Chestertown MD Real Estate & Homes for Sale

63 Properties Found

The median home value in Chestertown, MD is $245,000. 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 $245,000. 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!
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Beds:
4
Baths:
2 Full
Sq.Ft.:
2,284
Status:
NEW LISTING
MLS#:
MDKE117142
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
1.54 Acres
Year built:
1975
Contact:
William Norris, [email protected], 410-708-0956
Courtesy: Select Land & Homes, LLC
View additional info

Mill Creek Waterfront, situated at the end of a quiet cul-de-sac in Chesapeake Landing within a short ten minute drive to Chestertown or Rock Hall. This 1.5+ /- wooded acre point of land is bordered on two side s by the creek. One side slopes gently to the creek and the other offers elevated views of water, marsh and unspoiled woodland. An abundance of wildlife including deer, turkeys, herons, eagles and waterfowl frequent the property and surroundings. This site offers access to Mill Creek for canoe, kayak, and paddle board. The residence offers views of the creek from most rooms in the recently upgraded raised rancher. There are two bedrooms, living areas with fireplaces, and kitchens on both levels. The waterside barn is in need of repairs but serves as a perfect building for watersport equipment storage, woodshop, " man cave" or "she shed". This is the ideal property to getaway from it all and decompress from the hustle and bustle of a fast paced lifestyle. Utility easement runs with the property.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
2,408
Status:
NEW LISTING
MLS#:
MDKE117148
Type:
Single Family, Single Family-Detached
Subdivision:
Heather Heights
Lot size:
0.8 Acres
Year built:
1976
Contact:
Stacy Kendall, [email protected], 443-480-3453
Courtesy: Cross Street Realtors LLC
View additional info

This Heather Heights jewel has had quite the transformation - the main level features a tastefully updated/upgraded kitchen with breakfast nook, hardwood flooring, built-ins, separately zoned spacious master suite with reading/sitting room, walk-in closet with custom built-ins and laundry + large master bathroom... the upper level boasts 4 bedrooms and 2 full bathrooms. The basement offers generous storage capacity and game area, all of which is protected by a french drain system... The garage is even heated and cooled!

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
929
Status:
NEW LISTING
MLS#:
MDKE117144
Type:
Other
Subdivision:
Vicker's Row
Lot size:
0.02 Acres
Year built:
1900
Contact:
Stacy Kendall, [email protected], 443-480-3453
Courtesy: Cross Street Realtors LLC
View additional info

Turn-key Row Home in Downtown Chestertown provides great peace of mind for those looking to rid themselves of property maintenance... all you need to do is Lock and Leave. Brazilian Cherry Hardwood and Ceramic Tile Flooring, Custom Built-ins, High Ceilings, Fast Internet, Off-Street Parking, Storage, walk to dining, shopping, and the Chester River.

Beds:
6
Baths:
3 Full/1 Half
Sq.Ft.:
4,048
Status:
NEW LISTING
MLS#:
MDKE117086
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.15 Acres
Year built:
1910
Contact:
Lisa Raffetto, [email protected], 410-708-0174
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,066
Status:
NEW LISTING
MLS#:
MDQA145384
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
1 Acres
Year built:
1935
Contact:
Kristina Woodward, [email protected], 443-683-1041
Courtesy: Signature Realty Group, LLC
View additional info

INVESTOR ALERT!!! This three bedroom, one bath home sits on 1 acre in Chester Harbor! There is attic space for a potential extra bedroom. Convenient to Historic Chestertown for shopping and local events. Home being sold in AS IS? condition. Explore your imagination, turn this house into a home! Come check it out! Bring us your best offer!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,608
Status:
NEW LISTING
MLS#:
MDQA145374
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1972
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This delightful three bedroom , 2 bath Rancher is in move-in condition. Enjoy the large family room. Front porch overlooks a nice front yard. New roof and vinyl siding with a privacy fence surrounding the back yard. Paved driveway with a concrete pad.

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
1,664
Status:
NEW LISTING
MLS#:
MDKE117116
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District Chestertown
Lot size:
0.04 Acres
Year built:
1900
Contact:
Jody Baker, [email protected], 410-708-3536
Courtesy: Cross Street Realtors LLC
View additional info

A stately Victorian on a magnificently landscaped lot in the heart of the Historic District just two blocks from the Chester River. With an open design, high ceilings, intricate detailing, polished wide-plank hardwoods, an array of natural light and modern systems combining the best of today with the charm of yesterday. The wide-covered front porch and rear brick patio are perfect for quiet summer nights and entertaining!

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,582
Status:
NEW LISTING
MLS#:
MDKE117118
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.48 Acres
Year built:
2005
Contact:
Christine Burgess, [email protected], 410-708-3511
Courtesy: Keller Williams Select Realtors
View additional info

Gorgeous 4 bedroom/3 bath home on Mill Creek has been beautifully engineered and designed to evoke that "Welcome Home" feeling as you enter. The wooded lot is located on the Mill Creek, with it's panoramic water views, is an easy jaunt to the Chesapeake Bay by boat with 2-3 ft at the dock. The home comes completely furnished and is move in ready, as the owners are downsizing and would prefer to just hand over the keys. Radiant heat on the first floor will warm your toes on those crisp autumn days in the sun-filled living room, as the 3 sided fireplace set the mood for cozy evenings with a good book. Or just watch the stars from the wrap around deck. A floating staircase ascends to the open study or TV area with 2 additional bedrooms and a full bath. A second floor balcony, which opens from one of the bedrooms, affords a private getaway for a quiet moment. The 1st floor, light filled Master Bedroom opens to the deck with sliding doors, as does the 1st floor guest bedroom with its own private bath. The kitchen comes with stainless steel appliances and granite like countertops, an Island with standing breakfast bar and a few steps to the dining room for ease of serving. This property is a must see to appreciate, with it's quiet location on a cul-de-sac in a Chesapeake Landing neighborhood, the development has its own Marina and public area by the water and is just a few blocks away from Harbor House Restaurant among other local attractions. Just a 10 minute drive to Chestertown for shopping, dining and medical care, Farmers Market and events throughout the year.

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
1,632
Status:
NEW LISTING
MLS#:
MDKE117038
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.34 Acres
Year built:
1994
Contact:
Peter Heller, [email protected], 410-708-3301
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful home in highly sought after location. Featuring 2 bedrooms, 2.5 baths. Located at the end of a cul-de sac. Home is architecturally designed. Library with built -ins. Vaulted ceilings. Enclosed breezeway to garage. Beautiful deck and patio. Walking distance to everything the town has to offer. Pretty gardens throughout the property. Solar panels leased from Solar City.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,064
Status:
NEW LISTING
MLS#:
MDKE117128
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.06 Acres
Year built:
1920
Contact:
Kenneth Roderick, [email protected], 410-924-2810
Courtesy: RE/MAX Executive
View additional info

Solid investment property. Property is currently leased for a year through 5/15/2021. Rental market is strong because of close proximity to College and downtown. Fenced in rear yard allows privacy and shed has ample storage for yard accessories. If your are looking to add to your investment portfolio, take a look as this has positive cash flow. 24 hours showing notice required because house is tenant occupied. Lister must accompany. There is no sign on property.

Open House:

Saturday, 10/3 11:00-2:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,855
Status:
NEW LISTING
MLS#:
MDKE117106
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.16 Acres
Year built:
1800
Contact:
Miles Norris, [email protected], 410-708-5423
Courtesy: Select Land & Homes, LLC
View additional info

Renovated by the editor of Historic Houses of Kent County, the Davis Duplex is the perfect blend of historic charm and modern amenities. The property features a first floor master, multiple fireplaces, large upgraded kitchen, and built in bookshelves. The dual front doors enter into the formal dining and living room and the rear of the home has a spacious master with flex space above. Outside is a lovely slate patio and brick pathways that lead to the gardens and Downtown. Visit the property website at105smillst . com to schedule a private tour!

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
Contact:
Cindy Genther, [email protected], 443-480-1953
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:
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
Contact:
Doug Ashley, [email protected], 410-708-0480
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:
Active
MLS#:
MDKE117078
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.23 Acres
Year built:
1948
Contact:
Melinda Wimer, [email protected], 410-287-3691
Courtesy: Harlan C. Williams Co.
View additional info

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:
Active
MLS#:
MDKE117068
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Creek
Lot size:
5.05 Acres
Year built:
1993
Contact:
John Burke, [email protected], 443-206-3727
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:
Active
MLS#:
MDQA145180
Type:
Single Family, Single Family-Detached
Subdivision:
Pheasantfield
Lot size:
37.09 Acres
Year built:
1995
Contact:
Sarah Lipkowitz, [email protected], 301-502-7623
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:
Active
MLS#:
MDQA145178
Type:
Single Family, Single Family-Detached
Subdivision:
Pheasantfield
Lot size:
37.09 Acres
Year built:
1995
Contact:
Sarah Lipkowitz, [email protected], 301-502-7623
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.:
1,280
Status:
Active
MLS#:
MDKE117034
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.73 Acres
Year built:
2020
Contact:
Karen Clark, [email protected], 410-490-2183
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
Contact:
Retha Arrabal, [email protected], 410-810-0010
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
Contact:
Brett Schrader, [email protected], 410-490-6075
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
Contact:
BRIAN MORRIS, [email protected], 410-708-1984
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:
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
Contact:
Francis Hickman, [email protected], 410-778-9122
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
Contact:
Lisa Raffetto, [email protected], 410-708-0174
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
Contact:
Ed Beres, [email protected], 443-271-3561
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.

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