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Chestertown MD Real Estate & Homes for Sale

102 Properties Found

The median home value in Chestertown, MD is $185,500. 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 $185,500. 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 like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


Sort Results:
1–25 of 102 properties displayed
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Beds:
4
Baths:
2.00
Sq.Ft.:
2,358
Status:
NEW LISTING
MLS#:
MDKE115234
Type:
Single Family
Subdivision:
Country Club Estates
Lot size:
0.72 Acres
Year built:
1991
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Custom built home on the market for the first time! The open floor plan has 2 story living room. Balcony on the 2nd floor to bedrooms. Warm Honey tone wood details, mantel, and trim create a very inviting atmosphere. Wonderful home backs up to the stream that offers great views of birds and nature while providing privacy. Enjoy the screened-in porch in the warm weather or snuggle by the fireplace on cold evenings.A prestigeous neighborhood close to the Country Club, golfing, boating and downtown Chestertown!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,536
Status:
NEW LISTING
MLS#:
MDKE115294
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.23 Acres
Year built:
1976
Courtesy: Doug Ashley Realtors, LLC
View additional info

This 1536 sq foot home, sitting on a large lot in Tolchester Estates, has lots of potential! With a dry crawl space, all systems in good working condition, and recently inspected and maintained roof. Complete with two porches, water views, and a community beach with boat ramp only blocks away.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,440
Status:
NEW LISTING
MLS#:
MDKE115284
Type:
Single Family
Subdivision:
Fairlee
Lot size:
0.53 Acres
Year built:
1920
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Handyman special, needs work, lots of potential. Rt. 20, to right in Fairlee to Bayshore Road, property on the right.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,848
Status:
NEW LISTING
MLS#:
MDKE115262
Type:
Single Family
Subdivision:
Chestertown
Lot size:
22.38 Acres
Year built:
1984
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Farm set on 22 acres in a private setting is a true gem conveniently located just 2 miles from downtown Chestertown. The pristine horse farm has a 6-stall horse barn with hay loft, tack room and workshop. There is also two run-in sheds, machinery shed, an 8 acre hay field, and 10 acres of fenced pasture. Amenities enhancing the property include a stream with bass, a pergola, vegetable and flower gardens. Surrounded by mature landscaping, the 3 bedroom country home offers pastoral views, a first floor bedroom and full bath, and bright open kitchen. Anchored by a beautiful raised hearth fireplace, the living room opens to the screened porch. Founded in 1706, Chestertown is a picturesque walking town set on the banks of the Chester River with 18th century homes, cafes, pubs, galleries and shops. Enjoy the Chester River Walk, waterfront dining and marina or take a river cruise on the Chester River Packet. Residents enjoy the vibrant arts community, parks, walking trails and water activities. Annual events include the Chestertown Tea Party and Tall Ship Downrigging Weekend. Chestertown is also home to Washington College. Located about 90-minutes from Washington and Philadelphia.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,653
Status:
NEW LISTING
MLS#:
MDKE115196
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1975
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

One block away from the Chester River and two blocks away from Downtown Chestertown, this home offers an updated kitchen with two wall ovens, Avanza countertops, ceramic tile floor with a brick fireplace and skylight. The large addition on the back has 8 sliding glass doors with a French door and brick step entrance into the kitchen. All windows have been updated and boast interior blinds for ease & to keep dust to a minimum. The crawl space has lighting and is completely encapsulated. A black metal fence surrounds the back yard with gate and a white vinyl privacy fence is located on the street side allowing the extensive landscaping and brick patio to be completely closed in by fencing. This all brick home in this highly coveted area is waiting for you!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,016
Status:
NEW LISTING
MLS#:
MDKE115272
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.2 Acres
Year built:
1937
Courtesy: Cross Street Realtors LLC
View additional info

Bring your plans & start building! The footprint is solid, the water & sewer lines are BRAND NEW, the electric supply and breaker box are BRAND NEW, and the lot is HUGE with tons of potential! All within walking distance to everything Downtown Chestertown has to offer... shops, restaurants, parks & the new marina. The backyard abuts the Rail-to-Trail pathway, allowing for easy access to the Chester River waterfront, Washington College & beyond - up to the shopping centers. Easy to see, come visit this great opportunity soon! *The fine print: plans would have to be approved. Property is located within the Historic District.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
MDQA140308
Type:
Other
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1976
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Cute 3 BR, 1 BA rancher in water oriented community, good for 1st time home buyer, tenant occupied, call for an appointment.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,620
Status:
Active
MLS#:
MDKE115224
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.52 Acres
Year built:
2008
Courtesy: BHHS Fox & Roach-Newark
View additional info

Welcome to this charming Cape Cod in the community of Chesapeake Landing. The 2/3 Bedroom 2 bath cottage is nestled in the water oriented community with deeded access to Worton Creek. Bright airy open floor plan with cathedral ceiling, enclosed loft room and wrap around deck. Worton creek is but a few hundred foot walk from the front door. Home is nestled in a peaceful wooded section of Worton Creek and is not in the flood plain.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,378
Status:
Active
MLS#:
MDKE115248
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.42 Acres
Year built:
1963
Courtesy: Sommers Enterprises, Inc.
View additional info

This offering of one & 1/4 waterfront acres at the end of a cul de sac sits in a private, park-like setting on Worton Creek. The improved lot is fully bulkheaded with a dock. The well maintained three bedroom, two bath ranch with a waterside three season room has had periodic upgrades during its current ownership

Beds:
3
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
MDKE115216
Type:
Single Family
Subdivision:
Fairlee Cove
Lot size:
0.85 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Welcome to 'Knot Now Boat House', which has been a very tastefully remodeled home located on Fairlee Creek. This can be a full time residence or your Holiday retreat or week-end get away. Fully updated kitchen with new counter tops, cabinets, and stainless appliances, Wonderful color choices with paint,decorating and flooring. New HVAC system and tankless water heater. Has own private dock with power lift and jet ski ramps. Plenty of room for all your water toys. Detached garage with extra storage area. A must see if your seeking waterfront property with your own private dock.

Beds:
5
Baths:
2.00
Sq.Ft.:
3,008
Status:
Active
MLS#:
MDKE115238
Type:
Single Family
Subdivision:
Pomona
Lot size:
113 Acres
Year built:
1800
Courtesy: Coldwell Banker Residential Brokerage-Annapolis
View additional info

Hilltop Farm C. 1810 in historic Chestertown includes 113 acres with waterfront on Langford Creek off the Chester River. Property includes large 8 feet deep fresh water pond and impoundment.Perc test done in 2019 for new construction 3500 +sf on the waterfront portion of the farm to accommodate a new waterfront residence with privacy. Many options with the property operating as a residence, farm or combination. Great relationship with local farmer regarding crops and maintenance. This is a rare opportunity to own a piece of Eastern Shore history and build your dream home surrounded by wildlife on the shores of Langford Creek.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,602
Status:
Active
MLS#:
MDQA140134
Type:
Single Family
Subdivision:
Kingstown
Lot size:
0.26 Acres
Year built:
1953
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous opportunity for multiple uses with the property. House can be a residence or rent out with a couple of apartments or office space. Oversized Garage is bigger than the house at 1760 square feet! Have a shop or keep cars or boats with all this space! Zoned suburban commercial. House has newly refinished wood floors and multipurpose floor plan. NIce private yard and plenty of off street parking.

Beds:
4
Baths:
1.00
Sq.Ft.:
2,040
Status:
Active
MLS#:
MDKE115232
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.23 Acres
Year built:
1948
Courtesy: Harlan C. Williams Co.
View additional info
Beds:
3
Baths:
1.00
Sq.Ft.:
1,104
Status:
Active
MLS#:
MDKE115226
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.46 Acres
Year built:
1972
Courtesy: Doug Ashley Realtors, LLC
View additional info

Cute rancher located a few miles outside of Chestertown. Great living space. Kitchen has all of the major appliances. Laundry is located in the bath for easy access. Great backyard that overlooks farm fields. There is a one car detached garage. Currently used as a rental and has received a lead free certification.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,840
Status:
Active
MLS#:
MDKE115220
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.48 Acres
Year built:
1985
Courtesy: BHHS Fox & Roach - Hockessin
View additional info

Welcome to Tolchester Estates. This 2 bedroom 2 bath home would be perfect for a summer retreat or to live at year around offering stunning views of the Chesapeake Bay from your kitchen, dining room, and rear deck! This home is situated on nearly a half an acre with a 2 car detached garage. The property also features a well house w/ water treatment system and basement for additional storage and a gazebo to relax outdoors. Off the master bedroom there is a wonderful 8x15 sun room perfect for relaxing or additional space. The partially finished basement with walk out egress and a full bathroom offers endless possibilities. Put this home on your list to tour, you will not be disappointed.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,190
Status:
Active
MLS#:
MDKE115172
Type:
Single Family
Subdivision:
Historic District
Lot size:
0.13 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info
Beds:
2
Baths:
2.00
Sq.Ft.:
1,015
Status:
Active
MLS#:
MDKE115210
Type:
Townhouse
Subdivision:
Historic District Chestertown
Lot size:
0.02 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

Wonderful Water Street Condo with elevated views, a private balcony, and a boat slip to enjoy the Chester River. Large eat-in kitchen, beautifully renovated with stainless steel appliances, farmhouse sink and custom cabinets. The property also offers an open living room with gas fireplace and views of Chestertown's Historic District, in addition to a Master bedroom, two full bathrooms, and a second bedroom/office space. Perfectly situated to enjoy all the Chester River AND Chestertown's Historic District has to offer!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,464
Status:
Active
MLS#:
MDKE115148
Type:
Single Family
Subdivision:
Heather Heights
Lot size:
1.19 Acres
Year built:
1987
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Opportunity is knocking!! This beautiful home is located in Heather Heights conveniently situated between The Chester River Yacht and Country Club and Historic Chestertown. The home is turn key and well maintained with spacious rooms, wood floors, corian counters, large florida room overlooking the back yard, with attached garage. There are currently 4 bedrooms with the option to take the smallest bedroom and make it an office like the current owners have. Call to schedule your showing!!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,392
Status:
Active
MLS#:
MDKE115106
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
1.75 Acres
Year built:
1980
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Big Price Reduction! Here's your private waterfront getaway or retirement home! Peaceful views of the water and yard. Fish and kyack from your backyard or launch your motorboat at the community boat launch 200 feet away. Home in good condition has large rooms with lots of windows bringing in all the views. Open floor plan with wood burning fireplace in Living Room. Enjoy the deck under the retractable awning or relax in the large screened-in porch. Large garage, perfect for your boat, car collection or work shop. The upstairs has a large finished Family Room and Bedroom. This property has a lot of potential with 1.75 waterfront acres and a short walk to the boat launch and community area. Easy to see!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,244
Status:
Active
MLS#:
MDKE115174
Type:
Single Family
Subdivision:
Chestertown Historic District
Lot size:
0.08 Acres
Year built:
1900
Courtesy: RE/MAX Premiere Selections
View additional info

Welcome to this prime Historic District location in charming Chestertown! This home features Victorian style, original wide plank hardwood floors, many of the rooms feature chair rail, and cornices, with high ceilings. Two non-working slate fire places. Side entrance to patio and rear entrance to large level yard and one car garage and two car parking area.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,531
Status:
Active
MLS#:
MDKE115150
Type:
Single Family
Subdivision:
None Available
Lot size:
3.17 Acres
Year built:
1988
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Goose Landing is a 3.17 acre 4 bedroom 2.5 bathroom secluded waterfront home nestled on Fairlee Creek that boasts 350 feet of waterfront with panoramic views from almost every room, a 100 foot dock with swim platform. Fairlee Creek is fresh water year round and has some of the best swimming, water skiing, kayaking and fishing on the Chesapeake. The entrance to the Bay, as well as Great Oak Landing, are only a five minute boat ride away. The Public boat launch is 1/4 mile away. Take advantage of historic Chestertown and Rock Hall for shopping and dining as they are both only 9 miles away. Enjoy entertaining with a large great room, fireplace, several outside deck areas, screened in porch, patio, and plenty of yard. Fun time in the large family room/ Game Room and fireplace for cozy nights. Let everyone help and cook in this Kitchen! It's perfect for entertaining with large Breakfast bar overlooking the Great Room. First-floor master Bedroom suite. Take the spiral staircase to the 2nd floor with 3 bedrooms and another full bathroom. Freshly painted home and Deck. A separate workroom with electric and covered storage site can be for a footprint to build another structure. Peace, nature, beautiful water and a great home at a terrific price!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDKE115154
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.4 Acres
Year built:
2002
Courtesy: Keller Williams Select Realtors
View additional info

You'll simply fall in love with this charming Cape Cod. Located in sought after Coventry Farms and minutes from historic downtown Chestertown. This home has been meticulously maintained; fresh paint, new flooring, countertops, and more! 4 spacious bedrooms, 2 bath, living room, kitchen/dining combo opening to the large deck for easy summertime entertaining! Come see everything this delightful hom and Chestertown has to offer! There are no HOA or Front Foot Fees.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,096
Status:
Active
MLS#:
MDKE115122
Type:
Single Family
Subdivision:
Crestview I
Lot size:
0.76 Acres
Year built:
1989
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located in a lazy cul de sac just outside Chestertown town limits in the community of Crestview. This home offers a huge family room, living room with a wood burning fireplace and a full unfinished basement. Heat pump cools and heats plus there supplemental electric baseboard heat. The rear deck allows for shaded afternoon relaxation. The community offers acres of open space to enjoy and there is even a community pond.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,472
Status:
Active
MLS#:
MDKE115130
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Village Real Estate Company LLC
View additional info

Chestertown Victorian that is just a short walk to the library, shops, dining, and the river. This home has lots of potential with a fenced in yard and cute front porch.

Beds:
2
Baths:
1.00
Sq.Ft.:
768
Status:
Active
MLS#:
MDKE115114
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.09 Acres
Year built:
1949
Courtesy: RE/MAX Executive
View additional info

Tired of renting? Looking for an investment property? This might be your solution. This two bedroom, one bath home is not only affordable but convenient to downtown Chestertown. Living, dining and kitchen are open and inviting. Fixed stairs lead to unfinished attic space. Sit on the porch and enjoy a summer breeze. Off street parking located within the fenced yard. You will not need to spend hours mowing, yard is petite. Storage shed in back to keep the mower,tools and more. Basement with outside access. Investors....tenant in place and willing to stay!

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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 participates, and is provided by BRIGHT through a licensing agreement. 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. Copyright BRIGHT, All Rights Reserved

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