Homes Recently Sold in Chestertown, MD

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1-40 of 61 Homes
Sold, last 90 days
a view of a lake with houses in the back
a view of a lake with a house
a front view of a house with garden
a view of a lake with boats and trees in the background
an aerial view of residential house with yard
a living room with furniture fireplace and a large window
a living room with furniture pool table and a fireplace
a kitchen with stainless steel appliances granite countertop a stove top oven a sink a dining table and chairs
a kitchen with kitchen island granite countertop a sink and counter space
a kitchen with a sink stove and cabinets
a living room with furniture and a fireplace
a view of a dining room with furniture window and outside view
a view of a livingroom with furniture and windows in a room
a workspace with furniture and window
a bedroom with a bed and window
a spacious bedroom with a large bed and a window
a spacious bedroom with a bed and a window
a bathroom with a double vanity sink and a mirror
a bathroom with a double vanity sink a mirror and a bathtub
a bathroom with a shower and a sink
a bedroom with a bed a fireplace and a window
a room with furniture and a window
a bedroom with a bed and window
a bedroom with a bed and wooden floor
a bathroom with a granite countertop sink vanity mirror and toilet
a utility room with dryer and washer
a view of staircase with wooden floor and a rug
a bedroom with a bed and a large window
a spacious bedroom with a bed and chair
a view of a deck with chairs and a yard with wooden fence
a view of a wooden deck with a yard
a bathroom with a granite countertop sink and a mirror
a bathroom with a sink and a toilet
a view of a house with a yard and large tree
a front view of a house with a yard
a front view of a house with a yard
a view of a house with backyard sitting area and garden
a view of a house with a yard
a view of a lake with boats and trees in the background
a view of a lake with sitting area
aerial view of a lake with table and chairs
a view of an ocean with outdoor seating
a view of a house with a big yard and large trees
an aerial view of a city
a view of a lake
a view of a lake with a city
an aerial view of ocean and residential houses with outdoor space
an aerial view of a house with outdoor space
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
$1,550,000 | 7961 Quaker Neck Road, Chestertown, MD 21620
1/93
Closed 11/7/25Virtual Tour

$1,550,000

5
Bedrooms
4,167
Square Feet
0.47
Acres

7961 Quaker Neck Road, Chestertown, MD 21620

a view of a house with a swimming pool
a view of a house with a yard and large tree
a view of bathroom
a living room with furniture and a chandelier
a living room with furniture a two sinks and a ceiling fan
a living room with furniture and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture a fireplace and a window
a living room with furniture and a lamp
a living room with furniture
a living room with furniture and a table
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a view of a dining room with furniture and wooden floor
a view of a livingroom with furniture
a view of a workspace with furniture and a window
a bathroom with a sink toilet and shower
a bathroom with a sink a toilet and shower
a bedroom with a bed and a closet
a bedroom with a bed and a large mirror with a small space
a bedroom with a bed and a window
a bedroom with a bed and a dresser
$235,000 | 7521 Pine Avenue, Chestertown, MD 21620
1/24
Closed 1/20/26

$235,000

3
Bedrooms
1,040
Square Feet
0.56
Acres

7521 Pine Avenue, Chestertown, MD 21620

a front view of a house with a garden
a front view of a house with a garden
a view of empty room with wooden floor and fan
a view of an empty room with window and wooden floor
a view of empty room with wooden floor and fan
a view of an empty room with wooden floor and entryway
a view of wooden floor and windows in a room
a kitchen with granite countertop a refrigerator stove a sink and white cabinets with wooden floor
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a bathroom with a granite countertop sink and a mirror
a view of entryway and hall with wooden floor
a view of empty room with ceiling fan
a view of a livingroom with a ceiling fan and window
an empty room with window
a view of an empty room
an empty room with a window
a view of an empty room
a bathroom with a granite countertop sink and a mirror
a white toilet sitting next to a white sink
a garden with trees and a lake view
a view of a building with brick walls
a view of a building with a yard
a view of a building with a street
a view of a building with sitting area and garden
a view of a lake with houses
a view of a lake with boats and trees in the background
1/26
Closed 12/5/25New Construction

$264,900

3
Bedrooms
1,280
Square Feet
0.13
Acres

101 Metcalf Road, Chestertown, MD 21620

a house view with a garden space
a front view of a house with a garden
a view of a house with backyard porch and sitting area
a view of a park with large trees
a view of a house with a yard porch and sitting area
a view of a house with a yard table and chairs
a view of back yard of the house
a front view of a house with a porch
a view of a hallway with wooden floor and entryway
a view of a living room
a living room with furniture fireplace and a flat screen tv
a living room with furniture large window and wooden floor
a room with furniture and a chandelier
a kitchen with stainless steel appliances sink refrigerator and cabinets
a kitchen with sink refrigerator and cabinets
a kitchen with stainless steel appliances a refrigerator and a stove top oven
a living room with furniture and a large window
a bedroom with a bed and a window
a bedroom with a bed and a window
a bedroom with a bed and window
a bathroom with a sink a vanity and a mirror
a bedroom with a bed and a flat screen tv
a spacious bedroom with a bed and a table
a bathroom with a sink a toilet and a mirror
a view of ocean
a house view with a sitting space and garden
a view of a lake with houses in the back
a view of a lake with a big yard
a view of a lake with a yard and large trees
a view of a street sign
a view of street with sitting area
a view of a terrace
1/32
Closed 1/16/26

$364,000

3
Bedrooms
1,532
Square Feet
0.34
Acres

303 East Campus Avenue, Chestertown, MD 21620

$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
$475,000 | 101 Birch Run Road, Chestertown, MD 21620
1/38
Closed 12/11/25

$475,000

3
Bedrooms
1,961
Square Feet
0.42
Acres

101 Birch Run Road, Chestertown, MD 21620

$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
$290,000 | 107 Malone Avenue, Chestertown, MD 21620
1/27
Closed 1/16/26

$290,000

3
Bedrooms
1,200
Square Feet
0.35
Acres

107 Malone Avenue, Chestertown, MD 21620

a front view of house with yard and trees
a view of a city
an aerial view of residential houses with outdoor space and trees
a kitchen with a sink stove and refrigerator
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a kitchen with a sink dishwasher and white cabinets with wooden floor
a kitchen with a sink a stove cabinets and window
a open kitchen with stainless steel appliances granite countertop a sink dishwasher and white cabinets with wooden floor
a dining room with furniture window and wooden floor
a living room with furniture and a flat screen tv
a living room with furniture a large window and a chandelier
a room with wooden floor and furniture
a view of a livingroom with a window and wooden floor
a bathroom with a toilet sink and mirror
a bed room with a bed and a window
a bedroom with a bed and a chandelier
a bedroom with a bed and flat screen tv
a bathroom with a sink toilet and shower
a bedroom with a bed and a dresser
a bathroom with a sink toilet and shower
a house view with a seating space
a view of backyard with table and chairs and a large tree
a view of a house with backyard and sitting area
a view of a back yard with a chairs and table in the patio
a front view of a house with a yard and garage
front view of a house
a view of a house with a yard
a front view of a house with a yard
a swimming pool view
an aerial view of a houses with a yard
a view of a city
an aerial view of residential house with outdoor space and trees all around
a front view of a house with a yard and garage
1/33
Closed 12/1/25

$375,000

3
Bedrooms
1,842
Square Feet
0.71
Acres

907 North Meadowview Drive, Chestertown, MD 21620

a front view of a house with a yard and potted plants
a backyard of a house with table and chairs
a living room with furniture and a rug
a living room with fireplace furniture and a flat screen tv
a living room with furniture wooden floor and a window
a living room with furniture and a flat screen tv
a view of a house with a yard
a view of a dining room and livingroom with furniture wooden floor a chandelier
a dining room with furniture a chandelier and wooden floor
a dining table chairs and a living room with kitchen view
a kitchen with stainless steel appliances granite countertop a refrigerator a stove and a sink with wooden floor
a large kitchen with granite countertop a large counter top appliances a sink and cabinets
a living room with dining table and wooden floor
a front view of a house with a yard and large tree
a bathroom with a toilet a sink and a mirror
a white cabinet sitting next to a window
a bedroom with a bed and a chandelier
a bedroom with a bed and a couch next to a window
a view of walk in closet with clothes
a bathroom with a sink and a bathtub
a bathroom with a shower
a living room with furniture and a large window
a living room with television and a flat screen tv
a bathroom with a sink toilet and mirror
a bed sitting in a bedroom next to a window
a view of a bedroom from a hallway
a view of balcony with wooden floor and outdoor seating
a view of a deck with furniture and garden
a backyard of a house with table and chairs
a view of a house with swimming pool and sitting area
a view of a house with backyard and sitting area
unknown
1/32
Closed 1/7/26Virtual Tour

$415,000

3
Bedrooms
1,676
Square Feet
0.28
Acres

411 Greenwood Avenue, Chestertown, MD 21620

a front view of a house with garden
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a living room with furniture potted plant and window
a view of a dining room with furniture wooden floor and chandelier
a dining room with furniture a chandelier and wooden floor
a kitchen with a sink cabinets and window
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a bedroom with a bed and a window
a bedroom with a bed and wooden floor
a bedroom with a bed and wooden floor
a view of storage and utility room
a view of a room with gym equipment
an empty room with wooden floor and windows
a view of a room with wooden floor and a window
a view of a room with a large window
a front view of a house with a yard
a view of a golf course with a lake view
an aerial view of a residential house with a yard
an aerial view of a houses with outdoor space and city view
an aerial view of a golf course with houses
a view of a golf course with a lake view
a garden view with a lake view
a view of a city with a lake
a view of a city with lots of trees
a view of a house with a big yard and palm trees
a front view of a house with a yard and porch
an aerial view of a golf course with a garden
$264,900 | 24415 Chestertown Road, Chestertown, MD 21620
1/29
Closed 10/30/25

$264,900

2
Bedrooms
1,110
Square Feet
1
Acres

24415 Chestertown Road, Chestertown, MD 21620

a front view of a house with a garden
a kitchen with a sink stove and microwave
a kitchen with a refrigerator and cabinets
a kitchen with a sink appliances and cabinets
a view of a living room with washer and dryer
a utility room with dryer and washer
a living room with furniture and a window
a room with a bed and a window
a bathroom with a sink a toilet and shower curtain
a view of a hallway with closet
a bedroom with a bed and a flat screen tv
a bedroom with a bed and a closet
a bedroom with a bed and a window
an empty room with windows
a bedroom with a bed and a flat screen tv
a view of house with garden and tall trees
a front view of a house with a garden and trees
a view of a house with a big yard and large trees
a view of garden with trees
a view of a projector room
$255,000 | 318 Lincoln Drive, Chestertown, MD 21620
1/21
Closed 1/16/26

$255,000

3
Bedrooms
960
Square Feet
0.49
Acres

318 Lincoln Drive, Chestertown, MD 21620

a front view of house with yard and green space
a view of a house with a yard
a front view of a house with a yard and garden
a living room with couches rug and a large window
a living room with furniture and a flat screen tv
a living room with furniture and a floor to ceiling window
a view of a kitchen with granite countertop cabinets and a table
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a view of a hallway
a bedroom with a bed and a window
a view of a room with wooden floor and windows
a view of a bedroom with wooden floor and ceiling fan
a spacious bedroom with a bed and window
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
a bathroom with a sink toilet and a mirror
a bathroom with a bathtub and shower
a view of closet with wooden floor
a front view of a house with a garden
a view of a garden with a bench
a view of a house with a yard
a front view of a house with a garden and trees
a view of a house with a yard
a view of a house with a yard
a view of a building with sitting area
a front view of a building with garden
1/26
Closed 12/5/25

$287,500

3
Bedrooms
1,232
Square Feet
0.34
Acres

7483 Shortall Street, Chestertown, MD 21620

a view of a house with backyard and trees
a sign on the side of the house
a front view of a building with trees
front view of a house with a yard
a front view of a house with garden
a view of front door with a door
a very nice looking room with a large window
a workspace with furniture and window
a dinning table and chairs in the patio
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances kitchen island granite countertop a stove and a refrigerator
a very nice looking room with a large window
a living room with furniture and a large window
a building outdoor space with patio furniture
a view of a dining room with furniture a chandelier and wooden floor
a living room with furniture
a view of a dining room with furniture a chandelier and wooden floor
a living room with furniture and a window
a bed sitting in a bedroom next to a window
a bedroom with furniture and a large window
a bathroom with a sink toilet and shower
a bathroom with a sink toilet and shower
a view of wooden door
a view of entryway with wooden floor and a front door
a view of a park with large trees
a view of a yard with large trees
a view of backyard with tree
a view of road and trees
a view of a house with a yard
a sign that is on the wall of a building
a view of water heater room
a sign on the side of a building
a sign broad
an aerial view of a houses
a view of a city with ocean view
a view of an ocean and mountain
a view of a garden with a building
a backyard of a house with lots of green space
a front view of a house with garden
a house with tall trees in the background
a front view of a house with garden
a view of a house with backyard and trees
a backyard of apartments with large trees
a view of a park with large trees
a top view of a house with a yard
a picture of floor plan
$535,000 | 5179 Quaker Neck Road, Chestertown, MD 21620
$535,000 | 5179 Quaker Neck Road, Chestertown, MD 21620
1/48
Closed 11/5/25

$535,000

1
Bedrooms
1,148
Square Feet
3.22
Acres

5179 Quaker Neck Road, Chestertown, MD 21620

a living room with furniture and view of kitchen
a living room with furniture and a flat screen tv
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances a refrigerator stove microwave and cabinets
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a stove a sink and a microwave
a kitchen with stainless steel appliances granite countertop a white stove top oven and refrigerator
a utility room with dryer and washer
a large kitchen with a table and chairs
a kitchen with refrigerator cabinets and wooden floor
a living room with furniture and a wooden floor
a living room with furniture a table and a window
a bathroom with a sink toilet mirror and tub
a bedroom with a bed and a large window
a bedroom with a large bed and a window
a bedroom with a bed and a chandelier
a bathroom with a sink and a mirror
a bedroom with furniture and a window
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a view of a workspace with furniture and a window
a living room with furniture and a window
a children room with toys
a children room with toys and toys
a view of a workspace with furniture and a window
a workspace with furniture and fan
a bathroom with a sink a toilet and a mirror
a living room with furniture a flat screen tv and a window
a view of a dining room with furniture and wooden floor
front view of a house
a front view of a house
a front view of a house with a yard
a front view of a house with windows
a view of a backyard with furniture
a front view of a house with a yard
a view of a house with a yard
a front view of a house with a garden and yard
a view of a back yard of the house
a view of a patio with a table and chairs and a barbeque
a picture of a floor plan
a picture of a book and a bed
a picture of a bench in a wall
view of a bathroom with a shower
1/43
Closed 1/21/26

$379,900

5
Bedrooms
2,615
Square Feet
0.09
Acres

112 Silver Heel Drive, Chestertown, MD 21620

a front view of a house with a yard
a front view of a house with a yard porch and outdoor seating
a front view of a house with a yard
a picture of floor plan
a view of a livingroom with a fireplace
a view of empty room with wooden floor and fireplace
a open kitchen with stainless steel appliances granite countertop a refrigerator a stove and a wooden floors
a large kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a cabinets sink and stove
a kitchen with stainless steel appliances granite countertop a refrigerator stove and sink
a kitchen with stainless steel appliances granite countertop wooden cabinets a stove a sink and dishwasher
a view of empty room with wooden floor and fan
a bedroom with a bed and a dresser
a bedroom with a bed and a window
a view of an empty walk in closet
a bathroom with a bathtub and a shower
a bathroom with a sink and a mirror
a bed sitting in a bedroom next to a window
a bedroom with a bed and wooden floor
a bathroom with a sink a toilet and shower
a bathroom with a granite countertop toilet sink and mirror
a view of a porch with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a utility room with dryer and washer
a utility room with dryer and washer
a bathroom with a sink and a mirror
a view of an empty room with closet and a window
a picture of a floor plan
a view of entryway and hall with wooden floor
a view of an empty room
a view of entryway with an empty room and window
a spacious bedroom with a bed and a window
a living room with furniture
a bathroom with a sink a toilet and vanity
a bathroom with a shower and a bathtub
an empty room with a window
a view of an empty room
a view of an empty room
a view of a livingroom with furniture and a flat screen tv
a view of a chairs and tables in patio
a view of a house with a yard and garage
a view of a house with a yard
a front view of a house with a garden
a front view of house with yard barbeque and outdoor seating
a front view of a house with a garden
a view of a park with large trees
a view of a field with trees in the background
1/47
Closed 12/4/25

$700,000

4
Bedrooms
3,735
Square Feet
2.81
Acres

8951 Orchard Drive, Chestertown, MD 21620

a front view of a house with a garden
a front view of a house with a garden
a front view of a house with a yard table and chairs
a front view of a house with a yard and trees
a front view of house with yard and green space
a front view of a house with yard and green space
a house view with outdoor space and garden
a patio with a yard table and chairs
a view of swimming pool with outdoor seating
a view of a house with pool and chairs under an umbrella
a view of a patio with couple of furniture and a potted plant
a living room with furniture and a large window
a living room with fireplace furniture and a flat screen tv
a living room with furniture and a flat screen tv
a bedroom with a bed and furniture
a kitchen with stainless steel appliances granite countertop a refrigerator a stove top oven a sink dishwasher and white cabinets with wooden floor
a view of a dining room with furniture and wooden floor
a kitchen with granite countertop stainless steel appliances and wooden cabinets
a kitchen with stainless steel appliances kitchen island granite countertop a refrigerator oven a sink dishwasher and white cabinets with wooden floor
a view of a dining room with furniture window and outside view
a view of a dining table and chairs in a room
a living room with furniture
a living room with furniture and a rug
a living room with furniture and a potted plant
a workspace with a window
a bedroom with a bed and a chair
a view of an entryway with wooden floor
a bedroom with a bed and wooden floor
a bedroom with a bed and a flat screen tv
a bathroom with a toilet sink and mirror
a bathroom with a granite countertop sink toilet a mirror and a window
a living room with furniture
a bedroom with a bed and a window
a bedroom with a bed and a flat screen tv
a bathroom with a granite countertop sink toilet and a mirror
a view of backyard of house and garage
a view of a storage room with furniture fridge and stairs
$375,000 | 7653 Broad Neck Road, Chestertown, MD 21620
$375,000 | 7653 Broad Neck Road, Chestertown, MD 21620
1/39
Closed 1/8/26

$375,000

4
Bedrooms
1,790
Square Feet
0.91
Acres

7653 Broad Neck Road, Chestertown, MD 21620

a front view of a house with a yard
a front view of house with yard and green space
an aerial view of multiple house
a view of an entryway with wooden floor
a view of staircase with wooden floor and white walls
an empty room with windows
a view of an empty room with wooden floor and a window
a view of a livingroom with a fireplace
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a refrigerator a stove and a sink
a kitchen with stainless steel appliances granite countertop a sink a refrigerator and a stove
a large kitchen with a sink and large window
a dining room with furniture and window
a view of livingroom with kitchen
a kitchen with a stove a sink a window and dining table
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a front view of house with yard and green space
a view of a house with backyard and garden
a view of an empty room with window plants and wooden floor
a bathroom with a sink and a mirror
a utility room with dryer and washer
a view of a city with lots of flower around
an aerial view of residential house with outdoor space
a view of a hallway with wooden floor and stairs
an empty room with a window
a view of an empty room
an empty room with window and a ceiling fan
a bathroom with a sink a toilet and shower
a front view of a house with a garden
an aerial view of a house with a yard
a view of an empty room
a view of an empty room with a window
a view of an empty room with a window
a view of an empty room and window
a bathroom with a granite countertop sink a mirror and shower
an aerial view of residential house with outdoor space and trees
a view of an empty room with wooden floor
a view of an empty room
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
an aerial view of residential house with outdoor space and trees all around
a kitchen with stainless steel appliances a stove a sink dishwasher a microwave oven and a sink with wooden cabinets
a kitchen with a sink and cabinets
a bathroom with a sink a toilet a shower and a mirror
a view of an empty room with wooden floor
a view of an empty room with wooden floor
an aerial view of a house
a view of a roof deck with wooden floor and fence
a view of a roof deck with table and chairs a barbeque with wooden floor and fence
a view of a city
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
$585,000 | 103 Adela Way, Chestertown, MD 21620
1/90
Closed 11/13/25Virtual Tour

$585,000

4
Bedrooms
5,576
Square Feet
0.24
Acres

103 Adela Way, Chestertown, MD 21620

a view of a house with a yard
a view of a livingroom with wooden floor and a kitchen
a kitchen with white cabinets stainless steel appliances and a window
a kitchen with stainless steel appliances granite countertop white cabinets stove a sink and dishwasher
a kitchen with granite countertop white cabinets and white appliances
a large white kitchen with wooden floor and a large window
a view of kitchen with granite countertop cabinets and wooden floor
a view of empty room with wooden floor and fireplace
a view of entryway with wooden floor
a view of empty room with wooden floor and fan
an empty room with wooden floor and windows
a view of an entryway
wooden floor fireplace and windows in an empty room
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a bathroom with a toilet sink vanity and shower
a bathroom with a sink a toilet and shower
a bathroom with a toilet a sink and a mirror
an empty room with wooden floor and windows
a view of an empty room with wooden floor and a window
a view of storage and utility room with washer and dryer
a room with a closet
a view of an empty room and window
a view of storage and utility room
a view of a house with a yard and potted plants
a view of a back yard of the house
a view of backyard with green space
a front view of a house with a yard
a view of a house with yard and garage
a front view of house with yard and trees
a view of yard with trees
1/31
Closed 11/3/25

$435,000

3
Bedrooms
2,162
Square Feet
1.27
Acres

25800 Collins Avenue, Chestertown, MD 21620

a house that has a large window in front of a house
a picture of a bench in front of a wall
an aerial view of a houses
a view of a livingroom with kitchen space and wooden floor
a view of an empty room with window and wooden floor
an empty room with wooden floor ceiling fan and windows
a kitchen with stainless steel appliances a refrigerator and white cabinets
a kitchen with a sink a stove a refrigerator and white cabinets
a kitchen with stainless steel appliances granite countertop a refrigerator and white cabinets
a bathroom with a granite countertop sink and a mirror
a view of an empty room
an empty room with windows
a view of an empty room and a bathroom
an empty room with a ceiling fan and carpet
an empty room with wooden floor and windows
a view of a house with a yard
1/16
Closed 1/16/26

$240,000

3
Bedrooms
1,140
Square Feet
0.14
Acres

100 Metcalf Road, Chestertown, MD 21620

a view of a house with backyard and a patio
a front view of a house with garden
a view of a house with a yard
a view of a house with backyard
a front view of a house with patio and garden
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a living room with furniture and a flat screen tv
a utility room with dryer and washer
a room with storage and utility
a view of a dining room with furniture window and wooden floor
a living room with furniture a rug and a window
a bedroom with a bed and a chandelier
a bedroom with a bed and a chandelier
a white toilet sitting next to a bathroom sink
a view of entryway with wooden floor
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a bathroom with a granite countertop toilet and a sink
a kitchen with a table chairs refrigerator and wooden floor
a kitchen with stainless steel appliances a stove top oven a sink dishwasher and a refrigerator with wooden floor
an empty room with wooden floor and windows
a view of swimming pool with outdoor seating
a house view with a sitting space and garden
a front view of a house with garage
1/25
Closed 11/20/25

$230,000

3
Bedrooms
1,140
Square Feet
0.09
Acres

126 Metcalf Road, Chestertown, MD 21620

a front view of a house with garden
a front view of a house with garden
a view of entryway and hall with wooden floor
a living room with furniture a fireplace and a chandelier
a living room with furniture a flat screen tv and a fireplace
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and chandelier
a kitchen with stainless steel appliances kitchen island granite countertop a stove a sink and a microwave
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a bed room with furniture and a window
a bathroom with a sink double vanity and a mirror
a bedroom with a bed and a chandelier
a bathroom with a shower and a window
a bedroom with a bed and wooden floor
a bedroom with a bed and a chandelier
a living room with furniture and a window
a bathroom with a toilet a sink and a window
a bedroom with a bed and a couch
a bedroom with furniture and a window
a bathroom with a sink a toilet and shower
a kitchen with white cabinets and black appliances
a kitchen with stainless steel appliances white cabinets and a sink
a bathroom with a sink and a mirror
a picture of a bathroom
a picture of a floor plan
a picture of a floor plan
a view of outdoor space
a back yard of the house with a yard
a view of a backyard with table and chairs and a large tree
a view of a couches in backyard of house
front view of house with a yard
a view of a car in garage
a view of a entrance gate of the house and trees
a front view of a house with garden
front view of a house with a yard
a view of a house with backyard and garden
an aerial view of a city
a view of city and ocean
a view of city and ocean
1/39
Closed 11/5/25

$695,000

3
Bedrooms
2,492
Square Feet
0.20
Acres

110 South Mill Street, Chestertown, MD 21620

a front view of a house with a yard and large trees
a view of a backyard with garden and patio
a view of a porch with a table and chairs
a view of an empty room with a large window
a front view of a house with a yard and garage
a view of an entryway with a building
a spacious bedroom with a bed and a dresser
a view of an entryway with staircase
a kitchen with granite countertop a sink and a stove top oven
a kitchen with stainless steel appliances granite countertop a stove a sink and a microwave
a view of an empty room with a window
a bathroom with a toilet sink and mirror
a view of a house with porch
a view of an empty room with a window
a bathroom with a toilet a sink and mirror
a bathroom with a sink a toilet and a mirror
a view of a hallway with entryway
a view of a house with stairs and a ceiling fan
an empty room with windows and entrance
an empty room with windows
a bathroom with a sink a toilet and a mirror
a view of an empty room with a window
a view of a room with wooden floor and outdoor space
a view of a porch with wooden floor and outdoor space
a front view of a house with a yard
a view of a house with a porch
a view of outdoor space with seating
a view of a house with a backyard
a view of a fence
a view of a lake with boats and a lake view
a view of a house with a patio and a yard
a view of a patio with chairs and table
a view of a patio with table and chairs and potted plants
a view of a bench in a forest
a view of a lake with table and chairs
a view of a chairs and table on the deck with wooden floor and swimming pool
an aerial view of residential houses with outdoor space and trees all around
a view of a lake with houses in the background
a view of outdoor space and yard
a small pool with trees in the background
a front view of a house with a yard
a view of a lake with a city
a view of a sign board
a view of a city street from a building
$872,500 | 10761 Kasota Road, Chestertown, MD 21620
$872,500 | 10761 Kasota Road, Chestertown, MD 21620
$872,500 | 10761 Kasota Road, Chestertown, MD 21620
1/47
Closed 11/21/25

$872,500

3
Bedrooms
2,582
Square Feet
0.48
Acres

10761 Kasota Road, Chestertown, MD 21620

$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
$750,000 | 212 Landing Lane, Chestertown, MD 21620
1/36
Closed 12/1/25New Construction

$750,000

3
Bedrooms
Unavailable
Square Feet
Unavailable
Acres

212 Landing Lane, Chestertown, MD 21620

front view of a house with a yard
a front view of a house with a yard
a living room with furniture and a flat screen tv
a kitchen with stainless steel appliances granite countertop a refrigerator a stove a sink a dining table and chairs
a view of living room filled with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a table chairs sink refrigerator and cabinets
a kitchen with a table and chairs in it
a sign on the side of a building
a view of a park with large trees
a front view of a house with garden
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a table
a kitchen with sink a refrigerator and wooden cabinets
a living room with furniture and a flat screen tv
a view of a hallway with wooden floor and staircase
a bedroom with a bed a table and chair
a bedroom with a bed and a flat tv screen on dresser
a bathroom with double sink and a mirror
a bathroom with a granite countertop shower and a sink
a living room with furniture a flat screen tv and a fireplace
a bedroom with a bed and a flat screen tv
a bathroom with a toilet and a shower
a living room with furniture and a flat screen tv
a bedroom with a bed and a window
a view of livingroom with furniture and wooden floor
a living room with furniture and a large window
a bedroom with a bed and a window
a living room with furniture and a large window
a bedroom with a bed table chair and a window
a living room with furniture and a window
a bathroom with a granite countertop toilet sink and a mirror
a bathroom with a toilet and a shower
a living room with furniture and a flat screen tv
a utility room with dryer and washer
$795,000 | 201 Radcliffe Drive, Chestertown, MD 21620
1/36
Closed 11/7/25

$795,000

4
Bedrooms
2,736
Square Feet
0.28
Acres

201 Radcliffe Drive, Chestertown, MD 21620

a front view of a house with yard
a living room with furniture and a large window
a living room with furniture and a large window
a living room with furniture and a large window
a living room with fireplace furniture and a window
a living room with furniture and a rug
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a kitchen with granite countertop cabinets and window
a living room with furniture and a fireplace
a front view of a house with a garden
a living room with furniture and wooden floor
a living room with furniture and a fireplace
a living room with furniture and a flat screen tv
a front view of house with yard and trees around
a kitchen with a refrigerator a stove top oven and white cabinets
a kitchen with granite countertop white cabinets and a wooden floor
a living room with furniture and a table
a living room with furniture and a book shelf
a open kitchen with stainless steel appliances granite countertop a stove top oven a sink a counter space and cabinets
a view of a dining room and livingroom with furniture wooden floor a chandelier
a kitchen with stainless steel appliances granite countertop a stove a sink a refrigerator and a dining table
a bedroom with a bed and a table in it
a bed room with a bed and a window
a bedroom with a bed a chair and potted plant with the dresser
a bathroom with a sink and a mirror
a bathroom with a shower
a bathroom with a granite countertop sink mirror and double
a bedroom with a bed furniture and a book shelf
a bedroom with a bed and a flat screen tv
a workspace with furniture and a window
a view of a livingroom with workspace and a window
a living room with furniture and a window
a view of a storage room with furniture
a view of a room with gym equipment
a utility room with dryer and washer
a view of a patio with table and chairs and potted plants
a front view of a house with a garden
1/37
Closed 1/12/26

$590,000

4
Bedrooms
2,869
Square Feet
0.81
Acres

206 Valley Chestertown Md 21620, Chestertown, MD 21620

a view of a plants and large trees
a front view of a house with a garden
a view of outdoor space with green field and trees
a view of a big yard with plants and large trees
a view of a lake view
a map view of location
a yard
1/7
Closed 12/22/25

$80,000

3
Bedrooms
1,144
Square Feet
2
Acres

5700 Johnsontown Road, Chestertown, MD 21620

$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
$325,000 | 676 Deep Landing Road, Chestertown, MD 21620
1/24
Closed 1/23/26

$325,000

3
Bedrooms
1,468
Square Feet
0.59
Acres

676 Deep Landing Road, Chestertown, MD 21620

an aerial view of a golf course with chairs
a house view with a garden space
a view of a house with a big yard potted plants and large tree
a house view with swimming pool and garden
a view of a garden with a slide
a view of yard with swimming pool and green space
a view of a lake view
a view of yard with swimming pool and green space
a front view of a house with garden
a view of a park with a tree
a view of a swimming pool and lounge chairs in back yard of the house
a view of a patio with a yard
a view of a dining room with furniture and wooden floor
a kitchen with a sink stove and refrigerator
a kitchen with stainless steel appliances kitchen island granite countertop a refrigerator a stove and a sink
a kitchen with a stove a refrigerator and cabinets
a kitchen with stainless steel appliances a sink a stove and wooden floor
a view of a living room and dining room
a living room with lots of furniture and a chandelier
a living room with furniture fireplace and a large window
a dining room with wooden floor and large windows
a bedroom with a bed and a large window
a living room with furniture and a large window
a workspace with furniture window and wooden floor
a bedroom with furniture and a flat screen tv
a bedroom with a large bed and a large window
a bedroom with a large bed and a large window
a front view of house with yard and green space
a house view with a garden space
an aerial view of a city with lots of green space
a view of a city with a lake view
a view of a lake with a city view
an aerial view of a residential houses with outdoor space and seating
an aerial view of a residential houses with outdoor space and lake view
an aerial view of a houses with outdoor space and street view
a view of a house with a yard
an aerial view of a residential houses with outdoor space and street view
a view of a lake view
a backyard of a house with lots of green space
a vase of flowers sitting on a floor with a lake view
a view of a trees in a yard
a view of lake
a lake view with a yard
$1,150,000 | 23393 Cacaway Farm Lane, Chestertown, MD 21620
1/44
Closed 12/10/25Virtual Tour

$1,150,000

3
Bedrooms
4,446
Square Feet

23393 Cacaway Farm Lane, Chestertown, MD 21620

a front view of a house with balcony
a view of house with a deck and furniture
a view of a ocean with trees
a view of a swimming pool with a yard
a view of a garden with a lake
a view of a tree with a yard
a view of a garden with plants
an aerial view of a houses with a lake view
a backyard of a house with table and chairs
a living room with furniture and floor to ceiling windows
a living room with furniture and a large window
a living room with furniture fireplace and large windows
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture large windows and wooden floor
a kitchen with stainless steel appliances granite countertop a table chairs refrigerator and sink
a kitchen with stainless steel appliances a refrigerator sink and cabinets
a kitchen with stainless steel appliances a sink a stove a refrigerator and cabinets
a kitchen with counter top space and a stove
a very nice looking kitchen with a window
an outdoor sitting area with furniture
front view of a house with a porch
a bedroom with a bed and wooden floor
a bedroom with a bed and a window
a bedroom with a bed a mirror on dresser and a window
a bathroom with a toilet a sink and mirror
a bathroom with a sink a toilet and mirror
a view of a backyard with sitting area and garden
a view of a forest with a tree
a view of a livingroom with furniture
a view of entryway
a view of outdoor space with deck
a view of a two chairs in the balcony
a view of a porch with wooden floor and outdoor seating
a view of a porch with wooden floor and outdoor space
a bedroom with a bed and a large window with outer view
a bedroom with a bed and window
a bedroom with a bed and a window
a living room with furniture and large windows
a living room with furniture and a large window
a living room with furniture and floor to ceiling windows
a living room with furniture and large windows
a bedroom with a bed and a large window
a bedroom with a bed and wooden floor
a bedroom with a bed and wooden floor
a bedroom with a bed and a dresser in it
a bedroom with a bed and cabinets
a bed room with a bed and a window
a bathroom with a toilet and a sink
a utility room with dryer and washer
1/49
Closed 11/14/25

$905,000

4
Bedrooms
1,820
Square Feet
5.05
Acres

10050 Forrest Lane, Chestertown, MD 21620

a front view of a house with large trees
front view of a house
a view of a white house with iron fence
a view of living room and dining room
a view of an empty room with a window
a view of empty room with wooden floor and fan
a view of an empty room with a fireplace and a window
a view of washer and dryer with kitchen in the background
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a kitchen with a sink and cabinets
a kitchen with a sink and a refrigerator
a view of an entryway
a view of an entryway door
a bedroom with a bed and a chandelier
a bathroom with a toilet and a sink
a view of an entryway with wooden floor
a view of an entryway with wooden floor
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a view of an entryway with wooden floor
wooden floor in an empty room
a view of empty room with wooden floor
a bathroom with a sink a toilet and shower
a sign on the side of a building
a view of a balcony with wooden floor and a window
a view of empty room with wooden floor and fan
an empty room with wooden floor fan and windows
a bathroom with a sink a tub and a mirror
a view of an empty room with wooden floor and a window
an empty room with wooden floor chandelier fan and windows
a kitchen with a sink stove and cabinets
a bathroom with a granite countertop sink and a shower
a view of an empty room with a window
a view of a livingroom with a ceiling fan and window
a close view of a chairs
a view of a house with a balcony
a view of a house with a porch
a view of backyard with swimming pool
a view of a house with wooden fence
a front view of a house with a garden and trees
front view of a house with a yard
a view of a house with fountain and garden
an aerial view of a house with a yard and outdoor seating
a bird view of building
a view of a city
a view of a lake with a city view
an view of a city
a front view of a house with large trees
a balcony with table and chairs
a front view of a house with outdoor seating
$361,500 | 517 High Street, Chestertown, MD 21620
$361,500 | 517 High Street, Chestertown, MD 21620
1/51
Closed 12/19/25

$361,500

Unavailable
Bedrooms
Unavailable
Bathrooms
1,728
Square Feet
0.10
Acres

517 High Street, Chestertown, MD 21620

a front view of a house with a garden and plants
a view of a house with a big yard plants and large trees
a view of a park with large trees
a view of an outdoor space
a view of a lake with a yard
a view of a kitchen counter top space with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances a refrigerator a sink a stove top oven a wooden floor and cabinets
a kitchen with a refrigerator a stove top oven a sink dishwasher and wooden floor
a living room with furniture and a window
a living room with furniture and a flat screen tv
a living room with furniture and a floor to ceiling window
a living room with furniture and a fireplace
a bedroom with furniture and wooden floor
a view of a livingroom with furniture and window
a close view of a fireplace in a room
a living room with furniture wooden floor and a window
a view of wooden floor in a room
a living room with furniture and a fireplace
a view of walk in closet with wooden floor
a living room with furniture and a fireplace
a living room with furniture and a flat screen tv
a view of balcony with wooden floor
a bedroom with bed and a window
a kitchen with a sink cabinets and a stove
a bedroom with furniture and a wooden floor
a living room with furniture and a window
a bathroom with a sink toilet and window
a bedroom with a bed and wooden floor
a view of a living room and a rug
a view of swimming pool from a yard
a front view of a house with a garden
a front view of a house with a yard
a view of a house with a backyard and a garden
a view of a house with a yard and a pond
a view of a house with a big yard
a view of yard with green space
a front view of a house with a yard
a view of a lake with houses
a view of yard with outdoor seating and city view
a view of street with parked cars
a view of a swimming pool and a yard
1/41
Closed 1/15/26

$740,000

4
Bedrooms
2,350
Square Feet
1.44
Acres

10230 John Carvill Road, Chestertown, MD 21620

a living room with furniture and a wooden floor
a view of lake with green space
a front view of a house with a yard
a room with furniture and a wooden floor
a view of a dining room with furniture window and outside view
a living room with furniture fireplace and rug
a living room with furniture two night stand and a window
a kitchen with stainless steel appliances a sink cabinets and wooden floor
a spacious bedroom with a bed and a chandelier
a spacious bedroom with a bed a couch and dresser
a bathroom with a double vanity sink a large mirror and shower
a bedroom with a bed and a night stand
a bathroom with a sink vanity mirror and toilet
a bedroom with a bed and a window
a living room with furniture a rug and a table
a living room with furniture and a dining table
a living room with furniture and a potted plant
a view of a dining room with furniture window and outside view
1/18
Closed 10/27/25

$620,000

3
Bedrooms
2,280
Square Feet
0.68
Acres

7729 Country Club Lane, Chestertown, MD 21620

an aerial view of residential house with outdoor space and trees all around
a view of a lake with a yard and large trees
an aerial view of a house
an aerial view of a house with a yard
a view of a lake with a table and chairs
an aerial view of a house
a view of a lake with a lake
a view of lake and mountain
an aerial view of a house with a yard
a view of a lake with a park
an aerial view of a house with a yard
an aerial view of a house with yard and swimming pool
an aerial view of a residential houses with yard and swimming pool
an aerial view of a house with a yard
a view of a lake with a lake
1/15
Closed 1/12/26

$555,000

3
Bedrooms
1,600
Square Feet
0.63
Acres

26933 Mallard Road, Chestertown, MD 21620

$350,000 | 25195 Lovers Lane, Chestertown, MD 21620
Closed 12/15/25

$350,000

1
Bedrooms
1,002
Square Feet
8.72
Acres

25195 Lovers Lane, Chestertown, MD 21620

a front view of house with yard and trees
front view of a house with a yard
a front view of a house with garden
a view of swimming pool in front of house with yard and large trees
a front view of a house with a yard
a view of outdoor space
a big yard with lots of green space and plants
a backyard of a house with table and chairs
a front view of house with yard and trees
a view of a big yard with large trees
a front view of a house with garden
a view of a house with a small yard and large trees
a view of a backyard with plants and large trees
a front view of a house with a yard
a view of a house with a yard
a view of an empty room with wooden floor and a window
a view of an empty room with glass door and wooden floor
a view of an empty room with exposed radiator and fireplace
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a view of living room with furniture and wooden floor
a view of a livingroom with furniture and hardwood floor
a view of an empty room with wooden floor and a window
a view of a living room with hardwood floor
a view of an empty room with wooden floor fireplace and a window
a view of an empty room with wooden floor and windows
a view of empty room with wooden floor and fan
a view of an empty room with wooden floor fireplace and a window
an empty room with wooden floor and windows
an empty room with wooden floor and windows
a view of a porch
a view of entryway with wooden floor and stairs
a view of staircase with railing and a chandelier
a view of entryway with wooden floor
a view of a hallway with wooden floor and staircase
a view of entryway
a view of a hallway with wooden floor and staircase
a view of an outdoor space
a view of entryway
a view of an empty room with a window
a view of a door with an outdoor space
an empty room with wooden floor and windows
a view of empty room with wooden floor and fan
wooden floor in an empty room with a window
a living room with furniture and a flat screen tv
a view of outdoor space and wooden deck
a view of front door
a view of room with window
a view of a hallway with staircase
a bathroom with a sink a mirror and a shower
a view of a hallway with wooden floor and a bathroom
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
$775,000 | 8293 Brices Mill Road, Chestertown, MD 21620
1/59
Closed 11/8/25

$775,000

4
Bedrooms
2,836
Square Feet
36.2
Acres

8293 Brices Mill Road, Chestertown, MD 21620

$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
$4,221,800 | 23620 Land's End Road, Chestertown, MD 21620
1/77
Closed 11/24/25

$4,221,800

5
Bedrooms
9,852
Square Feet
80.51
Acres

23620 Land's End Road, Chestertown, MD 21620

Closed 12/19/25

$100,000

Unavailable
Bedrooms
2
Bathrooms
988
Square Feet
0.28
Acres

23137 Raleigh Road, Chestertown, MD 21620

Closed 12/11/25

$345,000

Unavailable
Bedrooms
1,068
Square Feet
2.05
Acres

23970 Langford Road, Chestertown, MD 21620

$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
$1,165,000 | 119 High Street, Chestertown, MD 21620
1/60
Closed 12/1/25

$1,165,000

5
Bedrooms
4,409
Square Feet
0.25
Acres

119 High Street, Chestertown, MD 21620

a view of a house with a big yard
a view of a house with a yard
a view of a lake with a mountain in the background
a view of an ocean and city
a view of a lake with a mountain
a view of a livingroom with wooden floor and a window
an empty room with windows
a view of a walk in closet
a view of empty room with wooden floor and fan
a view of a livingroom with a fireplace and a window
a view of empty room with wooden floor and fan
a view of empty room with wooden floor and fan
a view of an empty room with window and wooden floor
wooden floor in an empty room
a bathroom with a sink and a mirror
a view of an empty room with a window and a ceiling fan
a view of a room with a ceiling fan and a window
a bathroom with a toilet a sink and mirror
a bathroom with a shower curtain and a toilet
wooden floor in an empty room with a window
a kitchen with stainless steel appliances a refrigerator and a stove top oven
a kitchen with white cabinets and sink
a kitchen with stainless steel appliances a white stove top oven a sink a refrigerator and white cabinets
a view of a room with gym equipment
a view of parking garage with cars
a view of a pool with a yard
a front view of a house with a garden
aerial view of a house with yard and large tree
$250,000 | 124 Char Nor Manor Boulevard, Chestertown, MD 21620
$250,000 | 124 Char Nor Manor Boulevard, Chestertown, MD 21620
$250,000 | 124 Char Nor Manor Boulevard, Chestertown, MD 21620
1/31
Closed 11/11/25Virtual Tour

$250,000

2
Bedrooms
1,024
Square Feet
0.31
Acres

124 Char Nor Manor Boulevard, Chestertown, MD 21620

a white house in middle of the forest
a view of a house with a yard
a view of yard with tree
a view of a golf course with a tree
a view of a house with a tub and couches chair
a view of a chairs and tables in the patio
a bedroom with a bed and a flat screen tv
a living room with furniture and a window
a kitchen with sink a microwave and cabinets
a view of a dining room with furniture and window
a bedroom with a bed and a window
a bedroom with furniture and a flat screen tv
a workspace with furniture and window
a view of a bathroom from a hallway
a living room with a sink and a washer dryer
a bathroom with a sink toilet and shower
a view of a patio with a table chairs and a backyard
a view of outdoor space with trees
a house with trees in the background
1/19
Closed 11/10/25

$354,900

3
Bedrooms
1,253
Square Feet
2.08
Acres

2010 McGinnes Road, Chestertown, MD 21620

 
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