-6625 info@gowithaligned.com

1765 Greensboro Station Place Suite 900 McLean, VA 22102

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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
Aligned + Real Transparent (2)
      Home
      PORTFOLIO
      Home Search
      1. Browse Homes
      2. Falls Church
      3. Tysons Corner
      4. McLean Chase
      5. Great Falls
      6. Vienna
      7. Aldie Heights
      8. South Riding
      9. Broadlands
      10. Lansdowne
      11. Brambleton
      12. Hamilton
      13. Purcellville
      14. Clifton Crest
      15. Oakton
      16. Centerville
      17. Chantilly
      18. Fairfax City
      19. Herndon
      20. Sterling
      21. Reston
      Home Valuation
      NEIGHBORHOODS
      Real Estate Statistics
      1. Loudoun County
      2. Fairfax County
      Contact Us
      Prayer Request
      Partner Lender
Real Broker LLC

Aligned Real Estate Group

+1(703) 966-6625 info@gowithaligned.com

1765 Greensboro Station Place Suite 900 McLean, VA 22102

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.