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137 Properties
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137 Properties Available

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  • 515 N KENT ST, Chestertown, MD 21620
    4 Beds2 Baths2,220 SqFt
    1/37 37
    Coming Soon

    $509,900

    515 N KENT ST, Chestertown, MD 21620

    MLS# MDKE2005592

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 349 HIGH ST, Chestertown, MD 21620
    7 Beds4 Baths3,664 SqFt
    1/33 33
    Open Sun 12PM-2PM

    $395,000

    349 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2004076

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 105 PARMA RD, Chestertown, MD 21620
    3 Beds2 Baths1,232 SqFt
    1/5 5
    Coming Soon

    $326,500

    105 PARMA RD, Chestertown, MD 21620

    MLS# MDQA2014652

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • 224 VALLEY RD, Chestertown, MD 21620
    3 Beds2 Baths1,886 SqFt
    1/24 24
    New

    $450,000

    224 VALLEY RD, Chestertown, MD 21620

    MLS# MDKE2005546

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 116 HARLAN LOOP, Chestertown, MD 21620
    5 Beds4 Baths4,067 SqFt
    1/21 21
    New

    $538,000

    116 HARLAN LOOP, Chestertown, MD 21620

    MLS# MDKE2005610

    Listed by Samson Properties

    Bright MLS (BMLS)
  • 200 WASHINGTON AVE, Chestertown, MD 21620
    4 Beds4 Baths2,917 SqFt
    1/35 35
    New

    $795,000

    200 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2005538

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 200 FEY RD, Chestertown, MD 21620
    3 Beds2 Baths1,572 SqFt
    1/18 18
    New

    $374,900

    200 FEY RD, Chestertown, MD 21620

    MLS# MDQA2014600

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
  • 8978 ORCHARD DR, Chestertown, MD 21620
    4 Beds3 Baths3,820 SqFt
    1/44 44
    Coming Soon

    $675,000

    8978 ORCHARD DR, Chestertown, MD 21620

    MLS# MDKE2005500

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 103 ADELA WAY, Chestertown, MD 21620
    4 Beds4 Baths5,576 SqFt
    1/90 90
    New

    $615,000

    103 ADELA WAY, Chestertown, MD 21620

    MLS# MDKE2005594

    Listed by Douglas Realty LLC

    Bright MLS (BMLS)
  • 492 PEAR TREE POINT RD, Chestertown, MD 21620
    3 Beds2 Baths2,600 SqFt
    1/42 42
    Active

    $1,100,000

    492 PEAR TREE POINT RD, Chestertown, MD 21620

    MLS# MDQA2013108

    Listed by Meredith Fine Properties

    Bright MLS (BMLS)
  • 7729 COUNTRY CLUB LN, Chestertown, MD 21620
    3 Beds3 Baths2,280 SqFt
    1/18 18
    Active

    $635,000

    7729 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2005552

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 907 N MEADOWVIEW DR, Chestertown, MD 21620
    3 Beds3 Baths1,842 SqFt
    1/33 33
    Active

    $440,000

    907 N MEADOWVIEW DR, Chestertown, MD 21620

    MLS# MDKE2005540

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 10165 JOHN CARVILL RD, Chestertown, MD 21620
    3 Beds3 Baths2,774 SqFt
    1/20 20
    Active

    $549,000

    10165 JOHN CARVILL RD, Chestertown, MD 21620

    MLS# MDKE2005476

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 5700 JOHNSONTOWN RD, Chestertown, MD 21620
    3 Beds1 Bath1,144 SqFt
    1/7 7
    Active

    $125,000

    5700 JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005562

    Listed by Tesla Realty Group, LLC

    Bright MLS (BMLS)
  • 108 S KENT ST, Chestertown, MD 21620
    1 Bed2 Baths936 SqFt
    1/19 19
    Price Dropped by $10K

    $315,000

    108 S KENT ST, Chestertown, MD 21620

    MLS# MDKE2005496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 143 CHAR NOR MANOR BLVD, Chestertown, MD 21620
    3 Beds3 Baths2,073 SqFt
    3D
    Under Contract

    $868,000

    143 CHAR NOR MANOR BLVD, Chestertown, MD 21620

    MLS# MDQA2014274

    Listed by Redfin Corp

    Bright MLS (BMLS)
  • 201 BOUNDARY AVE, Chestertown, MD 21620
    4 Beds3 Baths3,096 SqFt
    1/49 49
    Under Contract

    $470,000

    201 BOUNDARY AVE, Chestertown, MD 21620

    MLS# MDQA2014272

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 112 METCALF RD, Chestertown, MD 21620
    3 Beds2 Baths1,280 SqFt
    1/20 20
    Price Dropped by $15K

    $265,000

    112 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2005498

    Listed by Engel & Volkers Annapolis

    Bright MLS (BMLS)
  • 600 ROSIN DR, Chestertown, MD 21620
    3 Beds3 Baths1,300 SqFt
    1/36 36
    Active

    $424,000

    600 ROSIN DR, Chestertown, MD 21620

    MLS# MDQA2014374

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 251 DEVON DR, Chestertown, MD 21620
    3 Beds3 Baths3,935 SqFt
    1/54 54
    Active

    $595,000

    251 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2005536

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 234 N COLLEGE AVE, Chestertown, MD 21620
    2 Beds1 Bath1,296 SqFt
    1/3 3
    Price Dropped by $10K

    $174,900

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2005434

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
  • 9194 N BAYVIEW AVE, Chestertown, MD 21620
    2 Beds2 Baths1,460 SqFt
    1/45 45
    Under Contract

    $698,000

    9194 N BAYVIEW AVE, Chestertown, MD 21620

    MLS# MDKE2005488

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 9190 N BAYVIEW AVE, Chestertown, MD 21620
    2 Beds1 Bath1,160 SqFt
    1/38 38
    Under Contract

    $319,500

    9190 N BAYVIEW AVE, Chestertown, MD 21620

    MLS# MDKE2005442

    Listed by Select Land & Homes, LLC

    Bright MLS (BMLS)
  • 141 PROSPECT ST, Chestertown, MD 21620
    4 Beds2 Baths1,156 SqFt
    1/16 16
    Active

    $175,000

    141 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2005504

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
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LPT Realty

Michael Blake

+1(703) 732-0795 mblakerealtor@gmail.com

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defaultdefault
      Home
      Buy
      1. All Listings
      2. Featured Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Sold Listings
      Connect
      1. Contact Us
      Market Snapshot
      Homes for Heroes
LPT Realty

Michael Blake

+1(703) 732-0795 mblakerealtor@gmail.com

TREC Consumer Protection Notice

TREC Information About Brokerage Services

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.