Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $214,750. This is higher than the county median home value of $183,500. The national median home value is $185,800. The average price of homes sold in Chestertown, MD is $214,750. Approximately 41.87% of Chestertown homes are owned, compared to 42.32% rented, while 15.82% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!


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Type:
Single Family-Detached
Sq.Ft.:
1,568
Status:
NEW LISTING
Beds:
4
Lot size:
0.46 Acres
Year built:
2012
Baths:
2.00
MLS#:
MDKE116126
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

One level home with some handicapped accessibility features including front ramp, wide doorways in master bedroom and bath with room for wheelchair, although not specifically a roll-in or lipless shower stall. Property almost half an acre (.45), level lot and faces farm fields across the street. At only eight years old it has good basic bones and, doesn't need much beyond cleaning, carpeting and decorating touches to be home. Three additional bedrooms and another full bath make this larger than it looks and a great buy at under $150k. DHCD Property.

Type:
Single Family-Detached
Sq.Ft.:
1,720
Status:
Active
Beds:
3
Lot size:
0.32 Acres
Year built:
1964
Baths:
2.00
MLS#:
MDKE116088
Subdivision:
College Heights

ADDITIONAL INFORMATION

Beautiful and well maintained home in Chestertown's College Heights, close to the college and all that Chestertown has to offer. Even provides quick access to route 213 for commuters. Possibilities are endless for this 1960's Rancher, could be your home or a solid investment for a lifetime. It's built like a rock and offers gleaming hardwood flooring, refinished bathrooms, large master bedroom, exceptional wood burning fireplace, and a full basement that could add another level to its beauty.

Type:
Single Family-Detached
Sq.Ft.:
1,456
Status:
Active
Beds:
3
Lot size:
0.8 Acres
Year built:
1986
Baths:
2.00
MLS#:
MDKE116102
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

Three bedroom ranch home located in HEATHER HEIGHTS, south of Chestertown, near Chester River Yacht and Country Club and a short walk to the Chester River. Large lot that backs up to open space and privacy.

Type:
Single Family-Detached
Sq.Ft.:
1,950
Status:
Active
Beds:
3
Lot size:
0.21 Acres
Year built:
1961
Baths:
2.00
MLS#:
MDKE116100
Subdivision:
College Heights

ADDITIONAL INFORMATION

Own this home less than the cost to rent! 3 bedrooms, a remodeled full bathroom, living room, office, and wood floors complete the main level. The lower level features a spacious kitchen opening to the family room, another full bathroom, laundry room and ceramic tile floors. Outside is a driveway for off street parking, a fully fenced backyard, and large shed with workbench and electric. Within walking distance to Downtown, Washington College, the hospital, and the Chestertown dog park, this is a great home for first time home buyers or investors looking for great return!

Type:
Single Family-Detached
Sq.Ft.:
1,592
Status:
Active
Beds:
3
Lot size:
0.49 Acres
Year built:
1975
Baths:
2.00
MLS#:
MDKE116096
Subdivision:
Morgnec

ADDITIONAL INFORMATION

Don't miss this 3BR, 2BA charming home with open country kitchen, large living room, den and spacious master bedroom with master bathroom and walk-in closet. Nicely situated with front and backyard overlooking farmland. Freshly painted, new septic and new HVAC! Just minutes to everything Chestertown has to offer; Washington College, restaurants, local shops, new marina and much more.

Type:
Single Family-Detached
Sq.Ft.:
4,715
Status:
Active
Beds:
4
Lot size:
2.05 Acres
Year built:
1995
Baths:
4.00
MLS#:
MDKE116070
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Hidden away in a private park-like setting, this wonderful waterfront retreat is ideally situated to take advantage of panoramic views and access to Worton Creek and the Bay beyond. This parcel is on a point of land with about 1000 feet of water frontage. The gracious Main House sits on the high ground of the property with the quaint and charming 2 BR 2 Bath Guest House below at waters edge - making it a great rental cottage. The main house consists of about 3500 sf and the guest house has about 1200 sf. Both have separate private lanes and easy access to the dock with boat lift and 3-4 MLW. When you enter the custom built main house, you are immediately drawn into the dramatic vaulted great room, designed like the bow of a ship, with water views all around plus an impressive wood burning fireplace. Glass doors open out to the wrap-around deck. Just off the great room is the expansive kitchen with center island, separate gas fireplace, and informal dining area with more windows framing the incredible views. The spacious separate dining room offers plenty of room for entertaining friends and family. The Master Bedroom with two closets and ensuite (radiant floor heat), adjoining screened porch and Hobby Room are all ideally located at one end of the home - well situated to take advantage of the water views. Three additional bedrooms plus office and two full baths are located at the other end of the home - also offering beautiful nature scenes and water views. Additionally, there are closets galore plus an oversized two car garage, lovely grounds, privacy and incredible water views - what more could you want? This is a one of a kind property - private but not isolated. In boating season, you can cruise right across to the Harbor House Restaurant for waterfront dining or over to fuel up your boat at the dock and head out for a day on the Bay and Worton Marina. By car, it is just 15 minutes from either Historic Chestertown or Rock Hall on the Bay - both towns offering a wide variety of dining, shopping and entertainment opportunities. BE SURE TO CLICK ON VIRTUAL TOUR ICON TO SEE INTERACTIVE FLOOR PLANS FOR HOUSE & GUEST HOUSE PLUS ADDITIONAL PHOTOS!

Type:
Single Family-Detached
Sq.Ft.:
1,503
Status:
Active
Beds:
n/a
Lot size:
0.09 Acres
Year built:
1939
Baths:
MLS#:
MDKE116074
Subdivision:
Chestertown

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
3,500
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
2009
Baths:
4.00
MLS#:
MDKE116060
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

Welcome to 118 Little Harbor Way, Unit 300 in Chester River Landing in Chestertown Maryland. This one of a kind Penthouse unit has panoramic views of the Chester River and Chester River Bridge. Enjoy your afternoon or evening relaxing on one of the two balconies facing the Chester River. The elevator will raise you to your Penthouse unit and open into the most beautiful condo that you will see. The open, bright floor plan featuring hardwood flooring , spacious rooms, beautiful crown moldings and wainscoting and so much more will cater to everyone's taste. The gourmet kitchen featuring granite counters, stainless appliances and enough storage to meet the needs of a professional chef won't disappoint. Awake in your Master Suite overlooking the river and the wildlife that the area has to offer. The walk-in dressing area and Master Bath are extremely large and beautifully designed. This home also includes a 30' boat slip in the community marina and also a single car detached garage .You must take a tour of this one of a kind Penthouse

Type:
Single Family-Detached
Sq.Ft.:
1,487
Status:
Active
Beds:
3
Lot size:
1.02 Acres
Year built:
1988
Baths:
2.00
MLS#:
MDKE116054
Subdivision:
Great Oak Estates

ADDITIONAL INFORMATION

Welcome Home to 22428 Great Oak Landing. Pull up to your very welcoming driveway complete with mature landscaping, room for boat, RV, and/or extra cars. Open concept floor plan and an updated kitchen with space to accommodate an eat in table. The beautiful kitchen overlooks the expanded dining area and large living room showcasing the vaulted ceilings and gorgeous beams that warm the space along with the fireplace and add character. The outdoors is sure to entertain with a screened in porch, inground swimming pool & patio, oversized shed all situated on a 1 acre lot. Schedule your showing today and move into this beautiful new home before throwing a housewarming pool party bash with your friends and family!

Type:
Single Family-Detached
Sq.Ft.:
794
Status:
Active
Beds:
2
Lot size:
0.65 Acres
Year built:
1950
Baths:
1.00
MLS#:
MDKE116048
Subdivision:
Fairlee

ADDITIONAL INFORMATION

Bungalow in the town of Fairlee. Cozy home with nice wood floors. Knotty Pine kitchen cabinets. Large lot has old shed/chicken coop and plenty of room for a large garden. No city taxes, but you have the benefit of public water and sewer. Easy to see.

Type:
Other
Sq.Ft.:
1,563
Status:
Active
Beds:
2
Year built:
2009
Baths:
3.00
MLS#:
MDKE116030
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

Shows great! Nice hardwood floors, beautiful millwork, built ins were custom made, granite counter tops, open floor plan, living room has a gas fireplace, private master bedroom suite with an electric fireplace and beautiful water views. Both bedrooms have a private bath, and there is a nice office with custom built ins. Beautiful Chester River water views from master suite, living room, kitchen and dining area. Walk out French doors to a private covered deck, overlooking the river, and a fire pit. Quality construction. There is a common propane tank that services the units through Peninsula Gas. Public water cost is covered thru condo fees. Locked common entrance/foyer is well decorated. Correct square footage is 1563

Type:
Single Family-Detached
Sq.Ft.:
1,584
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE116036
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the home, including original windows, beams, hardwood floors, bookcases, and more. 3 spacious bedrooms, all with restored hardwoods, master with ensuite bathroom (a rare find in a historic home)! Further family bathroom offering double vanities and tub/shower. Laundry and half bath on main level. Large great room addition on the back of the house, with sliders to deck, overlooking private back yard. Home was just completely renovated in 2019 including new 2 x Zone heat pump with central A/C, tankless hot water (propane), complete new wiring, new kitchen and baths, new windows, new stainless appliances, new/restored floors, and more!

Type:
Townhouse
Sq.Ft.:
1,876
Status:
Active
Beds:
3
Lot size:
0.05 Acres
Year built:
2005
Baths:
3.00
MLS#:
MDKE116012
Subdivision:
Oak Hollow

ADDITIONAL INFORMATION

Town-home located in Oak Hollow, a well managed town-home community. This unit is brick fronted with a one car garage. The master bedroom has a cathedral ceiling with large bath with separate shower and tub. There are 2 additional bedrooms on the upper level. The middle level has kitchen with sliders to a rear deck and a living room. The lower level has the garage and an additional room ready for you to finish the way you want it. Close to shopping and restaurants!

Type:
Single Family-Detached
Sq.Ft.:
3,692
Status:
Active
Beds:
4
Lot size:
0.28 Acres
Year built:
2010
Baths:
3.00
MLS#:
MDKE116020
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

This home looks like it has never been lived in!!!. When you enter the two story entrance foyer (pease take off your shoes) you will get a sense of what a new home looks like. The kitchen has wood floors and the dining room has tray ceilings. The family room has a wood burning fireplace that has never been used) and a stylish ceiling fan. There is even a tidy living room on the main level. The upper level has an owners suite and 3 additional bedrooms. The lower level overs a recreation room and a game room. Hunter Douglas insulated blinds are at most windows. This property backs to woods but has a front view of one of the larger community areas. The 2 car garage caps off one of the best homes and locations in Coventry Farms!

Type:
Single Family-Detached
Sq.Ft.:
3,204
Status:
Active
Beds:
4
Lot size:
2.05 Acres
Year built:
1990
Baths:
3.00
MLS#:
MDKE116014
Subdivision:
Orchard Hill

ADDITIONAL INFORMATION

Spacious multilevel home with 2 story entrance foyer. Recently updated kitchen with Quartz counters, newer looking cabinets and new stainless steel appliances. New flooring in the family room with wood burning fireplace. There is also a living room with a wood burning fireplace. There is a formal dining room and a rear screened porch. The laundry room is huge and has an additional refrigerator. The HVAC is all new as well!! Property backs to woods and farm land. The garage has space for a small workshop. One of the best locations in Orchard Hill!

Type:
Townhouse
Sq.Ft.:
2,200
Status:
Active
Beds:
3
Year built:
2007
Baths:
3.00
MLS#:
MDKE116006
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim in the lovely pool, walk the shell walking paths throughout the community and along the shoreline, go kayaking from the community launching area, or take a bike ride or walk into town. Lots of ways to enjoy the care-free Eastern Shore lifestyle!

Type:
Single Family-Detached
Sq.Ft.:
2,186
Status:
Active
Beds:
4
Lot size:
0.69 Acres
Year built:
1971
Baths:
2.00
MLS#:
MDKE116022
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

Just on the market, two story contemporary home located in water community area. Over 2,000 sq. ft., walk to beach and launching area and waterview. 4 BR, 2 BA with dining room and kitchen area, over a half an acre of ground, has a 40 X 24 ft. workshop with electric, and deck on the back of house, seller is offering new buyer's a home warranty.

Type:
Single Family-Detached
Sq.Ft.:
3,248
Status:
Active
Beds:
3
Lot size:
213 Acres
Year built:
1856
Baths:
3.00
MLS#:
MDKE115982
Subdivision:
None Available

ADDITIONAL INFORMATION

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.

Type:
Single Family-Detached
Sq.Ft.:
1,190
Status:
Active
Beds:
2
Lot size:
0.13 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE115990
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

This in town location is perfect - walk to shops and restaurants and enjoy all the activities that Chestertown has to offer. The home is in good condition with new carpet on the first floor. Updated kitchen as well. Come take a look!

Type:
Single Family-Detached
Sq.Ft.:
1,296
Status:
Active
Beds:
3
Lot size:
0.5 Acres
Year built:
1968
Baths:
2.00
MLS#:
MDKE115922
Subdivision:
Kent Acres

ADDITIONAL INFORMATION

This property checks all the boxes! Fantastic location, convenient to Chestertown, with a private, partially wooded lot backing to trees, with no HOA! The 3 bedroom, 2 bathroom ranch-style home offers an updated kitchen with durable composite tile floors, wood cabinets, Corian counters, stainless steel appliances, and a large kitchen island with wood top. The kitchen and dining areas open to the huge living room with beautiful hardwood floors and a wood burning fireplace. Refinished hardwood floors continue down the hall and into each of the bedrooms. The master suite offers an updated bathroom with ceramic tile flooring, double vanity with quartz counters, and a tiled shower with marble floor. A full, unfinished basement adds additional storage and usable space, while the carport offers covered parking. Freshly painted and landscaped, this property is move-in ready!

Type:
Single Family-Detached
Sq.Ft.:
6,105
Status:
Active
Beds:
5
Lot size:
0.97 Acres
Year built:
2002
Baths:
6.00
MLS#:
MDKE115970
Subdivision:
Tolchester

ADDITIONAL INFORMATION

An exceptional architect-designed 6,105 square foot home perched 100 feet-high on a bluff overlooking the Chesapeake Bay - the Chesapeake/Delaware shipping channel in full view. Included in the sale is the adjacent .66 acre parcel, "LOT PAR 1-2 ON A PL S/S MONTGOMERY AVE." You'll never tire of watching the ships and daily sunsets through the floor to ceiling windows. Floors throughout are finished in quarter-sawn red oak. Bluestone surrounds the house and continues into the entryway that provides a dramatic dining space with a 17-foot ceiling and a waterview as the backdrop. Sweeping open floor plan is graceful and elegant in its simplicity - full of light, angles, white walls and stunning views from every window. Plenty of gallery-like spaces to display your art. A chef-designed gourmet kitchen is a cook's dream, complete with a Thermador gas cooktop and electric double oven, two Subzero refrigerators, a Subzero freezer, under-counter Subzero refrigerator drawers, granite counters, and adjoining butler's pantry and many more custom features. A must see. First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Nationally known artisan-designed cherry stair rail leads to the guest floor with four bedrooms, three full baths and a huge bonus room, which could make a wonderful studio or game room. There are never-ending bay views from almost every room in the house. Heating and cooling is provided by a geothermal system. A three-car garage continues the house exterior design with matching trim and cedar shingles. Dock your boat at the premier marina just a three minute drive away. Nearby is Rock Hall with more marinas, shops, restaurants, and a world-class jazz venue called the Mainstay. Twelve miles away is historic Chestertown with Washington College and more shops and restaurants. Within two hours to Philadelphia, Baltimore and DC. By appointment only. This is one of the finest designed homes on the Eastern Shore. Be sure to allow plenty of time for your tour.

Type:
Single Family-Detached
Sq.Ft.:
1,340
Status:
Active
Beds:
3
Lot size:
0.5 Acres
Year built:
2015
Baths:
2.00
MLS#:
MDQA142208
Subdivision:
Pine Cove

ADDITIONAL INFORMATION

Buy this lovely one-level home in Queen Anne's County for less than you would rent. Better than new! No wait for permits, weather and contractors etc., no upcharge for option-add-ons. Landscaping is already established, there is already a deck , a shed and concrete driveway, and all the kinks are worked out. Very nice, dark, wood floors in the main living area, Laundry and Utility room. Large master with walk-in closet and en suite master bath with tub and separate shower. Spacious, dark, wood cabinets and warm, granite countertops and pantry. Water Softener. Slider to the rear deck. Attached 2 car garage. Alarm pre-wired. Additionally included: firepit and a new outdoor tent. The boat-ramp and the Chester River are about 150 yards walking distance. Centreville is about 20-25 minutes, the Bay Bridge is approximately 30-35 minutes away. This is a great home for anyone who wants to start homeownership, downsize or just relocate. *** Please take off shoes upon entering ***

Type:
Single Family-Detached
Sq.Ft.:
1,008
Status:
Active
Beds:
3
Lot size:
1.27 Acres
Year built:
1961
Baths:
1.00
MLS#:
MDKE115964
Subdivision:
None Available

ADDITIONAL INFORMATION

All new inside and out, freshly finished and ready for you to move in. New roof, windows, siding, gutters, crawl space encapsulated. Original hardwood flooring sanded and stained. New all-wood construction cherry kitchen cabinets. New HVAC, new well, and a HUGE Garage with an attached workshop. Beautifully situated in a peaceful, park-like setting.

Type:
Single Family-Detached
Sq.Ft.:
1,128
Status:
Active
Beds:
3
Lot size:
1.66 Acres
Year built:
1970
Baths:
1.00
MLS#:
MDKE115936
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Near Rock Hall, MD. Great 3 bedroom, bath Ranch home on 1.66 acres in Chestertown, MD. This home is a great starter home or for downsizing. It has a large living room and dining room off the kitchen. Hardwood floors. The yard is flat with open space that backs to woods. The front of the house faces farm fields. If you are looking for peace and quiet you will find it here. It is definitely worth a look. All HUD homes are sold "As Is".

Type:
Single Family-Detached
Sq.Ft.:
1,658
Status:
Active
Beds:
3
Lot size:
0.58 Acres
Year built:
1999
Baths:
2.00
MLS#:
MDQA141974
Subdivision:
Kingstowne Manor

ADDITIONAL INFORMATION

Very nice rancher in QA Co just minutes from downtown Chestertown. This home features a large LR with gas FP, wood floors, vaulted ceiling & skylights. Separate DR also has wood floors. Spacious kitchen has corian counters and a sunny bay window. A sunroom was added off the LR which leads to a deck. Fully fenced back yard. There is a new heat pump with propane backup and water heater. Pack your bags - this home is move in ready! Photos coming next week.

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Thomas H. O’Leary, Maryland License 665968, Xome Inc., License 665968, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Thomas H. O’Leary, D.C. License BR98378780, Xome Inc., License CO98372739, ThomasH.OLeary@Xome.com, 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Thomas H. O’Leary, PA License #RM423918, Xome Inc., PA License #RB067821, ThomasH.OLeary@Xome.com, 844-400-XOME (9663) 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626
Thomas H. O'Leary, NJ License # 1754747, Xome Inc. NJ License # 1861285, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

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