+1(302) 465-8055 bwindom2011@yahoo.com
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Recent Sold
  • Myers Realty
  • Move to Delaware
  • About
    1. About Us
    2. Reviews
  • Market Snapshot
    • 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
    ZIP Code: 21620
    Map
    122 Properties Available

    122 Properties Available

    • Newest Listings
    • Default
    • Price-High To Low
    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    10572 WATONGA RD, Chestertown, MD 21620
    1/25
    Open 6/13 12PM-2PM

    $325,000

    3 Beds2 Baths1,404 SqFt

    10572 WATONGA RD, Chestertown, MD 21620

    MLS# MDKE2006644

    Listed by Serhant

    Bright MLS (BMLS)
    104 ACORN DR, Chestertown, MD 21620
    1/22
    New

    $284,900

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

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

    $365,000

    3 Beds2 Baths1,248 SqFt

    23264 CLARISSA RD, Chestertown, MD 21620

    MLS# MDKE2006096

    Listed by TTR Sotheby's International Realty

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

    $120,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    FAIRLEE RD, Chestertown, MD 21620
    1/7
    New

    $75,000

    2.2 Acres

    FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2006672

    Listed by RE/MAX Chesapeake

    Bright MLS (BMLS)
    25416 COMMERCE LN, Chestertown, MD 21620
    1/39
    New

    $1,100,000

    2.03 Acres Lot

    25416 COMMERCE LN, Chestertown, MD 21620

    MLS# MDKE2006664

    Listed by Coldwell Banker Chesapeake Real Estate Company

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

    $119,900

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

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

    $1,650,000

    9 Beds7 Baths4,776 SqFt

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

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

    $265,000

    3 Beds1 Bath1,967 SqFt

    1904 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2017480

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    1906 PONDTOWN RD, Chestertown, MD 21620
    1/4
    New

    $110,000

    1.93 Acres

    1906 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2017476

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    222 MOUNT VERNON AVE, Chestertown, MD 21620
    1/29
    New

    $2,950

    4 Beds2 Baths1,656 SqFt

    222 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2006624

    Listed by Long & Foster Real Estate, Inc.

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

    $449,900

    4 Beds3 Baths2,160 SqFt

    10781 FERMOY RD, Chestertown, MD 21620

    MLS# MDKE2006640

    Listed by Real Broker, LLC - Chester

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

    $200,000

    4 Beds1 Bath2,920 SqFt

    21172 WYOMING AVE, Chestertown, MD 21620

    MLS# MDKE2006642

    Listed by Blue Star Real Estate, LLC

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

    $380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    8886 GEORGETOWN RD, Chestertown, MD 21620
    1/2
    New

    $85,000

    4.03 Acres

    8886 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2006634

    Listed by Samson Properties

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

    $3,000,000

    3 Beds4 Baths3,142 SqFt

    25440 LEARMAN RD, Chestertown, MD 21620

    MLS# MDKE2006468

    Listed by TTR Sotheby's International Realty

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

    $1,450,000

    4 Beds5 Baths4,257 SqFt

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    1010 TWIN CT, Chestertown, MD 21620
    1/14
    Active

    $2,400

    4 Beds2 Baths1,476 SqFt

    1010 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006610

    Listed by Kevin Dey Realty

    Bright MLS (BMLS)
    23741 L RD, Chestertown, MD 21620
    1/2
    Active

    $15,000

    1 Acres

    23741 L RD, Chestertown, MD 21620

    MLS# MDKE2006622

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    Active

    $450,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

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

    $285,000

    3 Beds1 Bath1,248 SqFt

    956 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006394

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    24295 LANGFORD RD, Chestertown, MD 21620
    1/71
    Price Dropped by $15K

    $430,000

    2 Beds3 Baths1,857 SqFt

    24295 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2006320

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    MAP 36 PARCEL 80 WATERTOWER RD, Chestertown, MD 21620
    1/3
    Active

    $55,000

    0.7 Acres

    MAP 36 PARCEL 80 WATERTOWER RD, Chestertown, MD 21620

    MLS# MDKE2006592

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    102 FLYING CLOUD DR, Chestertown, MD 21620
    1/41
    Active

    $339,900

    3 Beds3 Baths1,896 SqFt

    102 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006586

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6

    explore listings

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    site logo
    Myers Realty
    Brandon Windom
    1056 S State St, Dover, DE, 19901, USA

    +1(302) 465-8055

    bwindom2011@yahoo.com

    Get My App

    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.

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

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

    site logo
    Myers Realty
    Brandon Windom
    1056 S State St, Dover, DE, 19901, USA

    +1(302) 465-8055

    bwindom2011@yahoo.com

    Get My App

    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.

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

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