Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 09/18/2019 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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$3,400,000
4746 CLIFFS CITY RD, Chestertown MD 21620
5
BEDS
5
BATHS
5,174
SQFT
$657
$/SQFT
45.93
ACRES
1957
BUILT
"An elegant new offering located on the Chester River in Quaker Neck, just south of Historic Chestertown. This magnificent family residence has it all: ideal waterfront & wildlife habitat, a private pier w/ 3ft MLW, marvelous panoramic southern water views, a blend of open & wooded land, privacy, extensive gardens and is located in the premier estate area of Kent County."
$3,200,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$332
$/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 - $3,499,000 TO $3,200,000 
$3,200,000
4845 CLIFFS CITY RD, Chestertown MD 21620
7
BEDS
9
BATHS
9,651
SQFT
$332
$/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 - $3,499,000 TO $3,200,000 
$2,795,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
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 
$1,850,000
7250 PENTRIDGE LN, Chestertown MD 21620
4
BEDS
3
BATHS
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 
$1,750,000
6970 POMONA RD, Chestertown MD 21620
5
BEDS
2
BATHS
3,008
SQFT
$582
$/SQFT
113.00
ACRES
1800
BUILT
"Hilltop Farm C. 1810 in historic Chestertown includes 113 acres with waterfront on Langford Creek off the Chester River. Property includes large 8 feet deep fresh water pond and impoundment.Perc test done in 2019 for new construction 3500 +sf on the waterfront portion of the farm to accommodate a new waterfront residence with privacy. Many options with the property operating as a residence, farm or combination. Great relationship with local farmer regarding crops and maintenance. This is a rare opportunity to own a piece of Eastern Shore history and build your dream home surrounded by wildlife on the shores of Langford Creek."
$1,100,000
10718 TILDEN LN, Chestertown MD 21620
4
BEDS
3
BATHS
4,715
SQFT
$233
$/SQFT
2.06
ACRES
1995
BUILT
"Enjoy sweeping water views from three sides of this spectacular property. The custom built sprawling ranch home offers first floor living, is ideally situated on a point of land that provides broad water views, a private dock with protected water and easy access to the Chesapeake Bay, mature shade trees and gardens, a large deck overlooking the water, a separate guest house that is located close to the main house but can not be seen from the main house and has a separate driveway. The furniture in the fully furnished guest house may be included in the sale. The total square footage of both houses is over 4,000 sq ft but the main house is just over 3,000 sq ft. This is a rare offering that one must see to truly appreciate all that it has to offer."
* PRICE LOWERED - $1,250,000 TO $1,100,000 
$1,025,000
7999 QUAKER NECK RD, Chestertown MD 21620
4
BEDS
4
BATHS
4,402
SQFT
$233
$/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 - $1,100,000 TO $1,025,000 
$995,000
9326 N BAYVIEW AVE, Chestertown MD 21620
4
BEDS
5
BATHS
4,133
SQFT
$241
$/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 thru 2004 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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,050,000 TO $995,000 
$950,000
6910 PENTRIDGE LN, Chestertown MD 21620
3
BEDS
3
BATHS
3,440
SQFT
$276
$/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 - $998,000 TO $950,000 
$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 
$875,000
21124 TEXAS AVE, Chestertown MD 21620
3
BEDS
2
BATHS
2,425
SQFT
$361
$/SQFT
0.71
ACRES
2015
BUILT
"From the time you enter this property, it exceeds all expectations. Custom built, designed by owner, no space is without purpose. Great entertainment areas, efficient, energy smart, wood & tile flooring, top of the line materials from the construction to the lighting fixtures. There is nothing like this home. And then, there are the incredible bay views! Mahogany front door, Ipe porch, Hardiplank siding, NANA WALL opens to bring the outside in... screens, remotely controlled. Room for a garage, plenty of parking, over sized hot tub with adjustable privacy walls and outside shower. Waterviews from almost every room, Master suite w/ huge walk in shower, whirlpool tub, full vanity wall, walk-in closet, outside balcony. Main level has extensive seating areas in great room for breakfast bistro, cocktails, dining, wine bar, coffee station, cocktail station, large porches and balcony. Cozy living room with propane fireplace. Kitchen w/ top of the line appliances, walk in pantry/mud room. The list is too long to cover. This is a must see! Don't miss a photo, it all tells a story."
* PRICE LOWERED - $899,000 TO $875,000 
$839,000
21175 GEORGIA AVE, Chestertown MD 21620
3
BEDS
1
BATHS
1,504
SQFT
$558
$/SQFT
0.85
ACRES
1937
BUILT
"Eastern Shore Chesapeake Bay cottage with sweeping westerly views is set on 1.3 acres in Tolchester Estates. Built in 1930 and offering 200~ of waterfront with beach, the home captures stunning water views of the Chesapeake Bay. Tolchester Marina, a full service marina located just 1-mile away, has a private beach, restaurant, pool, and beach bar. Just 20 minutes away is downtown Chestertown set on the banks of the Chester River. The lovely walking town with 18th century homes offers a river walk, cafes, pubs, shops, theater and waterfront dining. Chestertown is also home to Washington College."
$825,000
108 N WATER ST, Chestertown MD 21620
5
BEDS
4
BATHS
3,031
SQFT
$272
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $874,000 TO $825,000 
$749,000
5748 LANGFORD BAY RD, Chestertown MD 21620
3
BEDS
3
BATHS
2,106
SQFT
$356
$/SQFT
1.35
ACRES
1949
BUILT
"A diamond in the rough with nearly all the desired features for waterfront property. Broad expansive 180 degree southwesterly views of Langford creek, four season sunsets, protected dock and slip. Crabbing, fishing, wake boarding, water skiing, paddle boarding, sailing all in your back yard. Just a few minutes from historic downtown Chestertown and very easy access to points north, Philadelphia and Wilmington or south, Washington DC and Northern Virginia."
* NEW LISTING 
$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."
* LISTED OVER 120 DAYS 
$635,000
8520 AIRY HILL RD, Chestertown MD 21620
4
BEDS
4
BATHS
2,492
SQFT
$255
$/SQFT
10.00
ACRES
2006
BUILT
"Eastern Shore Vermont style farmhouse built in 2006 is set on a rural 10-acre meadow backing up to woods. The farmland across the street is in conservation. This beautiful, thoughtfully designed home with two geo-thermal wells, high ceilings and large windows offers pastoral views of fields and woods, yet is surprisingly located just 5 minutes from the Chester River and Chestertown~s historic district. Maple hardwood floors, wood detail and a stunning Finnish Tulikivi soapstone wood stove create warm, bright interior spaces, while serene views from the screened porch and terrace invite outdoor living. Charming separate guest quarters, library, media room and a basement with large windows and high ceilings are among other desirable amenities. The property is also ideal for a horse farm. Founded in 1706, Chestertown is set on the banks of the Chester River where visitors and residents alike enjoy strolling along the brick walkways lined with 18th century homes, cafes, shops, live theater, river walk and waterfront dining. It is also home to Washington College, the Chester River Yacht and Country Club and Wilmer Park on the Chester River. Kent County also offers beaches, public landings, rails to trails for hiking and biking, the farmers market and Eastern Neck National Wildlife Refuge. Chestertown is located about 90-minutes from Washington and Philadelphia."
$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 
$600,000
7689 WATERVIEW LN, Chestertown MD 21620
4
BEDS
4
BATHS
4,138
SQFT
$145
$/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 - $625,000 TO $600,000 
$585,000
0 MUIRFIELD DR, Chestertown MD 21620
3
BEDS
3
BATHS
1.18
ACRES
"Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $580,000 TO $585,000 
$575,000
10050 FORREST LN, Chestertown MD 21620
4
BEDS
2
BATHS
1,820
SQFT
$316
$/SQFT
5.05
ACRES
1988
BUILT
"Best of all worlds in this waterfront home with easy water access and natural surroundings. Just feel the peace that engulfs you as you look out from the many windows of the great room. Boat, walk, bike, or drive to a marina, golf course, tennis, pool, restaurants and beach. A perfect Eastern Shore retreat. Co-broke commisssion will not be paid unless co-broke arranges and attends all showings"
* LISTED OVER 120 DAYS 
$535,000
7842 RADCLIFFE RD, Chestertown MD 21620
3
BEDS
2
BATHS
2,928
SQFT
$183
$/SQFT
1.38
ACRES
1955
BUILT
"Water views of the Chester River are a visual delight from this outstanding property on the Eastern Shore. Set on 1.3-acres in a highly-desirable residential area, the meticulously cared for home is just a walk away from Chester River Yacht & Country Club and is 1-mile from historic Chestertown. The open design creates generously sized, bright rooms with lovely views inviting outdoor living. Notable highlights such as wood detail, built in bookcases and a fireplace create a warm ambiance. The terrace overlooking gardens and the pond offers a serene setting, while the screened porch offers a lovely spot to enjoy the river views. Visitors and residents alike stroll around downtown Chestertown with its picturesque 18th century homes, brick walkways, Chester River Walk and marina. Enjoy the cafes, galleries, pubs, shops, live theater, farmers market, trails, First Friday, or take a river cruise on the Chester River Packet. There is a vibrant arts community and the town~s annual events include the Chestertown Tea Party, Harry Potter Festival and the Tall Ship Downrigging Weekend. Chestertown is home to Washington College and is located about 90-minutes from Washington and Philadelphia."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $547,000 TO $535,000 
$525,000
6100 PINE ACRES RD, Chestertown MD 21620
3
BEDS
2
BATHS
2,138
SQFT
$246
$/SQFT
3.28
ACRES
1966
BUILT
"Nature's paradise on Lovely Cove-enjoy a short and peaceful boat/kayak ride from your private dock to the East Fork of Langford Creek. This comfortable waterfront home celebrates 180 degrees water views, available from virtually all rooms. Outbuildings include garage area, workshop, storage, and potting shed. Over 3 1/4 acres of woods, cleared and privacy. Your own dock and 9 Ft. wide concrete launching ramp."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $550,000 TO $525,000 
$519,900
0 TURNBERRY CT, Chestertown MD 21620
3
BEDS
3
BATHS
2,200
SQFT
$236
$/SQFT
1.60
ACRES
"Spec home located on corner lot located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area~s finest builders."
* LISTED OVER 120 DAYS 
 
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