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Chestertown Real Estate, Homes and Condos for sale

All Chestertown homes currently listed for sale in Chestertown as of 03/01/2021 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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50
$6,500,000
6798 BROAD NECK RD, Chestertown MD 21620
5
BEDS
6
BATHS
11,840
SQFT
$549
$/SQFT
306.12
ACRES
1990
BUILT
"Walnut Point Farm ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/"
50
$6,500,000
6798 BROAD NECK RD, Chestertown MD 21620
5
BEDS
6
BATHS
11,840
SQFT
$549
$/SQFT
306.12
ACRES
1990
BUILT
"Walnut Point Farm ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/"
33
$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."
50
$2,750,000
5750 HONEST POINT LN, Chestertown MD 21620
4
BEDS
5
BATHS
6,050
SQFT
$455
$/SQFT
26.00
ACRES
1966
BUILT
"Presenting Honest Point Farm - Embrace the finest of Eastern Shore Living, Serenity and Nature at Honest Point Farm. Three Waterfront homes in Chestertown's Estate area all situated on 26 acres. This rare property consists of a beautifully maintained and updated main estate residence with breathtaking views and two charming guest homes- Winter Cottage and Summer Cottage. The main residence boasts 5 bedrooms (4 en-suite) a recently added expansive gourmet kitchen, renovated bathrooms, refinished hardwood floors, generator, 3 new heat pumps and a recently refinished waterside gunite pool. The guest homes each boast 2 bedrooms and one bath, perfect for company or as rentals. Ideally located, each dwelling has its own privacy and gorgeous views. Grounds also include an orchard, garden, wooded area, dock, in ground pool, barn, pond, various outbuildings with approximately 20 acres of woods. Given the acreage and all the fabulous amenities, this property is an exceptional offering! **Property Video in Virtual Tours**"
28
$2,450,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,250
SQFT
$467
$/SQFT
76.07
ACRES
1781
BUILT
"MOTIVATED SELLER LOOKING FOR OFFERS on this self-sustaining waterfront restored historic gem! Looking for separation and the ability to support yourself? Look no further than this 76 acre farm on the quiet Eastern Shore with on- site well and septic, underground utilities, rich soil for gardening, fruit trees, dairy barn, crabbing, stocked fishing pond and abundant waterfowl or deer hunting. Add the in-ground heated swimming pool, private dock with electric boat lift, sandy beach in low tide and charming 3BR 2 B guest house for family use or a successful source of Airbnb income. A tenant farmer tills 30 acres of corn or soybeans for more rent with more acreage possible. You can grow or obtain most of life's necessities and be self reliant! Owners could be creative in financing this1781 Eastern Shore beauty fully restored in the 90's. Entered down a tree line drive Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite addition, a new 3 BR Tenant House, dock with lift and an in-ground pool. Tenant house is a successful Airbnb source of income. Tenant farmed on 27 acres with more available. Perfect for todays lifestyle for the Sportsman while enjoying peaceful Eastern Shore outdoor life in a vibrant college town. New 301 road around Middletown makes an easy drive from Philadelphia, Wilmington. Owner is Licensed Real Estate Agent."
* PRICE LOWERED - $2,570,000 TO $2,450,000 
26
$2,450,000
24091 PROVIDENCE PLANTATION LN, Chestertown MD 21620
5
BEDS
6
BATHS
5,190
SQFT
$472
$/SQFT
76.07
ACRES
1781
BUILT
"MOTIVATED SELLER LOOKING FOR OFFERS on this self-sustaining waterfront restored historic gem! Looking for separation and the ability to support yourself? Look no further than this 76 acre farm on the quiet Eastern Shore with on- site well and septic, underground utilities, rich soil for gardening, fruit trees, dairy barn, crabbing, stocked fishing pond and abundant waterfowl or deer hunting. Add the in-ground heated swimming pool, private dock with electric boat lift, sandy beach in low tide and charming 3BR 2 B guest house for family use or a successful source of Airbnb income. A tenant farmer tills 30 acres of corn or soybeans for more rent with more acreage possible. You can grow or obtain most of life's necessities and be self reliant! 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 - $2,570,000 TO $2,450,000 
18
$1,650,000
7250 PENTRIDGE LN, Chestertown MD 21620
4
BEDS
3
BATHS
168.77
ACRES
2002
BUILT
"PENTRIDGE WOODS FARM, in an unspoiled corner of Maryland s Eastern Shore, could be a weekend refuge or your forever family home. On almost 170 private acres, with a modern and comfortable main house and a contemporary guest cottage down the road, this low-maintenance property has tilled fields, two ponds, and a dense forest. Pentridge Lane neighbors are a friendly community of mostly waterfront homes. Nearby Chestertown offers cultural and athletic events at Washington College, golf and sailing at the informal country club, a renowned farmers market on Saturdays, live music and theatre venues, a hospital, good schools, coffee shops and restaurants, and a thriving arts community. The area has long been a major sailing and cycling destination and is rapidly becoming an equestrian center. While Kent County fiercely preserves its agricultural heritage, it is less than a two-hour drive from Washington, Baltimore or Philadelphia and not much farther from the NYC area. The main house, designed by a Yale Architecture School grad as a modern farmhouse with a full basement, has four bedrooms, 2 baths, a large detached garage, and an interior courtyard garden. The center of the soaring open-plan main floor is a massive double-sided Finnish soapstone fireplace that divides the kitchen from the sitting area, with French doors opening onto the deck and brick courtyard. This floor also has a dining room/library, two bedrooms and a study/fourth bedroom. The second floor consists of a huge media room or studio and a large en-suite master bedroom. The distinctive two-story guesthouse (a short drive or ten minute walk from the main house) has a large deck and windows that wrap around the corners of the cube-shaped building. The guesthouse is currently a rental property but could easily revert to the owners personal use. About eighty acres are farmed under a shared profit/loss arrangement by a local farmer (qualifying the owner for agricultural property tax benefits). The "
* PRICE LOWERED - $1,850,000 TO $1,650,000 
18
$1,650,000
7250 PENTRIDGE LN, Chestertown MD 21620
4
BEDS
3
BATHS
168.77
ACRES
2002
BUILT
"PENTRIDGE WOODS FARM, in an unspoiled corner of Maryland s Eastern Shore, could be a weekend refuge or your forever family home. On almost 170 private acres, with a modern and comfortable main house and a contemporary guest cottage down the road, this low-maintenance property has tilled fields, two ponds, and a dense forest. Pentridge Lane neighbors are a friendly community of mostly waterfront homes. Nearby Chestertown offers cultural and athletic events at Washington College, golf and sailing at the informal country club, a renowned farmers market on Saturdays, live music and theatre venues, a hospital, good schools, coffee shops and restaurants, and a thriving arts community. The area has long been a major sailing and cycling destination and is rapidly becoming an equestrian center. While Kent County fiercely preserves its agricultural heritage, it is less than a two-hour drive from Washington, Baltimore or Philadelphia and not much farther from the NYC area. The main house, designed by a Yale Architecture School grad as a modern farmhouse with a full basement, has four bedrooms, 2 baths, a large detached garage, and an interior courtyard garden. The center of the soaring open-plan main floor is a massive double-sided Finnish soapstone fireplace that divides the kitchen from the sitting area, with French doors opening onto the deck and brick courtyard. This floor also has a dining room/library, two bedrooms and a study/fourth bedroom. The second floor consists of a huge media room or studio and a large en-suite master bedroom. The distinctive two-story guesthouse (a short drive or ten minute walk from the main house) has a large deck and windows that wrap around the corners of the cube-shaped building. The guesthouse is currently a rental property but could easily revert to the owner's personal use. About eighty acres are farmed under a shared profit/loss arrangement by a local farmer (qualifying the owner for agricultural property tax benefits)."
* NEW LISTING 
8
$605,000
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"
* PRICE INCREASED - $585,000 TO $605,000 
54
$595,000
114 WASHINGTON AVE, Chestertown MD 21620
5
BEDS
6
BATHS
4,100
SQFT
$145
$/SQFT
0.66
ACRES
1860
BUILT
"Welcome to the historic John . Stam house, the only A-rated Victorian in Chestertown according to the Secretary of the Interior. This property has so much to offer. A Gothic Revival Victorian with painted fire places, a double parlor with pocket doors, and entrance hall. Features such as hand painted plastered ceilings, Jenny doors, and original medallions, make this a one of a kind home. Dado chair rail and paneling, Bradbury and Bradbury Art Wallpapers, Soapstone fireplaces, China closet, and the list goes on. The details are such that the property really needs to be seen to be appreciated. Kitchen is completely upgraded with Delohghi stove and sub zero refrigerator. Waterfall in the back yard with gracious gardens make for a charming outdoor oasis. Carriage slate architectural shingle roof. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale which makes the total property approximately 1.3 acres. . Driveway with 6-8 parking spaces makes hosting guests easy."
39
$475,000
108 CHURCH ALY, Chestertown MD 21620
5
BEDS
1
BATHS
3,246
SQFT
$146
$/SQFT
0.08
ACRES
1730
BUILT
"GEDDES PIPER HOUSE. ca. 1730. Most unusual opportunity! Stately brick, preserved, Federal house in heart of Chestertown Historic District. Original architectural details abound including beautiful original random width pine floors, fine woodwork, original windows, nine fireplaces. The basement with brick floor also boast the original cooking fireplace. Spacious separate dining room adjacent to porch with brick floor and garden. Private garden of manageable size. Central air conditioning. Was home of Kent County Historical Society for years. Changing from museum house and offices may requires a few additions. The price of $475,00 reflects these possible desires. MD Hist. Trust Easements. One is transported to a significant architectural era. Situated on quiet street. One block to Historic Chestertown's Fountain Park, two blocks to Chester River and public Town Marina, shops, live theater, galleries. Four blocks to Washington College, 10th oldest college in America. PLEASE NOTE; All Buyer agents MUST attend all showings and inspections before and after Contract. All appointments must to requested by AGENT, not clients."
* PRICE LOWERED - $515,000 TO $475,000 
35
$455,000
251 DEVON DR, Chestertown MD 21620
3
BEDS
3
BATHS
3,935
SQFT
$116
$/SQFT
0.64
ACRES
2003
BUILT
"This Beautiful Brick home is located in Coventry Farms. Its backs up to woods, partially cleared, where you will enjoy lots of wildlife, including wild turkeys feeding. Very private setting with a patio that has a walk-out entrance from the awesome basement. The rear also bodes a balcony from the kitchen. This house is only 17 years old, but recently had all new windows installed plus $10,000.00 of interior upgrades. The home has a generator and solar panels for energy efficiency. Main floor has a formal dining room and formal living room, as well as a very workable kitchen. The Master bedroom is on one side of the house, while the other 2 bedrooms are on the opposite side. The basement has a game room with a propane fireplace, wet bar, 1/2 bath, bonus room, living room, and workshop. There is a chair lift from the main floor to the basement if needed, or it can be removed. Mature landscaping with a circular asphalt driveway that connects to the 2 car garage with an entrance to the main floor."
26
$445,000
225 RICHARD DR, Chestertown MD 21620
4
BEDS
3
BATHS
2,749
SQFT
$162
$/SQFT
0.37
ACRES
1977
BUILT
"Location, location, location! Wonderfully maintained one story brick rancher. Flexible floor plan allows for in-home office, primary bedroom with views of the water, fireplace, jacuzzi, skylights. Hardwood floors throughout and a brick floor screened porch with water views. This property has the best of both worlds, in town living and water views! A must see!"
27
$439,000
10145 3RD POINT RD, Chestertown MD 21620
3
BEDS
3
BATHS
3,292
SQFT
$133
$/SQFT
1.15
ACRES
2000
BUILT
"Don't miss your chance to own in Great Oak Landing. Make this summer a new beginning by the Bay. Play a round on the 9-hole executive golf course or enjoy the summer heat at the pool. Ask friends to join you for a drink at The Landing Restaurant or Jellyfish Joel's Beach Bar before heading to the sandy beach for a sunset bonfire. This is the the Eastern Shore Bay life at its best, just 20 minutes from historic Chestertown and 1.5 hours from Philadelphia. Access to amenities is optional HOA. Spacious colonial with wrap around porch and all the southern charm you need. Large living room with brick fireplace and eat in kitchen with Corian Counters. Off the kitchen there's a sunroom and a separate screened porch for afternoons in. First floor also features a formal dining room, laundry room and full bath. Upstairs you'll find 2 bedrooms, a large hall bath and the master suite with private bathroom and walk in closet. The property also has a 2 car garage with extra 3rd bay perfect for storage or a hobby room."
* PRICE LOWERED - $450,000 TO $439,000 
51
$399,900
6270 QUAKER NECK LANDING RD, Chestertown MD 21620
3
BEDS
2
BATHS
4.40
ACRES
"Charming country home minutes from downtown Chestertown! Located in the desirable Quaker Neck area and nearly 4.5 acres, it is only 1.5 miles from Quaker Neck Landing and the Chester River. The previous structure was torn down and it was fully renovated with a new well, BAT septic system and foam insulation in 2013. Talkie internet and Direct TV hooked up. New carpets in all bedrooms. HVAC central air/heat. 9ft ceilings on first floor, granite counter tops in kitchen and bathrooms, walk-in pantry, woodstove in grand living room with vaulted ceilings, oak floors, oversized master suite on 2nd floor with walk-in closet. A bonus room used as a guest room/office/den. French doors to screen porch overlooking gorgeous brick patio and landscaping. Electric inground dog fence. Large 2-bay garage with workshop area and lots of storage space. Electric is hooked up. Water-line in place to be hooked up. This is a must see!"
* NEW LISTING 
25
$369,000
409 BELL AVE, Chestertown MD 21620
5
BEDS
3
BATHS
3,500
SQFT
$105
$/SQFT
0.58
ACRES
1969
BUILT
"Gorgeous and rare 5 bedroom, 3 bath brick rancher in walking distance of historic downtown Chestertown. Large windows bring tons of natural light to every room. Fully fenced, large backyard includes a fantastic in-ground swimming pool surrounded by lush landscaping. Large Florida room just off the pool deck makes this home an entertainer s delight. Updated baths, including a recently added full bath on the lower level. Tax record is incorrect. This home actually includes almost 3500 finished square feet. Oversized 2 car side entry garage and large paved driveway provides ample parking. Beautiful eat-in kitchen with a large number of cabinets and counter space. Welcome Home! Pictures are from the prior listing. House in same condition but now with a 5th bedroom and 3rd full bath! 5k credit being offered."
* NEW LISTING 
36
$345,000
307 S QUEEN ST, Chestertown MD 21620
3
BEDS
3
BATHS
1,900
SQFT
$182
$/SQFT
0.05
ACRES
1999
BUILT
"The Chester River is just across the open space of Wilmer Park, from this townhome! The living room, with vaulted ceiling, fireplace and sky lights, is bright and roomy. Relax on the rear deck, tend to your flowers in the tidy garden or sit in your rocker on the front porch and watch people as they enjoy Wilmer Park. Gleaming wood floors are throughout the main level. There is a main level bedroom and full bath on main level. There is a den area on 2nd level that would make a great office or open up the wall and have sitting room off of the bedroom, as it was originally designed. Easy stroll to the Chester River and the Chestertown Marina. This is a great place to hang your hat part time or full time."
41
$295,000
103 S COLLEGE AVE, Chestertown MD 21620
2
BEDS
2
BATHS
1,536
SQFT
$192
$/SQFT
0.07
ACRES
1920
BUILT
"Updated home.. fenced back yard with a storage shed, zoned heat pumps. There is a patio and a third floor deck overlooking the semi private back yard. Brand new carpet throughout. Tiled floors in kitchen and Florida room, and fresh paint, inside and out. This home is adorable, just a couple of blocks from the wonderful historic Chestertown Shopping Area, and Washington College. One of the rooms upstairs has cut outs overlooking the stairway and owner will close those off to make another bedroom if desired. Shows well, no fridge or stove at present."
41
$289,000
106 N WATER ST, Chestertown MD 21620
6
BEDS
4
BATHS
4,048
SQFT
$71
$/SQFT
0.15
ACRES
1910
BUILT
"A real restoration opportunity on Water St. This Victorian is a project for someone who has a love of old houses.It needs attention. This house has a Mansard roof is covered in pressed tin. Hardwood floors throughout and high ceilings. Crown moldings, chair- railings built-ins and fireplaces. There is a total of 5 bedrooms and 3.5 baths. Wide covered porch in the front. Screened porch in the rear. 2 car garage and driveway for off street parking. Heat is not functioning, needs a new roof(part is covered with a tarp). Partial central air. Some views of the river over the 18th century houses from the second and third floors. This house has great potential and is a rare find for Water St. It is waiting to be restored to its former glory. Property is being sold in as-is condition; some restoration plans available."
* PRICE LOWERED - $318,000 TO $289,000 
33
$262,000
200 COURT ST, Chestertown MD 21620
0
BEDS
0
BATHS
1,503
SQFT
$174
$/SQFT
0.09
ACRES
1939
BUILT
"Great opportunity for someone wanting professional office space or would like to convert into a residence! RB professional zoning permits both! Was used as a law office for many years and would be ideal for the lawyer who is ready to branch out on their own. Recently has had mold remediation, documentation is available. The off street parking included is a premium in this location with 4+/- spaces available. Conveniently located in downtown Historic Chestertown and within the historic district. Formal appraisal completed in fall of 2019 and is currently listed under the appraised value."
* PRICE LOWERED - $289,900 TO $262,000 
45
$250,000
810 DOUBLE CREEK POINT ROAD, Chestertown MD 21620
4
BEDS
2
BATHS
1,400
SQFT
$179
$/SQFT
0.23
ACRES
2021
BUILT
"*NEW CONSTRUCTION* To be built. Lot cleared and ready! Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price in this competitive market to get what you want. You choose siding, shingles, cabinets, flooring and more. Very open floor plan with the entry, living room, dinning room and kitchen. Lot conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school district. Lot size not accurate. A bit over .5"
10
$245,000
211 DEVON DR, Chestertown MD 21620
3
BEDS
2
BATHS
1,456
SQFT
$168
$/SQFT
0.38
ACRES
1997
BUILT
"Coventry Farms Rancher! Enjoy one level living in the 3 bedroom 2 bath rancher with attached garage, and rear screened in porch. This home is close to the waterfront college town of Chestertown, with shops, and restaurants a short drive away. This is a Fannie Mae home. Submit all offers on Homepath site."
49
$245,000
111 CEE JAY ROAD, Chestertown MD 21620
4
BEDS
2
BATHS
1,400
SQFT
$175
$/SQFT
0.42
ACRES
2021
BUILT
"Photos are of model home. Lot is cleared, and footers are being put in. Your very own chance to own new construction, at a great price. Open kitchen, dining, and living area. 4 bedrooms, 2 full baths. Front, side, and back door. Very clean layout. Kitchen appliances included, wonderful laundry area. The sooner you act, the more options of specifications you may choose. Located 45 minutes from the bay bridge, in a rural area. Quiet and peaceful living! . A short easy commute to Middletown, Dover, Annapolis, DC, and the beautiful beaches. Located in QA County School District. Minutes away from downtown Chestertown and Centreville."
12
$239,900
106 OAK LEAF DR, Chestertown MD 21620
3
BEDS
3
BATHS
1,976
SQFT
$121
$/SQFT
0.08
ACRES
2003
BUILT
"Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living."
 
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