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Chesapeake City, MD Homes for Sale | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

    Safety & registry resources

    Review official public-safety information for any area from these government sources:

    • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
    • FBI: state sex-offender registry directory
    Save search
    3 bedsNew constructionWith a pool
    13 listings
    Sell

    Selling Options

    • What's my home worth?
    • Compare selling options
    • Get an instant cash offer
    • Buy before you sell

    Resources

    • How selling works
    • When should I sell?
    • Home selling tips
    • Pricing your home
    • What's worth fixing first
    • Find a seller's agent
    Home Loans
    Find an Agent

    Homes for Sale in Chesapeake City, MD

    Homes for Sale in Chesapeake City, MD

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    13 Listings
    Map

    Homes for Sale in Chesapeake City, MD

    13 Listings

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas
    1. 416 Mitton Rd — photoNew27Active

      $6,750,000

      4 bd · 4 ba · 4,141 sqft

      416 Mitton Rd, Chesapeake City, MD

      Leslie Carpenter · Patterson-Schwartz - Greenville

    2. 981 Court House Rd — photo39Active

      $295,000

      3 bd · 1 ba · 924 sqft

      981 Court House Rd, Chesapeake City, MD

      Michael A Saunders · Remax Vision

    3. 240 Randalia Rd — photo60Active

      $885,000

      3 bd · 3 ba · 2,480 sqft

      240 Randalia Rd, Chesapeake City, MD

      Samantha Kay Jackson · Keller Williams Realty

    4. 2871 Augustine Herman Hwy — photo4Active

      $298,000

      2 bd · 1 ba · 875 sqft

      2871 Augustine Herman Hwy, Chesapeake City, MD

      John J Burke · Gunther-McClary Real Estate

    5. 44 Buddy Blvd — photo20Active

      $69,000

      3 bd · 2 ba · 1,216 sqft

      44 Buddy Blvd, Chesapeake City, MD

      Jacqueline D Edmanson · Real-Trust-Associates, LLC.

    6. 2418 Old Telegraph Rd — photo52Active

      $849,000

      4 bd · 4 ba · 3,300 sqft

      2418 Old Telegraph Rd, Chesapeake City, MD

      Tracey Simms · Berkshire Hathaway HomeServices PenFed Realty

    7. 244 Cherry St — photo13Active

      $95,000

      99 bd · 99 ba · 2,436 sqft

      244 Cherry St, Chesapeake City, MD

      Yuliana Alex Goldin Dunn · Patterson-Schwartz-Middletown

    8. 42 Lamborn Ln — photoPrice Reduced17Active

      $250,000

      3 bd · 1 ba · 560 sqft

      42 Lamborn Ln, Chesapeake City, MD

      Jason M Zang · RE/MAX Chesapeake

    9. 34 Buddy Blvd — photoPrice Reduced20Active

      $90,000

      3 bd · 2 ba · 1,280 sqft

      34 Buddy Blvd, Chesapeake City, MD

      Jason M Zang · RE/MAX Chesapeake

    10. 246 Biddle St — photo57Active

      $699,999

      4 bd · 4 ba · 3,280 sqft

      246 Biddle St, Chesapeake City, MD

      Kristin N Lewis · Integrity Real Estate

    11. 320 Cecil St — photoPrice Reduced26Active

      $305,000

      3 bd · 2 ba · 2,263 sqft

      320 Cecil St, Chesapeake City, MD

      Suzanne C Armington · Long & Foster Real Estate, Inc.

    12. 943 Cayots Corner Rd — photoPrice Reduced33Active

      $109,999

      3 bd · 1 ba · 1,431 sqft

      943 Cayots Corner Rd, Chesapeake City, MD

      Byron K. Brooks · Thurston Wyatt Real Estate, LLC

    13. 1455 Cayots Corner Rd — photoPrice Reduced141Active

      $19,900,000

      4 bd · 5 ba · 0 sqft

      1455 Cayots Corner Rd, Chesapeake City, MD

      George W. Hobbs · Monument Sotheby's International Realty

    Explore Chesapeake City homes

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    Listing data & MLS disclosures

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    The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
    Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-02 04:09:15 UTC
  • Co-ops
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    • With a pool

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    Thomas O'Leary

    Realty.com

    Lic. #01-6355

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    Chesapeake City, MD community profile

    Population
    758
    Median income
    $81,500
    Housing units
    322
    People per sq. mi.
    25.4
    Area
    29.9 sq. mi.

    Source: HJN community data

    Chesapeake City housing market

    August 2026 · This period is still settling

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,687 sq. ft.

    Nearby areas

    ZIP codes

    • 21921 (104)
    • 21078 (92)
    • 21001 (87)
    • 21620 (56)
    • 21901 (55)
    • 21919 (28)
    • 21918 (18)
    • 21903 (16)

    Cities

    • Elkton (104)
    • Havre De Grace (92)
    • Aberdeen (87)
    • Chestertown (56)
    • North East (55)
    • Earleville (28)
    • Conowingo (18)
    • Perryville (16)