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Chestertown MD Real Estate & Homes for Sale

61 Properties Found

The median home value in Chestertown, MD is $253,950. This is higher than the county median home value of $192,000. The national median home value is $231,815. The average price of homes sold in Chestertown, MD is $253,950. Approximately 43% of Chestertown homes are owned, compared to 42% rented, while 15% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1–25 of 61 properties displayed
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Beds:
4
Baths:
2 Full
Sq.Ft.:
1,260
Status:
NEW LISTING
MLS#:
MDKE117090
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.51 Acres
Year built:
1955
Courtesy: Rock Hall Properties Real Estate
View additional info

Adorable, affordable 4 bedroom, 2 bath saltbox style home just outside the town of Chestertown. Over half an acre with room to roam, yet close to town amenities. 2012 renovation included new flooring, new kitchen and appliances, new bathrooms and new HVAC system. There's a rear deck for BBQs and outdoor dining, plus a basement with cement floor for extra storage.

Beds:
4
Baths:
3 Full
Sq.Ft.:
1,710
Status:
NEW LISTING
MLS#:
MDKE117088
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Center
Lot size:
0.31 Acres
Year built:
2006
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great house with 4 bedrooms and 3 full baths. Detached 2 car garage and basement provide plenty of storage. Public water and sewer. Master and 2 additional bedrooms on second floor. 4th bedroom on the main level. The master bedroom has its own private sitting room. Beautiful hardwood floors throughout the main living area. Entire house has been freshly painted. Back yard is fenced. Lovely front porch for sipping coffee in the mornings. Just a few miles outside of Chestertown.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,696
Status:
NEW LISTING
MLS#:
MDKE117070
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
4.74 Acres
Year built:
1910
Courtesy: Doug Ashley Realtors, LLC
View additional info

The old "Hilltop Hotel"! This was once a hotel that was visited by many who vacationed at Tolchester Beach Amusement Park. Some renovations and updates have been completed however there are many more that will require attention. HVAC has been updated to take care of the 1st and 2nd floors, some wiring has been updated and bathrooms have been updated. A new well and septic were installed 2002+/-. The wrap around porch was also renovated. The many windows have also been replaced. There are wood floors throughout most of the house. The work has been started but it it ready for a new owner to take over and add some finishing touches. There are even some of the original gas light fixtures on the third floor! The property is zoned Crossroads Commercial so if you would like to start a B&B at a basement bottom price then here is your chance.

Beds:
4
Baths:
1 Full
Sq.Ft.:
2,040
Status:
NEW LISTING
MLS#:
MDKE117078
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.23 Acres
Year built:
1948
Courtesy: Harlan C. Williams Co.
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Rancher with 2 car detached garage 24' x 30' on a private dead end street with lots of trees. 4 bedrooms 2 full baths

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,820
Status:
NEW LISTING
MLS#:
MDKE117068
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Creek
Lot size:
5.05 Acres
Year built:
1993
Courtesy: Gunther-McClary Real Estate
View additional info

Best of all worlds. with 5+ acres of private woodland. This waterfront home has very easy water access and natural surroundings. Located on Fairlee Creek, just minutes from the Chesapeake Bay. 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

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,136
Status:
NEW LISTING
MLS#:
MDQA145180
Type:
Single Family, Single Family-Detached
Subdivision:
Pheasantfield
Lot size:
37.09 Acres
Year built:
1995
Courtesy: Hagan Realty
View additional info

This 37-acre waterfront farm offers endless possibilities and an exceptional opportunity to generate multiple streams of income! The property backs to the Chester River and is one of the top duck hunting locations in the county. Kayak and canoe right from your own backyard or go across the street to Deep Landing to launch larger boats. The main level of the home boasts 3 bedrooms, 2 full baths, and new laminate flooring in a wood finish. The basement is a full in-law suite complete with a separate entrance, kitchen, living room, bedroom, full bath, and a bonus room that can be used as a bedroom or an office. The equestrian amenities are countless with a 25-stall barn, 11 pastures, a small indoor arena suitable for lunging or starting young horses, automatic waterers, 2 large run-in sheds, a large garage for vehicle or equipment storage, and more! The pastures were thoughtfully designed for handling foals and young horses and the wide trails through the woods are excellent for riding.

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,136
Status:
NEW LISTING
MLS#:
MDQA145178
Type:
Single Family, Single Family-Detached
Subdivision:
Pheasantfield
Lot size:
37.09 Acres
Year built:
1995
Courtesy: Hagan Realty
View additional info

This 37-acre waterfront farm offers endless possibilities and an exceptional opportunity to generate multiple streams of income! The property backs to the Chester River and is one of the top duck hunting locations in the county. Kayak and canoe right from your own backyard or go across the street to Deep Landing to launch larger boats. The main level of the home boasts 3 bedrooms, 2 full baths, and new laminate flooring in a wood finish. The basement is a full in-law suite complete with a separate entrance, kitchen, living room, bedroom, full bath, and a bonus room that can be used as a bedroom or an office. The equestrian amenities are countless with a 25-stall barn, 11 pastures, a small indoor arena suitable for lunging or starting young horses, automatic waterers, 2 large run-in sheds, a large garage for vehicle or equipment storage, and more! The pastures were thoughtfully designed for handling foals and young horses and the wide trails through the woods are excellent for riding.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,659
Status:
NEW LISTING
MLS#:
MDKE117060
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.55 Acres
Year built:
2004
Courtesy: Cross Street Realtors LLC
View additional info

Quality and class go hand in hand with this Country Club Estates beauty, which boasts vaulted & tray 9'+ ceilings, Brazilian Cherry hardwood floors throughout, GOURMET KITCHEN, breakfast bar, granite & silestone countertops, new kitchen appliances (3 years), limestone (raised) fireplace & mantle, french doors, Hurd windows, open/airy floor plan, bonus room above the two-car garage, backs to trees, large pond, and farmland. This won't last long!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,848
Status:
Active
MLS#:
MDKE117044
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Select Land & Homes, LLC
View additional info

Want to live on one of Chestertown's most desirable streets? Look no further! This lovely home boasts hardwood flooring, tall ceilings, elegant molding and trim, and ornate oversized windows. Main floor features an inviting living room, formal dining room, large kitchen, full bathroom and mudroom/laundry room. Upstairs you will find 4 large bedrooms. Two are located on the 2nd floor with a full bath and two others on the 3rd floor. There's space for everyone! Welcoming front porch is the perfect spot greet guests. Private and spacious backyard with patio and shed complete the picture for this gracious home. The possibilities are endless! Only 2 blocks from the Chester River. Close to restaurants, shops and schools. Make this place your home!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,480
Status:
Active
MLS#:
MDQA145108
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1986
Courtesy: Select Land & Homes, LLC
View additional info

Charming 3 bedroom ranch home close to Chestertown. This home features a remodeled kitchen that opens into a large family room over looking the backyard, wood burning fireplace in the living room, new roof, and a remodeled bathroom. The large backyard is fully fenced and offers lots of privacy. The oversized attached garage has a work bench and offers lots of storage space. This home has been well maintained and improved by the current owners!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE117034
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.73 Acres
Year built:
2020
Courtesy: Clark & Co Realty, LLC
View additional info

Under Construction, December/January Delivery.. .....Looking for a brand NEW home & the simple pleasures of one level living?? Look No Further!! Beautiful, Affordable Rancher on 3/4 acre corner lot.....this home features 3 bedrooms, 2 full baths and an open floor design that maximizes light throughout the gorgeous white kitchen, dining and living areas. Highlights include granite counter tops, high ceilings, hardwood floors, upgraded lighting, SS appliances and a front porch. Located close to a full range of local amenities. Quality Built, MHBR#3423. Not actual house - pictures are similar to home being built

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE117004
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,254
Status:
Active
MLS#:
MDKE117002
Type:
Single Family
Subdivision:
Tolchester
Lot size:
0.16 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. All rooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
4
Baths:
4 Full
Sq.Ft.:
4,820
Status:
Active
MLS#:
MDKE116996
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2.06 Acres
Year built:
1989
Courtesy: Taylor Properties
View additional info

Stunning 4 Bed 4 Full bath sitting on over 2 peaceful and secluded acres, circle driveway with plenty of garage space. Surrounded by farmland and yet only 2 miles from Chestertown. Inside you will find an open floor plan, cathedral ceilings, exposed wooded beams, a large brick wood burning fire place that's also plumbed with gas. Off the family room you'll notice a large formal dining area with a Solarium full of windows. In the kitchen you will see a large center island with a Commercial Grade Viking 6 burner gas cook top, a stainless Sub Zero fridge/freezer, double wall ovens and large stainless sink in the perfect kitchen Triangle. Granite counter, Custom CWP Cherry cabinets with a fold out mixer table. Flowing from the kitchen is the perfect sized living room with custom built in shelving, and surround sound. Office area & 1 full bath down stairs. Upstairs will lead you to a master suite with walk in closets, master bath with tile shower, soaking tub and double vanities. Also 3 other bedrooms and 2 full bathrooms located on the second floor. Out the back door will lead you to a screened in porch perfect for picking crabs and summer time dinners. Outside leads to a beautiful slate patio for grilling and hanging out when you invite family and friends over to your very own concrete pool, fully fenced in with diving board and self integrated shelf benches. Also a large hot tub to wind down in. This home is equipped with a propane Generac 20kw whole house back up generator. 2 Owned 500gal propane tanks, one for the Generator and one for 2 zones of forced air gas heat. For even more space, this home has a full basement, 90% finished of with 2 additional heat/AC zone mini splits. A full billiards room with pool table that conveys. Spacious attached 2 car garage, with additional detached 2 car garage with loft area. House had a New Roof 2020, great Talkie fiber internet, Well water with public sewer.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA144986
Type:
Other
Subdivision:
Ducks Neck
Lot size:
0.51 Acres
Courtesy: EXIT On The Bay
View additional info

THIS LOT HAS PREVIOUS SEPTIC AND WELL IN PLACE COUNTY HAS PREVIOUS IMPACT FEE RECORDED, COMMUNITY WATER ACCESS IS AT END OF MERGANSER DR. NEAR PROPERTY EST 600-800 ' PAST LOT DRIVEWAY.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,660
Status:
Active
MLS#:
MDKE116872
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District
Lot size:
0.11 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

TENANT OCCUPIED - 12 hour plus Notice Required. COVID PROTOCOL REQUIRED. Charm, character and natural light abound in this home which was expanded, renovated and updated inside and out in 2008. Pre-inspection recently done with good results. New heat-pump added to main level in 2020. Hard-plank siding on house and shed. Nice layout on main level includes gracious kitchen with wet bar, pantry/mud room, powder room, family room with wood stove insert, dining room and separate craft room. Second floor offers nice master bedroom with private tiled shower and soaking tub plus two additional bedrooms, ceramic tile 2nd full bath and bedroom level laundry. Third floor includes an additional finished 500 sq ft with 2 rooms, one of which could be 4th bedroom. Hardwood floors throughout. Privacy fenced back yard with deck overlooks space that will not be developed, and it includes a cute and functional shed. Off street parking included. Property is ideally located on a desirable street one block from college and an easy walk to downtown. Currently rented but available immediately subject to lease. Leased for $2400/month for good investment opportunity. Agent related to owners.

Beds:
3
Baths:
2 Full/2 Half
Sq.Ft.:
3,248
Status:
Active
MLS#:
MDKE116774
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
35.76 Acres
Year built:
1856
Courtesy: Cross Street Realtors LLC
View additional info

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.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,865
Status:
Active
MLS#:
MDQA144692
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.79 Acres
Year built:
1951
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy sunsets from the screened in porch and fires in the winter with one story living on the Chester River. Close to Chestertown on the Queen Anne's side. Large yard, shed, beach along 210 feet of waterfront. Pier with boat lift. A private paradise.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,393
Status:
Active
MLS#:
MDKE116906
Type:
Other
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Year built:
2015
Courtesy: RE/MAX Executive
View additional info

JUST REDUCED! Welcome to 114 Landing Lane in the Chester River Landing community located on the Chester River in historic Chestertown Maryland. This beautiful 3 Bedroom, 2.5 Bath, home is 2300 sq. ft (tax record is incorrect) and is awaiting it's next owner. Feel the pride of ownership in this home from the hardwood flooring, to the upgraded gourmet kitchen. The large great room featuring a gas fueled fireplace and large windows to allow in the natural light, situated just off the kitchen is a wonderful area to relax, read or just gather with family and friends. The second level of the home features an area that can be utilized as a den or large office. Proceed another half level upstairs to an expansive family room with dining area, 2 additional bedrooms and another full bath. There are two large rear decks on this home, one off the kitchen on the main level and a second off the family room on the second level. Enjoy the views of the Chester River from the 2nd level deck. Be advised that the tax record is showing an incorrect square footage on the home, the actual square footage is over 2300 sq. ft.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,690
Status:
Active
MLS#:
MDQA144792
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.45 Acres
Year built:
2001
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Lovely 3 bedroom, 2 bath Cape Cod in Chester Harbor. Situated on a large, very private lot with mature trees and super charming, expansive back yard. Nestled in near Rosin Creek this home is a walk to the community beach, convenient to Historic Chestertown, as well as, easy commute to metropolitan hubs. Perfect work from home spot! The home features, upgraded appliances, built in cabinets, hard wood flooring, spacious garage, main level bedroom and more!

Beds:
4
Baths:
6 Full
Sq.Ft.:
3,237
Status:
Active
MLS#:
MDKE116878
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.66 Acres
Year built:
1860
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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. Driveway with 6-8 parking spaces makes hosting guests easy.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,976
Status:
Active
MLS#:
MDKE116888
Type:
Townhouse
Subdivision:
Oakstreet
Lot size:
0.08 Acres
Year built:
2003
Courtesy: Benson & Mangold, LLC
View additional info
Beds:
4
Baths:
2 Full
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDKE116856
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Cross Street Realtors, LLC
View additional info

Gorgeous Split Foyer in the Byford Development, that is close to EVERYTHING! This property boasts 4 Bedrooms and 2 Full Baths, plus a bonus room. Beautifully updated from the kitchen to the lower level. Private back yard with room for fun. Hardwood floors throughout the first level. There is plenty of living space as well as a pellet stove on the lower level.

Beds:
4
Baths:
4 Full
Sq.Ft.:
2,737
Status:
Active
MLS#:
MDKE116838
Type:
Single Family, Single Family-Detached
Subdivision:
Chesmar
Lot size:
0.75 Acres
Year built:
1964
Courtesy: Gunther-McClary Real Estate
View additional info

This wonderful 4 bedroom family home has plenty indoor and outdoor space for everyone. The addition of entire second floor and garage along with first floor renovations were completed in 2008. Separate suite upstairs provides privacy from rest of the family. Only minutes from Chestertown by boat or car. The community of Chesmar, located on the north side of the river provides great boating along the Chester River. The double lot offers additional privacy and space on either side. The screened-in porch houses a hot tub to relax in at night without being bothered by bugs and the balcony off the family room on the second floor offers a beautiful view of the stars and moon over the river. Lots of storage inside and out for all the toys, kayaks and water gear. Walk out to the pier, board the boat and be on the river instantly for fishing , water skiing or to enjoy abundance of wildlife on a sunset cruise. This would make a terrific short term rental helping with the expenses of having a second home.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,428
Status:
Active
MLS#:
MDKE116756
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.04 Acres
Year built:
1880
Courtesy: Cross Street Realtors LLC
View additional info
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