Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 04/23/2019 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 Chestertown homes for sale or other Chestertown real estate, please contact us and one of our knowledgeable Chestertown REALTORS® would be pleased to assist you.


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$6,900,000
6798 BROAD NECK RD, Chestertown MD 21620
5
BEDS
6
BATHS
10,870
SQFT
$635
$/SQFT
300.00
ACRES
1990
BUILT
"300+/- acre waterfront estate with exceptional amenities. Main house with 7,500+/- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7'+.- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5+/- miles of shoreline."
* LISTED OVER 120 DAYS 
$6,900,000
6798 BROAD NECK RD, Chestertown MD 21620
5
BEDS
6
BATHS
10,870
SQFT
$635
$/SQFT
300.00
ACRES
1990
BUILT
"300+/- acre waterfront estate with exceptional amenities. Main house with 7,500+/- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7'+.- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5+/- miles of shoreline."
* LISTED OVER 120 DAYS 
$3,499,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$363
$/SQFT
164.13
ACRES
1965
BUILT
"Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,950,000 TO $3,499,000 
$3,499,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$363
$/SQFT
164.13
ACRES
1965
BUILT
"Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,950,000 TO $3,499,000 
$2,999,500
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,190
SQFT
$578
$/SQFT
76.07
ACRES
1800
BUILT
"A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st flr MBR suite, a new 3BR tenant house, dock with lift & an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of Eastern Shore outdoor Life. Agent/Owner."
* LISTED OVER 120 DAYS 
$2,999,500
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
4
BEDS
5
BATHS
5,250
SQFT
$571
$/SQFT
76.07
ACRES
1781
BUILT
"Owners will be creative in financing this1781 Eastern Shore beauty fully restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. Perfect for todays lifestyle enjoying peaceful Eastern Shore outdoor life in a vibrant college town. Owner is Licensed Real Estate Agent."
* LISTED OVER 120 DAYS 
$2,425,000
5240 JOHNSONTOWN RD, Chestertown MD 21620
4
BEDS
5
BATHS
2,656
SQFT
$913
$/SQFT
51.55
ACRES
1900
BUILT
"The location of the main house, 3 cottages, in-ground pool & pool house in the critical area buffer make this waterfront compound offering one that is extraordinary and extremely rare. Situated on the banks of Comegys Bight roughly 7.5 miles from Historic Chestertown is a 51.55-acre whimsical oasis with nature & riding trails, pastures, barns, farmland, woodlands... make this your Camelot..."
* LISTED OVER 120 DAYS 
$1,850,000
7250 PENTRIDGE LN, Chestertown MD 21620
4
BEDS
3
BATHS
4,214
SQFT
$439
$/SQFT
168.77
ACRES
2002
BUILT
"Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style woodstove (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound."
* LISTED OVER 120 DAYS 
$1,675,000
5268 QUAKER NECK RD, Chestertown MD 21620
5
BEDS
5
BATHS
4,748
SQFT
$353
$/SQFT
42.07
ACRES
1800
BUILT
"Quintessential Eastern Shore Waterfront Farm is set on 42-acres with 690 ft. of water frontage and long views of the East Fork of Langford Creek. Tree-lined drive leads to the well-maintained home, c.1800. Features include a new dock and boat lift, rip-rap shoreline, 33-tillable acres, and outbuildings. Lovely private setting is great for hunting. ."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,790,000 TO $1,675,000 
$1,600,000
6320 QUAKER NECK RD, Chestertown MD 21620
3
BEDS
3
BATHS
2,236
SQFT
$716
$/SQFT
12.35
ACRES
1800
BUILT
"Amazing sense of peace emphasized by the quiet of authentic 18th c.brick architecture. Methodically restored honoring its origins and yet made comfortable with 21st c. amenities. Lovely WF cove on Lankford Creek. Minutes from Chestertown on highy desirable Quaker Neck peninsula. Surrounded by farmland. Several important outbuildings offer many lifestyle opportunities. Rare 13 ac.offering!"
* LISTED OVER 120 DAYS 
$1,195,000
6870 PENTRIDGE CT, Chestertown MD 21620
5
BEDS
5
BATHS
3,848
SQFT
$311
$/SQFT
3.39
ACRES
1990
BUILT
"Impressive brick colonial waterfront home on the East Fork of Langford Creek, with its own private dock. Detached 4 car garage with copious storage. Interior features include a first floor Master Bedroom, theater, bar and game room, and gourmet kitchen. Come see the extraordinary interior details. Situated on 3.4 beautifully landscaped acres."
* LISTED OVER 120 DAYS 
$1,100,000
7999 QUAKER NECK RD, Chestertown MD 21620
4
BEDS
4
BATHS
4,402
SQFT
$250
$/SQFT
1.48
ACRES
1949
BUILT
"One of Chestertown's most prestigious addresses. Located on the river halfway between town and The Club. 1.48 acres of privacy. Professionally maintained and landscaped. The house has had one addition and two remodels. Large open floor plan,pool, guest/in-law suite,golf, gazebo, boating all make for endless entertaining possibilities."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,250,000 TO $1,100,000 
$1,050,000
9326 N BAYVIEW AVE, Chestertown MD 21620
4
BEDS
5
BATHS
4,133
SQFT
$254
$/SQFT
1.10
ACRES
1959
BUILT
"Expansive frontage on the Bay. Private, end of road lot. Large fenced pool with breathtaking bay view. House completely renovated in 2002 including infrastructure. 1st and 2nd floor Master Suites. Open den/study on second floor. Maintained steps and deck down to the water. Stone wood burning fireplace makes open living room extra cozy. Mature landscaping including vegetable garden. And of course spectacular bay views from every room. Separate artist studio and garden shed near pool. First floor master has private screened porch. Second floor master has private deck, coffee bar, gas fireplace and whirlpool bath."
$998,000
6910 PENTRIDGE LN, Chestertown MD 21620
3
BEDS
3
BATHS
3,440
SQFT
$290
$/SQFT
4.39
ACRES
2001
BUILT
"Peaceful,tranquil,beautiful and private just begin to describe this waterfront property on the East Fork of Langford.The grounds were designed by a landscape architect and are filled with indigenous plants and trees.The home is impeccably maintained with a bright open floor plan,new gourmet kitchen,hard wood floors,new systems and a view over the water of preserved land.Minutes from Chestertown."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,050,000 TO $998,000 
$998,000
4993 DEEP POINT DR, Chestertown MD 21620
3
BEDS
3
BATHS
1,584
SQFT
$630
$/SQFT
48.00
ACRES
1973
BUILT
"A rare offering in an ideal location. 48 acres of farm fields,woods, waterfrontage w/ deep water & expansive panoramic views, prime hunting including puddle & diving ducks, turkey, deer, rockfish, multiple blinds, pond, oak tree-lined driveway, ranch house situated in an excellent spot w/ spectacular water views,easy access to the water, large detached garage and additional shed/barn, privacy..."
$935,000
26 FAIRGALE FARM LN, Chestertown MD 21620
4
BEDS
4
BATHS
2,934
SQFT
$319
$/SQFT
20.18
ACRES
2018
BUILT
"Build your waterfront dream home on this little slice of heaven, offering the best of both worlds with 20+ acre of farmland and fringe woodlands on Fairlee Creek, with deeded slip at the private community dock with deep water! Hunting, fishing, horses, waterfront homestead...there are so many possibilities to enjoy the Eastern Shore lifestyle! Pictures show options & upgrades that can be built."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $975,000 TO $935,000 
$795,000
21175 GEORGIA AVE, Chestertown MD 21620
3
BEDS
1
BATHS
1.33
ACRES
1937
BUILT
"Seller assumes buyer will be tearing down (or completely rebuilding) existing structures. Value is based on 200' of Chesapeake Bayfront, a C shaped assemblage of 3 parcels, 8 lots which includes one allocation for water/sewer. Several nearby neighbors have built/rebuilt Million$+ properties worthy of Architectural Digest. Several pictures provided for inspiration purposes!"
* LISTED OVER 120 DAYS 
$795,000
22460 FAIRGALE FARM LN, Chestertown MD 21620
3
BEDS
3
BATHS
3,085
SQFT
$258
$/SQFT
3.12
ACRES
1999
BUILT
"Lovely home nestled amongst mature trees along the shoreline of Fairlee Creek. Built by the current owner, many well thought out features throughout. Currently first floor bedroom is used as a den with connected bath, gas fireplace. Cedar closets thru out house, wood floors, cedar board walls, outdoor shower and sink. Boat slip with lift at the community pier plus direct access to creek by steps."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $845,000 TO $795,000 
$775,000
10800 CLIFF RD, Chestertown MD 21620
5
BEDS
4
BATHS
4,866
SQFT
$159
$/SQFT
1.36
ACRES
1997
BUILT
"Custom built water front 5 bedroom 3.5 bath dream house in Great Oaks Community of Chestertown, MD! This +/- 5000 sq ft property is perfectly situated on an elevated bluff with absolutely breath taken water views and sunsets from almost every room in the house! The shoreline is protected by 150 ft of rip rap along with nice elevation. Pride of ownership is obvious as you walk thru this meticulously maintained estate. Features include 9 ft Ceilings, gourmet kitchen with luxury viking appliances, chef cutting board counter top with breakfast bar area, hardwood floors throughout majority of the main floor. The open floor plan has the kitchen area flowing into the great room that boasts a grand floor to ceiling, brick wood burning fireplace and a vaulted, shiplap pine ceiling with exposed beams. Nearby is an elegant formal dining room, and large gathering room, additional casual dining area with gas fireplace! The rest of the first floor is devoted to a master suite, walk in closet, master bath with tiled floor, corner soaking tub, and double sinks! And, two additional bedrooms and another full bathroom, and a laundry room. The 2nd floor includes two spacious bedrooms, a large living room area, full bathroom and an unfinished bonus room/or possible 6th bedroom (18x22~) with separate stair case to egress to the garage or outside. The property has an oversized two car garage with work bench area! One of the special features of the property is the basement has been turned into a state-of-the-art wine cellar with temperature/humidity controlled environment! A very special feature of the house is the grand screened in porch w/3 ceiling fans that spans the length of the majority of the house with panoramic views of the cheasapeake bay. In addition there is a large hot tub, upgraded Culligan whole house water filter, and two hot water heaters. This is a must see estate with a great waterside setting on a dead end street."
* NEW LISTING 
$729,000
8601 PIPPIN HILL LN, Chestertown MD 21620
5
BEDS
4
BATHS
5,367
SQFT
$136
$/SQFT
13.17
ACRES
2006
BUILT
"AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/stream & Every luxury & upgrade + 2500 sf basement. First floor master, 4 addtnl Brs, Phenomenal kitchen includes 3 ovens, double dishwasher, granite counters, custom Amish lighted, glass cab., custom tile floors, double sinks + veg sink, conv. micro, table space, serving counter, desk area. STUNNING wall of glass & two-story brick FIREPLACE in open family room w/balcony overlook. HUGE screened porch w/vaulted ceiling & brick floor. Amazing brick front porch w/entertainment area to capture every country view! IT'S WORTH A LOOK; YOU'LL FALL IN LOVE!"
* LISTED OVER 120 DAYS 
$729,000
8601 PIPPIN HILL LN, Chestertown MD 21620
5
BEDS
4
BATHS
5,367
SQFT
$136
$/SQFT
13.17
ACRES
2006
BUILT
"This is it!! Fabulous Custom-Built Home to the highest standards boasting a modern open floorplan, Chef's Designer kitchen including, What! - 3 Ovens!!, Outer Banks inspired wall of glass in family room w/FP, 5367 sf + 2500 sf basement & woodstove, 20x22 screened porch, second floor balcony overlooking FR & kit, gleaming hardwood flrs, Awesome home for entertaining perched on over 13 acres including a stream-Hurry!"
* LISTED OVER 120 DAYS 
$699,000
265 PEAR TREE POINT RD, Chestertown MD 21620
5
BEDS
4
BATHS
5,563
SQFT
$126
$/SQFT
21.06
ACRES
2005
BUILT
"Over 21 Acres Ready for your Horses & Existing Vineyard- Possible B&B! Entertainer's Delight- Nearly 5600 sq ft, 5 Bedrooms, 3.5 Baths. In-Ground Pool, Large Patio. Fenced Pasture. Large Outbuilding with 2 Stalls, Main-Level Master Suite w/ ADDITIONAL Potential In-Law Bedroom/Rec Room w/ Access to 1/2 Bath & Washer/Dryer, 3- Car Side-Load Garage,. 3 LARGE upper-level Bedrooms!"
* LISTED OVER 120 DAYS 
$699,000
265 PEAR TREE POINT RD, Chestertown MD 21620
5
BEDS
4
BATHS
5,563
SQFT
$126
$/SQFT
21.06
ACRES
2005
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $715,000 TO $699,000 
$695,000
102 N WATER ST, Chestertown MD 21620
4
BEDS
4
BATHS
3,960
SQFT
$176
$/SQFT
0.24
ACRES
1903
BUILT
"A Classic American Victorian, wrap around porch with balustrade. Many new appointments, including a new kitchen and new baths, while retaining the Victorian signatures of high ceilings, spacious rooms, fine wood floors, detailed wood trim, long windows, arched walls and graceful staircase. Rear and side gardens, 2 car detached garage with wine room and potting shed at the end of this Water St. driveway."
 
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