Chestertown MD Real Estate & Homes for Sale

117 Properties Found

The median home value in Chestertown, MD is $230,000. 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 $230,000. 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!
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Beds:
3
Baths:
3.00
Sq.Ft.:
2,200
Status:
NEW LISTING
MLS#:
MDKE116006
Type:
Townhouse
Subdivision:
Chester River Landing
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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!

Beds:
3
Baths:
3.00
Sq.Ft.:
3,001
Status:
NEW LISTING
MLS#:
MDKE116026
Type:
Single Family
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! Pool has been professionally closed and winterized.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,186
Status:
NEW LISTING
MLS#:
MDKE116022
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.69 Acres
Year built:
1971
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,152
Status:
NEW LISTING
MLS#:
MDQA142356
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1991
Courtesy: Chaney Homes, LLC
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Super cute cape cod! Great condition! hardwood throughout except for kitchen and 1 bedroom, new counter tops, kitchen floor, stainless steal appliances, new HVAC. Newer roof! Large fenced yard with deck and shed! Super cute curb appeal!! Great value at 215K

Beds:
3
Baths:
2.00
Sq.Ft.:
1,012
Status:
Active
MLS#:
MDKE116002
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.12 Acres
Year built:
1988
Courtesy: EXIT Preferred Realty
View additional info

Great investment opportunity!!! Three bedrooms, Two bath, No basement, Total of 1,012 Sq Ft. ~~HUD Case #244-044243~~ ~~HUD homes are Sold As Is.~~ ~~More info at www.HudHomeStore.com~~ Home backs to Washington College facilities. May be a great college rental opportunity, or alternative (off campus) housing for your student!!! Tax Record shows address as 126 Prospect. Deed references 126 Prospect Street, also known as 130 Prospect Street.

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

Beds:
2
Baths:
2.00
Sq.Ft.:
1,190
Status:
Active
MLS#:
MDKE115990
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.13 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDKE115922
Type:
Single Family
Subdivision:
Kent Acres
Lot size:
0.5 Acres
Year built:
1968
Courtesy: Cross Street Realtors, LLC
View additional info

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!

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,340
Status:
Active
MLS#:
MDQA142208
Type:
Single Family
Subdivision:
Pine Cove
Lot size:
0.5 Acres
Year built:
2015
Courtesy: Realty Navigator
View additional info

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 ***

Beds:
3
Baths:
2.00
Sq.Ft.:
1,792
Status:
Active
MLS#:
MDKE115972
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.72 Acres
Year built:
1993
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Looking for single floor living in Chestertown? Look no further! Well maintained handsome ranch in original section of Coventry Farm. New roof, updated appliances, newer systems, screened in porch, nicely landscaped with mature trees on .71 acre. 3 bedrooms, 2 full bathrooms, living room, separate dinning room and kitchen/family room. Attached 2 car garage. Public water and sewer with no deferred sewer charges. Close to shopping, restaurants, Washington College and the Historic District of Chestertown.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,796
Status:
Active
MLS#:
MDKE115930
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.27 Acres
Year built:
2006
Courtesy: Doug Ashley Realtors, LLC
View additional info

Come see, different floor plan than most. Spacious three levels of living with 9 ft. ceilings. Enter into foyer area with welcoming curved staircase. Hardwood flooring in foyer, dining and living rooms. Large open kitchen & breakfast room looking into living with over sized windows offering so much natural lighting. Gracious size master bedroom and bath with sizable walk in closet. Two additional bedrooms on main level. Second floor very open room for your choice of activities with bedroom and full bath. Walk out basement offers some natural lighting with finished off space and full bathroom. Two separate areas for storage and mechanical's. Garage is over sized with utility sink and separate side door. This house has so many options, pretty much has space for everyone and everything. Back yard backs up to trees and protected areas.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
MDKE115964
Type:
Single Family
Subdivision:
None Available
Lot size:
1.27 Acres
Year built:
1961
Courtesy: Gunther-McClary Real Estate
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE115938
Type:
Single Family
Subdivision:
Historic District Chestertown
Lot size:
0.14 Acres
Year built:
2015
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located in historic Chestertown, this home was built in 2015 and is gorgeous. Offers upgrades such as wood floors, gas fireplace, open living room/dining room, with an open kitchen. There is a first floor master suite, a laundry room, a screened porch, semi private picket fenced back yard. So much to love about this home! Detached garage with additional storage. There are three bedrooms all today, with threelarge rooms upstairs and a large bath. One of the rooms is a bonus room! Just a short jaunt to all the fun in downtown Chestertown.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,128
Status:
Active
MLS#:
MDKE115936
Type:
Single Family
Subdivision:
Chestertown
Lot size:
1.66 Acres
Year built:
1970
Courtesy: EXIT On The Bay
View additional info

Great Ranch home on 1.66 acres in Chestertown, MD. All HUD homes are sold "As Is", . This home has 3 bedrooms and 1 bath with original hardwood floors. Great buy near Rock Hall.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,658
Status:
Active
MLS#:
MDQA141974
Type:
Single Family
Subdivision:
Kingstowne Manor
Lot size:
0.58 Acres
Year built:
1999
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
6
Baths:
3.00
Sq.Ft.:
2,076
Status:
Active
MLS#:
MDKE115928
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Investment opportunity! Multi unit in Downtown Chestertown offers 3 units, 1st floor (largest) is a 3 bedroom 1 bath, washer/dryer & has rented for $950/month, 2nd floor is a 2 bedroom 1 bath and has rented for $850 but currently empty & 3rd floor (attic) is a studio (needs work) but can be rented at $450/month. Second floor unit was recently updated in 2018 with a new kitchen, mahogany porch, floors sanded and re-stained, windows sanded down and painted to make lead testing easier, new ceiling and so much more. All units are separately metered and have a great rental history. Make your money back in less then 10 years! If that doesn't interest you, convert it back into a single family home!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,776
Status:
Active
MLS#:
MDKE115908
Type:
Single Family
Subdivision:
Chestertown Historic District
Lot size:
0.19 Acres
Year built:
2011
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Charming cottage style home on the Eastern Shore was built in 2011 and is nestled in the Chestertown Historic District. The convenient location is a a walk away from Washington College, the Chester River Walk, Farmers Market, and downtown Chestertown shops, galleries, restaurants and cafes. Off-street parking and a finished basement with a terrace are among the amenities of this well-cared for home. An open floor plan evokes a casual ambiance. The bright, spacious kitchen has countertop seating and a dining area that opens to the deck and a peaceful view of woods and plantings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,456
Status:
Active
MLS#:
MDKE115894
Type:
Single Family
Subdivision:
Heather Heights
Lot size:
0.8 Acres
Year built:
1986
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great rancher in Heather Heights. Easy one floor living. Attached garage. 3 bedrooms, 2 bath. Nice rear deck over looking a great back yard. New carpeting, updated bathrooms, new stainless steal appliances, fresh paint. Close to town.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,152
Status:
Active
MLS#:
MDKE115906
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.02 Acres
Year built:
1920
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Enjoy living in Historic Chestertown, short distance to downtown, shopping, and restaurants and the Chester River. Well maintained 3 BR, 1 BA home, enclosed front porch with heat. Nice cozy home for first time homebuyers or investors.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,500
Status:
Active
MLS#:
MDKE115874
Type:
Single Family
Subdivision:
Fairlee Cove
Lot size:
1.8 Acres
Year built:
1996
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Exceptional architect designed Contemporary residence sited on a 1.8 acre private wooded lot enjoys 190' of protected waterfront, a 110' private dock and 3.5' MLW on Fairlee Creek; one of the prettiest bodies of navigable water in Kent County situated within just 1 nautical mile of the Chesapeake Bay. The property includes three separate living structures: the main house, an office/guest house. and a heated workshop/storage shed that, together, include approximately 3500 square feet of finished living space. The open floor plan interior of the main house features vaulted beaded board ceilings, strategically placed nooks and ledges to showcase art and collectibles, over sized windows and full-view glass doors overlooking the waterfront and easy care radiant heated tile floors. The cooks delight eat-in kitchen features stainless appliances, granite counter-tops, maple Brookhaven cabinetry, above and under-cabinet lighting, a large walk-in pantry, a built-in maple breakfast table, lovely views of surrounding gardens and the waterfront from the sink area through large space-enhancing corner windows and a double sided wood burning fireplace located between the kitchen and the dining area. A spacious private master bedroom and bath area includes a walk-in closet and a master bath with a tiled walk-in shower and Pearl brand whirlpool bathtub. Generously sized windows in the bedroom frame a serene verdant view through the trees to the water . The open living room features large windows and a brick wood-burning fireplace and opens to a screened porch that spans the waterfront side of the house. A 2011 addition includes a spacious cork floored Great Room with an outdoor deck seating area and a separate outdoor entrance. A discreet stairway leads from the Great Room to a bright and airy 2nd level studio that can, alternatively, serve as a third bedroom. A ships ladder stairway leads from the studio/bedroom up into a delightful tower space that offers birds-eye views of Fairlee Creek. An ingenious arrangement of a hallway and hide-away doors connects the Great Room and studio/bedroom to the first floor guest bedroom and bath; enabling use of this whole wing of the house as private guest or live-in quarters with its own private outdoor entrance. Additional main house rooms include a cozy den adjacent to the kitchen, a bright office area with water views and a separate laundry/utility room. The two outbuildings and carport connect to the main house via raised treated-wood walkways. The heated/air conditioned office/guest house includes a large main room, kitchenette, full bathroom and sleeping loft. The workshop includes a large built-in workbench and storage shelving. Rounding out this unique residential compound are a bluestone central courtyard patio, a roofed 2 car carport and a large outdoor equipment storage shed with sliding doors. Lush native and ornamental plant gardens watered with an automated in-ground irrigation system surround the house and point the way to steps leading down to the dock which has electric service. As if all of this isn't more than enough to support a great lifestyle, the property is located in easy walking distance to the Fairlee Creek Public Landing where area residents can easily off-load trailored boats, canoes and kayaks into Fairlee Creek and just a 15 minute drive to both historic downtown Chestertown and the lively waterfront town of Rock Hall. Plus, this property comes with a one year Home Warranty!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,128
Status:
Active
MLS#:
MDQA142002
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.48 Acres
Year built:
1961
Courtesy: Select Land & Homes, LLC
View additional info

An affordable Queen Anne's County waterfront! This property features a newer bulkhead, new BAT septic system, and navigable water. Inside the fully updated ranch home is a new kitchen with custom cabinets, granite counters, stainless steel appliances, new wood floors, a gas fireplace, new Andersen windows, 3 bedrooms and updated bathrooms. Downstairs is a full partially finished basement with a workshop. Enjoy the convenience of being close to Chestertown while utilizing the Queen Anne's County amenities!

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA141960
Type:
Single Family
Subdivision:
Blakefield
Lot size:
1 Acres
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

NEW CONSTRUCTION GETTING READY TO GET STARTED. 8 LOTS TO PICK FROM. 3 BED 2 BATH RANCHER WITH GARAGE. OR BRING THE BUILDER YOUR PLANS FOR A PRICE.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,850
Status:
Active
MLS#:
MDKE115886
Type:
Single Family
Subdivision:
Country Club Estates
Lot size:
0.73 Acres
Year built:
1990
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located in Country Club Estates, new carpet and fresh paint, this home offers so much. There is a detached 2 car garage, an attached 2 car garage 4/5 bedrooms, a media room, upstairs playroom area, storage galore. The living spaces on the first floor offer loads of space!. A double sided wood burning fireplace, large country kitchen, screened porch, first floor master, a second bathroom on the first floor, you could have three bedrooms on the first floor and 2 on the second. Shows great. Professionally landscaped, the lawn is manicured nicely!. Great curb appeal!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,800
Status:
Active
MLS#:
MDKE115880
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1948
Courtesy: Select Land & Homes, LLC
View additional info

A must see charming renovation in a private setting! The home features 3 bedrooms, 2 full bathrooms, hardwood and ceramic tile floors, efficient geothermal HVAC, a new roof, and hardiplank siding. Improved with a 4 zone home stereo system, horseshoe pit, outdoor shower and detached garage, this home is great for entertainment. Tolchester Marina and the Shanty Tiki Bar are within walking distance making this move in condition property is the perfect full time residence or weekend getaway. The sale includes 3 neighboring lots for a total of .459 acre to secure the private setting.

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