Chestertown, MD Homes for Sale & Real Estate

price
-
1-40 of 73 Homes
a view of grapes plant
$8,000 | Tonopah Road, Chestertown, MD 21620
1/2
Listed By Compass

$8,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Tonopah Road, Chestertown, MD 21620

$8,000 | Cogar Road, Chestertown, MD 21620
$8,000 | Cogar Road, Chestertown, MD 21620
1/2
Listed By Compass

$8,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Cogar Road, Chestertown, MD 21620

a view of a forest filled with trees
Listed By Compass

$8,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Lenapah Road, Chestertown, MD 21620

an aerial view of residential houses with outdoor space and lake view
front view of a building
an aerial view of a house with a lake view
a view of a city
a view of a lake with houses in the back
a view of a patio with couches table and chairs and potted plants
a view of a back yard
a view of a patio with chairs and plants
a view of a house with swimming pool and sitting area
a view of a terrace with sitting area
a view of a terrace with furniture and a garden
a view of a balcony with city view
a view of a balcony with wooden floor and iron stairs
a view of balcony and yard
a roof deck with lake view
a view of a lake with a lake
a view of a lake with a building in the background
a view of a lake with houses in the back
$695,000 | 118 Little Harbor Way, Unit 202, Chestertown, MD 21620
1/19
Coming Soon

$695,000

3
Bedrooms
1,600
Square Feet

118 Little Harbor Way, Unit 202, Chestertown, MD 21620

a front view of a house with garden
Coming SoonOpen: 1/3 02:00PM - 04:00PM

$475,000

4
Bedrooms
2,880
Square Feet
0.28
Acres

110 Trafford Drive, Chestertown, MD 21620

a front view of a house with a yard
a front view of a house with a yard
a view of a house with a backyard
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and a fireplace
a kitchen with a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher and white cabinets with wooden floor
a bedroom with furniture and a window
a view of a dining room with furniture wooden floor and chandelier
a living room with furniture and a large window
a living room with furniture and a large window
a bathroom with a sink toilet and shower
a bedroom with a bed and a painting on the wall
a picture of a floor plan
a view of a house with a tree in the background
a view of a patio with a table and chairs under an umbrella
a view of a wooden dinning table and chairs in the garden
a view of a house with backyard and sitting area
a view of a backyard with table and chairs and a large tree
a view of a house with a yard
a house view with a garden space
a view of a lake from a yard
a view of a wooden deck
$320,000 | 222 Dutchess Road, Chestertown, MD 21620
1/24

$320,000

3
Bedrooms
1,096
Square Feet
0.67
Acres

222 Dutchess Road, Chestertown, MD 21620

$29,000 | 23698 L Road, Chestertown, MD 21620
$29,000 | 23698 L Road, Chestertown, MD 21620
$29,000 | 23698 L Road, Chestertown, MD 21620
$29,000 | 23698 L Road, Chestertown, MD 21620
$29,000 | 23698 L Road, Chestertown, MD 21620
1/5

$29,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.6
Acres

23698 L Road, Chestertown, MD 21620

a view of brick house with large windows
a front view of a house with a yard
a front view of a house with a yard
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 empty room with wooden floor and fan
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 view of a lake with houses
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 garden with trees and a lake view
a view of a lake with boats and trees in the background
1/27
New Construction

$264,900

3
Bedrooms
1,280
Square Feet
0.09
Acres

109 Metcalf Road, Chestertown, MD 21620

a front view of a house with a yard
an aerial view of residential houses with outdoor space
an aerial view of residential houses with outdoor space
an aerial view of a house with a yard
a front view of a house with a yard
a front view of a house with a yard and garage
an aerial view of a city
a view of an empty room with a window
a living room with furniture and windows
a kitchen with stainless steel appliances kitchen island sink refrigerator and microwave
a kitchen with stainless steel appliances a refrigerator stove and sink
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with a refrigerator and a stove top oven
a bathroom with a toilet and a shower
an empty room with wooden floor
wooden floor in an empty room
a view of a hallway with wooden floor
an empty room with wooden floor and fan
1/18

$299,000

2
Bedrooms
920
Square Feet
0.13
Acres

611 Cannon Street, Chestertown, MD 21620

front view of a house with a yard
a view of a city with tall buildings
a picture of a bench in a room
an aerial view of a house with outdoor space and city view
a view of a city
an aerial view of a
a view of a city
an aerial view of a house with a garden and swimming pool
a view of a lake with a table and chairs
a view of a pathway both side of building
a view of a lake with a garden
a view of a lake with houses in back
a view of a terrace with sitting area
a view of a patio with table and chairs potted plants and large tree
an aerial view of a house with a yard and garden
an outdoor space with seating area and furniture
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
$765,900 | 37 Landing Lane, Chestertown, MD 21620
1/24
New Construction

$765,900

3
Bedrooms
1,964
Square Feet

37 Landing Lane, Chestertown, MD 21620

a front view of a house with a yard
a front view of a house with a yard
an aerial view of a house with a garden and large trees
unknown
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a view of a pathway both side of building
an outdoor space with seating area and furniture
an aerial view of a house with a yard and garden
a view of a lake with a table and chairs
a view of a lake with sitting area
a view of a terrace with sitting area
a view of a lake with houses in back
a view of a patio with table and chairs potted plants and large tree
a view of a lake with a garden
a view of a lake with a city
an aerial view of lake and residential houses with outdoor space
an aerial view of a city
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/24
New Construction

$813,900

3
Bedrooms
2,192
Square Feet
Unavailable
Acres

104 Landing Lane, Chestertown, MD 21620

a front view of a house
a front view of a house with a yard
a view of a city with tall buildings
a picture of a room with a white wall and sign
a picture of floor plan
a front view of a house with garden
a view of a city
an aerial view of a house with outdoor space and city view
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a view of a lake with a table and chairs
a view of a pathway both side of building
a view of a lake with a garden
a view of a lake with houses in back
a view of a terrace with sitting area
a view of a patio with table and chairs potted plants and large tree
an aerial view of a house with a yard and garden
an outdoor space with seating area and furniture
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/26
New Construction

$786,900

3
Bedrooms
1,964
Square Feet

35 Landing Lane, Chestertown, MD 21620

a front view of a house
a front view of a house with a yard
a view of a city with tall buildings
a picture of a room with a white wall and sign
a picture of floor plan
a front view of a house with garden
an aerial view of a house with outdoor space and city view
a view of a city
an aerial view of a
a view of a city
an aerial view of a house with a garden and swimming pool
a view of a lake with a table and chairs
a view of a pathway both side of building
a view of a lake with a garden
a view of a terrace with sitting area
a view of a patio with table and chairs potted plants and large tree
an aerial view of a house with a yard and garden
an outdoor space with seating area and furniture
a view of a lake with houses in back
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/26
New Construction

$753,500

3
Bedrooms
1,964
Square Feet

36 Landing Lane, Chestertown, MD 21620

a front view of a house
a front view of a house with windows
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a picture of a bathroom with a white sink and a window
unknown
a view of a pathway both side of building
a view of a lake with a city
a view of a lake with a garden
a view of a lake with a table and chairs
a view of a terrace with sitting area
a view of a lake with houses in back
an outdoor space with seating area and furniture
an aerial view of a house with a yard and garden
a view of a patio with table and chairs potted plants and large tree
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/23
New Construction

$839,500

3
Bedrooms
1,964
Square Feet

102 Little Harbor Way, Chestertown, MD 21620

a front view of a house with a porch
an aerial view of a house with outdoor space and city view
unknown
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a view of a lake with a table and chairs
a view of a pathway both side of building
a view of a lake with a garden
a view of a patio with table and chairs potted plants and large tree
an outdoor space with seating area and furniture
an aerial view of a house with a yard and garden
a view of a lake with houses in back
a view of a terrace with sitting area
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
$1,099,900 | 25 Landing Lane, Chestertown, MD 21620
1/22
New Construction

$1,099,900

4
Bedrooms
2,784
Square Feet

25 Landing Lane, Chestertown, MD 21620

a sign that is sitting on a brick wall
an aerial view of residential house with outdoor space and trees all around
en suite bathroom with a white and a shower curtain
a picture of a rug
a aerial view of a house with a yard and large trees
a view of deck with patio table and chairs
a view of a yard with a trees
a view of a yard
a view of a yard
a view of a yard with a trees
a view of a yard
a view of a yard with a trees
a view of a green yard
a view of field with trees in the background
a backyard of a house with lots of green space
a view of outdoor space and trees
a view of a yard
a bathroom with a yard
a backyard of a house with lots of green space and garden
a view of a yard with an outdoor space
a view of a yard
a view of a yard with an outdoor space
a view of a garden
$39,000 | Cloquet Road, Chestertown, MD 21620
1/24
Virtual Tour

$39,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.51
Acres

Cloquet Road, Chestertown, MD 21620

a front view of a house
a view of a house with a chairs in patio
an aerial view of a house with a yard
a front view of a house with a garden
a front view of a house with a yard and potted plants
a view of street with large trees
a front view of a house with a garden
a view of a patio with a dining table and chairs with wooden floor
an aerial view of a residential houses with outdoor space
an aerial view of a house with a yard and lake view
view of city and ocean
an aerial view of a houses with a yard
a house that has a tree in front of the house
a view of a patio with table and chairs potted plants with wooden floor and fence
a view of outdoor space and yard
a front view of a house with a yard
a view of outdoor space with trees all around
a view of a house with a large tree and sitting area
a view of a house with a yard
a view of living room with furniture and floor to ceiling window
a living room with furniture
a living room with furniture a flat screen tv and a refrigerator
a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a sink and a stove
a kitchen with stainless steel appliances kitchen island granite countertop a sink and cabinets
a view of livingroom with hardwood floor and flat screen tv
a view of an entryway
a very nice looking room with a large window
a balcony with furniture and a window
a kitchen with a sink a stove and cabinets
a kitchen with a sink a stove and a refrigerator
a living room with a black white checkered floor with a table and chair
a bedroom with furniture and a window
a bathroom with a sink a toilet and shower
a spacious bedroom with a large window and a chandelier
a view of a room with a large window
a view of a hallway with staircase
a view of an empty room
a view of kitchen with refrigerator and cabinets
a bathroom with a sink a toilet and shower
a view of a room with window and a wooden floor
a view of a bedroom with window and a bed
a view of an empty room with window and wooden floor
a view of a livingroom with wooden floor and a ceiling fan
a spacious bedroom with a bed and a chandelier
a bed room with a bed and a chandelier
a bathroom with a toilet sink and mirror
a bathroom with a granite countertop sink toilet and shower
a view of an empty room with a window
a view of a bedroom with a natural light
$499,900 | 8620 Park Drive, Chestertown, MD 21620
$499,900 | 8620 Park Drive, Chestertown, MD 21620
$499,900 | 8620 Park Drive, Chestertown, MD 21620
1/53

$499,900

4
Bedrooms
2,524
Square Feet
1.37
Acres

8620 Park Drive, Chestertown, MD 21620

a front view of a house with balcony
an outdoor space with furniture and garden
an aerial view of a house with a garden
a view of an ocean and beach
a front view of a house with a yard
a view of entryway and hall with wooden floor
a view of living room and dining room
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and wooden floor
a living room with furniture and a flat screen tv with wooden floor
a living room with furniture and a wooden floor
a kitchen with stainless steel appliances a stove a sink and cabinets
a kitchen with granite countertop a stove and a sink
a kitchen with stainless steel appliances a refrigerator a stove a sink and a microwave
a view of a dining room with furniture window and wooden floor
a living room with furniture and a fireplace
a living room with furniture and a window
a living room with furniture and a flat screen tv
a bathroom with a granite countertop sink toilet a large mirror and a window
a living room with couch and a large window
a living room with furniture and a large window
a view of a livingroom with furniture and front door
a view of a hallway with seating area
a bathroom with a toilet sink and shower
a living room with furniture and a window
a bathroom with a glass shower door
a bedroom with a bed and a dresser
a bedroom with a bed and window
a bedroom with a bed a lamp and wooden floor
a bedroom with a bed mirror and window
a view of a patio with table and chairs
a bathroom with a bathtub and a sink
a bathroom with a granite countertop sink mirror and shower
a bed sitting in a bedroom next to a window
a living room with a fireplace and a rug
a bathroom with a sink and toilet
a bedroom with a bed and a window
a view of a backyard with a garden
a view of a back yard
a front view of a house with a yard
a view of a balcony with chairs
a view of a garden with an outdoor seating
a front view of a house with a yard
a front view of a house with garden
a view of a garden with an outdoor space
a view of a flower in a yard
a view of outside with lake view
a view of a swimming pool and lounge chairs in the patio
a view of a lake with outdoor space
a view of a garden with a house
a view of a house with a yard
a lawn chairs sitting on a pier next to a yard
a view of a house with a patio
a view of a house with garden
a view of an ocean and beach
a view of a swimming pool with a yard
a view of an ocean and beach
a view of swimming pool
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
1/66

$2,350,000

6
Bedrooms
4,954
Square Feet
65.47
Acres

10121 Fairlee Road, Chestertown, MD 21620

a front view of a house with balcony
an outdoor space with furniture and garden
an aerial view of a house with a garden
a view of an ocean and beach
a front view of a house with a yard
a view of entryway and hall with wooden floor
a view of living room and dining room
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and wooden floor
a living room with furniture and a flat screen tv with wooden floor
a living room with furniture and a wooden floor
a kitchen with stainless steel appliances a stove a sink and cabinets
a kitchen with granite countertop a stove and a sink
a kitchen with stainless steel appliances a refrigerator a stove a sink and a microwave
a view of a dining room with furniture window and wooden floor
a living room with furniture and a fireplace
a living room with furniture and a window
a living room with furniture and a flat screen tv
a bathroom with a granite countertop sink toilet a large mirror and a window
a living room with couch and a large window
a living room with furniture and a large window
a view of a livingroom with furniture and front door
a view of a hallway with seating area
a living room with furniture and a window
a bathroom with a glass shower door
a bedroom with a bed and a dresser
a bedroom with a bed and window
a bedroom with a bed a lamp and wooden floor
a bedroom with a bed mirror and window
a view of a patio with table and chairs
a bathroom with a bathtub and a sink
a bathroom with a granite countertop sink mirror and shower
a living room with a fireplace and a rug
a bedroom with a bed and a window
a front view of a house with a yard
a view of a balcony with chairs
a view of a garden with an outdoor seating
a front view of a house with a yard
a front view of a house with garden
a view of a garden with an outdoor space
a view of a flower in a yard
a view of a swimming pool and lounge chairs in the patio
a view of a lake with outdoor space
a view of a garden with a house
a lawn chairs sitting on a pier next to a yard
a view of a house with garden
a view of an ocean and beach
a view of an ocean and beach
a view of swimming pool
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
$2,350,000 | 10121 Fairlee Road, Chestertown, MD 21620
1/66

$2,350,000

6
Bedrooms
4,954
Square Feet
65.47
Acres

10121 Fairlee Road, Chestertown, MD 21620

$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
$370,000 | 21111 Texas Avenue, Chestertown, MD 21620
1/16

$370,000

3
Bedrooms
1,680
Square Feet
0.41
Acres

21111 Texas Avenue, Chestertown, MD 21620

a view of a house with a yard
an aerial view of residential building with parking space
a kitchen with a sink a counter top space and stainless steel appliances
a kitchen that has a lot of cabinets and wooden floor
a dining room with furniture and window
a living room with furniture and a flat screen tv
a living room with furniture and large windows
a spacious bedroom with a bed a table and painting on the wall
a spacious bedroom with a bed and a chandelier
a bathroom with a toilet a sink and mirror
a view of walk in closet with clothes and shoes
a living room with furniture and large windows
a living room with furniture a large window with kitchen view
a utility room with dryer and washer
a bedroom with a bed rug and couch
a bedroom with furniture and a chandelier
a bathroom with a granite countertop sink a toilet and a mirror
a living room with furniture and a window
a bedroom with a bed and a table in it
a front view of house with yard and trees in the background
a front view of a house with a yard
a view of a yard with a house and large trees
a view of a house with a yard
a front view of a house with a big yard
a view of a garage with storage
a view of a garage with storage
a view of a city
a view of ocean and city
an aerial view of a city with lots of residential buildings ocean and mountain view in back
front view of a house with a yard
a view of a house with snow on the side of it
1/31

$370,000

3
Bedrooms
2,296
Square Feet
0.34
Acres

204 Rolling Road, Chestertown, MD 21620

a front view of a house with a yard
New Construction

$579,000

4
Bedrooms
2,400
Square Feet
1
Acres

216 Blakefield Drive, Chestertown, MD 21620

a front view of a house with a yard
a front view of a building with a garden
a kitchen with sink cabinets and wooden floor
a kitchen with a sink stove and cabinets
a large kitchen with granite countertop a large counter top a sink stainless steel appliances and cabinets
a large kitchen with kitchen island a white counter space a sink appliances and a cabinets
a living room with furniture and a flat screen tv
a living room with furniture and a table
a view of a dining room with furniture and wooden floor
an empty room with wooden floor and windows
an empty room with wooden floor and windows
a view of an empty room
a bathroom with a shower sink and mirror
a view of a balcony with chairs
a bathroom with a sink a toilet and shower
a utility room with sink dryer and washer
a view of a big room with wooden floor and windows
an empty room with wooden floor and windows
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 empty room with floor to ceiling window
a bathroom with a double vanity sink and mirror
a picture of a floor plan
a picture of a floor plan
a picture of a bench in front of a wall
a black and white photo of a living room
a picture of city view with lake view
an aerial view of a city with lots of residential buildings
an aerial view of a houses with a yard
an aerial view of multiple house
a front view of a house with a garden
1/32
New Construction

$878,000

3
Bedrooms
2,310
Square Feet
0.06
Acres

228 South Water Street, Chestertown, MD 21620

a view of a house with swimming pool
a living room with furniture
a living room with furniture
a bedroom with furniture and wooden floor
a living room with furniture
a living room with furniture and wooden floor
a dining room with furniture and window
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a refrigerator sink and stove
a kitchen with white cabinets and stainless steel appliances
a kitchen with stainless steel appliances a sink a stove a refrigerator cabinets and a window
a kitchen with stainless steel appliances granite countertop a refrigerator sink and stove
a bedroom with a bed and a chandelier
a bedroom with a large bed a chandelier and a window
a bathroom with a sink mirror and toilet
a bathroom with a toilet sink and shower
a bathroom with a sink a mirror and a vanity
a bathroom with a sink toilet and shower
an empty room with a window and a fan
wooden floor in an empty room
a view of empty room with wooden floor
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and a window
a bathroom with a sink a toilet and shower
wooden floor in an empty room with a window
a view of outdoor space and yard
an aerial view of residential houses with outdoor space
a view of a swimming pool with a yard
front view of a house with a yard
front view of a house with a yard
a front view of house with yard and trees
a front view of house with yard and trees
an aerial view of residential houses with outdoor space
an aerial view of a house with a yard
an aerial view of a city
a view of a city
an aerial view of residential building and ocean
a view of a city
a view of a city
a view of a city with an ocean
an aerial view of residential building with parking space
$399,000 | 304 Hadaway Drive, Chestertown, MD 21620
1/44

$399,000

4
Bedrooms
1,325
Square Feet
0.41
Acres

304 Hadaway Drive, Chestertown, MD 21620

$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
$598,000 | 311 Devon Drive, Chestertown, MD 21620
1/40
Open: 1/3 02:00PM - 04:00PM

$598,000

5
Bedrooms
3,504
Square Feet
0.28
Acres

311 Devon Drive, Chestertown, MD 21620

a view of a lake with houses
an aerial view of multiple house
an aerial view of a house with a lake view
a picture of a room with a fireplace lake view
a view of ocean with boats and trees in the background
1/5

$635,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.09
Acres

108 Little Harbor Way, Chestertown, MD 21620

a front view of house with yard
a front view of a house with a yard
an aerial view of a house with a garden and large trees
unknown
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a view of a pathway both side of building
an outdoor space with seating area and furniture
an aerial view of a house with a yard and garden
a view of a lake with a table and chairs
a view of a lake with sitting area
a view of a terrace with sitting area
a view of a lake with houses in back
a view of a patio with table and chairs potted plants and large tree
a view of a lake with a garden
a view of a lake with a city
an aerial view of lake and residential houses with outdoor space
an aerial view of a city
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/24
New Construction

$799,900

3
Bedrooms
2,092
Square Feet
Unavailable
Acres

106 Landing Lane, Chestertown, MD 21620

$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
$364,900 | 108 Flying Cloud Drive, Chestertown, MD 21620
1/21

$364,900

4
Bedrooms
1,936
Square Feet
0.09
Acres

108 Flying Cloud Drive, Chestertown, MD 21620

a front view of a house with a yard and garage
a living room with furniture a rug and a large window
a living room with furniture and wooden floor
a living room with furniture floor to ceiling window and wooden floor
a living room with furniture and a flat screen tv with wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture wooden floor and a chandelier
a kitchen with stainless steel appliances a sink a stove a refrigerator cabinets and dining table
a kitchen with a sink window and cabinets
a refrigerator freezer sitting inside of a kitchen
a utility room with dryer and washer
a bathroom with a sink mirror and toilet
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
an empty room with wooden floor and windows
a bedroom with a bed and a chandelier fan
a bathroom with a sink a toilet and a mirror
a bathroom with a shower curtain and a window
a view of a backyard with a tree
a view of a backyard with sitting area
$375,000 | 121 Primrose Road, Chestertown, MD 21620
1/22

$375,000

3
Bedrooms
2,034
Square Feet
0.34
Acres

121 Primrose Road, Chestertown, MD 21620

a front view of a house with a yard
a front view of a house with windows
an aerial view of a
an aerial view of a house with a garden and swimming pool
a view of a city
a picture of a bathroom with a white sink and a window
unknown
a view of a pathway both side of building
a view of a lake with a city
a view of a lake with a garden
a view of a lake with a table and chairs
a view of a terrace with sitting area
a view of a lake with houses in back
an outdoor space with seating area and furniture
an aerial view of a house with a yard and garden
a view of a patio with table and chairs potted plants and large tree
an aerial view of a city
an aerial view of lake and residential houses with outdoor space
a view of a city
a view of a swimming pool with sitting area
a view of living room and dining room
a view of people sitting in front of retail shops
a view of a lake in middle of the house
1/23
New Construction

$849,900

3
Bedrooms
1,980
Square Feet

104 Little Harbor Way, Chestertown, MD 21620

a front view of a house with a yard and trees
a front view of a house with garden
a front view of a house with garden
a view of a house with a yard and large tree
a living room with furniture and windows
a living room with furniture and a window
a view of a house with a yard
a view of a house with a yard
a front view of house with yard
a living room with furniture and a couch
a living room with furniture and a flat screen tv
a living room with furniture and a window
a view of a dining room with furniture wooden floor and a chandelier
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and wooden floor
a spacious bathroom with a sink a mirror and a bathtub
a kitchen with a sink refrigerator and window
a kitchen with white cabinets and appliances
an empty room with wooden floor and windows
a view of a room with gym equipment
a bedroom with a bed and a closet
a bedroom with a bed and a window
a utility room with cabinets washer and dryer
a view of a hallway to a livingroom with wooden floor and sink
a bedroom with a bed window and chair
a bedroom with a bed and a closet
a workspace with furniture and a book shelf
a room with furniture and wooden floor
a view of an empty room with wooden floor and a window
1/29

$469,000

4
Bedrooms
1,656
Square Feet
0.15
Acres

222 Mt Vernon Avenue, 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
$269,000 | 318 Lincoln Drive, Chestertown, MD 21620
1/21

$269,000

3
Bedrooms
960
Square Feet
0.49
Acres

318 Lincoln Drive, Chestertown, MD 21620

a picture of city view with lake view and ocean view
a view of kitchen with furniture and wooden floor
a view of empty room with wooden floor and fireplace
a bathroom with a bathtub and a shower
a view of entryway with wooden floor
a view of a room with wooden floor and furniture
a view of a bedroom with a bed and wooden floor
a bathroom with a sink and a painting on the wall
wooden floor in an empty room with a window
a kitchen with kitchen island granite countertop a sink and wooden cabinets
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and a window
a bathroom with a shower
a bathroom with a toilet and shower
a view of empty room with wooden floor and fan
a view of an empty room
a bathroom with a sink and a mirror
a view of wooden floor in a room
a bathroom with a shower and a sink
a bathroom with a shower
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and a window
a bathroom with a sink and a toilet
an empty room with wooden floor and windows
a view of a hallway with washer and dryer
a view of an entryway with hardwood and door
a view of a room with wooden floor and a window
an empty room with wooden floor
a bathroom with a toilet and a bathtub
a bathroom with a toilet and a sink
a view of empty room with wooden floor
a view of an empty room with wooden floor
a view of entryway with wooden floor
a view of construction area
a view of a back yard of the house
a view of a backyard with stairs
a view of a house with a yard
a close view of a swimming pool
a front view of a house with a yard
a view of city and ocean
a view of city and ocean
a view of a lake with a city
a view of a balcony with wooden floor
a view of a chairs and table in the balcony
a front view of a building with balcony
a view of a building with a street
a view of a building with many windows
a view of a city
$1,395,500 | 105 High Street, Chestertown, MD 21620
$1,395,500 | 105 High Street, Chestertown, MD 21620
1/51

$1,395,500

5
Bedrooms
3,243
Square Feet
0.06
Acres

105 High Street, Chestertown, MD 21620

a front view of a house
a view of a white house with large windows and a small yard
a view of door front of house
a front view of a house with a yard and garage
a backyard of a house
a living room with furniture and a window
a living room with furniture kitchen view and a dining table
a view of empty room with wooden floor and floor to ceiling window
a kitchen with stainless steel appliances granite countertop a sink a stove a refrigerator a dining table and chairs
a kitchen with stainless steel appliances a stove a sink island and a refrigerator
a bedroom with bed and window
an empty room with ceiling fan and windows
a bathroom with a toilet and a shower
a bedroom with bed and a potted plant
a view of hallway with chandelier fan
a bathroom with a toilet a sink and mirror
a bedroom with a bed and a potted plant
an empty room with a window and a fan
a utility room with dryer and washer
a view of storage and utility room
a picture of a bench in front of a door
a picture of a floor plan
a picture of a bench in front of a wall
a black and white photo of a picture of a floor
1/24

$449,900

3
Bedrooms
1,216
Square Feet
0.07
Acres

109 South College Avenue, Chestertown, MD 21620

a front view of a house with a yard
a front view of a house with a yard
a view of an empty room
a view of a house with a yard and sitting area
a view of a basketball court
a front view of a house with garden
a utility room with dryer and washer
a kitchen with granite countertop cabinets stainless steel appliances and a sink
a kitchen with a refrigerator and a stove top oven
a kitchen with a refrigerator and window
a view of a kitchen with a sink a washer and dryer next to a window
a view of a small space
a view of entryway
a view of an empty room
a white toilet sitting next to a bathtub and a shower
a view of a backyard with plants and large tree
a view of a house with a yard
a view of house with backyard and porch
a view of a park with large trees
a backyard of a house with lots of plants and large tree
$179,000 | 21316 Persimmon Drive, Chestertown, MD 21620
1/21

$179,000

2
Bedrooms
1,232
Square Feet
0.05
Acres

21316 Persimmon Drive, Chestertown, MD 21620

$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
$334,000 | 8750 Georgetown Road, Chestertown, MD 21620
1/25

$334,000

3
Bedrooms
1,900
Square Feet
1.03
Acres

8750 Georgetown Road, Chestertown, MD 21620

a front view of a house with a yard and trees
a view of a house with a yard
a view of a house with a yard
a view of a house with a backyard
a view of outdoor space with deck and yard
a room with a bed furniture and a window
a view of empty room
a bathroom with a bathtub
an empty room with wooden floor and windows
a bathroom with a sink and a toilet
a view of an empty room
a kitchen with stainless steel appliances a sink a stove a refrigerator a counter space and cabinets
a living room with furniture
a view of a room with gym equipment
$167,000 | 141 Prospect Street, Chestertown, MD 21620
$167,000 | 141 Prospect Street, Chestertown, MD 21620
1/16

$167,000

4
Bedrooms
1,156
Square Feet
0.18
Acres

141 Prospect Street, Chestertown, MD 21620

a backyard of a house with yard and tree
a view of a dining room with furniture and wooden floor
a living room with furniture and wooden floor
a living room with furniture and a window
a living room with furniture and a large window
a kitchen with a table and chairs in it
a dining room with furniture and window
a view of a dining room with furniture window and wooden floor
a kitchen with kitchen island a stove a refrigerator and a dining table with wooden floor
a view of a dining room with furniture and wooden floor
a kitchen with kitchen island granite countertop a sink cabinets and stainless steel appliances
a large kitchen with kitchen island a large counter top stainless steel appliances and cabinets
a living room with furniture a flat screen tv and a window
a living room with furniture and a wooden floor
a living room with furniture
a bathroom with a granite countertop sink toilet and mirror
a bathroom with a shower and a toilet
a bathroom with a sink and a mirror
a view of an empty room with a window
an empty room with windows and closet
a view of entryway
a view of a livingroom with a window
an empty room with windows and closet
a view of empty room with wooden floor and fan
a front view of house with yard and green space
front view of a house with a yard
a view of backyard of house with entertaining space
a view of backyard with trampoline
$349,900 | 23110 Old Fairlee Road, Chestertown, MD 21620
1/29

$349,900

3
Bedrooms
1,805
Square Feet
0.19
Acres

23110 Old Fairlee Road, Chestertown, MD 21620

a front view of a house with a yard and trees
a backyard of a house with lots of green space
a view of outdoor space and yard
a swimming pool with lots of tress in front of it
a view of a swimming pool with a yard
a patio table and chairs with potted plants
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove
a kitchen with stainless steel appliances granite countertop a sink refrigerator and cabinets
a view of a dining room with furniture and a chandelier
a bathroom with a toilet sink and shower curtain
a living room with furniture a flat screen tv and a floor to ceiling window
a bedroom with a bed and flat screen tv
a view of steet room
a living room with furniture and a window
a living room with furniture
a dinning table and chairs in a patio of the house
a bathroom with a sink and toilet
a kitchen with a sink stove and cabinets
a utility room with dryer and washer
a bedroom with a bed dresser and a window
a front view of a house with parking space
a view of a yard with a large trees
a view of a house with a yard
a front view of a house with a yard
a view of a house with a yard
$325,000 | 23043 Bay Shore Spur, Chestertown, MD 21620
$325,000 | 23043 Bay Shore Spur, Chestertown, MD 21620
1/27

$325,000

4
Bedrooms
2,630
Square Feet
1.65
Acres

23043 Bay Shore Spur, Chestertown, MD 21620

$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
$745,000 | 7844 Chester Court, Chestertown, MD 21620
1/51

$745,000

4
Bedrooms
3,248
Square Feet
1.01
Acres

7844 Chester Court, Chestertown, MD 21620

 
For Sale:

Discover Your Perfect Home

Explore Nearby Homes

Looking for Rentals?

Homes and Apartments for Rent in Chestertown