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154 Properties Available

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  • 101 S MILL ST, Chestertown, MD 21620
    1/39 39
    Coming Soon

    $ 515,000

    2 Beds3 Baths1,476 SqFt

    101 S MILL ST, Chestertown, MD 21620

    Single Family Home, Townhouse

    MLS# MDKE2006674

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 103 TRAFFORD DR, Chestertown, MD 21620
    1/65 65
    Open Sat 11AM-1PM

    $ 399,900

    3 Beds3 Baths1,944 SqFt

    103 TRAFFORD DR, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 7989 QUAKER NECK RD, Chestertown, MD 21620
    3D
    Open Sat 11AM-1PM

    $ 2,200,000

    5 Beds5 Baths4,305 SqFt

    7989 QUAKER NECK RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 202 ROYSTON SHORES RD, Chestertown, MD 21620
    1/72 72
    New

    $ 1,200,000

    4 Beds3 Baths2,292 SqFt

    202 ROYSTON SHORES RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDQA2017462

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 103 MAPLE AVE, Chestertown, MD 21620
    1/13 13
    Coming Soon

    $ 615,000

    4 Beds3 Baths4,536 SqFt

    103 MAPLE AVE, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006676

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 10572 WATONGA RD, Chestertown, MD 21620
    1/25 25
    Under Contract

    $ 325,000

    3 Beds2 Baths1,404 SqFt

    10572 WATONGA RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006644

    Listed by Serhant

    Bright MLS (BMLS)
  • 25750 COLLINS AVE, Chestertown, MD 21620
    1/50 50
    Coming Soon

    $ 468,000

    3 Beds2 Baths3,262 SqFt

    25750 COLLINS AVE, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006546

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 23264 CLARISSA RD, Chestertown, MD 21620
    1/30 30
    New

    $ 365,000

    3 Beds2 Baths1,248 SqFt

    23264 CLARISSA RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006096

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 104 ACORN DR, Chestertown, MD 21620
    1/26 26
    New

    $ 284,900

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    Townhouse

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 234 N COLLEGE AVE, Chestertown, MD 21620
    Exclusive Listing
    1/3 3
    New

    $ 120,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
  • 8796 MARYLAND PKWY, Chestertown, MD 21620
    1/60 60
    New

    $ 1,650,000

    9 Beds7 Baths4,776 SqFt

    8796 MARYLAND PKWY, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 110 PROSPECT ST, Chestertown, MD 21620
    1/6 6
    New

    $ 119,900

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
  • 205 RIVER RD, Chestertown, MD 21620
    1/68 68
    Pending

    $ 869,900

    4 Beds3 Baths2,877 SqFt

    205 RIVER RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDQA2017560

    Listed by Clark & Co Realty, LLC

    Bright MLS (BMLS)
  • 1904 PONDTOWN RD, Chestertown, MD 21620
    1/11 11
    New

    $ 265,000

    3 Beds1 Bath1,967 SqFt

    1904 PONDTOWN RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDQA2017480

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
  • 10781 FERMOY RD, Chestertown, MD 21620
    1/54 54
    Active

    $ 449,900

    4 Beds3 Baths2,160 SqFt

    10781 FERMOY RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006640

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
  • 213 BYFORD DR, Chestertown, MD 21620
    1/39 39
    Active

    $ 380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 21172 WYOMING AVE, Chestertown, MD 21620
    Active

    $ 200,000

    4 Beds1 Bath2,920 SqFt

    21172 WYOMING AVE, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006642

    Listed by Blue Star Real Estate, LLC

    Bright MLS (BMLS)
  • 25440 LEARMAN RD, Chestertown, MD 21620
    1/70 70
    Active

    $ 3,000,000

    3 Beds4 Baths3,142 SqFt

    25440 LEARMAN RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006468

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 100 PROSPECT ST, Chestertown, MD 21620
    1/21 21
    Under Contract

    $ 215,000

    3 Beds1 Bath1,373 SqFt

    100 PROSPECT ST, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006544

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
  • 22470 FAIRGALE FARM LN, Chestertown, MD 21620
    1/49 49
    Active

    $ 1,450,000

    4 Beds5 Baths4,257 SqFt

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 522 HIGH ST, Chestertown, MD 21620
    1/15 15
    Price Dropped by $25K

    $ 425,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • 118 GRANT CT, Chestertown, MD 21620
    3D
    Under Contract

    $ 457,500

    3 Beds2 Baths1,664 SqFt

    118 GRANT CT, Chestertown, MD 21620

    Single Family Home

    MLS# MDQA2017356

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
  • 7761 BROAD NECK RD, Chestertown, MD 21620
    1/4 4
    Pending

    $ 1,500,000

    5 Beds3 Baths2,700 SqFt

    7761 BROAD NECK RD, Chestertown, MD 21620

    Single Family Home

    MLS# MDKE2006542

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 956 WASHINGTON AVE, Chestertown, MD 21620
    1/29 29
    Active

    $ 285,000

    3 Beds1 Bath1,248 SqFt

    956 WASHINGTON AVE, Chestertown, MD 21620

    Manufactured Home

    MLS# MDKE2006394

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
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Mark's Home Team @ Cummings & Co Realtors

Mark Novak CCRL 531341

+1(410) 449-7770 [email protected]

111 Fulford Ave Suite B, Air, MD, 21014, United States
    • Meet Mark
    • Selling Plan
    • Client Love ❤️

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  • Baltimore, MD
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Mark's Home Team @ Cummings & Co Realtors

Mark Novak CCRL 531341

+1(410) 449-7770 [email protected]

111 Fulford Ave Suite B, Air, MD, 21014, United States
    • Meet Mark
    • Selling Plan
    • Client Love ❤️

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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

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.