Our website features the best real estate search for recently sold homes in Chesapeake City, MD and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.
You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.
Curious about what’s happening in the Chesapeake City, MD real estate market? Sign up for a Chesapeake City, MD Real Estate Market Report to see what’s active, under contract, and sold!
Considering selling or refinancing your home? Get an INSTANT property valuation now!
Coming soon! Showings to start June 12. There’s no place like home in charming North Chesapeake City! Just moments from the C&D Canal Trail and Schaefer’s Canal House, th...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .Amazing end-unit townhome with breathtaking unobstructed views of the C&D Canal in the North Side of Historic Chesapeake City! Offering 2,200+ sq. ft. of living space, th...
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .If you’ve ever dreamed of ending your day with a front-row seat to the sunset over the water, this home might feel like it was made for you. Welcome to 19 Tower Rd, tucke...
Listing courtesy of Patterson-Schwartz Real Estate. Contact:
Selling Office: .Bohemia River-area setting • Pond view • Ranch •Rear deck access from family room and primary bedroom • 1,961 SF main-level living • Unfinished basement with garage•Chesa...
Listing courtesy of BHHS Fox & Roach-Christiana. Contact:
Selling Office: .Charming Chesapeake City home with beautiful canal views directly across the street, offering front-row scenery of passing boats, water activity, and seasonal waterfront...
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: .PRICE ADJUSTMENT!! Step Back in Time at the Blue Max Inn Welcome to the Blue Max Inn, a charming and historic Bed & Breakfast nestled in the heart of Chesapeake City, Mar...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .Don't miss out on this charming ranch/rambler style home located in the picturesque Chesapeake City, MD. This property boasts 3 cozy bedrooms and 1 full bathroom, ideal f...
Listing courtesy of Patterson-Schwartz Real Estate. Contact:
Selling Office: .Enjoy this million dollar view of the historic C&D Canal at an affordable price! Located in Historic Chesapeake City, near shopping and dining. Just down the street fr...
Listing courtesy of Real-Trust-Associates, LLC.. Contact:
Selling Office: .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...
Listing courtesy of Sterling Real Estate LLC. Contact:
Selling Office: .REDUCED PRICE!! MOTIVATED SELLER!! Welcome to this charming ranch/rambler-style home located in the historic town of Chesapeake City, MD. This property features 3 bedroo...
Listing courtesy of Patterson-Schwartz-Newark. Contact:
Selling Office: .*** Stop by and see us this Saturday afternoon!!! Bring all offers!!!! *** Seller is including a 1 year Home Warranty! Welcome home to this beautiful 3-bedroom, 2 full...
Listing courtesy of Redfin Corp. Contact:
Selling Office: .Modernized Waterfront Living on the C&D Canal – Chesapeake City, MD This beautifully revitalized waterfront home on the C&D Canal offers a stunning transformation from d...
Listing courtesy of Patterson-Schwartz-Middletown. Contact:
Selling Office: .Welcome to this charming Colonial Traditional style home in Chesapeake City, MD! This delightful property features 3 bedrooms and 1.1 bathrooms spread across 2 levels/sto...
Listing courtesy of Patterson-Schwartz-Middletown. Contact:
Selling Office: .This 4-bedroom contemporary home is located in the water-access community of Creswell Forest. The main level features three bedrooms, while a beautiful wood spiral stairc...
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .There’s no place like home in this 3-bedroom, 2-bath ranch nestled in the water-oriented community of Harbour North! A welcoming covered front porch sets the tone as you ...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .Welcome to this charming three-story historic property ideally located one row back from the C&D Canal and within walking distance to Schaefer's Canal House Restaurant in...
Listing courtesy of Foraker Realty Co.. Contact:
Selling Office: .Tatman- Smithers House, built in 1856 and set in the heart of Chesapeake City’s beloved Historic District, 210 Bohemia Ave is the kind of home that doesn’t just tell a st...
Listing courtesy of Foraker Realty Co.. Contact:
Selling Office: .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 ra...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .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 offer...
Listing courtesy of Keller Williams Gateway LLC. Contact:
Selling Office: .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 drivewa...
Listing courtesy of VYBE Realty. Contact:
Selling Office: .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 b...
Listing courtesy of Contigo Real Estate. Contact:
Selling Office: .New Construction in South Chesapeake City
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .Historic Chesapeake City, a dream location! Nestled between homes built in the 1800's, this tremendous home was built in 2002. It fits well, having the charm of yesterye...
Listing courtesy of Patterson-Schwartz-Newark. Contact:
Selling Office: .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 sand...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .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 w...
Listing courtesy of Douglas Realty LLC. Contact:
Selling Office: .The Cooling-Coleman House is a charming historic home in the heart of Chesapeake City, offering endless possibilities. Zoned VC (Village Center), this property provides t...
Listing courtesy of Patterson-Schwartz Real Estate. Contact:
Selling Office: .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 excepti...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .Great Opportunity for this classic North Chesapeake City home on Biddle Street which parallels the C&D Canal. The home features 3 bedrooms 1 and 1/2 baths, wood floors a...
Listing courtesy of Real-Trust-Associates, LLC.. Contact:
Selling Office: .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 ...
Listing courtesy of Patterson-Schwartz-Newark. Contact:
Selling Office: .There’s no place like home! Discover your new sanctuary in this charming 3-bedroom home, nestled on just over 1.5 acres south of the canal. The living room welcomes you w...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .***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 a...
Listing courtesy of BHHS Fox & Roach - Hockessin. Contact:
Selling Office: .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 th...
Listing courtesy of Foraker Realty Co.. Contact:
Selling Office: .Lovely, detached home in quaint North Chesapeake City just a block away from the C & D Canal. A must see this home features many modern updates while keeping its early 20...
Listing courtesy of Patterson-Schwartz-Newark. Contact:
Selling Office: .FRESHLY PAINTED WHOLE EXTERIOR, GARAGE/IRON FENCING!!!!!! PHOTOS ARE GENERATED TO SHOW IDEAS!!! HOME IS CURRENTLY VACANT!!! Welcome to the Johnson-Lindsey House, a ...
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .BACK on the MARKET! Be sure to take advantage of this unusual opportunity. Welcome to the Kinter-Metz House, Circa 1854. This charming cottage is located at the corner of...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .This well-maintained manufactured home features 3 bedrooms, 2 full baths, and a rare private driveway in the Chesapeake Estates community. Recent updates include a 1-year...
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: .Remarkably exclusive waterfront home in Chesapeake City! 151 2nd Street is situated on 11 acres with 1600 feet of shoreline along the Elk River and features a private doc...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .COMPLETELY turn-key! Built in 1900 and recently updated, 2 bedroom, 1 full bath farmhouse situated in the historical waterfront town of Chesapeake City, Maryland and loca...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .Welcome to 18 Canterbury Ct in the desirable water-oriented community of Greenbrier! Homes in this peaceful, sought-after neighborhood rarely become available, so don’t m...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .Original Owner offering this charming home in downtown Chesapeake City. Plenty of character as you walk onto the front porch and into the home. The front living room ha...
Listing courtesy of RE/MAX Associates - Newark. Contact:
Selling Office: .Rare Waterfront/Waterview Gem on the C&D Canal ! – 638 Biddle St, Chesapeake City, MD – $550,000 Welcome to your dream retreat on the water! Nestled directly along the i...
Listing courtesy of Remax Vision. Contact:
Selling Office: .Discover this charming three-bedroom, two-bath rancher perfect for comfortable living and modern convenience located in a water oriented community. The updated kitchen fe...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .Welcome Home to 340 Cayots Corner! This 3 Bedroom, 1 Bathroom home has the space you need to create a life you desire. Boasting an array of sleek finishes throughout th...
Listing courtesy of Alberti Realty, LLC. Contact:
Selling Office: .Rural Chesapeake City location! Off the beaten path and in the heart of horse country, recently updated, 4 bedroom, 2 1/2 bath rancher situated on 4.19 private acres, off...
Listing courtesy of RE/MAX Chesapeake. Contact:
Selling Office: .This cute cottage is ready for you. Enjoy the peacefulness of North Chesapeake City. Close to the canal and fine dining. The owner removed a wall years ago to change the ...
Listing courtesy of Remax Vision. Contact:
Selling Office: .There’s no place like home! Welcome to your dream ranch home on over 1.3 acres in a highly sought-after location off of Town Point Road in Chesapeake City. This charming ...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .Adorable two-bedroom cottage in the water-oriented community of Hollywood Beach with a two-car garage is ready for new owners. This fabulous home has the necessary update...
Listing courtesy of Patterson-Schwartz Real Estate. Contact:
Selling Office: .Nestled in the highly sought-after Hollywood Beach community, just steps from the water, this charming three-bedroom, one-bath home is the perfect retreat for year-round ...
Listing courtesy of CENTURY 21 New Millennium. Contact:
Selling Office: .Welcome to this quaint and inviting 2-bedroom, 1-bath single-family home that offers the perfect blend of comfort and potential. Situated on nearly a quarter of an acre, ...
Listing courtesy of Keller Williams Gateway LLC. Contact:
Selling Office: .Discover the perfect blend of relaxation and outdoor fun in this charming 2-bedroom, 2-bath home, ideally located right across from the beach access in the community of T...
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .LOOK!!!! 5 Bedroom, 2 Bath, Rancher with 2 Car Garage and Full Basement on 3.31 Acres in Chesapeake City!!!! Just Outside of Town and Within 1 Mile of All Schools, Shoppi...
Listing courtesy of Key Realty, Incorporated. Contact:
Selling Office: .Motivated Seller! Experience Historic Charm with Modern Upgrades! Step into this beautifully restored early 1900s home in the heart of the sought-after Town of South Che...
Listing courtesy of Patterson-Schwartz Real Estate. Contact:
Selling Office: .PRICE REDUCED BELOW VALUE! Seller offering $25,000 seller credit for repairs (Estimates available) Live in your vacation home and take a three minute walk to the Two Rive...
Listing courtesy of VRA Realty. Contact:
Selling Office: .-- Highest and best offers by Sunday 2/16 at 5:00pm -- This beautiful 3-bedroom, 2-bathroom manufactured home sits on a desirable corner lot, offering privacy with gorgeo...
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: .Welcome to 244 Basil Ave, an inspired craftsman style new build situated on a 2.16 acre lot just outside the ever quaint Chesapeake City. A healthy walk or short bike ri...
Listing courtesy of RE/MAX Elite. Contact:
Selling Office: .Be among the lucky few who own a historic home in the much sought after south Chesapeake City, MD historic district. Nestled high above the canal, this quaint, two bedroo...
Listing courtesy of American Premier Realty, LLC. Contact:
Selling Office: .Experience true one level living in this newer ranch home close to the Elk River. OPEN LAYOUT! SUPER ROOMY BEDROOMS! 24X36 DETACHED GARAGE-ELECTRIC AND CONCRETE FLOOR...
Listing courtesy of EXIT Preferred Realty. Contact:
Selling Office: .OFFER DEADLINE, TUESDAY, 1/7 AT 5PM. There’s no place like home! Welcome to this charming 3-bedroom, 1-bathroom home in South Chesapeake City. Enjoy the ease of main-leve...
Listing courtesy of Integrity Real Estate. Contact:
Selling Office: .Beautifully maintained 3-bedroom, 2-bath ranch home with a 2-car garage in Chesapeake City, MD! This home is located in a water-oriented community just blocks from the co...
Listing courtesy of EXP Realty, LLC. Contact:
Selling Office: .This single family home is located in beautiful horse country & sits on .50 acre lot. Home features 4 bedrooms, 1 full bath, enclosed porch, living room & E/I kitchen. Ho...
Listing courtesy of RE/MAX Elite. Contact:
Selling Office: .
© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Estate Company participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Estate Company are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.