Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 12/06/2019 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
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."
* 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."
* PRICE LOWERED - $3,499,000 TO $3,200,000 
$2,925,000
23791 RICAUDS BRANCH RD, Chestertown MD 21620
3
BEDS
3
BATHS
3,248
SQFT
$901
$/SQFT
213.00
ACRES
1856
BUILT
"Middle Plantation Circa 1856, better known as Running Fox Farm, is one of the finest hunting farms in Kent County, Maryland - abundant deer, Canada and Snow geese, dove and turkey. The residence has been meticulously renovated, an extensive, well-documented project that includes upgrades such as 400 amp electric service and wiring, updated plumbing, custom restorations true to the period, and more. 213 acres with 166.6 prime soils, 60.5acres in CRP... all on FIVE 30+ acre subdivided, perc-approved lots."
$2,650,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,250
SQFT
$505
$/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."
* PRICE LOWERED - $2,795,000 TO $2,650,000 
$2,650,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,190
SQFT
$511
$/SQFT
76.07
ACRES
1781
BUILT
"Sellers offering creative financing for sale of this Beautifully Restored Historic Waterfront Farm plus Guest House, Inground Pool, Dock with lift and Tree lined drive. Exquisite restoration features magnificent 1st floor Master Suite with His and Hers baths and Walk-In Closets. A Sportsman Paradise with Hunting, Crabbinig and Boating in a vibrant college town on the Eastern Shore. Owner is a licensed Realtor."
* PRICE LOWERED - $2,795,000 TO $2,650,000 
$2,399,000
8744 S BAYVIEW DR, Chestertown MD 21620
5
BEDS
6
BATHS
6,105
SQFT
$393
$/SQFT
0.97
ACRES
2002
BUILT
"An exceptional architect-designed 6,105 square foot home perched 100 feet-high on a bluff overlooking the Chesapeake Bay - the Chesapeake/Delaware shipping channel in full view. Included in the sale is the adjacent .66 acre parcel, LOT PAR 1-2 ON A PL S/S MONTGOMERY AVE. You'll never tire of watching the ships and daily sunsets through the floor to ceiling windows. Floors throughout are finished in quarter-sawn red oak. Bluestone surrounds the house and continues into the entryway that provides a dramatic dining space with a 17-foot ceiling and a waterview as the backdrop. Sweeping open floor plan is graceful and elegant in its simplicity - full of light, angles, white walls and stunning views from every window. Plenty of gallery-like spaces to display your art. A chef-designed gourmet kitchen is a cook's dream, complete with a Thermador gas cooktop and electric double oven, two Subzero refrigerators, a Subzero freezer, under-counter Subzero refrigerator drawers, granite counters, and adjoining butler's pantry and many more custom features. A must see. First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Nationally known artisan-designed cherry stair rail leads to the guest floor with four bedrooms, three full baths and a huge bonus room, which could make a wonderful studio or game room. There are never-ending bay views from almost every room in the house. Heating and cooling is provided by a geothermal system. A three-car garage continues the house exterior design with matching trim and cedar shingles. Dock your boat at the premier marina just a three minute drive away. Nearby is Rock Hall with more marinas, shops, restaurants, and a world-class jazz venue called the Mainstay. Twelve miles away is historic Chestertown with Washington College and more shops and restaurants. Within two hours to Philadelphia, Baltimore and DC. By appointment only. This is one of the"
$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."
$1,650,000
5240 JOHNSONTOWN RD, Chestertown MD 21620
4
BEDS
5
BATHS
2,656
SQFT
$621
$/SQFT
51.55
ACRES
1900
BUILT
"Picture this ~ you drive past the crops, down the tree lined lane, past the barns and there is the river. You have arrived at your own piece of paradise ~ Grassymeade Farm. Situated on 51.55 picturesque acres with expansive views of the Chester River this charming waterfront compound offers something for everyone. Whether you~re looking for hunting, fishing, boating, equine activities and/or a private waterfront getaway you will find it in this special setting. There is a main farm style house with 4BR~s as well as 3 cottages perched on the banks of the Chester River. You will also find a private dock, a sandy beach, a hot tub and an in ground pool with pool house. Then there are the barns! The main barn has 8 stalls, a tack room, hay loft and a large workshop area. There are two more barns one with living space above. Plus 8 acres of fenced pasture with 2 run in sheds. Don~t miss this opportunity to own a unique property in the sought after Quaker Neck area."
$1,650,000
5240 JOHNSONTOWN RD, Chestertown MD 21620
4
BEDS
5
BATHS
2,656
SQFT
$621
$/SQFT
51.55
ACRES
1900
BUILT
"Picture this ~ you drive past the crops, down the tree lined lane, past the barns and there is the river. You have arrived at your own piece of paradise ~ Grassymeade Farm. Situated on 51.55 picturesque acres with expansive views of the Chester River this charming waterfront compound offers something for everyone. Whether you~re looking for hunting, fishing, boating, equine activities and/or a private waterfront getaway you will find it in this special setting. There is a main farm style house with 4BR~s as well as 3 cottages perched on the banks of the Chester River. You will also find a private dock, a sandy beach, a hot tub and an in ground pool with pool house. Then there are the barns! The main barn has 8 stalls, a tack room, hay loft and a large workshop area. There are two more barns one with living space above. Plus 8 acres of fenced pasture with 2 run in sheds. Don~t miss this opportunity to own a unique property in the sought after Quaker Neck area."
$1,275,000
8221 BROAD NECK RD, Chestertown MD 21620
5
BEDS
5
BATHS
5,794
SQFT
$220
$/SQFT
24.83
ACRES
1975
BUILT
"Rare (for Kent County) and exceptionally exciting, ultra-contemporary residence is situated on a promontory above twenty-five private pastoral acres. The combination of the position of the main house above the open natural grounds below featuring a breathtaking view of a pond with a mile-high fountain, a stream, woods and wildlife. You are on the level of the flight of birds. Sophistication, alluring and extremely comfortable are the words that come to mind. The owner has thought of even the most minor detail. One is part of nature and yet is able to enjoy all the amenities of today. This property satisfies the desire for privacy and nature while also offering a lap pool, sauna, exercise area, whirlpool tub, hot tub, expansive windows and multiple level deck. There is an apartment adjacent to carport/garage where caretaker lives but could also be additional guest quarters. After passing through the entrance gates one is enveloped by a feeling of privacy and a sense that you are entering a very special place."
$1,195,000
19 BYFORD CT, Chestertown MD 21620
5
BEDS
7
BATHS
7,505
SQFT
$159
$/SQFT
1.45
ACRES
1992
BUILT
"Impressive custom built brick waterfront home thoughtfully designed on the Chester River that combines classic elegance with modern open space living. Situated on a 1.45 acre lot just 2 blocks from downtown historic Chestertown , it is perfect for kayaking and canoeing! Main floor master suite, 4 bedrooms with baths, an in-law area, 3 car garage, and screened porch and deck both overlooking the river. The interior features high ceilings, built in shelving, and custom mouldings. Includes a pier with electric and water. Owner is a licensed real estate agent."
$1,185,000
5886 QUAKER NECK RD, Chestertown MD 21620
4
BEDS
3
BATHS
2,524
SQFT
$469
$/SQFT
9.71
ACRES
1920
BUILT
"Outstanding Waterfront property, with excellent deer, turkey, and waterfowl hunting with two impoundment ponds, an irrigation well, and 4.5 +/- tillable acres, on 9.75 acres nestled along Phillips Creek. The restored and renovated farmhouse features hardwood floors and exposed wood beams, as well as 4 bedrooms, 3 full bathrooms, separate living, dining and kitchen spaces and a wood burning fireplace. The partially wooded property offers a secluded respite, as well as a detached oversize garage, a concrete in-ground pool, floating dock, and abundant wildlife. Enjoy private Eastern Shore living within a few minutes of the Historic town of Chestertown."
$999,000
10718 TILDEN LN, Chestertown MD 21620
4
BEDS
3
BATHS
4,715
SQFT
$212
$/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 - $1,100,000 TO $999,000 
$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."
* 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."
* 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."
* PRICE LOWERED - $975,000 TO $935,000 
$895,000
105 RIVERVIEW PL, Chestertown MD 21620
3
BEDS
3
BATHS
1,486
SQFT
$602
$/SQFT
0.58
ACRES
1944
BUILT
"Eastern Shore waterfront compound with two separately deeded cottages on the Chester River offers coveted views looking across to the historic Chestertown waterfront, Wide Hall and the Chester River bridge. The main house has sweeping views of the river and is perfectly poised to see Sultana under sail, the Washington College boathouse, visiting Tall Ships and fireworks. Another cottage is set behind the main house with a pathway and in-ground pool between the two. Both houses have 1st floor bedrooms and 2 bedrooms upstairs. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants and pubs. Outdoor enthusiasts can enjoy the Chester River Walk and trails, or embark on a river cruise. Located in Queen Anne~s County, the property has 100-feet of shoreline, a 110-foot dock with 3-1/2 feet MLW and stunning sunsets."
$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
9767 RICHARDS RD, Chestertown MD 21620
3
BEDS
2
BATHS
3,500
SQFT
$236
$/SQFT
1.80
ACRES
1996
BUILT
"Exceptional architect designed Contemporary residence sited on a 1.8 acre private wooded lot enjoys 190' of protected waterfront, a 110' private dock and 3.5' MLW on Fairlee Creek; one of the prettiest bodies of navigable water in Kent County situated within just 1 nautical mile of the Chesapeake Bay. The property includes three separate living structures: the main house, an office/guest house. and a heated workshop/storage shed that, together, include approximately 3500 square feet of finished living space. The open floor plan interior of the main house features vaulted beaded board ceilings, strategically placed nooks and ledges to showcase art and collectibles, over sized windows and full-view glass doors overlooking the waterfront and easy care radiant heated tile floors. The cooks delight eat-in kitchen features stainless appliances, granite counter-tops, maple Brookhaven cabinetry, above and under-cabinet lighting, a large walk-in pantry, a built-in maple breakfast table, lovely views of surrounding gardens and the waterfront from the sink area through large space-enhancing corner windows and a double sided wood burning fireplace located between the kitchen and the dining area. A spacious private master bedroom and bath area includes a walk-in closet and a master bath with a tiled walk-in shower and Pearl brand whirlpool bathtub. Generously sized windows in the bedroom frame a serene verdant view through the trees to the water . The open living room features large windows and a brick wood-burning fireplace and opens to a screened porch that spans the waterfront side of the house. A 2011 addition includes a spacious cork floored Great Room with an outdoor deck seating area and a separate outdoor entrance. A discreet stairway leads from the Great Room to a bright and airy 2nd level studio that can, alternatively, serve as a third bedroom. A ships ladder stairway leads from the studio/bedroom up into a delightful tower space that offers birds-ey"
$799,000
108 N WATER ST, Chestertown MD 21620
5
BEDS
4
BATHS
3,031
SQFT
$264
$/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."
* PRICE LOWERED - $825,000 TO $799,000 
$795,000
22460 FAIRGALE FARM LN, Chestertown MD 21620
3
BEDS
4
BATHS
3,485
SQFT
$228
$/SQFT
3.13
ACRES
1999
BUILT
"Eastern Shore waterfront cottage on Fairlee Creek offers a boat slip with lift at the community pier. Elevated, secluded setting offers sweeping water views. A large deck overlooks the backyard leading to a wood stairway going down to the waterfront. Cedar panelling, wood floors and large brick fireplace create a welcoming cottage ambiance. The Master Suite upstairs opens to a deck with stunning views, and on the first floor is another convenient master suite. Other features include a finished basement with flexible space, a separate garage, workshop and potting shed. A quick walk away is the Fairgale community pond, picnic area and dock. The property is located just 15-minutes from Chestertown. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants, galleries and pubs. Outdoor enthusiasts can use the Chester River Walk, parks and trails, or embark on a river cruise."
$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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