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Chestertown MD Real Estate & Homes for Sale

140 Properties Found

The median home value in Chestertown, MD is $236,250. This is higher than the county median home value of $200,000. The national median home value is $209,892. The average price of homes sold in Chestertown, MD is $236,250. 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 140 properties displayed
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Open House:

Saturday, 11/2 2:00-4:00PM

Beds:
5
Baths:
5 Full
Sq.Ft.:
7,886
Status:
NEW LISTING
MLS#:
MDQA141916
Type:
Single Family, Single Family-Detached
Subdivision:
Hambleton Creek View
Lot size:
1.25 Acres
Year built:
2006
Courtesy: Chaney Homes, LLC
View additional info

Seeking Space? Style & Seclusion? Welcome Home! Nearly 7900 sf of Custom Designed Space Total! With Over 5300 sf above grade, and ANOTHER 2500+ in Walk-Out Bright Basement! 5 Bedrooms, 5 FULL Baths, Large, Open Spaces! Every Upgrade You Could Wish For! Inviting Foyer Opens to Sitting Room, Solarium Flooded w/ Natural Light, Game Room, Dining Room, Main-Level Office w/ Private Entry! 2-Story Family Room Open to Gourmet Kitchen & Morning Room! Upstairs, Master Suite Rivals Most Hotels w/ Sitting Room, Gas Fireplace, His & Hers Walk-in-Closets, Huge Master Bath w/ Separate Shower, Water Closet & Soaking Tub for Two! Each Bedroom Adjoins Full Bath! Basement Boasts Optional 5th Bedroom, Full Bath, Recreation Room, Media Room, Work-Out Room, Storage Space & Walk out Stairs to Fenced Backyard w Inground Pool & Waterfall, backing to Pond! Built to 'Wow' & Entertain, This Beauty Has IT ALL! You Deserve This One! 30 Mins from Bay Bridge, Close to Work & Play! HURRY to This Value, Before It's Your Competition Hosting Pool Parties Here Next Year!! Priced to SELL!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDQA141818
Type:
Single Family, Single Family-Detached
Subdivision:
Pearl Creek Estates
Lot size:
1.25 Acres
Year built:
2019
Courtesy: Coldwell Banker Waterman Realty
View additional info

Modern Split Level home To Be Built. Pick your own colors and finishes. Stick built, quality construction. Cathedral ceilings, hardwood floors, granite counter tops, Master Bedroom with attached bath. 2 car garage. Huge lower level for extra living space or bedroom. Peaceful setting. Large lot. Customize to your taste! Stock photos shown, may include upgrades.

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
5,794
Status:
NEW LISTING
MLS#:
MDKE115864
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
24.83 Acres
Year built:
1975
Courtesy: Maryland Heritage Properties
View additional info

Rare (for Kent County) and exceptionally exciting, ultra-contemporary residence is situated on a promontory above twenty-five private pastoral acres. The combination of the position of the main house above the open natural grounds below featuring a breathtaking view of a pond with a "mile-high" fountain, a stream, woods and wildlife. You are on the level of the flight of birds. "Sophistication", "alluring" and extremely "comfortable" are the words that come to mind. The owner has thought of even the most minor detail. One is part of nature and yet is able to enjoy all the amenities of today. This property satisfies the desire for privacy and nature while also offering a lap pool, sauna, exercise area, whirlpool tub, hot tub, expansive windows and multiple level deck. There is an apartment adjacent to carport/garage where caretaker lives but could also be additional guest quarters. After passing through the entrance gates one is enveloped by a feeling of privacy and a sense that you are entering a "very special place".

Beds:
2
Baths:
1 Full
Sq.Ft.:
992
Status:
NEW LISTING
MLS#:
MDQA141886
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.38 Acres
Year built:
1995
Courtesy: EXIT On The Bay
View additional info

This little cottage in the woods is as cute as a button. Full Dry basement to put in a workbench or make it into your personal gym. 2 bedrooms and good size kitchen for the chef. The dining room flows into the living room that has plenty of room. You will also appreciate the back deck to enjoy morning coffee or afternoon shade.All HUD owned homes are sold "As Is", All bids online only at www.hudhomestore.com. # 241-762346. All instructions are on the HUDhomestore.com www.olympusas-re.com

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,080
Status:
NEW LISTING
MLS#:
MDQA141822
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
6.51 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

12.34 TOTAL ACRES, Includes 2 Parcels in Queen Anne's County. Build your own home, hunting, fishing in private stocked pond, opportunities abound. Parcels must be sold together. Value is in the land, home structure is not safe but electric, well, and septic is on-site. Property sold strictly as-is. Second parcel listed separately, see MDQA141824

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,720
Status:
NEW LISTING
MLS#:
MDKE115862
Type:
Single Family, Single Family-Detached
Subdivision:
Heather Heights
Lot size:
0.93 Acres
Year built:
1979
Courtesy: Maryland REO Connection, LLC
View additional info

Great single family ranch located in Heather Heights. Loads of outdoor living space with nearly 1 acre lot, detached 2 car garage and shady enclosed porch ! Many recent updates to baths, flooring, and kitchen. MBR features private MBA with shower. Convenient location to downtown shopping and restaurants as well as the Chester River Yacht and Country Club. Bring the boat and move in !

Beds:
3
Baths:
2 Full
Sq.Ft.:
960
Status:
NEW LISTING
MLS#:
MDKE115850
Type:
Single Family, Single Family-Detached
Subdivision:
Georgetown
Lot size:
0.86 Acres
Year built:
1970
Courtesy: Clark & Co Realty, LLC
View additional info

This house is basically brand new! It has been completely renovated from top to bottom. All new stainless steel appliances, hot water heater, central air/heat, large 16x16 back deck, metal roof, siding, flooring, plumbing, you name it! On almost an acre of land with public water/sewer and a 16x12 shed that has electric. The house is located on a private, quiet street away from all the hustle and bustle of town but still a short drive away.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,368
Status:
NEW LISTING
MLS#:
MDQA141742
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1987
Courtesy: Cross Street Realtors, LLC
View additional info

Great 3 bedroom, 1 1/2 bath ranch-style home with ductless mini-splits for heat and air conditioning, fenced rear yard, two storage sheds and paved driveway. Offering large rooms, with an updated eat-in kitchen, formal dining room with beautiful and durable engineered wood floors, family room with gas fireplace and screened porch! Conveniently located in the water-access community of Chester Harbor and only minutes from Downtown Chestertown, this well-maintained and updated home is move-in ready!

Beds:
2
Baths:
1 Full
Sq.Ft.:
800
Status:
NEW LISTING
MLS#:
MDKE115846
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.54 Acres
Year built:
1943
Courtesy: Gunther-McClary Real Estate
View additional info

What's your pleasure? I cozy little getaway with spectacular views and 24/7 Sunsets or the perfect spot to start your retirement dreams with plenty of options available for future growth. How about both? This two bedroom cottage offer sweeping views of the Chesapeake and all the bay has to offer, with ships passing day and night and on clear days you can see as far as the Bay and Key bridges. This gem in the rough, is less than two hours from Philadelphia and Washington, DC making it the perfect location for a weekend of relaxing and regenerating on the screened in porch. The property also offers a large two car garage to keep all the water toys, kayaks, boats ect

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,371
Status:
NEW LISTING
MLS#:
MDKE115788
Type:
Single Family, Single Family-Detached
Subdivision:
Heather Heights
Lot size:
0.87 Acres
Year built:
1988
Courtesy: Cross Street Realtors LLC
View additional info

This large, well maintained home was completely renovated in 2004 and additional changes in 2010. Great flowing floor plan that invites both entertaining and plain old stay-at-home and relax! The open kitchen is the heart of the main level looking into the Great Room with 18' ceiling, fireplace and access to beautiful patios and rear yard. 5 Bedrooms, 1 with a fun "hideaway loft" and a second laundry room makeup the very spacious second level. In addition to the Great Room the first floor features a living room, a large bonus room with fireplace, a dining room and a 2nd laundry room. Two car attached garage too!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,001
Status:
NEW LISTING
MLS#:
MDKE115848
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.25 Acres
Year built:
2008
Courtesy: Keller Williams Legacy
View additional info

Immaculate 3BR/2.5 colonial w/ over 3000 sqft of finished living space in desirable Coventry Farms! Located just outside of Chestertown~s Historic District, this newly renovated home features an open floor plan w/ an abundance of natural light. New eat-in kitchen w/ SS appliances and granite countertops. Spacious bedrooms w/ new flooring and ceiling fan in each BR. Master BR w/ en-suite and walk-in closet. Large fully finished rec room w/ recessed lighting. Attached 2-car garage w/ fully fenced in rear yard and in-ground pool. This home is perfect for hosting family and friends. Nearby is Washington College featuring art, drama, sports, and a lifetime learning center. Welcome to Chestertown, situated close to local Marina~s, downtown Centreville, and the Chesapeake Bay Bridge! Enjoy the many activities Chestertown and the Chester River have to offer!

Beds:
5
Baths:
5 Full/2 Half
Sq.Ft.:
7,505
Status:
NEW LISTING
MLS#:
MDKE115726
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Court
Lot size:
1.45 Acres
Year built:
1992
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Impressive custom built brick waterfront home thoughtfully designed on the Chester River that combines classic elegance with modern open space living. Situated on a 1.45 acre lot just 2 blocks from downtown historic Chestertown , it is perfect for kayaking and canoeing! Main floor master suite, 4 bedrooms with baths, an in-law area, 3 car garage, and screened porch and deck both overlooking the river. The interior features high ceilings, built in shelving, and custom mouldings. Includes a pier with electric and water. Owner is a licensed real estate agent.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,290
Status:
NEW LISTING
MLS#:
MDKE115840
Type:
Single Family, Single Family-Detached
Subdivision:
Langford
Lot size:
36.17 Acres
Year built:
1900
Courtesy: Cross Street Realtors, LLC
View additional info

Two parcels totaling 36.17 acres comprising of 2 impoundment ponds, a fish pond and the balance of wooded and tillable acreage. Improved by a 2,290 sq/ft Farm house featuring wide plank wood floors throughout, Main level Master Suite. Large screened porch off the country kitchen overlooking the fish pond. Excellent deer, waterfowl, and turkey hunting. Very private. Shown by appointment only, no drive-ins.~

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,290
Status:
Active
MLS#:
MDKE115686
Type:
Single Family, Single Family-Detached
Subdivision:
Langford
Lot size:
36.17 Acres
Year built:
1900
Courtesy: Cross Street Realtors, LLC
View additional info

Two parcels totaling 36.17 acres comprising of 2 impoundment ponds, a fish pond and the balance of wooded and tillable acreage. Improved by a 2,290 sq/ft Farm house featuring wide plank wood floors throughout, Main level Master Suite. Large screened porch off the country kitchen overlooking the fish pond. Excellent deer, waterfowl, and turkey hunting. Very private. Shown by appointment only, no drive-ins.~

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,328
Status:
Active
MLS#:
MDQA141736
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.34 Acres
Year built:
1979
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fully updated river view home with master bedroom and screened porch with river views. Rear deck facing the woods. Utility shed, fire pit, 500-gallon underground propane tank with a connected gas grill. Gas fireplaces in the living room and master bedroom. 3/4 finished basement and attic that can be finished. Sprinkler and security systems installed.

Open House:

Saturday, 10/26 10:00-12:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,530
Status:
Active
MLS#:
MDKE115792
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.71 Acres
Year built:
1994
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Well maintained brick rancher on 1.7 acre lot with nice landscaping. Ample room sizes with high ceilings. Screened in porch. Partially finished basement. Whole house generator. Very peaceful setting where you can see both the sunrise and the sunset. Close to town. Public sewer. Easy living. Home has a nice flow with big windows and tons of storage.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,240
Status:
Active
MLS#:
MDKE115826
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.03 Acres
Year built:
2014
Courtesy: Taylor Properties
View additional info

Custom Built 4 Bed 2.5 Bath Boasting 2240Sqft sitting on a 1 acre private wooded lot just a few miles from town or the boat ramp. This home has many great custom features you will find inside. From the beautiful artistic Maple Island in the kitchen, granite counters, stainless steel appliances. Acacia hardwood floors along with tile. Open floor plan flows through the rooms. Gorgeous wainscot & crown molding. Upstairs the large master suite has a luxurious bath, jet tub, tile shower and a double vanity. 2nd level Full laundry room upstairs. Rear and side decking connecting to a 1 car garage with the other half as a storage room. This home is really something you have to see in person to appreciate the craftsmanship that was put in to building it.

Beds:
5
Baths:
1 Full
Sq.Ft.:
3,246
Status:
Active
MLS#:
MDKE115820
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.08 Acres
Year built:
1730
Courtesy: Maryland Heritage Properties
View additional info

GEDDES PIPER HOUSE. Most unusual opportunity. Fine brick, Federal house in heart of Chestertown Historic District. Nine fireplaces, graceful stair hall, original details abount PLUS central AC. Private garden. MD Hist. Trust Easements. One block to Fountain Park, two blocks to Chester River and Marina, shops, live theatre, galleries. Four blocks to Washington College.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,642
Status:
Active
MLS#:
MDKE115728
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.08 Acres
Year built:
1995
Courtesy: Cross Street Realtors LLC
View additional info

Gorgeous Victorian replica, 1995 build in the Historic District. Seller is offering a $4,000 appliance credit! BRAND NEW windows and siding; refinished mahogany hardwood flooring; elevator access from the basement to the 2nd floor; 3rd floor artists studio; spa room for ultimate relaxation; off street parking lot; only 1 block from the new marina and all that Downtown Chestertown has to offer.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,456
Status:
Active
MLS#:
MDKE115798
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.98 Acres
Year built:
1989
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy the wildlife and the quiet life! This much loved home is on the market for the first time by long time owners! Interior photos coming soon. A beautiful woodland setting surrounds this traditional ranch home and its two story/two car detached garage in Chesapeake Landing. The welcoming brick entrance patio and the attractive rear deck expand the living space and connect you to the outdoors. The two car garage has a workshop on the second floor. There is also a nice solid shed on a concrete foundation. Pick your own flooring: Sellers are offering $5,000 credit at settlement because the carpet & vinyl could use an update! This sale also Includes parcel 0878 (lots 203, 204, 205) across the street for an additional half acre of wooded view and privacy. The additional lots probably will not perc for building, but have been enjoyed as a view, nature trail, and extra space! The house needs cosmetic updates, but it is otherwise well-maintained. It is entirely livable as it is with functional appliances and a neutral decor. Spread out and enjoy the extra space of the additional lots and generous garage. This property is comfortable and private without being isolated. The optional community association offers waterfront facilities to members for only $40 per year & boat slips for an additional fee. Walk or 3 minute ride to Harbor House Restaurant and nearby deep water marina. Less than 15 minutes by car to the shops, restaurants, and festivals of historic Chestertown. Additional photos coming soon!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,441
Status:
Active
MLS#:
MDKE115800
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.18 Acres
Year built:
1928
Courtesy: Select Land & Homes, LLC
View additional info

Tudor-style home in the heart of Chestertown. This 2500 square foot home boasts 3 Bedrooms and 2 1/2 baths. Built-ins and hardwoods throughout. Main level has a large family room with fireplace, galley style kitchen and separate dining area. Second floor features a master bedroom and bathroom, 2 guest bedrooms and 1 full bath. Property is currently operating as an office. Close to Washington College, schools, shopping, and downtown.

Beds:
3
Baths:
3 Full
Sq.Ft.:
1,486
Status:
Active
MLS#:
MDQA141672
Type:
Single Family, Single Family-Detached
Subdivision:
Kingstown
Lot size:
0.58 Acres
Year built:
1944
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore waterfront compound with two cottages on the Chester River offers coveted views looking across to the historic Chestertown waterfront, Wide Hall and the Chester River bridge. The main house has sweeping views of the river and is perfectly poised to see Sultana under sail, the Washington College boathouse, visiting Tall Ships and fireworks. Another cottage is set behind the main house with a pathway and in-ground pool between the two. Both houses have 1st floor bedrooms and 2 bedrooms upstairs. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants and pubs. Outdoor enthusiasts can enjoy the Chester River Walk and trails, or embark on a river cruise. Located in Queen Anne~s County, the property has 100-feet of shoreline, a 110-foot dock with 3-1/2 feet MLW and stunning sunsets.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,485
Status:
Active
MLS#:
MDKE115704
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale
Lot size:
3.13 Acres
Year built:
1999
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore waterfront cottage on Fairlee Creek offers a boat slip with lift at the community pier. Elevated, secluded setting offers sweeping water views. A large deck overlooks the backyard leading to a wood stairway going down to the waterfront. Cedar panelling, wood floors and large brick fireplace create a welcoming cottage ambiance. The Master Suite upstairs opens to a deck with stunning views, and on the first floor is another convenient master suite. Other features include a finished basement with flexible space, a separate garage, workshop and potting shed. A quick walk away is the Fairgale community pond, picnic area and dock. The property is located just 15-minutes from Chestertown. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants, galleries and pubs. Outdoor enthusiasts can use the Chester River Walk, parks and trails, or embark on a river cruise.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDKE115678
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.17 Acres
Year built:
1926
Courtesy: Cross Street Realtors LLC
View additional info

This renovated, meticulously maintained, & upgraded home is MOVE-IN READY! Refinished hardwood floors throughout, updated baths, modern kitchen with stainless steel appliances, ample back porch & private master deck, large & beautiful fully fenced backyard, full basement with storage & laundry, central A/C, & fully foam insulated. This highly sought after street is just a few blocks from downtown, neighbors the Washington College campus, & is convenient to the shopping centers. Chestertown, MD is Eastern Shore Life at its best... come experience it for yourself!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,144
Status:
Active
MLS#:
MDKE115782
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC
View additional info

Coventry charmer with a fenced back yard, deck with new awning makes this an "outdoor room". Family room is open to the kitchen/breakfast area. Partially finished basement for playroom, office/den, you choose. Three nice bedrooms with great light, well landscaped lot. Move in ready, nicely painted.

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