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Chestertown MD Real Estate & Homes for Sale

106 Properties Found

The median home value in Chestertown, MD is $250,000. This is higher than the county median home value of $192,000. The national median home value is $232,276. The average price of homes sold in Chestertown, MD is $250,000. 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!
Learn more about Chestertown Real Estate.


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1–25 of 106 properties displayed
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Beds:
3
Baths:
2 Full
Sq.Ft.:
1,600
Status:
NEW LISTING
MLS#:
MDKE116266
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.05 Acres
Year built:
1900
Courtesy: Select Land & Homes, LLC
View additional info

This Historical home has undergone a tasteful renovation to include 3 bedrooms, 2 full bathrooms, new plumbing and HVAC. Home offers an open floor plan with decorative touches which include wide plank pine floors, shiplap, original doors with hardware and original mouldings. The courtyard garden with brick patio and walkway lead to Downtown, waterfront, shops and restaurants. Bike trails and park for your enjoyment are nearby. The delightful, turnkey home blends history with comfort and convenience.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,176
Status:
NEW LISTING
MLS#:
MDKE116202
Type:
Single Family, Single Family-Detached
Subdivision:
Washington Park
Lot size:
0.47 Acres
Year built:
1998
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This 1200sq ft., 3 BR, 1 Bath home was built in the 90~s and though it has always had ~strong bones~, many improvements have been made since the current owner purchased it in 2008. In September 2017 the asphalt roof was replaced. New kitchen cabinets, countertops & sink were installed in the summer of 2018. Laminate wood flooring was originally in the kitchen and has been added to the living room, hallway and left front bedroom since 2016. The other 2 bedrooms have ww carpeting & 6 of the original windows have been replaced since purchase. Electric has been kept updated with newer GFI and some USB outlets being added within the past 2 years. The property is pie shaped and approximately .41 acres with lovely, mature shade trees lining one entire side of the yard and the back. There is a 10x12 wooden deck on the back and a covered front porch with a built in bench. Washington Park has a neighborhood park that has recently been updated with playground equipment, benches, picnic tables and a brand new pavilion and basketball court. Fun for all!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,800
Status:
NEW LISTING
MLS#:
MDKE116256
Type:
Condo
Subdivision:
Scott's Point
Year built:
2009
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy panoramic views of the Chester River from this tastefully finished waterfront condo in Historic Chestertown. Decks on all three levels provide a great space to relax while enjoying the breezes off the river. The gourmet kitchen opens to the dining/living area which features a gas fireplace. There are 2 deeded boat slips - one has a 10,000# aluminum boat lift and the other has an EZ dock for 2 jet skis. Scott's Point offers carefree waterfront living within walking distance of restaurants, parks and shops.

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
936
Status:
NEW LISTING
MLS#:
MDKE116246
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.04 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great downtown Chestertown location! Recently updated home is set in the Historic District and is just a walk away from Washington College, the University of Maryland Medical Center, the Chester River, restaurants, shops and walking trails. The delightful home evokes cottage charm with wood floors and bead board detail, while outside, the fenced backyard with plantings offers an inviting seating area. Founded in 1706, Chestertown is a charming riverfront town. Residents and visitors alike can enjoy the Chester River Walk, strolling downtown, embarking on a river cruise and having fun at annual events. Located about 90 minutes from Washington, D.C. and Philadelphia.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,596
Status:
NEW LISTING
MLS#:
MDKE116228
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Bay Estates
Lot size:
0.53 Acres
Year built:
1948
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Waterfront Home with commanding views of Langford Bay and the Chester River is set in a quiet, rural community just 15 minutes from historic Chestertown. Enjoy boating and water activities with the 4-ft MLW deep water dock. Designed to maximize the spectacular water views, the 3 bedroom brick home features an open design, a first floor master suite, office, flex room and garage. Founded in 1706, Chestertown is a lovely walking town with shops, theater, waterfront dining, cafes and oyster bar. Residents and visitors alike participate in annual events and enjoy the Chester River Walk and river cruises. Located about 90 minutes from Washington, D.C. and Philadelphia.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,310
Status:
NEW LISTING
MLS#:
MDQA143120
Type:
Single Family, Single Family-Detached
Subdivision:
Pearl Creek Estates
Lot size:
1.58 Acres
Year built:
2020
Courtesy: Coldwell Banker Waterman Realty
View additional info

New construction to be built. 3 Bedrooms, 2 Full Baths. Modern open floor plan. Master suite with separate shower and jetted soaking tub. Hardwood floors. Cathedral ceilings. Granite counter tops. Walk in closets. Two car garage. Beautiful peaceful setting. Large 1.58 acre lot. Quality stick built construction.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,756
Status:
NEW LISTING
MLS#:
MDKE116250
Type:
Single Family, Single Family-Detached
Subdivision:
Crestview
Lot size:
0.5 Acres
Year built:
1989
Courtesy: Davis Real Estate, Inc.
View additional info

Move in condition Cape Cod Home in Crestview. Near Washington Square Shopping Center, Churches, Washington College and a mile from downtown Historic Chestertown. Master bedroom on the first floor, large rear deck, attached garage and fenced rear yard.

Open House:

Saturday, 2/29 12:00-2:00PM

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,950
Status:
NEW LISTING
MLS#:
MDKE116218
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
1.01 Acres
Year built:
1958
Courtesy: Doug Ashley Realtors, LLC
View additional info

Location, Location, Location! Rare opportunity to own a home adjoining Chester River Yacht and Country Clubs 18 hole championship club course! Located on the dogleg of the 15th hole, you are just a short distance to club house. This home has large rooms with wood flooring throughout most of this home. The family/dining area combine with a wood burning fireplace a central focal point for family gatherings or for the occasional party with neighbors and friends. There is a Florida/sun room that has views of golf course and exits to the rear brick patio, perfect for weekend barbecues. There are 4 bedrooms, all with built ins. The kitchen opens to the family/dining areas. There is a partial basement where you will find the mechanical s and there is a 2nd with unfinished pine wood floors that could easily be renovated to be a large owners suite, additional family area or just leave it the way it is so that you have plenty of storage. Finally there is a detached 2 car garage that actually has 3 garage doors, 2 for your cars and one for your lawn toys. Close to Historic Downtown Chestertown and the Marina!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,650
Status:
NEW LISTING
MLS#:
MDQA143010
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.35 Acres
Year built:
1986
Courtesy: Home Selling Assistance Plus, LLC
View additional info

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.

Open House:

Saturday, 3/14 10:00-1:00PM

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,664
Status:
NEW LISTING
MLS#:
MDKE116220
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.4 Acres
Year built:
1959
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
1
Baths:
1 Full
Sq.Ft.:
1,297
Status:
Active
MLS#:
MDQA143004
Type:
Single Family, Single Family-Detached
Subdivision:
Crumpton
Lot size:
19.33 Acres
Year built:
1978
Courtesy: Cross Street Realtors LLC
View additional info

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.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,404
Status:
Active
MLS#:
MDKE116212
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.41 Acres
Year built:
1999
Courtesy: Doug Ashley Realtors, LLC
View additional info

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.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,492
Status:
Active
MLS#:
MDKE116192
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.16 Acres
Year built:
1880
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,292
Status:
Active
MLS#:
MDKE116196
Type:
Single Family, Single Family-Detached
Subdivision:
Georgetown
Lot size:
0.36 Acres
Year built:
1900
Courtesy: The Hogans Agency Inc.
View additional info

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

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,545
Status:
Active
MLS#:
MDKE116182
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.69 Acres
Year built:
1968
Courtesy: Gunther-McClary Real Estate
View additional info

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.

Beds:
2
Baths:
1 Full
Sq.Ft.:
884
Status:
Active
MLS#:
MDQA142890
Type:
Single Family, Single Family-Detached
Subdivision:
Queen Annes County
Lot size:
0.34 Acres
Year built:
1963
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,135
Status:
Active
MLS#:
MDKE116174
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.15 Acres
Year built:
1900
Courtesy: Maryland Heritage Properties
View additional info

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.

Beds:
3
Baths:
2 Full
Sq.Ft.:
960
Status:
Active
MLS#:
MDKE116186
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2 Acres
Year built:
1992
Courtesy: Village Real Estate Company LLC
View additional info

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!!

Beds:
3
Baths:
1 Full
Sq.Ft.:
880
Status:
Active
MLS#:
MDKE116180
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.28 Acres
Year built:
1955
Courtesy: Keller Williams Select Realtors
View additional info

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.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,588
Status:
Active
MLS#:
MDKE116146
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.69 Acres
Year built:
1974
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,160
Status:
Active
MLS#:
MDKE116154
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.08 Acres
Year built:
1920
Courtesy: Long & Foster Real Estate, Inc.
View additional info
Beds:
5
Baths:
3 Full
Sq.Ft.:
3,316
Status:
Active
MLS#:
MDKE116148
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.12 Acres
Year built:
1900
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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.

Beds:
3
Baths:
1 Full
Sq.Ft.:
993
Status:
Active
MLS#:
MDKE116152
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.69 Acres
Year built:
1962
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,050
Status:
Active
MLS#:
MDQA142776
Type:
Single Family, Single Family-Detached
Subdivision:
The Flyway
Lot size:
1 Acres
Year built:
2020
Courtesy: Benson & Mangold, LLC
View additional info

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!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,463
Status:
Active
MLS#:
MDKE116142
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.32 Acres
Year built:
1967
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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

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