Chesapeake City, MD homes for sale & real estate

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COMING SOON

151 2nd St, Chesapeake City, MD 21915
151 2nd St, Chesapeake City, MD 21915
151 2nd St, Chesapeake City, MD 21915
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 dock with a boat lift and jet ski lift, plus a boat ramp. At low tide, the property reveals a gorgeous, massive sandy beach just around the point. Inside, the open, expansive main level features oak hardwood flooring and neutral colors that carry throughout most of the home. The large living area with wood-burning fireplace has plenty of room to gather with family and friends. The sunroom features breathtaking panoramic water views – a great spot to sit and watch the ships as they travel through the intracoastal waterway

$1,299,900

3 beds2.5 baths2,328 sq ft

151 2nd St, Chesapeake City, MD 21915

11 acre lot • 2 garage spots • Built 1995

(410) 398-9200

317 George St, Chesapeake City, MD 21915
317 George St, Chesapeake City, MD 21915
317 George St, Chesapeake City, MD 21915
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 yesteryears but the conveniences of today. The covered porch is large and inviting, room for parties/ social gatherings and a rear enclosed private patio were the builders favorites. The main floor offers a unique living room with cathedral ceiling, fireplace with restored woodwork and built in shelves for displaying/storage. Kitchen/Dining/Sitting room is all open and is the HUB of the house. Loads of cabinets, corian countertops and wonderful built in computer/office area. Owners suite includes two walk in closets and private bat

$629,000

3 beds3.5 baths3,792 sq ft

317 George St, Chesapeake City, MD 21915

4,792 sq ft lot • 2 garage spots • Built 2002

(302) 733-7000

314 Bohemia Ave, Chesapeake City, MD 21915
314 Bohemia Ave, Chesapeake City, MD 21915
314 Bohemia Ave, Chesapeake City, MD 21915
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 along the famous C & D Canal, you can enjoy the many town events, shops, cafe, waterfront restaurant, ice cream shop, marina, and more! This home has been carefully renovated to make it shine and have modern conveniences while maintaining its Victorian charm. The wrap-around front porch welcomes

$599,800

5 beds2 baths2,687 sq ft

314 Bohemia Ave, Chesapeake City, MD 21915

6,272 sq ft lot • 2 parking spots • Built 1850

(717) 826-9758

1455 Cayots Corner Rd, Chesapeake City, MD 21915
1455 Cayots Corner Rd, Chesapeake City, MD 21915
1455 Cayots Corner Rd, Chesapeake City, MD 21915
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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 synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class

$29,800,000

4 beds4 baths— sq ft

1455 Cayots Corner Rd, Chesapeake City, MD 21915

Exercise room • Equestrian facility • Wide-plank staircase

(302) 654-6500

4 Mallard Dr, Chesapeake City, MD 21915
4 Mallard Dr, Chesapeake City, MD 21915
4 Mallard Dr, Chesapeake City, MD 21915
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
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-old hot water heater, 7-year-old roof on both the home and shed, and a 3-year-old washer. Lot rent is $789/month and covers water, sewer, and trash pickup. The landscaped yard offers mature plants, trees, and vines for added privacy and a tranquil setting, plus a shed for storage. Conveniently located near marinas, restaurants, and historic downtown Chesapeake City. Schedule your tour today!

$86,999

3 beds2 baths1,000 sq ft

4 Mallard Dr, Chesapeake City, MD 21915

Mature plants • Private driveway • Near restaurants

(410) 879-8080

Property at 26 Wallamsey Ln, Chesapeake City, MD 21915, 3 beds, 2.5 baths

$589,900

3 beds2.5 baths3,145 sq ft

26 Wallamsey Ln, Chesapeake City, MD 21915

(302) 999-9999

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 306 Bohemia Ave, Chesapeake City, MD 21915, 4 beds, 1.5 baths

$515,000

4 beds1.5 baths2,176 sq ft

306 Bohemia Ave, Chesapeake City, MD 21915

(410) 885-2200

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

$99,900

3 beds2 baths1,568 sq ft

3 Buddy Blvd, Chesapeake City, MD 21915

(410) 398-3434

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

$1,198,000

4 beds3 baths2,016 sq ft

19 Tower Rd, Chesapeake City, MD 21915

(410) 275-2118

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

Property at 23 Buddy Blvd, Chesapeake City, MD 21915, 3 beds, 2 baths

$105,000

3 beds2 baths1,680 sq ft

23 Buddy Blvd, Chesapeake City, MD 21915

(410) 255-3690

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Nearby homes that match your criteria

NEW 25 HRS AGO

209 Casparus Way, Elkton, MD 21921
209 Casparus Way, Elkton, MD 21921
209 Casparus Way, Elkton, MD 21921
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Location, Location, Location! Welcome to your waterfront paradise—2.5 stunning acres on the Elk River with unmatched views and endless potential! Start your mornings with breathtaking sunrises from the deck, relax on your private beach at low tide, or head out on the water from your private dock—perfect for boating, jet skis, and exploring the Chesapeake Bay. This 5-bedroom, 2-bath home offers a spacious open floor plan centered around a massive great room with floor-to-ceiling brick fireplace and panoramic river views. The primary suite features an en-suite bath and walk-in closet, while four additional bedrooms provide plenty of space for family or guests. The lower level is u

$1,599,000

5 beds2 baths2,916 sq ft

209 Casparus Way, Elkton, MD 21921

Private beach • Private dock • Massive great room

(302) 453-3200

OPEN SAT, 10AM TO 6PM

437 Crownleaf Dr, Middletown, DE 19709
437 Crownleaf Dr, Middletown, DE 19709
437 Crownleaf Dr, Middletown, DE 19709
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
* SUMMER SAVINGS HAPPENING NOW! * Say hello to 437 Crownleaf Drive, our stunning Emerson Farmhouse! Step in off your front porch and be greeted by a grand double story entry way with your formal dining room off to one side, and home office on the other. Moving inward, an open layout seamlessly connects the double story family room with cozy fireplace, gourmet kitchen (complete w/ quartz counters, tile backsplash, and upgraded cabinetry), and included morning room, creating an ideal setting for gatherings. Additionally, on the first level you will find a spacious flex room and laundry room with included Whirlpool washer and dryer! The upper-level features 3 guest bedrooms, a hall bath, and

$768,457

4 beds3.5 baths4,202 sq ft

437 Crownleaf Dr, Middletown, DE 19709

Formal dining room • Gourmet kitchen • Cozy fireplace

(856) 424-3339

34 Bay Blvd, Newark, DE 19702
34 Bay Blvd, Newark, DE 19702
34 Bay Blvd, Newark, DE 19702
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
COMING SOON - Beautiful home located in desirable Bay Point community in the Appoquinimink school district. You will know this is the one from the moment you walk through the door. As you enter the Grand Foyer you are greeted by hard wood flooring which spans through the foyer, office, kitchen, dining room, sunroom living room and sitting room. Located to your left is a private office with French style doors. To the right is a living room that flows into the dining room. From the dining room, or the living room, you can enter the sunroom with 2 sets of French style doors and could also be used as a second office. You'll enjoy cooking in the open kitchen with double wall oven, lots of cabine

$845,000

4 beds3.5 baths4,675 sq ft

34 Bay Blvd, Newark, DE 19702

0.75 acre lot • 3 garage spots • Pool

(302) 285-5100

104 Dungarvan Dr, Middletown, DE 19709
104 Dungarvan Dr, Middletown, DE 19709
104 Dungarvan Dr, Middletown, DE 19709
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Welcome to 104 Dungarvan Dr, a true gem of a home with charm and beauty, located in one of the most exclusive and sought-after communities in Middletown, DE. The curb appeal, accented by mature trees and a stunning brick exterior with classic shutters flanking the windows, makes for a glowing first impression. The one-acre lot offers privacy and sprawling usable space while still maintaining a community feel in the premier and coveted Chesterfield neighborhood, where homes are rarely available. Upon entering through the front door, you will immediately be captivated by the charm of the cased openings and ornate crown molding. To the left of the foyer, a formal living space features the same

$620,000

4 beds2.5 baths2,725 sq ft

104 Dungarvan Dr, Middletown, DE 19709

1 acre lot • 2 garage spots • Built 1990

(302) 688-7653

79 Riverview Ave, Earleville, MD 21919
79 Riverview Ave, Earleville, MD 21919
79 Riverview Ave, Earleville, MD 21919
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Recent upgrades have made this Fantastic. .. Home on a TRIPLE lot in sought after Community of Hacks Point ever more attractive. This 3br , 1 bath home is the Perfect summer get away that is Being Sold AS-IS! Featuring Waterviews as well as communtiy beach, swim area along the beaches to enjoy breathtaking views and is also walking distance to 5 Marina's. HOA - Dues are voluntary and only $125.00 a year and include a nice community hall up the street that was recently renovated! The lot is actually 3 seperate parcels that is all being sold as 1 including the home. Prime location for boaters of any caliber from kayaking to motor boating to sailing the Chesapeake Bay!

$299,900

3 beds1 bath994 sq ft

79 Riverview Ave, Earleville, MD 21919

5,140 sq ft lot • 8 parking spots • Built 1935

(302) 426-2211

VIDEO TOUR

28 S Shore Rd, Elkton, MD 21921
28 S Shore Rd, Elkton, MD 21921
28 S Shore Rd, Elkton, MD 21921
ABOUT THIS HOME
Chesapeake City, MD Homes for Sale
Waterfront Living + Income/Guest Potential on the C & D Canal. Welcome to your private oasis—4285 sq ft Water Front Rancher with 3 Beds | 2 Baths, plus a 696 sq ft Carriage House with 1 Bed | 1 Bath. Both are situated on nearly an acre of land with commanding waterfront canal views, a sandy swim beach, and a deep-water dock equipped with two 10,000-lb lifts. Watch the big ships come up and down the C & D Canal. The Main Residence is located at 28 Shore and features a fresh paint job in designer neutrals, complemented by new luxury vinyl plank flooring throughout. The Water-view Primary Suite – wake up to sunrise over the Canal, enjoy dual walk-in closets, and unwin

$1,250,000

3 beds2 baths4,285 sq ft

28 S Shore Rd, Elkton, MD 21921

Sandy swim beach • Deep-water dock • Waterfront living

(410) 885-1606

Property at 733 Mckinneytown Rd, North East, MD 21901, 4 beds, 2.5 baths

$599,888

4 beds2.5 baths2,404 sq ft

733 Mckinneytown Rd, North East, MD 21901

(410) 705-2565

Property at 609 Channel Ct, Newark, DE 19702, 4 beds, 2.5 baths

$825,000

4 beds2.5 baths3,775 sq ft

609 Channel Ct, Newark, DE 19702

(302) 688-7653

Property at 114 Saint Augustine Ct, Middletown, DE 19709, 5 beds, 3.5 baths

$749,995

5 beds3.5 baths3,775 sq ft

114 Saint Augustine Ct, Middletown, DE 19709

(888) 543-4829

Property at 12 Riverview Ave, Earleville, MD 21919, 3 beds, 1.5 baths

$429,000

3 beds1.5 baths1,840 sq ft

12 Riverview Ave, Earleville, MD 21919

(410) 697-8100

Property at 24 Ferry Point Ln, Earleville, MD 21919, 4 beds, 3 baths

$649,000

4 beds3 baths2,558 sq ft

24 Ferry Point Ln, Earleville, MD 21919

(410) 398-9200

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 329 Bronzeleaf Dr W, Middletown, DE 19709, 4 beds, 2.5 baths

$669,900

4 beds2.5 baths2,955 sq ft

329 Bronzeleaf Dr W, Middletown, DE 19709

(856) 424-3339

Property at 64 S Shore Rd, Elkton, MD 21921, 3 beds, 2.5 baths

$714,999

3 beds2.5 baths1,712 sq ft

64 S Shore Rd, Elkton, MD 21921

(302) 368-1621

Property at 1487 Bunker Hill Rd, Middletown, DE 19709, 3 beds, 2.5 baths

$858,242

3 beds2.5 baths2,426 sq ft

1487 Bunker Hill Rd, Middletown, DE 19709

(302) 533-8606

Property at 1481 Bunker Hill Rd, Middletown, DE 19709, 4 beds, 3.5 baths

$1,188,918

4 beds3.5 baths3,345 sq ft

1481 Bunker Hill Rd, Middletown, DE 19709

(302) 533-8606

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

$621,990

4 beds2.5 baths2,879 sq ft

TBD Mckinneytown Rd, North East, MD 21901

(410) 705-2565

Property at Shagbark Ln, Elkton, MD 21921

$99,000

— beds— baths— sq ft

Shagbark Ln, Elkton, MD 21921

(410) 287-3629

Property at LOT 2 Old Elk Neck Rd, North East, MD 21901

$94,900

— beds— baths— sq ft

LOT 2 Old Elk Neck Rd, North East, MD 21901

(410) 287-8080

Property at Glebe Rd, Earleville, MD 21919

$105,000

— beds— baths— sq ft

Glebe Rd, Earleville, MD 21919

(410) 287-8080

Average home prices near Chesapeake City, MD

Cities

Zip Codes

21915 homes for sale
$434,450

Chesapeake City, MD real estate trends

$603K

Sale price

+22.7%
since last year

$226

Sale $/sq ft

-19.4%
since last year

Under list price

3.3%

Days on market

Down payment

—

Total homes sold

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