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Chestertown, MD
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Newest Listings
118 LITTLE HARBOR WAY 201 CHESTERTOWN MD 21620
1 / 34
$675,000
CondominiumFor Sale
Coming Soon
2
BEDS
3
TOTAL BATHS
1,600
SQFT
118 LITTLE HARBOR WAY 201
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Cross Street Realtors LLC
112 METCALF ROAD CHESTERTOWN MD 21620
1 / 4
$249,500
TownhouseFor Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,280
SQFT
112 METCALF ROAD
CHESTERTOWN, MD21620
CHESTER ARMS Subdivision
Listing courtesy of Rosendale Realty
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
New Listing - 6 days on site
1 / 13
$850,000
Commercial SaleFor Sale
Active
3,527
SQFT
201 N LYNCHBURG STREET
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Associates-Hockessin
105 PEARL CREEK LANE CHESTERTOWN MD 21620
Open House Sat, Jan 31, 10 AM
1 / 73
$449,000
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,961
SQFT
105 PEARL CREEK LANE
CHESTERTOWN, MD21620
PEARL CREEK ESTATES Subdivision
Listing courtesy of Taylor Properties
23055 OLD FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 1
$330,000
Single Family ResidenceFor Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,628
SQFT
23055 OLD FAIRLEE ROAD
CHESTERTOWN, MD21620
FAIRLEE Subdivision
Listing courtesy of Benson & Mangold, LLC
109 WATER STREET CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 69
$650,000
TownhouseFor Sale
Active
4
BEDS
2
TOTAL BATHS
2,064
SQFT
109 WATER STREET
CHESTERTOWN, MD21620
DOWNTOWN CHESTERTOWN Subdivision
Listing courtesy of Cross Street Realtors LLC
HOFFECKER ROAD CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 11
$212,000
LandFor Sale
Active
10.05
ACRES
QUEEN ANNES
COUNTY
HOFFECKER ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
24339 CHESTERTOWN ROAD CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 36
$269,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
960
SQFT
24339 CHESTERTOWN ROAD
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
206 S WATER STREET CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 45
$585,000
Single Family ResidenceFor Sale
Active
4
BEDS
4
TOTAL BATHS
2,008
SQFT
206 S WATER STREET
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of TTR Sotheby's International Realty
129 PARMA ROAD CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 41
$330,000
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,170
SQFT
129 PARMA ROAD
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
141 PROSPECT STREET CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 16
$165,000
Single Family ResidenceFor Sale
Active
4
BEDS
2
TOTAL BATHS
1,156
SQFT
141 PROSPECT STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Taylor Properties
22681 WOOD YARD LANE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 2
$15,000
LandFor Sale
Active
0.52
ACRES
KENT
COUNTY
22681 WOOD YARD LANE
CHESTERTOWN, MD21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
201 GREENWOOD AVENUE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 62
$495,000
Single Family ResidenceFor Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
3,984
SQFT
201 GREENWOOD AVENUE
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
104 IRIS ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 36
$379,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,700
SQFT
104 IRIS ROAD
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
6746 QUAKER ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 49
$445,000
Mixed UseFor Sale
Active
3
TOTAL BATHS
3,371
SQFT
6746 QUAKER ROAD
CHESTERTOWN, MD21620
QUAKER NECK Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
6746 QUAKER NECK ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 50
$445,000
Single Family ResidenceFor Sale
Active
5
BEDS
3
TOTAL BATHS
3,371
SQFT
6746 QUAKER NECK ROAD
CHESTERTOWN, MD21620
QUAKER NECK Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
10800 CLIFF ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 94
$1,495,000
Single Family ResidenceFor Sale
Active Under Contract
5
BEDS
4
TOTAL BATHS
5,241
SQFT
10800 CLIFF ROAD
CHESTERTOWN, MD21620
GREAT OAK ESTATES Subdivision
Listing courtesy of Taylor Properties
22481 GOOSE HOLLOW DRIVE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 18
$379,500
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,296
SQFT
22481 GOOSE HOLLOW DRIVE
CHESTERTOWN, MD21620
GOOSE HOLLOW Subdivision
Listing courtesy of Realty Mark Cityscape
24775 LANGFORD ROAD CHESTERTOWN MD 21620
1 / 36
$319,900
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,008
SQFT
24775 LANGFORD ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Advantage Realty
23698 L ROAD CHESTERTOWN MD 21620
1 / 5
$29,000
LandFor Sale
Active
2.6
ACRES
KENT
COUNTY
23698 L ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Taylor Properties
303 CEDAR STREET CHESTERTOWN MD 21620
1 / 26
$333,900
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
2,577
SQFT
303 CEDAR STREET
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Select Land & Homes, LLC
218 CAMELOT DRIVE CHESTERTOWN MD 21620
1 / 45
$525,000
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
3,932
SQFT
218 CAMELOT DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Coldwell Banker Realty
109 METCALF ROAD CHESTERTOWN MD 21620
1 / 27
$264,900
TownhouseFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,280
SQFT
109 METCALF ROAD
CHESTERTOWN, MD21620
CHESTER ARMS Subdivision
Listing courtesy of Real Broker, LLC
CLOQUET ROAD CHESTERTOWN MD 21620
1 / 32
$39,000
LandFor Sale
Active
1.51
ACRES
KENT
COUNTY
CLOQUET ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty
110 TRAFFORD DRIVE CHESTERTOWN MD 21620
1 / 26
$475,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,880
SQFT
110 TRAFFORD DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of RE/MAX Advantage Realty
#37 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$765,900
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#37 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
#36 LANDING LANE CHESTERTOWN MD 21620
1 / 26
$753,500
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#36 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
#35 LANDING LANE CHESTERTOWN MD 21620
1 / 26
$786,900
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#35 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
#25 LANDING LANE CHESTERTOWN MD 21620
1 / 22
$1,099,900
CondominiumFor Sale
Active
4
BEDS
4
TOTAL BATHS
2,784
SQFT
#25 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
104 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$813,900
CondominiumFor Sale
Active
3
BEDS
4
TOTAL BATHS
2,192
SQFT
104 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
102 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 23
$839,500
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
102 LITTLE HARBOR WAY
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
213 CENTRAL DRIVE CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 23
$314,900
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,232
SQFT
213 CENTRAL DRIVE
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
311 DEVON DRIVE CHESTERTOWN MD 21620
1 / 40
$598,000
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
3,504
SQFT
311 DEVON DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
21111 TEXAS AVENUE CHESTERTOWN MD 21620
1 / 16
$370,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,680
SQFT
21111 TEXAS AVENUE
CHESTERTOWN, MD21620
TOLCHESTER ESTATES Subdivision
Listing courtesy of Keller Williams Select Realtors of Easton
GEORGETOWN ROAD CHESTERTOWN MD 21620
1 / 7
$89,500
LandFor Sale
Active
3.92
ACRES
KENT
COUNTY
GEORGETOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
108 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
1 / 21
$364,900
Single Family ResidenceFor Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
1,936
SQFT
108 FLYING CLOUD DRIVE
CHESTERTOWN, MD21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of Cross Street Realtors LLC
EAST STREET CHESTERTOWN MD 21620
1 / 8
$88,900
LandFor Sale
Active Under Contract
0.48
ACRES
QUEEN ANNES
COUNTY
EAST STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
108 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 5
$635,000
LandFor Sale
Active
0.09
ACRES
KENT
COUNTY
108 LITTLE HARBOR WAY
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
121 PRIMROSE ROAD CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 22
$350,000
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
2,034
SQFT
121 PRIMROSE ROAD
CHESTERTOWN, MD21620
SARAH SKIPPER LANDS Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
611 CANNON STREET CHESTERTOWN MD 21620
1 / 18
$299,000
Single Family ResidenceFor Sale
Active
2
BEDS
2
TOTAL BATHS
920
SQFT
611 CANNON STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
106 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$799,900
CondominiumFor Sale
Active
3
BEDS
4
TOTAL BATHS
2,092
SQFT
106 LANDING LANE
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
104 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 23
$849,900
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,980
SQFT
104 LITTLE HARBOR WAY
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
LITTLE HARBOR WAY 1 CHESTERTOWN MD 21620
1 / 25
$1,459,000
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
2,231
SQFT
LITTLE HARBOR WAY 1
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
204 ROLLING ROAD CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 31
$345,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,296
SQFT
204 ROLLING ROAD
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
105 HIGH STREET CHESTERTOWN MD 21620
1 / 51
$1,395,500
Single Family ResidenceFor Sale
Active
5
BEDS
5
TOTAL BATHS
3,243
SQFT
105 HIGH STREET
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
216 BLAKEFIELD DRIVE CHESTERTOWN MD 21620
1 / 49
$579,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,400
SQFT
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD21620
BLAKEFIELD Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
222 MOUNT VERNON AVENUE CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 29
$455,000
Single Family ResidenceFor Sale
Active
4
BEDS
2
TOTAL BATHS
1,656
SQFT
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Long & Foster Real Estate, Inc.
304 HADAWAY DRIVE CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 44
$350,000
Single Family ResidenceFor Sale
Active
4
BEDS
2
TOTAL BATHS
1,325
SQFT
304 HADAWAY DRIVE
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Cummings & Co. Realtors
10121 FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 67
$2,350,000
FarmFor Sale
Pending
6
BEDS
5
TOTAL BATHS
4,954
SQFT
10121 FAIRLEE ROAD
CHESTERTOWN, MD21620
MELITOTA Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
8620 PARK DRIVE CHESTERTOWN MD 21620
1 / 53
$499,900
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,524
SQFT
8620 PARK DRIVE
CHESTERTOWN, MD21620
TOLCHESTER Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
10121 FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 67
$2,350,000
Single Family ResidenceFor Sale
Pending
6
BEDS
5
TOTAL BATHS
4,954
SQFT
10121 FAIRLEE ROAD
CHESTERTOWN, MD21620
MELITOTA Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
7844 CHESTER COURT CHESTERTOWN MD 21620
1 / 51
$745,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
3,248
SQFT
7844 CHESTER COURT
CHESTERTOWN, MD21620
HEATHER HEIGHTS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
8750 GEORGETOWN ROAD CHESTERTOWN MD 21620
1 / 25
$334,000
Manufactured HomeFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,900
SQFT
8750 GEORGETOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
228 S WATER ST CHESTERTOWN MD 21620
1 / 32
$878,000
TownhouseFor Sale
Active
3
BEDS
4
TOTAL BATHS
2,310
SQFT
228 S WATER ST
CHESTERTOWN, MD21620
HISTORIC CHESTERTOWN Subdivision
Listing courtesy of Gunther-McClary Real Estate
127 WOOD DUCK LANE CHESTERTOWN MD 21620
1 / 26
$215,000
Mobile HomeFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,666
SQFT
127 WOOD DUCK LANE
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Point Realty
222 DUTCHESS ROAD CHESTERTOWN MD 21620
1 / 24
$320,000
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,096
SQFT
222 DUTCHESS ROAD
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Gunther-McClary Real Estate
118 LITTLE HARBOR WAY 202 CHESTERTOWN MD 21620
1 / 19
$695,000
CondominiumFor Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,600
SQFT
118 LITTLE HARBOR WAY 202
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Benson & Mangold, LLC
108 PRIMROSE ROAD CHESTERTOWN MD 21620
1 / 49
$375,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,722
SQFT
108 PRIMROSE ROAD
CHESTERTOWN, MD21620
SARAH SKIPPER LANDS Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
CLARISSA ROAD CHESTERTOWN MD 21620
1 / 1
$10,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
CLARISSA ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Samson Properties
8833 GEORGETOWN ROAD CHESTERTOWN MD 21620
1 / 47
$364,000
Single Family ResidenceFor Sale
Pending
4
BEDS
2
TOTAL BATHS
1,625
SQFT
8833 GEORGETOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
404 SPRING ROAD CHESTERTOWN MD 21620
1 / 11
$19,500
LandFor Sale
Active Under Contract
0.99
ACRES
QUEEN ANNES
COUNTY
404 SPRING ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of The Parker Group
423 CALVERT STREET CHESTERTOWN MD 21620
1 / 20
$135,000
TownhouseFor Sale
Pending
3
BEDS
2
TOTAL BATHS
1,136
SQFT
423 CALVERT STREET
CHESTERTOWN, MD21620
CALVERT HOMES Subdivision
Listing courtesy of Redfin Corp
119 DARDEN ROAD CHESTERTOWN MD 21620
1 / 2
$315,000
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,424
SQFT
119 DARDEN ROAD
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Compass
103 METCALF RD CHESTERTOWN MD 21620
1 / 25
$259,900
TownhouseFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,280
SQFT
103 METCALF RD
CHESTERTOWN, MD21620
CHESTER ARMS Subdivision
Listing courtesy of Real Broker, LLC
23110 OLD FAIRLEE ROAD CHESTERTOWN MD 21620
Price Change - a week ago
1 / 29
$339,900
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,805
SQFT
23110 OLD FAIRLEE ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Real Broker LLC
21316 PERSIMMON DRIVE CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 21
$169,000
TownhouseFor Sale
Pending
2
BEDS
1
TOTAL BATH
1,232
SQFT
21316 PERSIMMON DRIVE
CHESTERTOWN, MD21620
TOLCHESTER Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
100 ADELA WAY CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 67
$500,000
Single Family ResidenceFor Sale
Active
4
BEDS
4
TOTAL BATHS
3,799
SQFT
100 ADELA WAY
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty
23043 BAY SHORE SPUR CHESTERTOWN MD 21620
1 / 27
$325,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,630
SQFT
23043 BAY SHORE SPUR
CHESTERTOWN, MD21620
FAIRLEE Subdivision
Listing courtesy of Rock Hall Properties Real Estate
7989 QUAKER NECK ROAD CHESTERTOWN MD 21620
1 / 90
$2,500,000
Single Family ResidenceFor Sale
Active
5
BEDS
5
TOTAL BATHS
4,305
SQFT
7989 QUAKER NECK ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
116 HARLAN LOOP CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 21
$509,000
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
4,067
SQFT
116 HARLAN LOOP
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Samson Properties
BUCK NECK LANDING ROAD CHESTERTOWN MD 21620
1 / 2
$10,000
LandFor Sale
Active
0.55
ACRES
KENT
COUNTY
BUCK NECK LANDING ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Rosendale Realty
TONOPAH RD. CHESTERTOWN MD 21620
1 / 2
$40,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
TONOPAH RD.
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of The Hogans Agency
JOHNSONTOWN ROAD CHESTERTOWN MD 21620
1 / 16
$35,000
LandFor Sale
Active Under Contract
0.9
ACRES
KENT
COUNTY
JOHNSONTOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty
200 WASHINGTON AVENUE CHESTERTOWN MD 21620
1 / 35
$695,000
Single Family ResidenceFor Sale
Pending
4
BEDS
4
TOTAL BATHS
2,917
SQFT
200 WASHINGTON AVENUE
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Cross Street Realtors LLC
251 DEVON DRIVE CHESTERTOWN MD 21620
1 / 54
$595,000
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
3,935
SQFT
251 DEVON DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
COGAR ROAD CHESTERTOWN MD 21620
1 / 2
$8,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
COGAR ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Compass
TONOPAH ROAD CHESTERTOWN MD 21620
1 / 2
$8,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
TONOPAH ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Compass
234 N COLLEGE AVENUE CHESTERTOWN MD 21620
Short Sale
1 / 3
$164,000
Single Family ResidenceFor Sale
Active Under Contract
2
BEDS
1
TOTAL BATH
1,296
SQFT
234 N COLLEGE AVENUE
CHESTERTOWN, MD21620
 
Listing courtesy of Cummings & Co Realtors
134 CHAR NOR MANOR BOULEVARD CHESTERTOWN MD 21620
1 / 42
$279,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,128
SQFT
134 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD21620
CHAR NOR MANOR Subdivision
Listing courtesy of Meredith Fine Properties
165 CHAR NOR MANOR BOULEVARD CHESTERTOWN MD 21620
1 / 67
$409,900
Single Family ResidenceFor Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
2,258
SQFT
165 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD21620
CHAR NOR MANOR Subdivision
Listing courtesy of RE/MAX Executive
23069 RALEIGH ROAD CHESTERTOWN MD 21620
1 / 10
$175,000
Single Family ResidenceFor Sale
Pending
2
BEDS
2
TOTAL BATHS
1,160
SQFT
23069 RALEIGH ROAD
CHESTERTOWN, MD21620
FAIRLEE Subdivision
Listing courtesy of Keller Williams Select Realtors of Annapolis
BUCK NECK ROAD CHESTERTOWN MD 21620
1 / 1
$9,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
BUCK NECK ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
KINGLET ROAD CHESTERTOWN MD 21620
1 / 2
$9,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
KINGLET ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
GEORGETOWN RD CHESTERTOWN MD 21620
1 / 5
$60,000
LandFor Sale
Active
3
ACRES
KENT
COUNTY
GEORGETOWN RD
CHESTERTOWN, MD21620
 
Listing courtesy of Doug Ashley Realtors, LLC
LENAPAH RD CHESTERTOWN MD 21620
1 / 1
$8,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
LENAPAH RD
CHESTERTOWN, MD21620
 
Listing courtesy of Compass
329 HIGH STREET CHESTERTOWN MD 21620
Price Change - yesterday
1 / 19
$1,190,000
Mixed UseFor Sale
Active
4,500
SQFT
329 HIGH STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Cross Street Realtors LLC
CROMWELL CLARK ROAD CHESTERTOWN MD 21620
1 / 19
$3,000,000
LandFor Sale
Active
87.34
ACRES
KENT
COUNTY
CROMWELL CLARK ROAD
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of The Land Group
CAULKS FIELD ROAD CHESTERTOWN MD 21620
1 / 8
$150,000
LandFor Sale
Active
2
ACRES
KENT
COUNTY
CAULKS FIELD ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Allegiance
GEORGETOWN ROAD SE CHESTERTOWN MD 21620
1 / 3
$150,000
LandFor Sale
Active
2
ACRES
KENT
COUNTY
GEORGETOWN ROAD SE
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Allegiance
LITTLE HARBOR WAY 1 CHESTERTOWN MD 21620
1 / 29
$1,800,000
CondominiumFor Sale
Active
4
BEDS
4
TOTAL BATHS
3,540
SQFT
LITTLE HARBOR WAY 1
CHESTERTOWN, MD21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
OLD MORGNEC ROAD CHESTERTOWN MD 21620
1 / 1
$59,000
LandFor Sale
Active
1.37
ACRES
KENT
COUNTY
OLD MORGNEC ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
TOWHEE ROAD CHESTERTOWN MD 21620
1 / 4
$10,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
TOWHEE ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
MELITOTA ROAD CHESTERTOWN MD 21620
1 / 1
$29,000
LandFor Sale
Active Under Contract
2
ACRES
KENT
COUNTY
MELITOTA ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of The Hogans Agency
FISH HATCHERY ROAD CHESTERTOWN MD 21620
1 / 7
$10,000
LandFor Sale
Active
0.37
ACRES
KENT
COUNTY
FISH HATCHERY ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
BUNTING ROAD CHESTERTOWN MD 21620
1 / 4
$10,000
LandFor Sale
Pending
0.34
ACRES
KENT
COUNTY
BUNTING ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
BELTRAM RD CHESTERTOWN MD 21620
1 / 6
$10,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
BELTRAM RD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
109 WILTON ROAD CHESTERTOWN MD 21620
1 / 31
$344,900
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,392
SQFT
109 WILTON ROAD
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
HAACKE DRIVE LOT 3 CHESTERTOWN MD 21620
1 / 5
$225,000
LandFor Sale
Pending
0.96
ACRES
KENT
COUNTY
HAACKE DRIVE LOT 3
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
SCHEELER ROAD LOT 2 CHESTERTOWN MD 21620
1 / 7
$250,000
LandFor Sale
Pending
0.93
ACRES
KENT
COUNTY
SCHEELER ROAD LOT 2
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
24543 CHESTERTOWN ROAD CHESTERTOWN MD 21620
Short Sale
1 / 55
$425,000
Single Family ResidenceFor Sale
Pending
3
BEDS
2
TOTAL BATHS
3,280
SQFT
24543 CHESTERTOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Executive
1 - 100of115 listings (115 total matches)


The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.


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    Accessibility Statement

    Accessibility Statement

    • execuhome.com
    • January 28, 2026

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    We firmly believe that the internet should be available and accessible to anyone, and are committed to providing a website that is accessible to the widest possible audience, regardless of circumstance and ability. To fulfill this, we aim to adhere as strictly as possible to the World Wide Web Consortium’s (W3C) Web Content Accessibility Guidelines 2.1 (WCAG 2.1) at the AA level. These guidelines explain how to make web content accessible to people with a wide array of disabilities. Complying with those guidelines helps us ensure that the website is accessible to all people: blind people, people with motor impairments, visual impairment, cognitive disabilities, and more. This website utilizes various technologies that are meant to make it as accessible as possible at all times. We utilize an accessibility interface that allows persons with specific disabilities to adjust the website’s UI (user interface) and design it to their personal needs. Additionally, the website utilizes an AI-based application that runs in the background and optimizes its accessibility level constantly. This application remediates the website’s HTML, adapts Its functionality and behavior for screen-readers used by the blind users, and for keyboard functions used by individuals with motor impairments. If you’ve found a malfunction or have ideas for improvement, we’ll be happy to hear from you. You can reach out to the website’s operators by using the following email [email protected]

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    Notes, comments, and feedback

    Despite our very best efforts to allow anybody to adjust the website to their needs, there may still be pages or sections that are not fully accessible, are in the process of becoming accessible, or are lacking an adequate technological solution to make them accessible. Still, we are continually improving our accessibility, adding, updating and improving its options and features, and developing and adopting new technologies. All this is meant to reach the optimal level of accessibility, following technological advancements. For any assistance, please reach out to [email protected]