Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 02/15/2019 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
"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."
$6,900,000
6798 BROAD NECK RD, Chestertown MD 21620
5
BEDS
6
BATHS
10,870
SQFT
$635
$/SQFT
300.00
ACRES
"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 
$3,950,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$409
$/SQFT
164.13
ACRES
"Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale."
* LISTED OVER 120 DAYS 
$3,950,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$409
$/SQFT
164.13
ACRES
"Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale."
* LISTED OVER 120 DAYS 
$2,999,500
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,190
SQFT
$578
$/SQFT
76.07
ACRES
"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."
$2,999,500
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
6
BEDS
6
BATHS
5,250
SQFT
$571
$/SQFT
76.07
ACRES
"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 floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of the Eastern Shore outdoor life. Owner is Licensed Real Estate Agent."
$2,425,000
5240 JOHNSONTOWN RD, Chestertown MD 21620
4
BEDS
5
BATHS
2,656
SQFT
$913
$/SQFT
51.55
ACRES
"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 
$2,395,000
5793 QUAKER NECK LANDING RD, Chestertown MD 21620
5
BEDS
5
BATHS
5,800
SQFT
$413
$/SQFT
65.13
ACRES
"The Kentfields Farm-A country Estate for all seasons - Kentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful Eastern Shore. This 65 acre estate on Jarrett Creek, just off the Chester River and Chesapeake Bay. The home provides a comfortable Eastern Shore lifestyle. A unique living/sporting/entertaining property."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,500,000 TO $2,395,000 
$1,850,000
7250 PENTRIDGE LN, Chestertown MD 21620
4
BEDS
3
BATHS
4,214
SQFT
$439
$/SQFT
168.77
ACRES
"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."
$1,675,000
5268 QUAKER NECK RD, Chestertown MD 21620
5
BEDS
5
BATHS
4,748
SQFT
$353
$/SQFT
42.07
ACRES
"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
"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
3.39
ACRES
"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
"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 
$998,000
6910 PENTRIDGE LN, Chestertown MD 21620
3
BEDS
3
BATHS
3,440
SQFT
$290
$/SQFT
4.39
ACRES
"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
"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
"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 
$899,000
406 RIVER RD, Chestertown MD 21620
3
BEDS
5
BATHS
5,200
SQFT
$173
$/SQFT
0.61
ACRES
"Great Opportunity!! This beautifully built brick home has stunning water views from almost every room. The property boasts 3 bedrooms w/ 4.5 baths, slate roof, bulkhead, swimming pool, hot tub, back patio area, 2nd floor deck overlooking the river, finished bonus room w/ bath, and beautiful irrigated gardens w/ walkways.The property is being sold as-is."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $949,000 TO $899,000 
$795,000
21175 GEORGIA AVE, Chestertown MD 21620
3
BEDS
1
BATHS
1.33
ACRES
"Seller assumes buyer will be tearing down (or completely rebuilding) existing structures. Value is based on 200' of Chesapeake Bayfront, a C shaped assemblage of 3 parcels, 8 lots which includes one allocation for water/sewer. Several nearby neighbors have built/rebuilt Million$+ 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
"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 
$729,500
9840 WHITE SWAN CT, Chestertown MD 21620
4
BEDS
5
BATHS
4,682
SQFT
$156
$/SQFT
2.72
ACRES
"Located in an exclusive water-oriented community, this magnificent home offers an open plan design for those who enjoy entertaining and being active. The prominent eye-catching architectural style of the interior accents a classic paint scheme throughout. Various seating spaces, lavish main level master suite, large kitchen, sunroom, bonus room, 4 zones, 3-bay garage, deeded boat slip with 4' MLW"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $769,000 TO $729,500 
$729,000
8601 CHESTERTOWN RD, Chestertown MD 21620
5
BEDS
4
BATHS
5,367
SQFT
$136
$/SQFT
13.17
ACRES
"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
"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
"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!"
$699,000
265 PEAR TREE POINT RD, Chestertown MD 21620
5
BEDS
4
BATHS
5,563
SQFT
$126
$/SQFT
21.06
ACRES
* LISTED OVER 120 DAYS  * PRICE LOWERED - $715,000 TO $699,000 
 
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