+1(323) 974-2911 joshluberisse@gmail.com
  • Home
  • Listings
  • Buy
    1. All Listings
    2. Featured Listings
    3. Philadelphia
    4. West Kensington
    5. Warehouse District
    6. Winchester Park
    7. West Logan
    8. Walton Park
    9. Wynnefield
    10. Whitman
    11. Yorktown
    12. University City
    13. Wynnefield Heights
    14. Wissahickon
    15. Upper Holmesburg
    16. Washington Square West
    17. Wissinoming
    18. Walnut Hill
    19. Woodland
    20. West Fairmount Park
    21. West Philadelphia
    22. West Oak Lane
    23. Upper North Philadelphia
    24. New York
    25. Midwood
    26. Mill Basin
    27. Sheepshead Bay
    28. Flatbush
    29. Park Slope
    30. Bensonhurst
    31. Canarsie
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Sold Listings
  • Real Broker LLC
  • Neighborhoods
  • About
    1. My Team
    2. About Us
    3. Contact Us
  • 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
    Chestertown, MD
    Map
    127 Properties Available

    127 Properties Available

    The average price in the selected areas has remained stable. Learn more
    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    23110 OLD FAIRLEE RD, Chestertown, MD 21620
    1/29
    Exclusive Listing
    Price Dropped by $10K

    $349,900

    3 Beds1 Bath1,805 SqFt

    23110 OLD FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2005676

    Listed by Real Broker LLC

    Bright MLS (BMLS)
    10800 CLIFF RD, Chestertown, MD 21620
    1/94
    Open Sat 2PM-4PM

    $1,495,000

    5 Beds4 Baths5,241 SqFt

    10800 CLIFF RD, Chestertown, MD 21620

    MLS# MDKE2005898

    Listed by Taylor Properties

    Bright MLS (BMLS)
    201 GREENWOOD AVE, Chestertown, MD 21620
    1/62
    Under Contract

    $495,000

    4 Beds3 Baths3,984 SqFt

    201 GREENWOOD AVE, Chestertown, MD 21620

    MLS# MDKE2006030

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    104 IRIS RD, Chestertown, MD 21620
    1/36
    Open Sat 12PM-2PM

    $379,000

    3 Beds2 Baths1,700 SqFt

    104 IRIS RD, Chestertown, MD 21620

    MLS# MDQA2015798

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    22481 GOOSE HOLLOW DR, Chestertown, MD 21620
    1/18
    Open Sun 1PM-3PM

    $379,500

    3 Beds2 Baths1,296 SqFt

    22481 GOOSE HOLLOW DR, Chestertown, MD 21620

    MLS# MDKE2006012

    Listed by Realty Mark Cityscape

    Bright MLS (BMLS)
    218 CAMELOT DR, Chestertown, MD 21620
    1/45
    Open Sat 12PM-2PM

    $525,000

    5 Beds4 Baths3,932 SqFt

    218 CAMELOT DR, Chestertown, MD 21620

    MLS# MDKE2005982

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    204 ROLLING RD, Chestertown, MD 21620
    1/31
    Open 1/17 11AM-1PM

    $345,000

    3 Beds2 Baths2,296 SqFt

    204 ROLLING RD, Chestertown, MD 21620

    MLS# MDKE2005896

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    121 PRIMROSE RD, Chestertown, MD 21620
    1/22
    Open 1/18 10AM-12PM

    $350,000

    3 Beds3 Baths2,034 SqFt

    121 PRIMROSE RD, Chestertown, MD 21620

    MLS# MDQA2015570

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    222 MOUNT VERNON AVE, Chestertown, MD 21620
    1/29
    Open Sun 1PM-3PM

    $465,000

    4 Beds2 Baths1,656 SqFt

    222 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2005876

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    7844 CHESTER CT, Chestertown, MD 21620
    1/51
    Open Sun 12PM-2:30PM

    $745,000

    4 Beds3 Baths3,248 SqFt

    7844 CHESTER CT, Chestertown, MD 21620

    MLS# MDKE2005796

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    100 ADELA WAY, Chestertown, MD 21620
    1/71
    Open Sat 12PM-2PM

    $500,000

    4 Beds4 Baths3,799 SqFt

    100 ADELA WAY, Chestertown, MD 21620

    MLS# MDKE2005636

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
    141 PROSPECT ST, Chestertown, MD 21620
    1/16
    New

    $165,000

    4 Beds2 Baths1,156 SqFt

    141 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006036

    Listed by Taylor Properties

    Bright MLS (BMLS)
    24775 LANGFORD RD, Chestertown, MD 21620
    1/36
    New

    $319,900

    3 Beds1 Bath1,008 SqFt

    24775 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2005992

    Listed by RE/MAX 1st Choice - Middletown

    Bright MLS (BMLS)
    6746 QUAKER NECK RD, Chestertown, MD 21620
    1/50
    New

    $445,000

    5 Beds3 Baths3,371 SqFt

    6746 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2006014

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    110 TRAFFORD DR, Chestertown, MD 21620
    1/26
    New

    $475,000

    4 Beds3 Baths2,880 SqFt

    110 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2005964

    Listed by RE/MAX Advantage Realty

    Bright MLS (BMLS)
    303 CEDAR ST, Chestertown, MD 21620
    1/26
    Under Contract

    $333,900

    3 Beds3 Baths2,577 SqFt

    303 CEDAR ST, Chestertown, MD 21620

    MLS# MDKE2005970

    Listed by Select Land & Homes, LLC

    Bright MLS (BMLS)
    21111 TEXAS AVE, Chestertown, MD 21620
    1/16
    Under Contract

    $370,000

    3 Beds2 Baths1,680 SqFt

    21111 TEXAS AVE, Chestertown, MD 21620

    MLS# MDKE2005932

    Listed by Keller Williams Select Realtors of Easton

    Bright MLS (BMLS)
    109 METCALF RD, Chestertown, MD 21620
    1/27
    Active

    $264,900

    3 Beds2 Baths1,280 SqFt

    109 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2005968

    Listed by Real Broker, LLC

    Bright MLS (BMLS)
    676 DEEP LANDING RD, Chestertown, MD 21620
    1/24
    Under Contract

    $315,000

    3 Beds3 Baths1,468 SqFt

    676 DEEP LANDING RD, Chestertown, MD 21620

    MLS# MDQA2015466

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    #25 LANDING LN, Chestertown, MD 21620
    1/22
    Active

    $1,099,900

    4 Beds4 Baths2,784 SqFt

    #25 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005954

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    102 LITTLE HARBOR WAY, Chestertown, MD 21620
    1/23
    Active

    $839,500

    3 Beds3 Baths1,964 SqFt

    102 LITTLE HARBOR WAY, Chestertown, MD 21620

    MLS# MDKE2005950

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    104 LANDING LN, Chestertown, MD 21620
    1/24
    Active

    $813,900

    3 Beds4 Baths2,192 SqFt

    104 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005952

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    #35 LANDING LN, Chestertown, MD 21620
    1/26
    Active

    $786,900

    3 Beds3 Baths1,964 SqFt

    #35 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005956

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    #37 LANDING LN, Chestertown, MD 21620
    1/24
    Active

    $765,900

    3 Beds3 Baths1,964 SqFt

    #37 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005960

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    default
        Home
        Listings
        Buy
        1. All Listings
        2. Featured Listings
        3. Philadelphia
        4. West Kensington
        5. Warehouse District
        6. Winchester Park
        7. West Logan
        8. Walton Park
        9. Wynnefield
        10. Whitman
        11. Yorktown
        12. University City
        13. Wynnefield Heights
        14. Wissahickon
        15. Upper Holmesburg
        16. Washington Square West
        17. Wissinoming
        18. Walnut Hill
        19. Woodland
        20. West Fairmount Park
        21. West Philadelphia
        22. West Oak Lane
        23. Upper North Philadelphia
        24. New York
        25. Midwood
        26. Mill Basin
        27. Sheepshead Bay
        28. Flatbush
        29. Park Slope
        30. Bensonhurst
        31. Canarsie
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Sold Listings
        About
        1. My Team
        2. About Us
        3. Contact Us
        Market Snapshot
    Real of Pennsylvania

    Josh Luberisse License ID: 10401377519

    +1(323) 974-2911 joshluberisse@gmail.com

    500 Office Center Drive, Suite 400, Fort, Washington

    NYS Housing and Anti Discrimination Disclosure  

    NYS Fair Housing and Anti Discrimination Notice

    PA Customer Notice

    Get My App

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

    Powered by Lofty Inc. Copyright 2026. 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.
    default
        Home
        Listings
        Buy
        1. All Listings
        2. Featured Listings
        3. Philadelphia
        4. West Kensington
        5. Warehouse District
        6. Winchester Park
        7. West Logan
        8. Walton Park
        9. Wynnefield
        10. Whitman
        11. Yorktown
        12. University City
        13. Wynnefield Heights
        14. Wissahickon
        15. Upper Holmesburg
        16. Washington Square West
        17. Wissinoming
        18. Walnut Hill
        19. Woodland
        20. West Fairmount Park
        21. West Philadelphia
        22. West Oak Lane
        23. Upper North Philadelphia
        24. New York
        25. Midwood
        26. Mill Basin
        27. Sheepshead Bay
        28. Flatbush
        29. Park Slope
        30. Bensonhurst
        31. Canarsie
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Sold Listings
        About
        1. My Team
        2. About Us
        3. Contact Us
        Market Snapshot
    Real of Pennsylvania

    Josh Luberisse License ID: 10401377519

    +1(323) 974-2911 joshluberisse@gmail.com

    500 Office Center Drive, Suite 400, Fort, Washington

    NYS Housing and Anti Discrimination Disclosure  

    NYS Fair Housing and Anti Discrimination Notice

    PA Customer Notice

    Get My App

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

    Powered by Lofty Inc. Copyright 2026. 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.