• Home
  • Buy
    1. All Listings
    2. Featured Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Recent Sold
  • Real Broker
  • Rent
    1. Rental Listings
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. 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
    152 Properties Available

    152 Properties Available

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    10540 TONOPAH RD, Chestertown, MD 21620
    1/21
    Coming Soon

    $279,000

    3 Beds2 Baths1,404 SqFt

    10540 TONOPAH RD, Chestertown, MD 21620

    MLS# MDKE2006880

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    123 HEATH RD, Chestertown, MD 21620
    1/54
    Open 8/6 2PM-4PM
    3D

    $349,000

    3 Beds2 Baths1,792 SqFt

    123 HEATH RD, Chestertown, MD 21620

    MLS# MDQA2017994

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    115 METCALF RD, Chestertown, MD 21620
    1/10
    Open Sat 11AM-1PM

    $259,900

    3 Beds2 Baths1,280 SqFt

    115 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006826

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    226 S WATER ST, Chestertown, MD 21620
    1/31
    Open Sat 11AM-1PM

    $898,000

    3 Beds4 Baths2,172 SqFt

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2006354

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    533 ROUND TOP RD, Chestertown, MD 21620
    Coming Soon

    $225,000

    4 Beds2 Baths1,800 SqFt

    533 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2018038

    Listed by EXP Realty, LLC

    Bright MLS (BMLS)
    129 TRAFFORD DR, Chestertown, MD 21620
    1/15
    Coming Soon

    $480,000

    3 Beds3 Baths3,176 SqFt

    129 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006878

    Listed by Elevated Real Estate Solutions

    Bright MLS (BMLS)
    109 PARMA RD, Chestertown, MD 21620
    1/4
    Coming Soon

    $315,000

    3 Beds2 Baths1,288 SqFt

    109 PARMA RD, Chestertown, MD 21620

    MLS# MDQA2018184

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    240 ROUND TOP RD, Chestertown, MD 21620
    Coming Soon

    $295,000

    3 Beds2 Baths1,132 SqFt

    240 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2018166

    Listed by Clark & Co Realty, LLC

    Bright MLS (BMLS)
    207 LINCOLN DR, Chestertown, MD 21620
    1/24
    New

    $135,000

    4 Beds2 Baths1,152 SqFt

    207 LINCOLN DR, Chestertown, MD 21620

    MLS# MDKE2006894

    Listed by Monument Sotheby's International Realty

    Bright MLS (BMLS)
    7828 COUNTRY CLUB LN, Chestertown, MD 21620
    1/68
    Under Contract

    $799,000

    3 Beds3 Baths2,857 SqFt

    7828 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2006736

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    7903 RADCLIFFE RD, Chestertown, MD 21620
    1/5
    Coming Soon

    $625,000

    3 Beds4 Baths4,037 SqFt

    7903 RADCLIFFE RD, Chestertown, MD 21620

    MLS# MDKE2006890

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    1010 TWIN CT, Chestertown, MD 21620
    1/25
    New

    $375,000

    4 Beds2 Baths1,476 SqFt

    1010 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006874

    Listed by Kevin Dey Realty

    Bright MLS (BMLS)
    202 PINE ST, Chestertown, MD 21620
    Coming Soon

    $205,000

    3 Beds1 Bath1,341 SqFt

    202 PINE ST, Chestertown, MD 21620

    MLS# MDKE2006888

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    107 CONLEY DR, Chestertown, MD 21620
    1/24
    New
    3D

    $240,000

    3 Beds1 Bath1,140 SqFt

    107 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006828

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    21146 MONTANA AVE, Chestertown, MD 21620
    1/56
    New

    $289,900

    2 Beds2 Baths1,500 SqFt

    21146 MONTANA AVE, Chestertown, MD 21620

    MLS# MDKE2006858

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    8312 BROAD NECK RD, Chestertown, MD 21620
    1/47
    Active

    $380,000

    3 Beds2 Baths3,292 SqFt

    8312 BROAD NECK RD, Chestertown, MD 21620

    MLS# MDKE2006854

    Listed by Pearson Smith Realty, LLC

    Bright MLS (BMLS)
    8999 ORCHARD DR, Chestertown, MD 21620
    1/74
    Active

    $824,900

    5 Beds4 Baths4,353 SqFt

    8999 ORCHARD DR, Chestertown, MD 21620

    MLS# MDKE2006786

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    21324 PERSIMMON DR, Chestertown, MD 21620
    1/21
    Price Dropped by $10K
    3D

    $189,000

    2 Beds1 Bath1,232 SqFt

    21324 PERSIMMON DR, Chestertown, MD 21620

    MLS# MDKE2006816

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    PRESTON LANE, Chestertown, MD 21620
    1/41
    Pending

    $525,000

    3 Beds3 Baths2,824 SqFt

    PRESTON LANE, Chestertown, MD 21620

    MLS# MDKE2006820

    Listed by Shoreline Realty

    Bright MLS (BMLS)
    210 N QUEEN ST, Chestertown, MD 21620
    1/36
    Under Contract

    $735,000

    4 Beds3 Baths2,730 SqFt

    210 N QUEEN ST, Chestertown, MD 21620

    MLS# MDKE2006744

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    109 CEDAR ST, Chestertown, MD 21620
    1/22
    Under Contract

    $325,000

    3 Beds3 Baths1,397 SqFt

    109 CEDAR ST, Chestertown, MD 21620

    MLS# MDKE2006792

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    200 MANOR AVE, Chestertown, MD 21620
    1/34
    Active

    $325,000

    4 Beds2 Baths2,198 SqFt

    200 MANOR AVE, Chestertown, MD 21620

    MLS# MDKE2006808

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    121 METCALF RD, Chestertown, MD 21620
    1/10
    Active

    $264,900

    3 Beds2 Baths3,920 Sqft Lot

    121 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006678

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    10720 FORESTON RD, Chestertown, MD 21620
    1/42
    Active

    $335,000

    3 Beds2 Baths1,412 SqFt

    10720 FORESTON RD, Chestertown, MD 21620

    MLS# MDKE2006800

    Listed by Compass

    Bright MLS (BMLS)
    • 1
    • 2
    • 3
    • 4
    • 5
    • ...
    • 7

    explore listings

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    site logo
      • Home
        Rent
        1. Rental Listings
      • Buy
        1. All Listings
        2. Featured Listings
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Market Snapshot
    Real Broker
    Taha Duran

    +1(301) 346-2534 tahatherealtor@gmail.com

    9841 Washingtonian Blvd Ste 200, Gaithersburg, Maryland 20878, USA

    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.
    site logo
      • Home
        Rent
        1. Rental Listings
      • Buy
        1. All Listings
        2. Featured Listings
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Market Snapshot
    Real Broker
    Taha Duran

    +1(301) 346-2534 tahatherealtor@gmail.com

    9841 Washingtonian Blvd Ste 200, Gaithersburg, Maryland 20878, USA

    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.