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Chestertown MD Real Estate & Homes for Sale

20 Properties Found

The median home value in Chestertown, MD is $328,000. This is higher than the county median home value of $178,000. The national median home value is $277,796. The average price of homes sold in Chestertown, MD is $328,000. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% 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.


1–20 of 20 properties displayed
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Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,714
Status:
NEW LISTING
MLS#:
MDKE2001966
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.15 Acres
Year built:
2016
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located in the historic district of Chestertown! Well maintained with an open floor plan and currently tenant occupied. The gleaming wood floors on the main level gleam! Amazing 2" x 6" exterior wall construction w/concrete crawl space, fire suppression system, granite kitchen counter tops. Large pantry. Master bedroom on the main level with double vanities and walk in closet. The exterior is finished with Hardiplank siding. Shared driveway. All photos were taken in 2017. New updated photos coming as soon as professional photographer provides.

Open House:

Saturday, 10/8 12:00-2:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,978
Status:
NEW LISTING
MLS#:
MDKE2001932
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.33 Acres
Year built:
2003
Courtesy: Doug Ashley Realtors, LLC
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Large Contemporary Rancher on a corner lot, located in Chesapeake Landing, a water orientated community with direct access to Worton creek and minutes from downtown Chestertown. All one level living and only 19 years young! Fully renovated kitchen in 2016 with ceramic tile floors, SS appliances and oak cabinets, Laundry and pantry. Pass through breakfast bar area opens up to living room with Gas fireplace, cathedral ceilings, and french doors leading to back yard. Master Bedroom has sizable walk in closet and separate vanity. Heated ceramic floors in bathroom and walk in shower. A large, partially finished bonus room (22' x 20') with walk out entrance to a fenced in yard is currently being used as a crafting room but would make a great extra entertaining area or home office/workshop! Features 2 french doors, windows, and separate pull down attic space above. Large shed on property is partially finished inside and has electric running to it. Expected on market: Oct 1, 2022. Please No Drive Byâs. Tenant occupied and dogs on property.

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,535
Status:
NEW LISTING
MLS#:
MDKE2001850
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale
Lot size:
20.08 Acres
Year built:
1999
Courtesy: TTR Sotheby's International Realty
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An Eastern Shore Haven: twenty picturesque acres, 10+/- wooded, with exceptional hunting in a trophy whitetail deer corridor and where wild turkey roam and roost. A gorgeous and classic 1999 custom built home, modeled after a Nantucket fishing Captain's cottage, with nine foot ceilings, solid wood doors, Kolbe&Kolbe windows, a comfortable screened porch, wood burning fireplaces, and a gourmet, open concept kitchen. Above the garage is the caretakers apartment with a private entrance, featuring one bedroom, full bathroom, and kitchenette. Fenced acreage, turn-out sheds, automatic waterers, a three stall barn with connected paddocks, and all the necessary amenities. The idyllic pond and gazebo offer the perfect spot to picnic and relax. The gunite "sport" pool is accompanied by a shaded pergola and a storage shed.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,147
Status:
NEW LISTING
MLS#:
MDKE2001862
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
2 Acres
Year built:
1999
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Immaculately kept home in Orchard Hill set on 2 acres, featuring 3 bedrooms, 2.5 baths. Additional rooms could serve as extra bedrooms if desired. Thick crown molding and chair rail. Gleaming hardwood floors. Vaulted ceilings. Gourmet kitchen with stainless steel appliances. Stunning owners suite with multiple large closets. Washer and dryer in the owners suite. Additional washer/dryer on the second floor. Upstairs features 2 bedrooms and another full bath as well as 2 extra rooms (1 finished) that could be bedrooms, storage or office space. A second staircase leads to another second floor living area that is currently set up as a living room but again could serve multiple purposes. 3 heating/AC zones which have all been replaced in 2016-2019. Extremely well cared for. Beautiful inside and out!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2004760
Type:
Other
Subdivision:
Chestertown
Lot size:
20.65 Acres
Year built:
1900
Courtesy: Benson & Mangold, LLC
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Magnificent Building Site on the Chester River. Being sold together⦠two lots totaling 30+ acres of property along the Chester River in Queen Anneâs County. Private lane with large oak trees towering over the driveway, high (30â+/-) elevation, 1,200â+ of Shoreline. The property is generally surrounded by about 5,500 acres of property that is subject to a conservation easement and includes an easement for recreational use of those 5,500 acres. One of the lots also includes a grandfathered pier and boat house. The property is one of several created as part of the subdivision of what was once referred to as Grasslands Plantation and is subject to some covenants that run in favor of the other property owners. The largest portion of the surrounding land is now owned by Washington College, which conducts migratory bird research there. MLW is 20â at pier!!!!!! That is not a typo. Northwestern Exposure. Outstanding location with rolling farm fields and close proximity to Historic Chestertown MD and easy commute to Wilmington/Philly/NJ/NY as well as Balt/Washington/NOVA.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,770
Status:
Active
MLS#:
MDKE2001924
Type:
Single Family, Single Family-Detached
Subdivision:
Venaringham
Lot size:
0.84 Acres
Year built:
1997
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Lovely rancher on over 3/4 of an acre. Private country settling but only 10 minutes to town. Bedrooms are split with the owner's suite on one side and the two additional bedrooms on the other side. Nice wood stove in the living room for a warm, cozy heat during the winter. Beautiful hardwood floors throughout most of the house. Formal dining room. Deck off the living room with pretty views of the back yard. Large uninished basement. $300 road maintenance fee.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,820
Status:
Active
MLS#:
MDKE2001726
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1986
Courtesy: The Hogans Agency Inc.
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Welcome to the Byford Heights community! This home is comfortable and inviting and offers one floor ease of living . Study with vaulted ceiling and skylights and sliding glass door to the backyard could also be used as a fourth bedroom! Living Room and Dining Room also have sliding glass doors to the backyard where the pool and patio are located. Hardwood floors throughout entire house. Primary bedroom has walk in closet. Dry walled garage with overhead storage. Mature landscaping. Great location - walk to historic downtown Chestertown for shopping and restaurants and the water! It is also Convenient to the Hospital and College.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,503
Status:
Active
MLS#:
MDKE2001848
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.1 Acres
Year built:
1939
Courtesy: Long & Foster Real Estate, Inc.
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A unique property for sale, and a rare opportunity in this charming historic town. The building is in the process of renovation. Currently down to the studs, much of the preparation work to rebuild is done, ready for the next phase. Plans have been approved by the city and would be made available to qualified prospective buyers. Located downtown, bordered on one side by the broad lawns and trees of the Kent County Courthouse, and on the other by charming historic homes. 5 minute walk to the Chester River and town amenities, galleries, restaurants, farmerâs market, boutiques, artists studios, parks and nature walks. Up to 3 Bedrooms/2.5 Bathrooms possible.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,464
Status:
Active
MLS#:
MDQA2004528
Type:
Single Family, Single Family-Detached
Subdivision:
The Grove
Lot size:
1.03 Acres
Year built:
2005
Courtesy: Brenton Realty Group
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Need Space??? Well here it is! Bring Your family and bring you Boat, RV, Collector Cars...Golf Cart...etc.... Home features 4 Bedrooms 2.5 bath. 2 Car Attached Garage PLUS a Detached Pole Building 30x48 with 12' Doors! Inside the home is plenty of room also. Eat-in kitchen with Breakfast bar and lots of Cabinets! Separate Dining Room, Living Room and Large Family Room. Upstairs you will find a Spacious Primary Bedroom with Full bath and Walk-in Closet. 3 extra generous size rooms and another Full Bath. Nice level lot with extensive landscaping. Within Minutes to the Chester River and Historial Chestertown and Centreville. Eastern Shore Living at its Best!

Beds:
4
Baths:
1 Full/1 Half
Sq.Ft.:
1,855
Status:
Active
MLS#:
MDKE2001774
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.12 Acres
Year built:
1920
Courtesy: Doug Ashley Realtors, LLC
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Welcome to 626 High St, she is just adorable. The hardwood floors throughout this 3 level home have withstood the test of time and are gorgeous! You immediately feel at home! Lovely fixtures, which are probably original to this home add to the charm. The dining room is very generous in size. The main level has an office, powder room, a nice kitchen with an eat in breakfast bar. There are four bedrooms, and 1.5 baths all total. This home has been a rental for a few years, but the owners have maintained it very well. There are just a couple of tweaks to be made, and the owners are working on that as well. The owner has explored the possibility of a possible building lot on the Lynchburg side. There may be a possibility of that with local zoning approval. Nothing is set in stone, but the new owner could explore further, if desired. In the historic district, four blocks to downtown, but close to Chestertown's Rail for Trails, which is a nice, paved path through Chestertown. Enjoy Washington College and all it has to offer to the community, local restaurants, a thriving artists community, music, the farmer's market, artisans, charming shops, and friendly welcoming people! There is a health food store, coffee shops, two grocery stores, hardware store, a local golf course at Chester River Yacht and County Club, bocci and pickle ball teams you can join! Like to kayak and canoe? You can easily do both on the Chester River, or Radcliffe Creek.

Beds:
2
Baths:
1 Full
Sq.Ft.:
966
Status:
Active
MLS#:
MDKE2001744
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.4 Acres
Year built:
1968
Courtesy: RE/MAX Excellence Realty
View additional info

Huge price reduction over 45K!!!!....bring all offers!!! SFH with 2 bedrooms, 1 bath, one level living situated on .40 acres of land, Living/Dining room combo, Table pace kitchen, Den off living room, screened porch off back, the home has room for improvements or expansion

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,140
Status:
Active
MLS#:
MDKE2001742
Type:
Townhouse
Subdivision:
Chester Arms
Lot size:
0.09 Acres
Year built:
2022
Courtesy: D N K Real Estate, LLC
View additional info

Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranquility of upper shore living. This is a unique opportunity to buy an affordable, yet brand new home located centrally in town a short walking distance to local stores, restaurants and the new YMCA. Your new home is a short drive from Washington College and Chestertown's historic waterfront district. This NEW CONSTRUCTION two story 3 BR duplex style townhome is complete and ready to move-in with no HOA fees or regulations. This end unit home has a private front, back and side yard with off street driveway. Inside, a modern open concept floor plan, upgraded stainless steel appliances, granite countertops and bright white cabinetry are a welcome invitation to comfortable living. There are multiple linen and storage closets to keep your living area organized. All living areas have easy to clean and maintain durable vinyl plank flooring. This townhome has 3 generous bedrooms and 1 full bathrooms upstairs and a 1/2 bathroom on the main floor. All bathrooms have matching granite countertops in modern design which coordinate with the main living area. This private lot offers a back porch with oversized private storage closet.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
4,446
Status:
Active
MLS#:
MDKE2001648
Type:
Single Family, Single Family-Detached
Subdivision:
Kent County
Year built:
1990
Courtesy: Gunther-McClary Real Estate
View additional info

This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach. Great room was added in 2001, with a loft and cat walk to offer added living area. The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included. A south facing direction on the water side offers wonderful & welcoming breezes throughout the summer. It is improved by 2 car heated garage built in 2006 plus a smaller area for storage with a bonus area above. The area above has radiant floor heat. New BAT septic was installed in last two years, with the county becoming the operator of the new sewage treatment area. Please do not drive down Cacaway Farm Lane without an appointment. This is a private lane.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2001612
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.06 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,490
Status:
Active
MLS#:
MDKE2001598
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.09 Acres
Year built:
2022
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2001618
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.09 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

Beds:
4
Baths:
2 Full/2 Half
Sq.Ft.:
2,698
Status:
Active
MLS#:
MDKE2001488
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.28 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC
View additional info

Back on the market due to a buyer financing problem. Move in ready home! On the main level, there are formal living and dining rooms and a kitchen that is adjacent to a beautiful breakfast room. You will enjoy lots of light streaming into the first floor. The kitchen has loads of storage with pantry and lots of upper and lower cabinets. The dining room offers a tray ceiling, and plenty of room for your dining room furniture. Upper level boasts of 4 large bedrooms and two full size bathrooms. The backyard has a freshly painted fence, and lots of room for your furry friends. The house has freshly painted exteriors and is nicely landscaped. The basement is large and a clean slate, that you can certainly finish. The two car garage has lots of space for storage. The home overlooks the main park and is centrally located.

Beds:
3
Baths:
2 Full
Sq.Ft.:
3,153
Status:
Active
MLS#:
MDKE2001246
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estates
Lot size:
1.91 Acres
Year built:
1975
Courtesy: Select Land & Homes, LLC
View additional info

Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime!

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,144
Status:
Active
MLS#:
MDQA2002828
Type:
Single Family, Single Family-Detached
Subdivision:
Ducks Neck
Lot size:
18.1 Acres
Year built:
1988
Courtesy: Select Land & Homes, LLC
View additional info

Wonderful Chester River get-a-way with extensive accessible river frontage. Private setting with approximately 3-4 acres of solid ground with 12-14 acres of marshland which offers excellent waterfowl hunting! Included is a 2 bedroom, 1 1/2 bath elevated, (over a 3-car garage) ranch style home. Views of unspoiled farmland across the river. These types of properties are hard to find and rarely come on the market! Deep Landing public boat ramp located is just down the road. Located in Queen Anne County just minutes to downtown Chestertown and easy access to Rt 301. Waterfowl shoreline permit in documents.

Beds:
1
Baths:
1 Full
Sq.Ft.:
600
Status:
Active
MLS#:
MDQA2000234
Type:
Single Family, Single Family-Detached
Subdivision:
Kingstown
Lot size:
0.34 Acres
Year built:
1945
Courtesy: EShore
View additional info

Waterfront Lot with dilapidated residence. Existing well and septic.

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