Chesapeake City Real Estate, Homes and Condos for sale

All Chesapeake City homes currently listed for sale in Chesapeake City as of 07/22/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Chesapeake City homes for sale or other Chesapeake City real estate, please contact us and one of our knowledgeable Chesapeake City REALTORS® would be pleased to assist you.


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$935,000
7 BLUFF RD, Chesapeake City MD 21915
4
BEDS
2
BATHS
3,200
SQFT
$292
$/SQFT
0.86
ACRES
1962
BUILT
"This Elk River 4 bdr ranch with a 3 car garage,offers a spacious 4 season sun porch,outdoor patio, remodeled kitchen and baths, hardwood floors, 2 fireplaces and most of all a beautiful view of the Elk River with sunsets. Sloping lawn to a sandy beach plus 200' dock with 3 boat lifts, jet ski lift and new boat shed.This gem is located in a quiet community of North Bluff and only minutes to Chesapeake City by boat or car."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $980,000 TO $935,000 
$899,000
333 WALNUT DR, Chesapeake City MD 21915
6
BEDS
6
BATHS
10,300
SQFT
$87
$/SQFT
14.23
ACRES
1998
BUILT
"This is a MUST SEE! 6-7 bedrooms, 5.5 baths, in-ground pool, indoor basketball court, all on 14+ acres in beautiful downtown Chesapeake City! This home is situated on a private wooded setting and is over 10,000 square feet. So many possibilities! This home even has an in-law suite with a kitchen, living area, eating area, two bedrooms lots of closet space and a full bath as well! Please call to set up a showing."
* LISTED OVER 120 DAYS 
$750,000
135 PORT HERMAN RD, Chesapeake City MD 21915
4
BEDS
5
BATHS
5,263
SQFT
$143
$/SQFT
3.23
ACRES
1997
BUILT
"Beautiful, custom estate home in Port Herman overlooking the river. The home is situated down a long driveway for privacy! There are oak floors on three levels of the home and custom woodwork throughout. The first floor has a large kitchen for entertaining and both the library and the formal living room have wood burning fireplaces. Rounding out the first floor is a Florida room, a formal dining room, a breakfast room with a wet bar, an office with a separate entrance, and a grand foyer with a curved stairway to the second floor. The second floor has a large master with an en suite bath and walk in closet as well as three other bedrooms and two more bathrooms. The bonus room over the garage is finished with oak flooring and has a separate entrance from the outside. The third floor also has oak flooring and has room for a game room or overflow guest space. This property must be seen to be appreciated. There is an adjacent perced 10 acre parcel with an outbuilding/barn also available for $200,000."
$649,900
21 PORT HERMAN DR, Chesapeake City MD 21915
3
BEDS
3
BATHS
2,902
SQFT
$224
$/SQFT
0.30
ACRES
1995
BUILT
"Condominium ownership with flexibility. Open spaces are taken care of, but you can do your flower beds to suit you and outdoor maintenance is by the homeowner. House is detached so you can be apart from everyone else and enjoy the peace and quiet of the Villas. A beautiful beach, outdoor deck and pavilion await you. Enjoy your own boat slip, slip #5 with 10,000 lbs lift, slip will hold a 25-30 foot boat. The monthly Condo Fee is $390 and there are no capital projects scheduled. Come and walk along the beach and get a real feel for this beautiful waterfront community along the Elk River. House boasts a main floor set of bedrooms and 2 full baths. The Master bedroom has a seating area and opens to a wonderful screened in porch. The master bath is open and airy with jetted tub and stall shower along with granite counters and two sinks. The basement is finished, large laundry area with storage, a lower family room exists and also a room used for exercise equipment. As you work your way to the upper level, the views are simply beautiful. Kitchen and upper family room are on hardwood floors and are open and airy. As you sit at the dining room table you are greeted with the open cathedral ceiling of the living room. And as if to tease you to come to the open air, the living area opens to a spacious second story open yet covered deck to enjoy the beautiful views of the elk river. Simply a must see property. Lots to love!!"
$459,000
2 SHADY DR, Chesapeake City MD 21915
3
BEDS
3
BATHS
2,073
SQFT
$221
$/SQFT
32.56
ACRES
1980
BUILT
"Cute Cape Cod Water Front Home On Herring Creek, Great For Kayaks And Fishing ~ Sale Includes The House With Over 36 Acres Of Beautiful Wildlife Sanctuary! Oversized Garage And Shop Has 2 Front Facing Garage Doors And A Machine Bay In The Rear. Older Home In Need Of Updates, Make It Your Own Paradise. CALL FOR A SHOWING! 443-553-2256"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $495,000 TO $459,000 
$399,999
56 VANDERLYN DR, Chesapeake City MD 21915
3
BEDS
3
BATHS
2,764
SQFT
$145
$/SQFT
1.75
ACRES
1995
BUILT
"Welcome to your new home in this contemporary custom ranch on large private lot in desirable community! From the open-concept kitchen and living space with vaulted ceilings to the large deck overlooking the shaded backyard with mature trees, there is plenty of room and privacy for all to enjoy. The single level open architecture makes this house ideal for entertaining and spending time with family. Bonus feature-large addition not pictured could be used as second master, fourth bedroom, family game room or whatever your family desires! Large windows and doors provide ample natural light to the interior of the home. Bring your boat and toys, the three-car garage has plenty of storage, not including the workshop in the partial basement. Situated in a quiet, water-oriented neighborhood just off the Elk & Bohemia Rivers, this home is truly one of a kind."
* PRICE LOWERED - $410,000 TO $399,999 
$359,900
824 MOUNT NEBO RD, Chesapeake City MD 21915
3
BEDS
2
BATHS
1,972
SQFT
$183
$/SQFT
2.48
ACRES
1925
BUILT
"The owner spared no expense in this home. Gutted down to the studs. Gorgeous modern farmhouse. Beautiful hardwood flooring. Amazing staircase. Gorgeous cherry cabinets, built in window seats with butcher block cutting, featuring Corian counter tops. Featuring an awesome walk in pantry. Large laundry/mud room. Both bathrooms, feature tiled flooring & tiled surround with glass doors. Imagine yourself spending hours on the wrap around porch, having bonfires. Walk to restaurants, marina & boutiques. Dreamed of living in a water front town? This could be the one."
$342,900
95 PORT HERMAN DR #7B, Chesapeake City MD 21915
2
BEDS
2
BATHS
1,200
SQFT
$286
$/SQFT
1987
BUILT
"This is a charming 2-bedroom, 2-bath very recently updated condo on the beautiful inter-coastal waterway! See the ships pass by as you relax on your second-floor veranda. Port Herman Condominiums, such a wonderful place to enjoy the peace and quiet of Maryland's Eastern Shore. Port Herman, with her beach and pier await you as you wander down to the sandy shore to experience all the wonder of the area. Remember, you are close to three major highways, Route 40, Route I-95 and Route US 301. Close to Delaware for tax free shopping too! The condo boasts fresh paint, carpet and numerous upgrades. As the nights get cooler, come in and enjoy the warm glow of the fireplace. When friends arrive and want to head out to dinner, you have choices! Stop out to Chesapeake City for the restaurants and the shops or head down to the Sassafras River for some enjoyable local fare, either way, this area has many destinations for your enjoyment and fulfillment. Call today to schedule your tour!"
* NEW LISTING 
$328,000
100 BIDDLE ST, Chesapeake City MD 21915
4
BEDS
1
BATHS
1,470
SQFT
$223
$/SQFT
0.01
ACRES
1900
BUILT
"This listing is for 100 and 106 Biddle Street plus an unimproved lot in between the two home. #100 is a 2 story 4 BR home, #106 is a ranch with 3 BR on a corner lot. Canal views from all 3 properties. Easy access to Schaefer's Canal House and the canal bike trail."
$300,000
1197 TOWN POINT RD, Chesapeake City MD 21915
3
BEDS
2
BATHS
2,012
SQFT
$149
$/SQFT
1.70
ACRES
1986
BUILT
"Beautiful, spacious 3 bedroom, 2 bath home in a country setting, close to marinas. Updated appliances, flooring, HVAC, hot water heater, etc! You don't want to miss this out! Schedule your tour today!"
$299,000
108 GEORGE ST, Chesapeake City MD 21915
2
BEDS
2
BATHS
1,692
SQFT
$177
$/SQFT
0.04
ACRES
2007
BUILT
"NEW PRICING $299,000.00. Beautiful canal views. So many potential uses for this property. Property includes 2nd floor apt. w/separate entrance. Apt. rental history has remained consistent yearly. Hardwood floors in great condition. 2 kitchens with 2 stainless steel refrigerators, 2 stoves, 2 microwaves, 2 dishwashers, 2 washer/dryers. BRING ALL OFFERS"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $320,000 TO $299,000 
$289,000
208 GEORGE ST, Chesapeake City MD 21915
3
BEDS
2
BATHS
1,656
SQFT
$175
$/SQFT
0.03
ACRES
1896
BUILT
"Business and Home! Storefront/Office w/spacious rental / residence 2BR, 1BA, w/ W/D on 2nd FL. Partial Waterview of C & D upstairs! Approx. 16' x 61' Bldg, open floor plan, back entrance for 2nd FL Rental, with History! Don't miss! Call for your showing today!"
$269,000
58 WOODSIDE DR, Chesapeake City MD 21915
3
BEDS
2
BATHS
1,333
SQFT
$202
$/SQFT
0.34
ACRES
2001
BUILT
"Beautifully maintained, open-floor plan inviting contemporary rancher in popular water-oriented community of Harbour View/Elk River Basin. Perfect get-away house or comfortable year-round residence. Short walk to neighborhood water-access area with picnic tables, canoe/kayak storage racks and ramp. Large marina next door. Five minutes away from restaurants, shops and entertainment in historic downtown Chesapeake City. Master bath with whirlpool tub and separate shower. Rear deck, shed and play-equipment area. Home pre-wired for home generator. New detached Amish-built garage. Nice basement drywalled, wired for ceiling lights, freshly painted, and ready for final finishing. Includes separate workshop area. Water filter and conditioner. Sump pump with power-fail backup. Neighborhood has summer mosquito spraying and winter snow removal."
$264,900
16 HARBOR RD, Chesapeake City MD 21915
4
BEDS
2
BATHS
1,764
SQFT
$150
$/SQFT
0.34
ACRES
1988
BUILT
"Ready for summer? Bring your boat, kayak or paddle boards! Come see this renovated 4 bedroom home featuring 2 full baths, wood flooring, granite counter tops and more! Water access community which includes a boat ramp, sandy beach and a community area. Bar and Restaurant in community. Minutes from the town of Chesapeake City. USDA financing available, buy with $0 down!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $269,000 TO $264,900 
$250,000
2640 AUGUSTINE HERMAN HWY, Chesapeake City MD 21915
2
BEDS
1
BATHS
954
SQFT
$262
$/SQFT
16.00
ACRES
1952
BUILT
"Total of approximately 17.4+/- Acres Chesapeake City. This property includes Parcels: 164; 163; 207; 223 & 225 for a total of approximately 17.4+/- Acres. This brick ranch is situated on .5790+/- acres. Cyclone fenced area behind house. Living room features wood burning fireplace with mantle. Wood floors throughout except kitchen has tile flooring. All appliances included. Full unfinished basement with walk out door. This would be great for hunters, wild life and nature lovers, etc. Lots of woods for your enjoyment."
$250,000
67 WOODSIDE DR, Chesapeake City MD 21915
3
BEDS
2
BATHS
1,608
SQFT
$155
$/SQFT
0.45
ACRES
1996
BUILT
"Price reduced Seller motivated! This updated, immaculate home ready to move into is priced to sell with over 1600 sq ft of beautiful living space PLUS a $30,000 screened in porch! It is in the water oriented community of Elk River Basin which boasts a private community beach, boat ramp and a playground. There are 3 spacious bedrooms with room for a possible fourth in the lower level which also has a plumbed in area for a third bath. The owners have made many improvements including an incredible screened in porch, dormers added and fresh paint to name a few.Roof and gutters approx 5 yrs old. It is in move in condition. Hurry and enjoy the summer in Chesapeake City and the surrounding area with all that it has to offer!"
* PRICE LOWERED - $255,000 TO $250,000 
$225,000
51 PORT HERMAN DR #9A, Chesapeake City MD 21915
1
BEDS
1
BATHS
860
SQFT
$262
$/SQFT
1988
BUILT
"Meticulously maintained first floor WATERFRONT CONDO overlooking the Elk River in Chesapeake City! Kitchen features Italian marble counter tops, custom cabinetry, stainless steel appliances, farmhouse sink, built in microwave, and under-cabinet lighting. Master bath features stunning complete tile surround shower. Open concept living and dining areas, featuring a gas fireplace, can be arranged to your liking. Recessed lighting throughout most of the home! Deck views are second to none, be it a beautiful summer sunset or a cargo ship heading to or from the C&D Canal! Common area, beach, dock, and more included with condo dues! Whether a permanent residence or vacation getaway, this space is all you'll ever need!"
$210,000
421 BIDDLE ST, Chesapeake City MD 21915
2
BEDS
2
BATHS
1,204
SQFT
$174
$/SQFT
0.14
ACRES
1900
BUILT
"Reduced Price!! Charming, totally renovated 2 bedroom, 1.5 bath in North Chesapeake city. Off street parking, fenced in back yard with shed. Adorable front porch and screened in side/back porch. A must see-schedule your showing today!"
* PRICE LOWERED - $225,000 TO $210,000 
$174,500
217 BOHEMIA AVE, Chesapeake City MD 21915
3
BEDS
3
BATHS
1,408
SQFT
$124
$/SQFT
0.08
ACRES
1870
BUILT
"Come and see this charming house built in 1870 in the Historic District of Chesapeake City. See the old world details in the shutters, porch, 2 staircases, wide plank hardwood floors and antique doors. This home features 3 bedrooms, 2 1/2 bathrooms, granite kitchen counters, a recently renovated master bathroom, a walk in closet and main level laundry. Call today for more information or to schedule a showing."
* NEW LISTING 
$173,000
80 BAYVIEW RD, Chesapeake City MD 21915
3
BEDS
2
BATHS
1,544
SQFT
$112
$/SQFT
0.34
ACRES
1989
BUILT
"Property being sold AS-IS no warranties expressed or implied. Inspections are for informational purpose only. Short sale offers subject to lenders approval. Don't move forward with inspections or attorney until we receive 3rd party approval. If you decide to complete inspections prior to bank approval it will be at your discretion. There is consideration associated with the short sale to buyer. Buyer to pay short sale faciliatory fee of $2500.00"
* SHORT SALE 
$89,900
2940 AUGUSTINE HERMAN HWY, Chesapeake City MD 21915
3
BEDS
1
BATHS
1,046
SQFT
$86
$/SQFT
0.24
ACRES
1950
BUILT
"Tenant Occupied Rental until. Currently has a year lease and tenant pays 1,200 per month. Great Tenant! House has new furnace, new carpet, new kitchen cabinets and a few other updates. SOLD AS IS!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $93,000 TO $89,900 
 
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