• Home
  • My Listings
    1. Featured Listings
    2. Sold Listings
    3. Property Portfolio
  • Communities
    1. Annapolis
    2. Severna Park
    3. Arnold
  • Sell My Home
  • Services
  • Real Estate Professional
  • Resources
    1. Affordability Calculator
    2. Mortgage Calculator
    3. Market Snapshot
  • About
    1. My Story
    2. My Resume
    3. Client Survey
    4. Testimonials
    5. Contact Me
  • Home Valuation
  • Did You Hear About Your Neighbor
    • Register
    • Sign In
    Filters Reset
    1 Filter
    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
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Baths
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Reset
    0 Filters
    0 Filters Applied

    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
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Baths
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Days On Site
    Advanced
    Less Than
    Days
    Unit Level

    SqFt
    Switch to Acre
    Sqft
    Sqft
    Lot Size
    Switch to Acre
    Sqft
    Sqft
    Price per Sqft
    Monthly HOA Fee
    Year Built
    Stories
    Kitchens
    Acres
    Full Bathrooms
    Half Bathrooms
    Frontage
    Tax Amount
    Land Lease Fee
    Keyword
    Maintenance Fee
    Assessed Value

    Fireplace Number

    Parking Space
    Garage Space
    Carport Spaces

    Open House
    Has Picture
    New
    Hot
    Virtual Tour
    3D Tour
    Price Reduced
    Save Search (1)
    Save your search to get Alerts
    149 Properties
    Map

    149 Properties Available

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    The average price in the selected areas has remained stable. Learn more
    • MELITOTA RD, Chestertown, MD 21620
      2 Acres
      Under Contract

      $29,000

      MELITOTA RD, Chestertown, MD 21620

      MLS# MDKE2004834

      Listed by The Hogans Agency

      Bright MLS (BMLS)
    • LOT 24 & 25 BUCK NECK RD, Chestertown, MD 21620
      0.42 Acres
      1/6 6
      Under Contract

      $8,000

      LOT 24 & 25 BUCK NECK RD, Chestertown, MD 21620

      MLS# MDKE2004828

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • BELTRAM RD, Chestertown, MD 21620
      0.34 Acres
      1/6 6
      Active

      $10,000

      BELTRAM RD, Chestertown, MD 21620

      MLS# MDKE2004756

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • BUNTING RD, Chestertown, MD 21620
      0.34 Acres
      1/4 4
      Active

      $10,000

      BUNTING RD, Chestertown, MD 21620

      MLS# MDKE2004758

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • FISH HATCHERY RD, Chestertown, MD 21620
      0.37 Acres
      1/7 7
      Active

      $10,000

      FISH HATCHERY RD, Chestertown, MD 21620

      MLS# MDKE2004754

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • 22681 WOOD YARD LN, Chestertown, MD 21620
      0.51 Acres
      1/2 2
      Active

      $15,000

      22681 WOOD YARD LN, Chestertown, MD 21620

      MLS# MDKE2004720

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • HAACKE DRIVE LOT 3, Chestertown, MD 21620
      0.96 Acres
      1/5 5
      Active

      $225,000

      HAACKE DRIVE LOT 3, Chestertown, MD 21620

      MLS# MDKE2004648

      Listed by Select Land & Homes, LLC

      Bright MLS (BMLS)
    • SCHEELER ROAD LOT 2, Chestertown, MD 21620
      0.93 Acres
      1/7 7
      Active

      $250,000

      SCHEELER ROAD LOT 2, Chestertown, MD 21620

      MLS# MDKE2004650

      Listed by Select Land & Homes, LLC

      Bright MLS (BMLS)
    • BUCK NECK LANDING RD, Chestertown, MD 21620
      0.34 Acres
      Active

      $9,500

      BUCK NECK LANDING RD, Chestertown, MD 21620

      MLS# MDKE2004072

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • LOT 9 PRESTWICK DR, Chestertown, MD 21620
      1.95 Acres
      1/20 20
      Active

      $185,000

      LOT 9 PRESTWICK DR, Chestertown, MD 21620

      MLS# MDKE2003918

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 860 & 870 HIGH ST, Chestertown, MD 21620
      1/92 92
      Price Dropped by $2.0M

      $375,000

      860 & 870 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2003850

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 349 & 351 HIGH ST, Chestertown, MD 21620
      3,664 SqFt
      1/47 47
      Under Contract

      $395,000

      349 & 351 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2003720

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • PARCEL BUCK NECK LDG RD, Chestertown, MD 21620
      0.34 Acres
      1/6 6
      Active

      $10,000

      PARCEL BUCK NECK LDG RD, Chestertown, MD 21620

      MLS# MDKE2003874

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • ELM RD, Chestertown, MD 21620
      0.09 Acres
      1/3 3
      Active

      $20,000

      ELM RD, Chestertown, MD 21620

      MLS# MDKE2003590

      Listed by Coldwell Banker Chesapeake Real Estate Company

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

      $55,000

      MAP 36 PARCEL 80 WATERTOWER RD, Chestertown, MD 21620

      MLS# MDKE2003624

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 206 CANNON ST, Chestertown, MD 21620
      1.56 Acres
      1/9 9
      Active

      $1,150,000

      206 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2003620

      Listed by Benson & Mangold, LLC

      Bright MLS (BMLS)
    • ELM RD, Chestertown, MD 21620
      0.33 Acres
      Active

      $40,000

      ELM RD, Chestertown, MD 21620

      MLS# MDKE2003416

      Listed by The Hogans Agency

      Bright MLS (BMLS)
    • MONTGOMERY AVENUE, Chestertown, MD 21620
      0.11 Acres
      1/2 2
      Active

      $40,000

      MONTGOMERY AVENUE, Chestertown, MD 21620

      MLS# MDKE2003418

      Listed by The Hogans Agency

      Bright MLS (BMLS)
    • LOTS 253-254 CARIMON RD, Chestertown, MD 21620
      0.34 Acres
      1/3 3
      Under Contract

      $9,500

      LOTS 253-254 CARIMON RD, Chestertown, MD 21620

      MLS# MDKE2003110

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • REDFIELD RD, Chestertown, MD 21620
      0.34 Acres
      1/2 2
      Active

      $38,000

      REDFIELD RD, Chestertown, MD 21620

      MLS# MDKE2002842

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • SPINNAKER RD, Chestertown, MD 21620
      0.56 Acres
      1/2 2
      Active

      $38,000

      SPINNAKER RD, Chestertown, MD 21620

      MLS# MDKE2002844

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • FISH HATCHERY RD, Chestertown, MD 21620
      0.34 Acres
      1/2 2
      Active

      $37,000

      FISH HATCHERY RD, Chestertown, MD 21620

      MLS# MDKE2002848

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • CAULKS FIELD RD, Chestertown, MD 21620
      2 Acres
      1/2 2
      Active

      $28,000

      CAULKS FIELD RD, Chestertown, MD 21620

      MLS# MDKE2002846

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • 23710 L RD, Chestertown, MD 21620
      0.5 Acres
      1/2 2
      Active

      $24,000

      23710 L RD, Chestertown, MD 21620

      MLS# MDKE2002838

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • 1
    • ...
    • 3
    • 4
    • 5
    • 6
    • 7
    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 MAP

        Home
        My Listings
        1. Featured Listings
        2. Sold Listings
        3. Property Portfolio
        Communities
        1. Annapolis
        2. Severna Park
        3. Arnold
        Sell My Home
        Services
        Resources
        1. Affordability Calculator
        2. Mortgage Calculator
        3. Market Snapshot
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
        Home Valuation
        Did You Hear About Your Neighbor
    VA305_primary_cabProud Partner of FGP

    Berkshire Hathaway HomeServices PenFed Realty

    Jared Schwartz Lic# 5012305

    +1(301) 906-5301 jared.schwartz@penfedrealty.com

    1997 Annapolis Exchange Pkwy 101, Annapolis, MD, 21401, USA

    Get My App

    Powered by Lofty Inc. Copyright 2025. 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 MAP

        Home
        My Listings
        1. Featured Listings
        2. Sold Listings
        3. Property Portfolio
        Communities
        1. Annapolis
        2. Severna Park
        3. Arnold
        Sell My Home
        Services
        Resources
        1. Affordability Calculator
        2. Mortgage Calculator
        3. Market Snapshot
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
        Home Valuation
        Did You Hear About Your Neighbor
    VA305_primary_cabProud Partner of FGP

    Berkshire Hathaway HomeServices PenFed Realty

    Jared Schwartz Lic# 5012305

    +1(301) 906-5301 jared.schwartz@penfedrealty.com

    1997 Annapolis Exchange Pkwy 101, Annapolis, MD, 21401, USA

    Get My App

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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