Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $250,000. 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 $250,000. 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.:
1,650
Status:
NEW LISTING
Beds:
4
Lot size:
0.35 Acres
Year built:
1986
Baths:
2.00
MLS#:
MDQA143010
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

This is a fully transformed house, just like new! Move in and enjoy! MBR wing is private, has cable TV H/U on wall, and the other 3 BR's on the opposite side of house. The Den can be used as a Family Room as it has cable TV H/U on wall, or use it for meeting clients if you work from home; they can enter through the back den door to keep your home space private. Open Floorplan is perfect for family gatherings. Cook in the gorgeous gourmet Kitchen with Chimney Hood and Island, high end granite countertops w/undermount SS sink, Samsung Stainless Appliances while your friends hang out in the Living Room. The Samsung full sized stacked washer & dryer are in a separate laundry room. Fall in love with the Custom vanities in the tiled bathrooms. The Hall bath has curved tub & tiled walls, and the MBA has beautiful glass walled shower with rolling door and double sinks. All new LVT throughout living areas, carpet in BR's. New architectural shingle Roof, tilt-in Low-E windows, siding, gutters, HVAC and HWH. The garage is perfect for a workshop w/utility sink, or can be used for a small vehicle, plus there is a storage shed in the yard. Enjoy the outdoors under the covered front porches, rain or shine. With all New insulation in attic, crawl space and walls, All new electric, plumbing, lighting, and sprinkler system to reduce your insurance costs, you will love the ease of raising your family here.. Close to tax-free Delaware shopping, Washington College, and quaint town of Chestertown with all it's history. HOA is not mandatory, but provides access to pier/ramp/playground. Professional Pictures will be posted on Monday.

Type:
Single Family-Detached
Sq.Ft.:
2,664
Status:
NEW LISTING
Beds:
4
Lot size:
0.4 Acres
Year built:
1959
Baths:
2.00
MLS#:
MDKE116220
Subdivision:
College Heights

ADDITIONAL INFORMATION

Spacious brick rancher in College Heights. Remodeled kitchen and gleaming hardwood floors. Finished lower level adds an additional bedroom and bath as well as a large family room. Ample room in the back yard. Many more pictures will be coming next week. Subject to existing lease which ends 7/1/2020.

Type:
Single Family-Detached
Sq.Ft.:
1,080
Status:
Active
Beds:
3
Lot size:
0.1 Acres
Year built:
1970
Baths:
1.00
MLS#:
MDKE116214
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Rancher located in the historic district of Chestertown with a nice manageable lot. House needs some work but location and price make it a great for a rehab. Close to schools, downtown Chestertown and Washington College.

Type:
Single Family-Detached
Sq.Ft.:
1,297
Status:
Active
Beds:
1
Lot size:
19.33 Acres
Year built:
1978
Baths:
1.00
MLS#:
MDQA143004
Subdivision:
Crumpton

ADDITIONAL INFORMATION

19.33 Acres of riverfront property on the Chester! Private and peaceful wooded setting ideal for the outdoors sportsman, hunters, boaters & outdoor enthusiasts! T-dock 100' +/- with 2 mooring pilings. Cozy cabin to warm up in after a long day with 2 brick fireplaces & woodstove.

Type:
Single Family-Detached
Sq.Ft.:
1,404
Status:
Active
Beds:
3
Lot size:
0.41 Acres
Year built:
1999
Baths:
2.00
MLS#:
MDKE116212
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Updated three bedroom, 2 bath home in a semi private .41 acre lot. New flooring throughout, kitchen has been updated, deck, two storage shed, landscaped lot, one bedroom on the first floor and two bedrooms upstairs with two full baths. Shows well, and is in move in condition. Easy to show.

Type:
Single Family-Detached
Sq.Ft.:
2,492
Status:
Active
Beds:
4
Lot size:
0.16 Acres
Year built:
1880
Baths:
3.00
MLS#:
MDKE116192
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

This home features the charm of a historic home with the amenities and energy efficiency of a modern home. There are beautiful hardwood floors throughout. The first floor flows nicely from the living/dining room at the front to the sunny kitchen and family room at the rear. The home was completely remodeled in 2009 with low E windows, new roof, insulation, heating and AC system. The front porch looks out over the lovely tree-lined streets in one of Chestertown's nicest historic districts and the rear opens to a pretty garden. There is off street parking accessible from an alley which runs behind the house. A very short walk down the street offers a beautiful view of the Chester River. Also within walking distance are the shops and restaurants in downtown Chestertown. Don't miss out on the opportunity to own this lovely home.

Type:
Single Family-Detached
Sq.Ft.:
1,292
Status:
Active
Beds:
3
Lot size:
0.36 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDKE116196
Subdivision:
Georgetown

ADDITIONAL INFORMATION

Small bungalow, quiet street, public utilities, priced to sell.

Type:
Single Family-Detached
Sq.Ft.:
1,545
Status:
Active
Beds:
3
Lot size:
0.69 Acres
Year built:
1968
Baths:
3.00
MLS#:
MDKE116182
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

As soon as you enter, you will notice the expansive views of Mill Creek. Beautifully situated on an elevated location. New dredging runs in front of property, giving access to deep water. Newly constructed and renovated in 2013 with highest quality finishes, such as wood floors, granite counters, marble tile baths and thoughtful design, making the views impressive from every room in the house. There is a master suite on the first floor with a sumptuous bath; an expansive deck facing the water, and a gentle slope down to the dock.A full, dry, walk-out basement is the perfect location for a workshop and storage for water toys. Come see soon.

Type:
Single Family-Detached
Sq.Ft.:
884
Status:
Active
Beds:
2
Lot size:
0.34 Acres
Year built:
1963
Baths:
1.00
MLS#:
MDQA142890
Subdivision:
Queen Annes County

ADDITIONAL INFORMATION

Welcome to Chester Harbor a quaint water front community located in Queen Annes County just minutes from Chestertown and an easy commute to Annapolis or Wilmington. This property is on the main street of the community on a large corner lot. A two bedroom ranch with great bones and is in good shape and ready for new owners. This home is priced for the first time home buyer and the potential is unlimited . There is water access from the community park and marina. Call for an appointment to see this diamond in the rough.

Type:
Single Family-Detached
Sq.Ft.:
2,135
Status:
Active
Beds:
3
Lot size:
0.15 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE116174
Subdivision:
Historic Chestertown

ADDITIONAL INFORMATION

204 NORTH WATER is the perfect marriage between early 20th century and 21st century. The era in which it was built featured many gracious details all retained and meticulously restored. One is struck by the inviting front porch, the Victorian details of balustrades, true working shutters, metal roof and Wisteria mounted along porch eaves. So typical of the time. Adding to the gracious lifestyle is the square ENTRANCE HALL where the original stairway is situated so the side of the stairway is featured as a focal point of the entrance including its handsome newel posts, railings and gentle rise to the second floor. To the left is the LIVING ROOM with fully-functioning original pocket doors between the entrance hall, living room and the separate, spacious DINING ROOM. The wood floors throughout are beautifully finished and original. In both the living room and dining room the ceiling in the bay windows have been imaginatively designed to house modern recessed lighting. Here there are custom designed radiator covers. The like-new condition of the woodwork, walls, decorative mantel and tile coupled with the lighting adds to the dramatic feeling of these social spaces. Of note are the architecturally designed ceilings and crown molding. Adjacent to the dining rooms and kitchen is a new-screened porch that flows to the gardens. The new, very large, quite contemporary, inviting and well-equipped KITCHEN and FAMILY AREA beautifully complement the original traditional architecture. The floor is heated. On the second level there are three gracious bedrooms (or two bedrooms and an office/library). All meticulously restored. The two front rooms enjoy a view of the Chester River and Chester River Bridge. The third room with built-in bookshelves offers a view of the garden and outbuilding. A new, modern bath is nearby. All baths and the powder room feature inlaid tiles from Portugal and Italy as artistic features. Here is a heated towel rack. A "back" stairway leads to the MASTER BEDROOM AND MASTER BATH. This very private space offers views of the Chester River and inlaid Portuguese tile display above double windows and window seat. An attractive master bath was added that features a folding glass shower door. ALL the baths have heated toilet seats, handsome tile work, modern fixtures and heated floors. The OUTBUILDING in situated in a slight rise in the garden a brick walk away from the main house. It is heated, has its own electrical service, exhaust fan, window air conditioner and is fully insulated. A great space for a workshop, office or studio. There is a timed sprinkler system for the garden beds and plantings. All new PLUMBING including a unique individual direct line to each faucet for both hot and cold water. All new WIRING. This ca. 1900, handsome, "very modern Victorian lady" is a very special experience that offers a lovely traditional yet contemporary lifestyle. 204 North Water is located in Chestertown in the County of Kent on Maryland's Eastern Shore. Here is found Washington College (10th oldest college in America), live theatre, newly redesigned and constructed MARINA, specialty shops, thriving Center of the Arts. There is a continuous calendar of fine Cultural events. The award-winning Farmers Market offers fruits and vegetables and artisans' wares all year. Sporting events are a top priority on the Chester River and Chesapeake Bay. This small, primarily agricultural Kent County also offers a precious, serene National Refuge & many public boat ramps; It is a special destination for visiting, relaxing, weddings, sailing, peace and plenty.

Type:
Single Family-Detached
Sq.Ft.:
960
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1992
Baths:
2.00
MLS#:
MDKE116186
Subdivision:
None Available

ADDITIONAL INFORMATION

YOU WILL LOVE THIS HOME! Just step inside and explore all the space for everyone! The original ranch home has been expanded to over 1,800+ sq ft with room for everyone in any stage of life! A luxurious private master suite with HUMONGOUS walk in closet, space for a king size bed, morning room area, and large en suite bath with 2 sinks and ceramic tile floor. There is a formal living room for holidays and guests. The large central kitchen is the hub of this family home and opens onto the sunny dining area with pellet stove an a GIGANTIC family room with space for everything and everyone. A separate rec room that opens onto the rear patio can be a flexible space for a multitude of needs. The screened car port makes for a great place to have everyone over for crabs in the summer and the large 2 acre lot is 3/4 wooded for hunting and recreation! This home has so much to offer and not far from Chestertown or Rock Hall, come take a look today and see for yourself!!

Type:
Single Family-Detached
Sq.Ft.:
880
Status:
Active
Beds:
3
Lot size:
0.28 Acres
Year built:
1955
Baths:
1.00
MLS#:
MDKE116180
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

OWN A HOME FOR THE PRICE OF A RENTAL! MONTHLY PAYMENTS UNDER $1000 will get you a completely remodeled rancher. All new walls, flooring, recessed lighting, paint. Brand new kitchen with tasteful palette, new appliances, cabinets, granite counters. Ceramic tile bath. New exterior siding, roof, windows. New plumbing, electric & HVAC system. No septic, home is on public sewer line. Newly installed water softener. Home backs to wooded area for privacy. Relax on the deck and enjoy peaceful Tolchester Estates. Just a short distance to the Tolchester Beach Marina.

Type:
Single Family-Detached
Sq.Ft.:
1,588
Status:
Active
Beds:
3
Lot size:
0.69 Acres
Year built:
1974
Baths:
2.00
MLS#:
MDKE116146
Subdivision:
Country Club Estates

ADDITIONAL INFORMATION

Easy one floor living in Country Club Estates. Lovely views of the golf course with the Chester River in the distance from the family room and screened-in porch. Attached one car garage. New laminate flooring throughout. Close to town, river and Chester River Yacht and County Club yet has the peaceful, country living feel. Great combo of public sewer and well water. Ready for your updates.

Type:
Single Family-Detached
Sq.Ft.:
1,160
Status:
Active
Beds:
3
Lot size:
0.08 Acres
Year built:
1920
Baths:
1.00
MLS#:
MDKE116154
Subdivision:
None Available

ADDITIONAL INFORMATION

Type:
Single Family-Detached
Sq.Ft.:
3,316
Status:
Active
Beds:
5
Lot size:
0.12 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE116148
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Gorgeous Victorian Two-Unit Home in Need of a Facelift. She's a Beauty Located in a Beautiful Historic Waterfront Town! Pretty Street, Nice Front and Rear Yards, Rear Shed, Off Street Parking in Rear. Inside Has Fantastic Heart of Pine Flooring, Spacious Rooms and a Great Floor Plan. Main Level (Unit B) has a Covered Front Porch for Relaxing and Entertaining, 2Br, 2Ba, Living Room, Table Space Kitchen, Separate Laundry Room and Rear Yard Space w/Shed. Upper Level (Unit A) has 3Br, 1Ba, Living Room, Table Space Kitchen and a Deck/Balcony. Interior Space is Clean But Could Use Some Freshening Up. Live In One Unit and Rent the other, or Rent Both Units as a Full Investment Property. AirBnB, Would also be Easy to Convert Back to a One Single Family Home. Chestertown Is Lovely Town and Has So Much to do. This is also a popular destination for community events, festivals, boating, wine, art, food and shopping.

Type:
Single Family-Detached
Sq.Ft.:
993
Status:
Active
Beds:
3
Lot size:
0.69 Acres
Year built:
1962
Baths:
1.00
MLS#:
MDKE116152
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

Nice investment property, tenant occupied. Tenant would like to stay.

Type:
Single Family-Detached
Sq.Ft.:
2,050
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
2020
Baths:
3.00
MLS#:
MDQA142776
Subdivision:
The Flyway

ADDITIONAL INFORMATION

Custom built quality rancher by Stansbury & Sons on a 1+\- acre corner lot in the Flyways. House will feature tiled bathroom, granite countertops in kitchen and bath, LVT flooring, stainless kitchen appliances, washer and dryer, heat pump and gas fireplace. Includes two car garage with bonus room above, 12' by 16' covered back porch, front porch and large windows for natural lighting. It is conveniently located between Chestertown and Church Hill with easy access to RT 301. Chestertown is home to fine dining, arts and entertainment plus Washington College. Two county parks, boat ramp , and Church Hill Theater are all within a short distance. Home will be ready to occupy this spring and buyer can pick out finishes. This house reflects the pride of the builder's craftsmanship. Call and schedule your showing today!

Type:
Single Family-Detached
Sq.Ft.:
1,463
Status:
Active
Beds:
3
Lot size:
0.32 Acres
Year built:
1967
Baths:
1.00
MLS#:
MDKE116142
Subdivision:
College Heights

ADDITIONAL INFORMATION

Nice brick rancher, in town location, close to College and shopping, nice starter home for anyone, easy to show, lockbox, call agent for combo.

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
4
Lot size:
168.77 Acres
Year built:
2002
Baths:
3.00
MLS#:
MDKE116136
Subdivision:
None Available

ADDITIONAL INFORMATION

Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound.

Type:
Single Family-Detached
Sq.Ft.:
1,568
Status:
Active
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.:
1,456
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.:
1,503
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.:
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

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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

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