Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 05/23/2019 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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$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 
$2,795,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
4
BEDS
5
BATHS
5,250
SQFT
$532
$/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  * PRICE LOWERED - $2,999,500 TO $2,795,000 
$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 
$1,600,000
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 
$1,100,000
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 
$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 
$874,000
108 N WATER ST, Chestertown MD 21620
5
BEDS
4
BATHS
3,031
SQFT
$288
$/SQFT
0.21
ACRES
1925
BUILT
"This stately colonial is located on the famed Water Street in the historic district of Chestertown. The home features 1 off street parking space and one on street parking space, high-end upgrades including Wolf appliances, Sub Zero refrigerator, Granite counters, Rinnai instant hot water, radiant floor heating in the kitchen, Generac whole house generator, Honeywell commercial dehumidifier in the basement, slate roof and extensive landscaping with a sprinkler system. The owners have done a great job preserving features from the original era. With the large flowing rooms downstairs and the added porches and patio, this home is perfect for entertaining. A classic Chestertown beauty! Call to schedule your showing today."
$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 Oak 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."
$735,000
105 CHESTER VIEW, Chestertown MD 21620
3
BEDS
2
BATHS
1,987
SQFT
$370
$/SQFT
3.84
ACRES
1964
BUILT
"Queen Anne's county waterfront over looking Chestertown. Perfect view of sunsets from this side. Enjoy the Chester river and private pond from this nearly 4 acre parcel. Upgrades include new kitchen, wiring, septic (BAT system), well, irrigation system, bulkheading, 100 ft dock complete with lift. Water and electric on the dock. Great crabbing from this location. Current owners ice skate on the pond in the winter."
$729,000
8601 PIPPIN HILL LN, Chestertown MD 21620
5
BEDS
4
BATHS
5,367
SQFT
$136
$/SQFT
13.17
ACRES
2006
BUILT
"OPEN 5/18, 12-2PM 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
"OPEN 5/18, 12-2pm 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 
$699,990
244 RIVER RD, Chestertown MD 21620
4
BEDS
3
BATHS
2,182
SQFT
$321
$/SQFT
0.89
ACRES
1962
BUILT
"Enjoy the best of Chestertown waterfront living! This beautifully updated home nestles on the shoreline of the Chester River with breathtaking views across the bridge from historic Chestertown. Meticulously renovated in 2015, this property is open and airy with superior custom molding and craftsmanship to be seen in every room. Kitchen boasts stainless steel appliances with granite counters and ceramic tile floor. The Kitchen flows into the Dining Room with its custom built large wooden cabinet, hardwood floors, stunning decorative chandelier, and bay window. The Living Room offers soothing wood burning fireplace and hardwood floors. A large Sun Room stretching across the entire river side of the property with walls of Anderson sliding glass doors allows for abundant natural light and gorgeous water views. Perfect for entertaining! The side hallway leads to the main level master bedroom and offers custom shuttered windows, spacious closet, decorative ceiling fan, and hardwood floors leading into the luxurious private Owner's Bath. This custom ceramic tile oasis offers walk in shower surrounded by a glass enclosure, decorative mirror built into the wall overlooking large vanity, and wonderful storage. The other two spacious bedrooms on the main level boast hardwood floors, large closets along with custom built bookcases and plantation style shutters for the windows. The second main level full bath offers a custom ceramic tile walk in shower with bench and sliding glass enclosure. The steps ascending to the upper level lead to a Recreation Room/Office and another private suite complete with vaulted ceilings, large skylights and private full bathroom. The lower level has a full basement with a french drainage system, extra large cedar closet for storage, laundry area, and access to a deep one car garage that leads to the"
$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."
$649,000
509 FEY RD, Chestertown MD 21620
4
BEDS
4
BATHS
2,906
SQFT
$223
$/SQFT
1.70
ACRES
1958
BUILT
"Just Reduced! Minutes from Chestertown, shops, Washington College, restaurants and cultural events. One level living on the Chester River on one and a half acres. Private dock and a nice sandy beach - you will feel like you are on vacation every day. Waterviews from almost every room and the most amazing sunsets. LARGE screened-in porch and decks. Large kitchen and pantry with lots of storage. Three car garage and workshop. Whole house generator. Perfect second home with a separate wing for your guests. Welcome home to the Eastern Shore of Maryland."
* PRICE LOWERED - $699,000 TO $649,000 
$625,000
7689 WATERVIEW LN, Chestertown MD 21620
4
BEDS
4
BATHS
4,138
SQFT
$151
$/SQFT
0.46
ACRES
1994
BUILT
"Beautiful home placed along the 13th fairway of the Chester River Yacht & Country Club. Sit in the pool, porch, hot tub, enjoy the manicured golf course with views of the Chester River in the distance.1st & 2nd floor masters sitting room, washer/dryer on each floor. 9' ceilings, oak floors, den & withdrawing room, good flow for entertaining. Just relax and enjoy; right here! Past garage turned into first floor master."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $649,000 TO $625,000 
$610,000
121 LYONS LN, Chestertown MD 21620
4
BEDS
3
BATHS
2,327
SQFT
$262
$/SQFT
1.90
ACRES
1990
BUILT
"Premium materials and finishes,including yellow pine floors reclaimed from Camden Yards,really set this waterfront cape apart.Crown moulding,wainscoting,panel doors,fireplace,sun room and master on first floor are among the many amenities.Studio with AC/Heat is surrounded by a Williamsburg Garden and a gazebo sits waterside.Very private. Adjacent .44 perc approved lot can be purchased separately. Walk to C-town."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $669,000 TO $610,000 
 
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