Kathy Christensen
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Chestertown MD Real Estate & Homes for Sale

133 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!
Learn more about Chestertown Real Estate.


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Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,584
Status:
NEW LISTING
MLS#:
MDKE116036
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the home, including original windows, beams, hardwood floors, bookcases, and more. 3 spacious bedrooms, all with restored hardwoods, master with ensuite bathroom (a rare find in a historic home)! Further family bathroom offering double vanities and tub/shower. Laundry and half bath on main level. Large great room addition on the back of the house, with sliders to deck, overlooking private back yard. Home was just completely renovated in 2019 including new 2 x Zone heat pump with central A/C, tankless hot water (propane), complete new wiring, new kitchen and baths, new windows, new stainless appliances, new/restored floors, and more!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,876
Status:
NEW LISTING
MLS#:
MDKE116012
Type:
Townhouse
Subdivision:
Oak Hollow
Lot size:
0.05 Acres
Year built:
2005
Courtesy: Doug Ashley Realtors, LLC
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Town-home located in Oak Hollow, a well managed town-home community. This unit is brick fronted with a one car garage. The master bedroom has a cathedral ceiling with large bath with separate shower and tub. There are 2 additional bedrooms on the upper level. The middle level has kitchen with sliders to a rear deck and a living room. The lower level has the garage and an additional room ready for you to finish the way you want it. Close to shopping and restaurants!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
3,692
Status:
NEW LISTING
MLS#:
MDKE116020
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.28 Acres
Year built:
2010
Courtesy: Doug Ashley Realtors, LLC
View additional info

This home looks like it has never been lived in!!!. When you enter the two story entrance foyer (pease take off your shoes) you will get a sense of what a new home looks like. The kitchen has wood floors and the dining room has tray ceilings. The family room has a wood burning fireplace that has never been used) and a stylish ceiling fan. There is even a tidy living room on the main level. The upper level has an owners suite and 3 additional bedrooms. The lower level overs a recreation room and a game room. Hunter Douglas insulated blinds are at most windows. This property backs to woods but has a front view of one of the larger community areas. The 2 car garage caps off one of the best homes and locations in Coventry Farms!

Open House:

Thursday, 12/12 11:00-2:00PM

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
832
Status:
NEW LISTING
MLS#:
MDQA142388
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.52 Acres
Year built:
1981
Courtesy: Doug Ashley Realtors, LLC
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Cute as a button cottage! Wood flooring, beautifully updated with a wonderful gas fireplace, built in cabinets and shelving. Lots of thought went into this home. All on one level, the crawlspace has been encapsulated, it's water proof and you can use that for extra storage. Acreage is .52 and has some fruit bearing trees on the property. Super cute, inside and out. There is a detached workshop, an attached front loading garage, that could be another bedroom. Great location, about five minutes from Chestertown, and the historic district. Join the HOA for a small yearly fee ($25.00) and have access from Rosin Creek out to the Chester River. This is a very nice area. There is a play ground area.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
3,204
Status:
NEW LISTING
MLS#:
MDKE116014
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
2.05 Acres
Year built:
1990
Courtesy: Doug Ashley Realtors, LLC
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Spacious multilevel home with 2 story entrance foyer. Recently updated kitchen with Quartz counters, newer looking cabinets and new stainless steel appliances. New flooring in the family room with wood burning fireplace. There is also a living room with a wood burning fireplace. There is a formal dining room and a rear screened porch. The laundry room is huge and has an additional refrigerator. The HVAC is all new as well!! Property backs to woods and farm land. The garage has space for a small workshop. One of the best locations in Orchard Hill!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
NEW LISTING
MLS#:
MDKE116006
Type:
Condo, Townhouse
Subdivision:
Chester River Landing
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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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:
2 Full/1 Half
Sq.Ft.:
3,001
Status:
NEW LISTING
MLS#:
MDKE116026
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.25 Acres
Year built:
2008
Courtesy: Keller Williams Legacy
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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 Full
Sq.Ft.:
2,186
Status:
NEW LISTING
MLS#:
MDKE116022
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.69 Acres
Year built:
1971
Courtesy: Long & Foster Real Estate, Inc.
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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 Full
Sq.Ft.:
1,152
Status:
NEW LISTING
MLS#:
MDQA142356
Type:
Single Family, Single Family-Detached
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 Full/1 Half
Sq.Ft.:
3,248
Status:
Active
MLS#:
MDKE115982
Type:
Single Family, Single Family-Detached
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:
1 Full/1 Half
Sq.Ft.:
1,190
Status:
Active
MLS#:
MDKE115990
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDKE115922
Type:
Single Family, Single Family-Detached
Subdivision:
Kent Acres
Lot size:
0.5 Acres
Year built:
1968
Courtesy: Cross Street Realtors, LLC
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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:
5 Full/1 Half
Sq.Ft.:
6,105
Status:
Active
MLS#:
MDKE115970
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
1,340
Status:
Active
MLS#:
MDQA142208
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
1,792
Status:
Active
MLS#:
MDKE115972
Type:
Single Family, Single Family-Detached
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:
3
Baths:
1 Full
Sq.Ft.:
1,068
Status:
Active
MLS#:
MDKE115924
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.34 Acres
Year built:
1962
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Home located in terrific neighborhood of Quaker Estates, just a few minutes to all the amenities Chestertown has to offer. The home does require some TLC and your personal updates to make it shine again! Large backyard with dog kennels and a wonderful screened-in area under roof for summer entertaining without the weather worries.

Beds:
4
Baths:
4 Full
Sq.Ft.:
3,796
Status:
Active
MLS#:
MDKE115930
Type:
Single Family, Single Family-Detached
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:
2 Full
Sq.Ft.:
1,584
Status:
Active
MLS#:
MDQA141946
Type:
Single Family, Single Family-Detached
Subdivision:
Kingstown
Lot size:
0.48 Acres
Year built:
1989
Courtesy: Cross Street Realtors LLC
View additional info

This adorable three bedroom home has A LOT to offer! On a desirable street on the Queen Anne's side of 21620, freshly painted throughout, brand new kitchen range, new master bath vanity, private tree-lined lot, spacious rooms, and attached two car garage off of the paved driveway. Move quickly, this home will NOT last!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,344
Status:
Active
MLS#:
MDKE115902
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.14 Acres
Year built:
1956
Courtesy: Doug Ashley Realtors, LLC
View additional info

Location, location, location! Renovated in 2004-2005 this home is a short distance from Washington College, hospital and historic downtown Chestertown! Wood floors throughout the main level. Large master suite. Master bath offers radiant floor heat. Spacious family area on the second level. Tankless propane water heater. House has been used as a rental for the last 12 years and has a "Lead Free" certification.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,008
Status:
Active
MLS#:
MDKE115964
Type:
Single Family, Single Family-Detached
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:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE115938
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
1,128
Status:
Active
MLS#:
MDKE115936
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
1,658
Status:
Active
MLS#:
MDQA141974
Type:
Single Family, Single Family-Detached
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 Full
Sq.Ft.:
2,076
Status:
Active
MLS#:
MDKE115928
Type:
Single Family, Single Family-Detached
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:
2 Full/1 Half
Sq.Ft.:
1,776
Status:
Active
MLS#:
MDKE115908
Type:
Single Family, Single Family-Detached
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.

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