1,798

Chesapeake City, MD Homes

Section Image
  • 42 Buddy Blvd, Chesapeake City, MD 21915
    42 Buddy Blvd, Chesapeake City, MD 21915
    /2

    $139,900

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    42 Buddy Blvd, Chesapeake City, MD 21915

    NEW home coming SOON! Located in Chesapeake Estates, take a tour on this brand NEW 3 bed 2 bath single family home! Featuring open concept floor plans, kitchen appliance packages, driveways, and spacious yards to BBQ and garden in. Our community amenities include on-site management and 24-hour emergency maintenance. *Must complete a community application and be approved for residency. Lot rent is

    Celine Geigel Arx Housing, LLC

    42 Buddy Blvd, Chesapeake City, MD 21915
  • 2314 Old Telegraph Rd, Chesapeake City, MD 21915
    2314 Old Telegraph Rd, Chesapeake City, MD 21915
    2314 Old Telegraph Rd, Chesapeake City, MD 21915
    /43

    $690,000 Sold Jun 13, 2025

    2314 Old Telegraph Rd, Chesapeake City, MD 21915

    • 4 Beds
    • 2.5 Baths
    • 2,830 Sq Ft
    • Built 2000

    Last Sold Summary

    • $244/SF
    • 4 Days On Market

    Current Estimated Value $687,740

    Last Listing Agent Wanda Jackson RE/MAX Chesapeake

    2314 Old Telegraph Rd, Chesapeake City, MD 21915
    • 984 Biddle St, Chesapeake City, MD 21915
      984 Biddle St, Chesapeake City, MD 21915
      984 Biddle St, Chesapeake City, MD 21915
      /8

      Est $193,736 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,512 Sq Ft

      984 Biddle St, Chesapeake City, MD 21915

      984 Biddle St, Chesapeake City, MD 21915
  • 614 Biddle St, Chesapeake City, MD 21915
    614 Biddle St, Chesapeake City, MD 21915
    614 Biddle St, Chesapeake City, MD 21915
    /42

    $685,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,310 Sq Ft

    614 Biddle St, Chesapeake City, MD 21915

    Experience refined waterfront living in the heart of historic Chesapeake City. This elegant canal-front ranch offers unobstructed, ever-changing views of grand vessels passing by ---enjoyed from both the enclosed patio and expansive deck designed for relaxed sophistication and entertaining. The thoughtfully designed main level features two bedrooms and two beautifully appointed baths,

    Linda McKinnon Patterson-Schwartz-Newark

    614 Biddle St, Chesapeake City, MD 21915
  • 2617 Augustine Herman Hwy, Chesapeake City, MD 21915
    2617 Augustine Herman Hwy, Chesapeake City, MD 21915
    2617 Augustine Herman Hwy, Chesapeake City, MD 21915
    /22

    $280,000 Sold Feb 21, 2025

    2617 Augustine Herman Hwy, Chesapeake City, MD 21915

    • 2 Beds
    • 1 Bath
    • 1,184 Sq Ft
    • Built 1958

    Last Sold Summary

    • $236/SF
    • 0 Days On Market

    Current Estimated Value $291,261

    Last Listing Agent Michele Burch Patterson-Schwartz-Middletown

    2617 Augustine Herman Hwy, Chesapeake City, MD 21915
    • 256 Cayots Corner Rd, Chesapeake City, MD 21915
      256 Cayots Corner Rd, Chesapeake City, MD 21915
      256 Cayots Corner Rd, Chesapeake City, MD 21915
      /26

      Est $173,262 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,122 Sq Ft

      256 Cayots Corner Rd, Chesapeake City, MD 21915

      256 Cayots Corner Rd, Chesapeake City, MD 21915
  • 58 Buddy Blvd, Chesapeake City, MD 21915
    58 Buddy Blvd, Chesapeake City, MD 21915
    58 Buddy Blvd, Chesapeake City, MD 21915
    /7

    $116,900

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    58 Buddy Blvd, Chesapeake City, MD 21915

    NEW home coming SOON! Located in Chesapeake Estates, take a tour on this brand NEW 3 bed 2 bath single family home! Featuring open concept floor plans, kitchen appliance packages, driveways, and spacious yards to BBQ and garden in. Our community amenities include on-site management and 24-hour emergency maintenance. *Must complete a community application and be approved for residency. Lot rent is

    Celine Geigel Arx Housing, LLC

    58 Buddy Blvd, Chesapeake City, MD 21915
  • 64 Shipwatch Ln, Chesapeake City, MD 21915
    64 Shipwatch Ln, Chesapeake City, MD 21915
    64 Shipwatch Ln, Chesapeake City, MD 21915
    /84

    $1,100,000 Sold Dec 05, 2025

    64 Shipwatch Ln, Chesapeake City, MD 21915

    • 3 Beds
    • 3.5 Baths
    • 2,760 Sq Ft
    • Built 1994

    Last Sold Summary

    • $399/SF
    • 77 Days On Market

    Last Listing Agent Jason Zang RE/MAX Chesapeake

    64 Shipwatch Ln, Chesapeake City, MD 21915
    • 191 Basil Ave, Chesapeake City, MD 21915
      191 Basil Ave, Chesapeake City, MD 21915
      191 Basil Ave, Chesapeake City, MD 21915
      /42

      Est $739,236 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,480 Sq Ft

      191 Basil Ave, Chesapeake City, MD 21915

      191 Basil Ave, Chesapeake City, MD 21915
  • 3 Buddy Blvd, Chesapeake City, MD 21915
    3 Buddy Blvd, Chesapeake City, MD 21915
    3 Buddy Blvd, Chesapeake City, MD 21915
    /16

    $99,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    3 Buddy Blvd, Chesapeake City, MD 21915

    Honey stop the car!! NEW PRICE!! GREAT DEAL! Wow** *Affordable year round doublewide within minutes to public boat launching, dining & shops to peruse. Sit & relax in Pell Gardens & watch the boats, ships go through the C&D Canal. Enjoy the historical town of Chesapeake City. Venture across to the North side of Chesapeake City and travel along the canal on the Ben Cardin C& D Canal Trail

    Dottie Walker Empower Real Estate, LLC

    3 Buddy Blvd, Chesapeake City, MD 21915
  • 319 Bohemia Ave, Chesapeake City, MD 21915
    319 Bohemia Ave, Chesapeake City, MD 21915
    319 Bohemia Ave, Chesapeake City, MD 21915
    /25

    $290,000 Sold Oct 29, 2025

    319 Bohemia Ave, Chesapeake City, MD 21915

    • 3 Beds
    • 1.5 Baths
    • 1,678 Sq Ft
    • Built 1869

    Last Sold Summary

    • $173/SF
    • 8 Days On Market

    Last Listing Agent Amber Durand Patterson-Schwartz Real Estate

    319 Bohemia Ave, Chesapeake City, MD 21915
    • 1160 Town Point Rd, Chesapeake City, MD 21915
      1160 Town Point Rd, Chesapeake City, MD 21915
      1160 Town Point Rd, Chesapeake City, MD 21915
      /27

      Est $1,137,731 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 5,269 Sq Ft

      1160 Town Point Rd, Chesapeake City, MD 21915

      1160 Town Point Rd, Chesapeake City, MD 21915
  • 51 Woodside Dr, Chesapeake City, MD 21915
    51 Woodside Dr, Chesapeake City, MD 21915
    51 Woodside Dr, Chesapeake City, MD 21915
    /66

    $420,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    51 Woodside Dr, Chesapeake City, MD 21915

    Welcome to 51 Woodside Drive, a charming Rancher nestled in the serene neighborhood of Harbour North, Chesapeake City, MD. This beautiful 3-bedroom, 2-bathroom home offers 1836 sq. ft. of comfortable living space, perfect for families and those seeking a peaceful retreat.Step inside to discover a cozy gas fireplace that invites warmth and comfort to your living area. The spacious double sink

    cory willems Keller Williams Gateway LLC

    51 Woodside Dr, Chesapeake City, MD 21915
  • 8 Woodside Dr, Chesapeake City, MD 21915
    8 Woodside Dr, Chesapeake City, MD 21915
    8 Woodside Dr, Chesapeake City, MD 21915
    /32

    $404,000 Sold Oct 09, 2025

    8 Woodside Dr, Chesapeake City, MD 21915

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft
    • Built 2003

    Last Sold Summary

    • $221/SF
    • 9 Days On Market

    Last Listing Agent Linda McKinnon Patterson-Schwartz-Newark

    8 Woodside Dr, Chesapeake City, MD 21915
    • 80 Bayview Rd, Chesapeake City, MD 21915
      80 Bayview Rd, Chesapeake City, MD 21915
      80 Bayview Rd, Chesapeake City, MD 21915
      /26

      Est $345,257 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,544 Sq Ft

      80 Bayview Rd, Chesapeake City, MD 21915

      80 Bayview Rd, Chesapeake City, MD 21915
  • 288 Randalia Rd, Chesapeake City, MD 21915
    288 Randalia Rd, Chesapeake City, MD 21915
    288 Randalia Rd, Chesapeake City, MD 21915
    /45

    $574,900 Under Contract

    • 4 Beds
    • 3 Baths
    • 3,600 Sq Ft

    288 Randalia Rd, Chesapeake City, MD 21915

    Welcome to this completely renovated 4BR/3BA sprawling rancher tucked into the landscape on a spacious 3.31 acre lot in Chesapeake City! Park on your newly paved driveway, just steps from the two-car garage and the covered front porch, and open the door into your forever home. Step inside a home filled with natural light, a crisp clean interior with a soft color palette, recessed and luxury

    Jordan Larigan VYBE Realty

    288 Randalia Rd, Chesapeake City, MD 21915
  • 0 Mt Nebo Rd Unit MDCC2016700, Chesapeake City, MD 21915
    0 Mt Nebo Rd Unit MDCC2016700, Chesapeake City, MD 21915
    0 Mt Nebo Rd Unit MDCC2016700, Chesapeake City, MD 21915
    /10

    $150,000 Sold Jun 27, 2025

    0 Mt Nebo Rd Unit MDCC2016700, Chesapeake City, MD 21915

    • Land
    • 1.53 Acres
    • $98,039 per Acre

    Last Sold Summary

    • 20 Days On Market

    Last Listing Agent Kathy Shearon Integrity Real Estate

    0 Mt Nebo Rd Unit MDCC2016700, Chesapeake City, MD 21915
    • 100 Woodside Dr, Chesapeake City, MD 21915
      100 Woodside Dr, Chesapeake City, MD 21915
      100 Woodside Dr, Chesapeake City, MD 21915
      /22

      Est $421,030 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      100 Woodside Dr, Chesapeake City, MD 21915

      100 Woodside Dr, Chesapeake City, MD 21915
  • 8 Iler Ln, Chesapeake City, MD 21915
    8 Iler Ln, Chesapeake City, MD 21915
    8 Iler Ln, Chesapeake City, MD 21915
    /55

    $300,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    8 Iler Ln, Chesapeake City, MD 21915

    DEED COMBINING 2 PARCELS AND SURVEY IN DOCUMENTS- Affordable move-in ready opportunity! Lovingly maintained by the original owners for over 50 years, 3 bedroom, 1 bath rancher situated on a peaceful .82 acre lot and located just steps from the historical, downtown area of Chesapeake City, Maryland in the Bo Manor School District. Main level highlights include beautiful well maintained hardwood

    Wanda Jackson RE/MAX Chesapeake

    8 Iler Ln, Chesapeake City, MD 21915
  • 244 Basil Ave, Chesapeake City, MD 21915
    244 Basil Ave, Chesapeake City, MD 21915
    244 Basil Ave, Chesapeake City, MD 21915
    /39

    $668,500 Sold Feb 28, 2025

    244 Basil Ave, Chesapeake City, MD 21915

    • 4 Beds
    • 3.5 Baths
    • 2,312 Sq Ft
    • Built 2023

    Last Sold Summary

    • $289/SF
    • 13 Days On Market

    Current Estimated Value $680,534

    Last Listing Agent Travis L. Dorman RE/MAX Elite

    244 Basil Ave, Chesapeake City, MD 21915
    • 26 Forest Ln, Chesapeake City, MD 21915
      26 Forest Ln, Chesapeake City, MD 21915
      26 Forest Ln, Chesapeake City, MD 21915
      /54

      Est $448,345 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft

      26 Forest Ln, Chesapeake City, MD 21915

      26 Forest Ln, Chesapeake City, MD 21915
  • 314 Bohemia Ave, Chesapeake City, MD 21915
    314 Bohemia Ave, Chesapeake City, MD 21915
    314 Bohemia Ave, Chesapeake City, MD 21915
    /90

    $520,000 Sold Dec 17, 2025

    314 Bohemia Ave, Chesapeake City, MD 21915

    • 5 Beds
    • 2 Baths
    • 2,687 Sq Ft
    • Built 1850

    Last Sold Summary

    • $194/SF
    • 144 Days On Market

    Last Listing Agent Stephanie Torres Contigo Real Estate

    314 Bohemia Ave, Chesapeake City, MD 21915
    • 47 N Saint Augustine Rd, Chesapeake City, MD 21915
      47 N Saint Augustine Rd, Chesapeake City, MD 21915
      47 N Saint Augustine Rd, Chesapeake City, MD 21915
      /26

      Est $300,291 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,032 Sq Ft

      47 N Saint Augustine Rd, Chesapeake City, MD 21915

      47 N Saint Augustine Rd, Chesapeake City, MD 21915
  • 241 Bank St, Chesapeake City, MD 21915
    241 Bank St, Chesapeake City, MD 21915
    241 Bank St, Chesapeake City, MD 21915
    /106

    $950,000 Sold Jun 05, 2025

    241 Bank St, Chesapeake City, MD 21915

    • 7 Beds
    • 6.5 Baths
    • 5,487 Sq Ft
    • Built 1859

    Last Sold Summary

    • $173/SF
    • 24 Days On Market

    Current Estimated Value $937,391

    Last Listing Agent Amber Durand Patterson-Schwartz Real Estate

    241 Bank St, Chesapeake City, MD 21915
    • 313 Bohemia Ave, Chesapeake City, MD 21915
      313 Bohemia Ave, Chesapeake City, MD 21915
      313 Bohemia Ave, Chesapeake City, MD 21915
      /29

      Est $579,227 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,774 Sq Ft

      313 Bohemia Ave, Chesapeake City, MD 21915

      313 Bohemia Ave, Chesapeake City, MD 21915
  • 140 Hollywood Beach Rd, Chesapeake City, MD 21915
    140 Hollywood Beach Rd, Chesapeake City, MD 21915
    140 Hollywood Beach Rd, Chesapeake City, MD 21915
    /31

    $350,000 Sold May 16, 2025

    140 Hollywood Beach Rd, Chesapeake City, MD 21915

    • 2 Beds
    • 1 Bath
    • 1,216 Sq Ft
    • Built 1950

    Last Sold Summary

    • $288/SF
    • 4 Days On Market

    Current Estimated Value $325,862

    Last Listing Agent Amber Durand Patterson-Schwartz Real Estate

    140 Hollywood Beach Rd, Chesapeake City, MD 21915
    • 210 George St, Chesapeake City, MD 21915
      210 George St, Chesapeake City, MD 21915
      210 George St, Chesapeake City, MD 21915
      /32

      Est $526,707 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,934 Sq Ft

      210 George St, Chesapeake City, MD 21915

      210 George St, Chesapeake City, MD 21915
  • 2 Mallard Dr, Chesapeake City, MD 21915
    2 Mallard Dr, Chesapeake City, MD 21915
    2 Mallard Dr, Chesapeake City, MD 21915
    /38

    $120,000 Sold Mar 07, 2025

    2 Mallard Dr, Chesapeake City, MD 21915

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2000

    Last Sold Summary

    • $92/SF
    • 68 Days On Market

    Last Listing Agent Cassandra Peters Long & Foster Real Estate, Inc.

    2 Mallard Dr, Chesapeake City, MD 21915
    • 79 River Rd, Chesapeake City, MD 21915
      79 River Rd, Chesapeake City, MD 21915
      79 River Rd, Chesapeake City, MD 21915
      /46

      Est $603,954 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,134 Sq Ft

      79 River Rd, Chesapeake City, MD 21915

      79 River Rd, Chesapeake City, MD 21915
  • 151 2nd St, Chesapeake City, MD 21915
    151 2nd St, Chesapeake City, MD 21915
    151 2nd St, Chesapeake City, MD 21915
    /53

    $1,300,000 Sold Aug 21, 2025

    151 2nd St, Chesapeake City, MD 21915

    • 3 Beds
    • 2.5 Baths
    • 2,328 Sq Ft
    • Built 1995

    Last Sold Summary

    • $558/SF
    • 11 Days On Market

    Current Estimated Value $1,283,485

    Last Listing Agent Jason Zang RE/MAX Chesapeake

    151 2nd St, Chesapeake City, MD 21915
    • 981 Court House Point Rd, Chesapeake City, MD 21915
      981 Court House Point Rd, Chesapeake City, MD 21915
      981 Court House Point Rd, Chesapeake City, MD 21915
      /10

      Est $223,622 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 924 Sq Ft

      981 Court House Point Rd, Chesapeake City, MD 21915

      981 Court House Point Rd, Chesapeake City, MD 21915
  • 6 Tower Rd, Chesapeake City, MD 21915
    6 Tower Rd, Chesapeake City, MD 21915
    6 Tower Rd, Chesapeake City, MD 21915
    /43

    $414,000 Sold May 01, 2025

    6 Tower Rd, Chesapeake City, MD 21915

    • 2 Beds
    • 2 Baths
    • 1,426 Sq Ft
    • Built 1981

    Last Sold Summary

    • $290/SF
    • 2 Days On Market

    Last Listing Agent Susan Hubbell Gunther-McClary Real Estate

    6 Tower Rd, Chesapeake City, MD 21915
    • 46 Elk Rd, Chesapeake City, MD 21915
      46 Elk Rd, Chesapeake City, MD 21915
      46 Elk Rd, Chesapeake City, MD 21915
      /34

      Est $418,919 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft

      46 Elk Rd, Chesapeake City, MD 21915

      46 Elk Rd, Chesapeake City, MD 21915
  • 238 Hollywood Beach Rd, Chesapeake City, MD 21915
    238 Hollywood Beach Rd, Chesapeake City, MD 21915
    238 Hollywood Beach Rd, Chesapeake City, MD 21915
    /32

    $380,000 Sold May 15, 2025

    238 Hollywood Beach Rd, Chesapeake City, MD 21915

    • 3 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1985

    Last Sold Summary

    • $266/SF
    • 49 Days On Market

    Current Estimated Value $394,857

    Last Listing Agent Thomas Marryott CENTURY 21 New Millennium

    238 Hollywood Beach Rd, Chesapeake City, MD 21915
    • 227 Bank St, Chesapeake City, MD 21915
      227 Bank St, Chesapeake City, MD 21915
      227 Bank St, Chesapeake City, MD 21915
      /42

      Est $419,213 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,532 Sq Ft

      227 Bank St, Chesapeake City, MD 21915

      227 Bank St, Chesapeake City, MD 21915
  • 3695 Augustine Herman Hwy, Chesapeake City, MD 21915
    3695 Augustine Herman Hwy, Chesapeake City, MD 21915
    3695 Augustine Herman Hwy, Chesapeake City, MD 21915
    /35

    $1,875,000 Sold May 30, 2025

    3695 Augustine Herman Hwy, Chesapeake City, MD 21915

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft
    • Built 2003

    Last Sold Summary

    • $992/SF
    • 14 Days On Market

    Current Estimated Value $1,972,000

    Last Listing Agent A. John Price Patterson-Schwartz Real Estate

    3695 Augustine Herman Hwy, Chesapeake City, MD 21915
    • 601 Biddle St, Chesapeake City, MD 21915
      601 Biddle St, Chesapeake City, MD 21915
      601 Biddle St, Chesapeake City, MD 21915
      /41

      Est $457,523 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,032 Sq Ft

      601 Biddle St, Chesapeake City, MD 21915

      601 Biddle St, Chesapeake City, MD 21915
  • 26 Wallamsey Ln, Chesapeake City, MD 21915
    26 Wallamsey Ln, Chesapeake City, MD 21915
    26 Wallamsey Ln, Chesapeake City, MD 21915
    /34

    $531,000 Sold Oct 06, 2025

    26 Wallamsey Ln, Chesapeake City, MD 21915

    • 3 Beds
    • 2.5 Baths
    • 3,145 Sq Ft
    • Built 1999

    Last Sold Summary

    • $169/SF
    • 96 Days On Market

    Last Listing Agent Iris Cong BHHS Fox & Roach - Hockessin

    26 Wallamsey Ln, Chesapeake City, MD 21915
    • 768 Bethel Rd, Chesapeake City, MD 21915
      768 Bethel Rd, Chesapeake City, MD 21915
      768 Bethel Rd, Chesapeake City, MD 21915
      /33

      Est $315,506 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,272 Sq Ft

      768 Bethel Rd, Chesapeake City, MD 21915

      768 Bethel Rd, Chesapeake City, MD 21915
  • 156 Basil Ave, Chesapeake City, MD 21915
    156 Basil Ave, Chesapeake City, MD 21915
    156 Basil Ave, Chesapeake City, MD 21915
    /19

    $475,000 Sold Dec 08, 2025

    156 Basil Ave, Chesapeake City, MD 21915

    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft
    • Built 2025

    Last Sold Summary

    • $220/SF
    • 0 Days On Market

    Last Listing Agent Brian Tuohey RE/MAX Chesapeake

    156 Basil Ave, Chesapeake City, MD 21915

Showing Results 41 - 80, Page 2 of 18

Maryland Cecil County Chesapeake City

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group