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Chesapeake City, MD Homes for Sale

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  • /45

    $499,999

    • 4 Beds
    • 1.5 Baths
    • 2,176 Sq Ft

    306 Bohemia Ave, Chesapeake City, MD 21915

    FRESHLY PAINTED WHOLE EXTERIOR, GARAGE/IRON FENCING!!!!!! PHOTOS ARE GENERATED TO SHOW IDEAS!!! HOME IS CURRENTLY VACANT!!! Welcome to the Johnson-Lindsey House, a rare opportunity to own a piece of Chesapeake City’s history. Located in the heart of the Historic District, this Federal-style home was built around 1850 by Joseph W. Lindsey, the town’s sawmill and lumber yard owner. Zoned

    Agent Photo

    Tinamarie Reamy

    Coldwell Banker Chesapeake Real Estate

    (410) 449-1459

    306 Bohemia Ave, Chesapeake City, MD 21915
  • /32

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    19 Tower Rd, Chesapeake City, MD 21915

    Waterfront Home on the Elk River!Experience breathtaking views as ships from around the world glide by from your own backyard. This spacious and versatile home features 4+ bedrooms and 3 full baths, offering incredible potential to customize and make it your own. The main level boasts 2 bedrooms, a welcoming great room with a cozy fireplace, a dining area, and an eat-in kitchen—perfect for

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 498-8122

    19 Tower Rd, Chesapeake City, MD 21915
  • /74

    $1,299,900

    • 3 Beds
    • 3 Baths
    • 3,867 Sq Ft

    87 Deer Run, Chesapeake City, MD 21915

    Welcome to your private Elk River waterfront paradise, nestled on 2.28 acres in Chesapeake City, MD! Affectionately known as “The Landing,” 87 Deer Run is a truly exceptional retreat featuring meticulously landscaped grounds, a rip-rapped shoreline, a sandy beach, and stunning sunset views over the water. Step inside and you’re greeted by a warm and inviting foyer accented by a propane fireplace.

    Jason Zang RE/MAX Chesapeake

    87 Deer Run, Chesapeake City, MD 21915
  • /84

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 3,457 Sq Ft

    64 Shipwatch Ln, Chesapeake City, MD 21915

    Remarkable, pristine Elk River waterfront home at the Villas at Port Herman! 64 Shipwatch provides a rare opportunity to own a piece of real estate just steps from a sandy beach that overlooks ships as they pass through the intracoastal waterway. The home itself overflows with impeccable water views and brilliant outdoor spaces that will make every day feel like a vacation. Highlights include the

    Jason Zang RE/MAX Chesapeake

    64 Shipwatch Ln, Chesapeake City, MD 21915
  • /30

    $799,900

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft

    53 Pleasure Shores Cir, Chesapeake City, MD 21915

    Rare WATERFRONT Property/ Vacation home for Sale... a true Turnkey Opportunity! Just a bit downstream from Chesapeake City, Md, near Port Herman and Hollywood Beach. Less than one hour from Delco, PA. Property is being sold fully furnished. Comes with an 85' foot dock (new decking). Dock has one Boat Lift and 2 Jet Ski Lifts. Catch Crabs and Fish right off the end of the dock! Home features 4

    Ralph Harvey ListWithFreedom.com

    53 Pleasure Shores Cir, Chesapeake City, MD 21915
  • /46

    $1,200,000

    • 6 Beds
    • 5.5 Baths
    • 3,757 Sq Ft

    280 Hollywood Beach Rd, Chesapeake City, MD 21915

    Best of everything on the water. Build you own dock or ask about the possible deep water community boat slips. Community boat ramp. You will own a private sandy beach 100 feet wide off your deck. No better views anywhere. Total of five bedrooms and three full baths. Finished en suite above garage with separate entrance and full bath. Oversized garage with full garage doors on both ends.

    Rodman Mullins Sterling Real Estate LLC

    280 Hollywood Beach Rd, Chesapeake City, MD 21915
  • /117

    $1,489,000

    • 9 Beds
    • 10 Baths
    • 7,044 Sq Ft

    300 Bohemia Ave, Chesapeake City, MD 21915

    PRICE ADJUSTMENT!!Step Back in Time at the Blue Max InnWelcome to the Blue Max Inn, a charming and historic Bed & Breakfast nestled in the heart of Chesapeake City, Maryland. This beautiful Victorian Inn offers a unique blend of old-world elegance and modern comforts, making it a beloved retreat in Chesapeake City which is along the Chesapeake and Delaware Canal.Operating under the

    Joseph A Zang III RE/MAX Chesapeake

    300 Bohemia Ave, Chesapeake City, MD 21915
  • /29

    $1,500,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,761 Sq Ft

    3192 Augustine Herman Hwy, Chesapeake City, MD 21915

    Amazing opportunity! 40 acres of preserved farmland with 4 pastures in South Chesapeake City horse country convenient to Fair Hill, Delaware Park, marinas, and golf courses plus convenient to Chesapeake City restaurants on the canal.. Expanded 4 bedroom, 2 bath brick and vinyl ranch with sunroom, primary bedroom with walk-in closet and access to the hall bath and laundry. Full walk out basement

    David Landon Patterson-Schwartz-Newark

    3192 Augustine Herman Hwy, Chesapeake City, MD 21915
  • /32

    $329,999 Open Thu 5PM - 7PM

    • 3 Beds
    • 1.5 Baths
    • 1,896 Sq Ft

    321 Cecil St, Chesapeake City, MD 21915

    Coming Soon — 321 Cecil St, Chesapeake City, MDShowings Begin Wednesday., Aug. 27th | Open House: Thurs. Aug. 28, 6:00–7:30 PMStep into charm, history, and location! This beautifully updated 3-bedroom, 1.5-bath, two-story home sits just over a block from the renowned C&D Canal walking and biking trail—a scenic 14-mile path stretching from Delaware to Maryland, offering views of one of the

    Julie Strickler Remax Vision

    321 Cecil St, Chesapeake City, MD 21915
  • /7

    $116,900

    • 3 Beds
    • 2 Baths

    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.

    Celine Geigel Arx Housing, LLC

    58 Buddy Blvd, Chesapeake City, MD 21915
  • /2

    $139,900

    • 3 Beds
    • 2 Baths

    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.

    Celine Geigel Arx Housing, LLC

    42 Buddy Blvd, Chesapeake City, MD 21915
  • /10

    $116,900

    • 3 Beds
    • 2 Baths

    15 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.

    Celine Geigel Arx Housing, LLC

    15 Buddy Blvd, Chesapeake City, MD 21915
  • /7

    $119,900

    • 3 Beds
    • 2 Baths

    13 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.

    Celine Geigel Arx Housing, LLC

    13 Buddy Blvd, Chesapeake City, MD 21915
  • /34

    $379,900

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    534 Biddle St, Chesapeake City, MD 21915

    Enjoy this million dollar view of the historic C&D Canal at an affordable price! This 2 Bedroom, 1 bath home features a large deck, opening to a flower garden and patio, overlooking the canal. This home is 2 doors down from the entrance to the C&D Canal walking and biking trail. Other amenities include a concrete driveway, and a garden shed in a private fenced yard. The home has been

    Norman Wehner Real-Trust-Associates, LLC.

    534 Biddle St, Chesapeake City, MD 21915
  • /32

    $399,000

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

    8 Woodside Dr, Chesapeake City, MD 21915

    Welcome to this charming split-level home in the heart of Chesapeake City, MD! This home boasts 3 bedrooms and 2.1 bathrooms. This cozy residence is the perfect place to call home. Upon entering up to the main level, you will be greeted by a spacious living area with an open floor plan that is adjacent to the dining area and kitchen. The kitchen is equipped with modern appliances, granite

    Linda McKinnon Patterson-Schwartz-Newark

    8 Woodside Dr, Chesapeake City, MD 21915
  • /141

    $29,800,000

    • 4 Beds
    • 5 Baths

    1455 Cayots Corner Rd, Chesapeake City, MD 21915

    Rarely... does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is

    George Hobbs Monument Sotheby's International Realty

    1455 Cayots Corner Rd, Chesapeake City, MD 21915
  • /90

    $599,800

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

    314 Bohemia Ave, Chesapeake City, MD 21915

    If you are looking for a beautifully designed Victorian home in a quaint waterfront small town with a marina, this is the one for you! This turn-key historical home has been thoughtfully designed with an Airbnb or vacation home use in mind, complete with custom decor and carefully selected antiques, to instantly transport you into another world. Only steps from the small town of Chesapeake City

    Stephanie Torres Contigo Real Estate

    314 Bohemia Ave, Chesapeake City, MD 21915
  • /34

    $559,900

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

    26 Wallamsey Ln, Chesapeake City, MD 21915

    ***Motivated Seller***Don’t miss out on this stunning log cabin nestled in a water-oriented community that offers a private beach, boat ramp, mooring, and dock, plus 99 acres of scenic community land, tennis and basketball courts. This impressive home spans over 3,000 finished square feet and exudes rustic charm with its authentic log construction, gleaming hardwood floors, and soaring

    Iris Cong BHHS Fox & Roach - Hockessin

    26 Wallamsey Ln, 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
  • /24

    $105,000

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

    23 Buddy Blvd, Chesapeake City, MD 21915

    Welcome Home to this 3 bedroom, 2 bath home located in Chesapeake Estates complete with a beautiful front deck and side deck . Enter into the large living room with bay window, the beautiful open floor plan flows into the kitchen and dining room with a wood burning fire place and slider to garden and shed area. The master suite offers a large master bath with a large tub, stand up shower, and

    Stacie Burris Douglas Realty, LLC

    23 Buddy Blvd, Chesapeake City, MD 21915
  • /36

    $289,000 Open Thu 5:30PM - 7:30PM

    • 2 Beds
    • 1 Bath
    • 1,192 Sq Ft

    535 Biddle St, Chesapeake City, MD 21915

    Welcome to 535 Biddle Street, Chesapeake City, MD! Available for showings Thursday 8/28. OPEN HOUSE Thursday 8/28 5:30pm-7:30pm. This charming two-bedroom home offers the perfect blend of historic character and small-town charm with modern updates throughout all with a partial view of the C&D Canal! The home features a newly renovated kitchen, designed with both style and functionality in mind.

    Annabelle Charlton Foraker Realty Co.

    535 Biddle St, Chesapeake City, MD 21915

Frequently Asked Questions

What are the most popular zip codes in Chesapeake City, MD?
The most popular zip codes in Chesapeake City, MD include 21915, 21921, 19709, 19702 and 19701.
What are the most popular neighborhoods near Chesapeake City, MD?
The most popular neighborhoods near Chesapeake City, MD are Kirkwood, Saint Georges, Old Town, Main Street District and Bulle Rock.
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