Chesapeake City, MD homes for sale & real estate

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ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 lighting, LVP flooring, crown moldings, and so much more. The main living space boasts an open concept living room with a wood burning fireplace, a dining room with sliding doors to a screened in porch and a stunning kitchen. A door from the dining room gives you access to a mudroom with laundry, the ga

$599,900

4 beds3 baths3,600 sq ft

288 Randalia Rd, Chesapeake City, MD 21915

Covered front porch • Screened in porch • Newly paved driveway

(410) 220-4648

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Welcome to 321 Cecil St, Chesapeake City, MD. Step 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 busiest canals in the world. Watch ships and barges pass by from around the globe! Built in 1874, this nearly 2,000 sq. ft. home (only $171/sq. ft. !) blends timeless character with modern updates. The renovated kitchen and bathroom provide convenience and style, while the cozy private fenced backyard, 2-car detached garage, and additional shed add both charm and practical

$325,000

3 beds1.5 baths1,896 sq ft

321 Cecil St, Chesapeake City, MD 21915

9,016 sq ft lot • 2 garage spots • Built 1874

(410) 287-3629

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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. Just beyond lies the spectacular Great Room, showcasing a soaring cathedral ceiling, a stone fireplace with a wood-burning insert, and breathtaking panoramic views of the water—offering a front-row seat to ships passing through the Intracoastal Waterway. The updated kitchen

$1,299,900

3 beds3 baths3,867 sq ft

87 Deer Run, Chesapeake City, MD 21915

Sandy beach • Propane fireplace • Elk river waterfront

(410) 398-9200

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 insulated and has modern windows, a modern furnace and hot water heater. Lots of potential!

$379,900

2 beds1 bath1,200 sq ft

534 Biddle St, Chesapeake City, MD 21915

Large deck • Modern furnace • Modern windows

(410) 287-1260

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 kitchen, complete with granite counters, stainless steel appliances, cream cabinetry, and barstool seating area. The versatile dining space is set off by a three-sided fireplace and can serve just as perfectly a breakfast spot for morning coffee as it can for dinner. Room for you and your guests is

$1,179,000

3 beds3.5 baths3,457 sq ft

64 Shipwatch Ln, Chesapeake City, MD 21915

3.6 acre lot • 2 garage spots • Built 1994

(410) 398-9200

Property at 1455 Cayots Corner Rd, Chesapeake City, MD 21915, 4 beds, 4 baths

$29,800,000

4 beds4 baths— sq ft

1455 Cayots Corner Rd, Chesapeake City, MD 21915

(302) 654-6500

Property at 314 Bohemia Ave, Chesapeake City, MD 21915, 5 beds, 2 baths

$599,800

5 beds2 baths2,687 sq ft

314 Bohemia Ave, Chesapeake City, MD 21915

(717) 826-9758

Property at 19 Tower Rd, Chesapeake City, MD 21915, 4 beds, 3 baths

$1,075,000

4 beds3 baths2,016 sq ft

19 Tower Rd, Chesapeake City, MD 21915

(410) 275-2118

Property at 53 Pleasure Shores Cir, Chesapeake City, MD 21915, 4 beds, 2 baths

$799,900

4 beds2 baths1,600 sq ft

53 Pleasure Shores Cir, Chesapeake City, MD 21915

(855) 456-4945

Property at 280 Hollywood Beach Rd, Chesapeake City, MD 21915, 6 beds, 5.5 baths

$1,200,000

6 beds5.5 baths3,757 sq ft

280 Hollywood Beach Rd, Chesapeake City, MD 21915

(302) 479-9600

Property at 3 Buddy Blvd, Chesapeake City, MD 21915, 3 beds, 2 baths

$99,000

3 beds2 baths1,568 sq ft

3 Buddy Blvd, Chesapeake City, MD 21915

(410) 398-3434

Property at 300 Bohemia Ave, Chesapeake City, MD 21915, 9 beds, 10 baths

$1,489,000

9 beds10 baths7,044 sq ft

300 Bohemia Ave, Chesapeake City, MD 21915

(410) 398-9200

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ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Nestled in the serene community of Pembrey, this exquisite ranch-style residence offers a luxurious lifestyle defined by its stunning water features and unparalleled access to the Elk River. Spanning over 1.55 acres, this property is a true sanctuary. As you approach the home, the charming brick and vinyl siding exterior invites you in, while the meticulously landscaped grounds set the stage for a tranquil retreat. Step inside to discover a thoughtfully designed layout that maximizes space and natural light. With 2,476 square feet of finished living area, this home boasts three spacious bedrooms and two full bathrooms, providing ample room for relaxation and entertainment. The heart of this

$525,000

3 beds2 baths2,476 sq ft

20 Lance Ct, Elkton, MD 21921

1.55 acre lot • $23 HOA • 2 garage spots

(610) 869-8711

OPEN SAT, 11AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
If you are looking for luxury, privacy and a blend of traditional spaces with great entertainment potential 67 Bay Boulevard has ALL this and MUCH more. This stunning home sits on just over 1.4 acres in the highly sought-after Bay Pointe community, consisting of only 100 luxury homes on spacious lots. You'll immediately notice the exceptional care and craftsmanship that has gone into this home from the moment you arrive. The meticulously landscaped grounds lead you up the expansive driveway to a three-car garage. A stone paver walkway takes you to an elegant covered front porch. Step inside and you’re greeted by a two-story grand foyer that sets the tone for the elegance found throu

$850,000

5 beds3 baths3,600 sq ft

67 Bay Blvd, Newark, DE 19702

1.42 acre lot • $38 HOA • 3 garage spots

(302) 299-1100

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Spectacular opportunity to make this spacious home your own. Located a block from the river in Hack's Point, you will enjoy deeded water rights. Use as a vacation home or vacation all year around. Conveniently located easy commuting distances to Dover, Wilmington, Newark or Aberdeen. Just over an hour to Philadelphia, Baltimore & Annapolis. This large home is well appointed and includes 4 bedrooms, 3 1/2 baths upper and lower living areas. This home can easily accommodate multigenerational living if desired. There is a frond porch, a back deck and a balcony, nicely sized lot. Bring the boat, bring the toys- plenty of parking in the garage, the driveway and yard! This is a fantastic ar

$420,000

4 beds3.5 baths2,678 sq ft

80 Parkside Dr, Earleville, MD 21919

7,841 sq ft lot • 2 garage spots • Car-dependent

(410) 275-8101

OPEN SAT, 10AM TO 6PM

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
* Now selling final homes for 2025! * This stunning 4-bedroom, 3.5-bath home with 3,900+ sq. ft. of thoughtfully designed living space won’t be available for long! From the moment you step onto the welcoming front porch and into the grand double-story entryway, you’ll feel the difference this home makes. A formal dining room sets the stage for memorable gatherings, while the open-concept family room with a cozy fireplace flows seamlessly into the gourmet kitchen—complete with quartz countertops, tile backsplash, upgraded cabinetry, and an included morning room for extra light and space. The first level also features a private home office and spacious mudroom, designed fo

$729,000

4 beds3.5 baths2,955 sq ft

447 Crownleaf Dr, Middletown, DE 19709

0.63 acre lot • $50 HOA • 2 garage spots

(856) 424-3339

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Deepwell Farm is a gorgeous 57+/- acre working horse farm near the waterfront Maryland village of Chesapeake City. Just 15 minutes to Interstate 95, convenient to Baltimore, Philadelphia and their suburbs. The farm is currently laid out as boarding, training, breeding, and Hunter/Jumper show facility, but suitable for numerous other disciplines. The horse facilities include 30 stalls in several different barns, one being a beautiful center isle training barn with a covered 6 horse Eurociser and nearby 100 x 200 indoor arena. Additional 150 x 350 outdoor arena, extensive pastures and paddocks with 15 run-in sheds, riding trails about the farm and through the woods. The property has 3 income

$1,899,000

5 beds3.5 baths7,452 sq ft

2 Preakness Pl, Warwick, MD 21912

57.81 acre lot • 2 garage spots • Pool

(410) 885-1606

ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
This well maintained residence offers a spacious two bedrooms and two baths, plus a versatile bonus room on the lower level with a walk out and bathroom rough in, perfect for a home office, guest suite, or entertainment space. The over-sized two car garage provides ample storage and convenience, all situated on a generous . 83 acre wooded lot with a large shed and large rear deck. The home features a brand (2025) new roof and new HVAC system in 2022, ensuring peace of mind and added durability. Well-cared for and move-in ready, this property combines comfort, functionality, and charm. Don’t miss your chance to own a stunning home in a tranquil setting—schedule your private tour

$375,000

2 beds2 baths1,695 sq ft

32 Crestwood Dr, Elkton, MD 21921

0.83 acre lot • 2 garage spots • Car-dependent

(410) 287-8080

Property at 83 Trent Rd, Elkton, MD 21921, 4 beds, 2.5 baths

$547,000

4 beds2.5 baths2,352 sq ft

83 Trent Rd, Elkton, MD 21921

(410) 287-8080

Property at 457 Crownleaf Dr, Middletown, DE 19709, 4 beds, 3.5 baths

$629,800

4 beds3.5 baths2,857 sq ft

457 Crownleaf Dr, Middletown, DE 19709

(856) 424-3339

Property at 102 Dungarvan Dr, Middletown, DE 19709, 4 beds, 4 baths

$625,000

4 beds4 baths4,125 sq ft

102 Dungarvan Dr, Middletown, DE 19709

(302) 285-5100

Property at 727 Mckinneytown Rd, North East, MD 21901, 4 beds, 2.5 baths

$599,888

4 beds2.5 baths2,848 sq ft

727 Mckinneytown Rd, North East, MD 21901

(410) 705-2565

Property at 230 Mckinneytown Rd, North East, MD 21901, 5 beds, 3 baths

$369,900

5 beds3 baths3,054 sq ft

230 Mckinneytown Rd, North East, MD 21901

(410) 287-0037

Property at 1039 Old Elk Neck Rd, Elkton, MD 21921, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths2,050 sq ft

1039 Old Elk Neck Rd, Elkton, MD 21921

(717) 461-7201

Property at 135 Ayshire Dr, Middletown, DE 19709, 5 beds, 4 baths

$1,079,997

5 beds4 baths5,658 sq ft

135 Ayshire Dr, Middletown, DE 19709

(888) 543-4829

Property at 137 Elk Ranch Park Rd, Elkton, MD 21921, 4 beds, 3 baths

$1,050,000

4 beds3 baths3,174 sq ft

137 Elk Ranch Park Rd, Elkton, MD 21921

(703) 242-0005

Property at 85 Clearfield Ct, Elkton, MD 21921, 5 beds, 5 baths

$950,000

5 beds5 baths6,413 sq ft

85 Clearfield Ct, Elkton, MD 21921

(301) 652-0643

Property at 209 Casparus Way, Elkton, MD 21921, 5 beds, 2 baths

$1,475,000

5 beds2 baths2,916 sq ft

209 Casparus Way, Elkton, MD 21921

(302) 453-3200

Property at 34 Bay Blvd, Newark, DE 19702, 4 beds, 3.5 baths

$845,000

4 beds3.5 baths4,675 sq ft

34 Bay Blvd, Newark, DE 19702

(302) 285-5100

Property at 40 Lower Beach Dr, North East, MD 21901, 3 beds, 1 bath

$549,000

3 beds1 bath1,111 sq ft

40 Lower Beach Dr, North East, MD 21901

(410) 287-8080

Property at 113 Anna Ct, Middletown, DE 19709, 4 beds, 4.5 baths

$799,990

4 beds4.5 baths5,925 sq ft

113 Anna Ct, Middletown, DE 19709

(302) 285-5100

Property at 39 Wood Chip Rd, Elkton, MD 21921

$94,000

— beds— baths— sq ft

39 Wood Chip Rd, Elkton, MD 21921

(410) 885-1606

Average home prices near Chesapeake City, MD

Cities

Zip Codes

21915 homes for sale
$699,900

Chesapeake City, MD real estate trends

$285K

Sale price

+3.6%
since last year

$264

Sale $/sq ft

-17.2%
since last year

Under list price

3.3%

Days on market

Down payment

—

Total homes sold

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