+1(443) 397-1773 moveswithmikeshia@gmail.com
  • Home
  • Book a Consult
  • Free Guides
  • Mortgage Calculator
  • Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty
  • Buy
    1. All Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • About
    1. About Us
    2. Contact Us
    • Register
    • /
    • Sign In
    Price
    • Any
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • $ 800,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 1,000,000
      Beds Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
      Baths Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
    • List
    • Mixed
    • Map
    City: Chestertown, MD
    Price Reduced
    Map
    23 Properties Available In Chestertown

    23 Properties Available In Chestertown

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    MD >Chestertown >
    Market Insights
    Image
    Address
    Price
    Beds
    Baths
    Area
    Status
    MLS®
    9126 FAIRLEE RD, Chestertown, MD 21620

    9126 FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2006764 Listed by Chesapeake Real Estate Associates, LLC

    $299,500

    3
    2
    1,216 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006764
    329 UNION CHURCH RD, Chestertown, MD 21620

    329 UNION CHURCH RD, Chestertown, MD 21620

    MLS# MDQA2018610 Listed by Chesapeake Real Estate Associates, LLC

    $549,900

    4
    3
    2,464 SqFt
    Active
    Bright MLS (BMLS) MLS# MDQA2018610
    234 N KENT ST, Chestertown, MD 21620

    234 N KENT ST, Chestertown, MD 21620

    MLS# MDKE2007128 Listed by TTR Sotheby's International Realty

    $300,000

    5
    2
    1,802 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDKE2007128
    8820 CUMBERLAND ST, Chestertown, MD 21620

    8820 CUMBERLAND ST, Chestertown, MD 21620

    MLS# MDKE2007156 Listed by RE/MAX Advantage Realty

    $281,500

    3
    2
    1,080 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007156
    24775 LANGFORD RD, Chestertown, MD 21620

    24775 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2007012 Listed by RE/MAX Chesapeake

    $305,000

    3
    1
    1,008 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007012
    104 LINCOLN DR, Chestertown, MD 21620

    104 LINCOLN DR, Chestertown, MD 21620

    MLS# MDKE2007032 Listed by RE/MAX Executive

    $275,000

    3
    1
    960 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007032
    115 CHESTER ARMS DR, Chestertown, MD 21620

    115 CHESTER ARMS DR, Chestertown, MD 21620

    MLS# MDKE2006958 Listed by Samson Properties

    $259,000

    3
    2
    1,140 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006958
    216 BIRCH RUN RD, Chestertown, MD 21620

    216 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2006896 Listed by TTR Sotheby's International Realty

    $730,000

    3
    3
    2,176 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006896
    23208 BUCK NECK RD, Chestertown, MD 21620

    23208 BUCK NECK RD, Chestertown, MD 21620

    MLS# MDKE2006980 Listed by Real Broker, LLC - Chester

    $319,900

    3
    3
    1,650 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDKE2006980
    10540 TONOPAH RD, Chestertown, MD 21620

    10540 TONOPAH RD, Chestertown, MD 21620

    MLS# MDKE2006880 Listed by Doug Ashley Realtors, LLC

    $267,000

    3
    2
    1,404 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006880
    234 N COLLEGE AVE, Chestertown, MD 21620

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670 Listed by Cummings & Co Realtors

    $79,000

    2
    1
    1,296 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006670
    222 DUTCHESS RD, Chestertown, MD 21620

    222 DUTCHESS RD, Chestertown, MD 21620

    MLS# MDQA2014830 Listed by Gunther-McClary Real Estate

    $298,000

    3
    2
    1,096 SqFt
    Active
    Bright MLS (BMLS) MLS# MDQA2014830
    TOWHEE RD, Chestertown, MD 21620

    TOWHEE RD, Chestertown, MD 21620

    MLS# MDKE2007066 Listed by The Parker Group

    $40,000

    --
    --
    0.55 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2007066
    CANNON ST, Chestertown, MD 21620

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006944 Listed by Taylor Properties

    $281,000

    --
    --
    0.29 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2006944
    CANNON ST, Chestertown, MD 21620

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006940 Listed by Taylor Properties

    $196,000

    --
    --
    0.22 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2006940
    620 CANNON ST, Chestertown, MD 21620

    620 CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006922 Listed by Taylor Properties

    $85,000

    --
    --
    0.07 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2006922
    201 N LYNCHBURG ST, Chestertown, MD 21620

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006844 Listed by RE/MAX Associates-Hockessin

    $450,000

    --
    --
    4,342 Sqft Lot
    Active
    Bright MLS (BMLS) MLS# MDKE2006844
    109 2ND ST, Chestertown, MD 21620

    109 2ND ST, Chestertown, MD 21620

    MLS# MDQA2017232 Listed by Cross Street Realtors LLC

    $125,000

    --
    --
    1.8 Acres
    Active
    Bright MLS (BMLS) MLS# MDQA2017232
    201 N LYNCHBURG ST, Chestertown, MD 21620

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006082 Listed by RE/MAX Associates-Hockessin

    $695,000

    --
    --
    4,342 Sqft Lot
    Active
    Bright MLS (BMLS) MLS# MDKE2006082
    REDFIELD RD, Chestertown, MD 21620

    REDFIELD RD, Chestertown, MD 21620

    MLS# MDKE2002842 Listed by Paul Wesley Real Estate

    $19,000

    --
    --
    0.34 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2002842
    SPINNAKER RD, Chestertown, MD 21620

    SPINNAKER RD, Chestertown, MD 21620

    MLS# MDKE2002844 Listed by Paul Wesley Real Estate

    $19,000

    --
    --
    0.56 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2002844
    FISH HATCHERY RD, Chestertown, MD 21620

    FISH HATCHERY RD, Chestertown, MD 21620

    MLS# MDKE2002848 Listed by Paul Wesley Real Estate

    $18,500

    --
    --
    0.34 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2002848
    23710 L RD, Chestertown, MD 21620

    23710 L RD, Chestertown, MD 21620

    MLS# MDKE2002838 Listed by Paul Wesley Real Estate

    $12,000

    --
    --
    0.5 Acres
    Active
    Bright MLS (BMLS) MLS# MDKE2002838
    • 1

    explore listings in Chestertown

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    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.
    site logo
    Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty
    Mikeshia Lindsey
    License ID: 5011891 and RS-0039676
    +1(443) 397-1773
    moveswithmikeshia@gmail.com
    302 Park Row, Chestertown, MD 21620-1544, United States, Chestertown, MD 21620-1544

    Get My App

    • Home
    • Mortgage Calculator
    • About
      1. About Us
      2. Contact Us
    • Book a Consult
    • Buy
      1. All Listings
    • Free Guides
    • Sell
      1. Sell My Home
      2. Home Valuation

    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.
    site logo
    Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty
    Mikeshia Lindsey
    License ID: 5011891 and RS-0039676
    +1(443) 397-1773
    moveswithmikeshia@gmail.com
    302 Park Row, Chestertown, MD 21620-1544, United States, Chestertown, MD 21620-1544

    Get My App

    • Home
    • Mortgage Calculator
    • About
      1. About Us
      2. Contact Us
    • Book a Consult
    • Buy
      1. All Listings
    • Free Guides
    • Sell
      1. Sell My Home
      2. Home Valuation

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

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