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Chestertown, MD
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Newest Listings
110 PROSPECT STREET CHESTERTOWN MD 21620
New Listing - 8 hours on site
1 / 6
$119,900
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
2,210
SQFT
110 PROSPECT STREET
CHESTERTOWN, MD21620
 
Listing courtesy of ANR Realty, LLC
205 RIVER ROAD CHESTERTOWN MD 21620
New Listing - 3 days on site
1 / 68
$869,900
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,877
SQFT
205 RIVER ROAD
CHESTERTOWN, MD21620
SARAH SKIPPER LANDS Subdivision
Listing courtesy of Clark & Co Realty, LLC
8886 GEORGETOWN ROAD CHESTERTOWN MD 21620
New Listing - 4 days on site
1 / 2
$85,000
LandFor Sale
Active
4.03
ACRES
KENT
COUNTY
8886 GEORGETOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Samson Properties
10572 WATONGA ROAD CHESTERTOWN MD 21620
Open House Sat, Jun 13, 12 PM
1 / 25
$325,000
Single Family Residence
Coming Soon
3
BEDS
2
TOTAL BATHS
1,404
SQFT
10572 WATONGA ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Serhant
21172 WYOMING AVENUE CHESTERTOWN MD 21620
New Listing - 4 days on site
1 / 1
$200,000
Single Family ResidenceFor Sale
Active
4
BEDS
1
TOTAL BATH
2,920
SQFT
21172 WYOMING AVENUE
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Blue Star Real Estate, LLC
10781 FERMOY ROAD CHESTERTOWN MD 21620
New Listing - 4 days on site
1 / 54
$449,900
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
2,160
SQFT
10781 FERMOY ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Real Broker, LLC - Chester
213 BYFORD DRIVE CHESTERTOWN MD 21620
New Listing - 7 days on site
1 / 39
$380,000
Single Family ResidenceFor Sale
Active
4
BEDS
2
TOTAL BATHS
1,277
SQFT
213 BYFORD DRIVE
CHESTERTOWN, MD21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
8796 MARYLAND PARKWAY CHESTERTOWN MD 21620
New Listing - a week on site
1 / 60
$1,650,000
Commercial SaleFor Sale
Active
5,000
SQFT
8796 MARYLAND PARKWAY
CHESTERTOWN, MD21620
TOLCHESTER Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
202 ROYSTON SHORES ROAD CHESTERTOWN MD 21620
1 / 72
$1,200,000
Single Family Residence
Coming Soon
4
BEDS
3
TOTAL BATHS
2,292
SQFT
202 ROYSTON SHORES ROAD
CHESTERTOWN, MD21620
ROYSTON SHORES Subdivision
Listing courtesy of Cross Street Realtors LLC
1906 PONDTOWN ROAD CHESTERTOWN MD 21620
New Listing - a week on site
1 / 4
$110,000
LandFor Sale
Active
1.93
ACRES
QUEEN ANNES
COUNTY
1906 PONDTOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Keller Williams Flagship
1904 PONDTOWN ROAD CHESTERTOWN MD 21620
New Listing - a week on site
1 / 11
$265,000
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,967
SQFT
1904 PONDTOWN ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Keller Williams Flagship
23741 L ROAD CHESTERTOWN MD 21620
New Listing - a week on site
1 / 2
$15,000
LandFor Sale
Active
1
ACRES
KENT
COUNTY
23741 L ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Benson & Mangold, LLC
522 HIGH STREET CHESTERTOWN MD 21620
New Listing - a week on site
1 / 15
$450,000
Single Family ResidenceFor Sale
Active
2
BEDS
3
TOTAL BATHS
1,518
SQFT
522 HIGH STREET
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Benson & Mangold, LLC
8796 MARYLAND PARKWAY CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 60
$1,650,000
Single Family ResidenceFor Sale
Active
9
BEDS
7
TOTAL BATHS
4,776
SQFT
8796 MARYLAND PARKWAY
CHESTERTOWN, MD21620
TOLCHESTER Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
956 WASHINGTON AVENUE CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 29
$285,000
Manufactured HomeFor Sale
Active
3
BEDS
1
TOTAL BATH
1,248
SQFT
956 WASHINGTON AVENUE
CHESTERTOWN, MD21620
CHESTER HEIGHTS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
7761 BROAD NECK ROAD CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 4
$1,500,000
Single Family Residence
Pending
5
BEDS
3
TOTAL BATHS
2,700
SQFT
7761 BROAD NECK ROAD
CHESTERTOWN, MD21620
BROAD NECK Subdivision
Listing courtesy of TTR Sotheby's International Realty
25440 LEARMAN ROAD CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 70
$3,000,000
Single Family ResidenceFor Sale
Active
3
BEDS
4
TOTAL BATHS
3,142
SQFT
25440 LEARMAN ROAD
CHESTERTOWN, MD21620
QUAKER NECK Subdivision
Listing courtesy of TTR Sotheby's International Realty
118 GRANT COURT CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 37
$457,500
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,664
SQFT
118 GRANT COURT
CHESTERTOWN, MD21620
BLAKEFIELD Subdivision
Listing courtesy of RE/MAX Executive
127 WOOD DUCK LANE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 23
$138,000
Manufactured Home
Pending
3
BEDS
2
TOTAL BATHS
1,666
SQFT
127 WOOD DUCK LANE
CHESTERTOWN, MD21620
DUCKS NECK Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
102 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 41
$339,900
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,896
SQFT
102 FLYING CLOUD DRIVE
CHESTERTOWN, MD21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of Long & Foster Real Estate, Inc.
22470 FAIRGALE FARM LANE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 49
$1,450,000
Single Family ResidenceFor Sale
Active
4
BEDS
5
TOTAL BATHS
4,257
SQFT
22470 FAIRGALE FARM LANE
CHESTERTOWN, MD21620
FAIRGALE PROPERTIES Subdivision
Listing courtesy of Gunther-McClary Real Estate
423 CALVERT STREET CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 30
$185,000
TownhouseFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,136
SQFT
423 CALVERT STREET
CHESTERTOWN, MD21620
CALVERT HOMES Subdivision
Listing courtesy of Compass
23683 L ROAD CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 3
$6,000
LandFor Sale
Active
0.69
ACRES
KENT
COUNTY
23683 L ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Alex Cooper Auctioneers, Inc.
21363 LYNN LANE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 28
$205,000
TownhouseFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,314
SQFT
21363 LYNN LANE
CHESTERTOWN, MD21620
TOLCHESTER Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
SANDY BOTTOM ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 6
$79,000
LandFor Sale
Active
1.95
ACRES
KENT
COUNTY
SANDY BOTTOM ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Village Real Estate Company LLC
304 HADAWAY DRIVE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 38
$322,500
Single Family ResidenceFor Sale
Active
4
BEDS
2
TOTAL BATHS
1,325
SQFT
304 HADAWAY DRIVE
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Redfin Corporation
228 MERGANSER DRIVE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 13
$75,000
LandFor Sale
Active
0.51
ACRES
QUEEN ANNES
COUNTY
228 MERGANSER DRIVE
CHESTERTOWN, MD21620
DUCKS NECK Subdivision
Listing courtesy of Benson & Mangold, LLC
100 PROSPECT STREET CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 21
$215,000
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,373
SQFT
100 PROSPECT STREET
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Real Broker, LLC - Chester
202 VALLEY ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 1
$325,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,427
SQFT
202 VALLEY ROAD
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of TTR Sotheby's International Realty
110 S QUEEN STREET CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 29
$525,000
Mixed Use
Pending
778
SQFT
110 S QUEEN STREET
CHESTERTOWN, MD21620
HISTORIC DISTRICT Subdivision
Listing courtesy of Cross Street Realtors LLC
8629 AIRY HILL ROAD CHESTERTOWN MD 21620
1 / 45
$425,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,440
SQFT
8629 AIRY HILL ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Keller Williams Realty
109 2ND STREET CHESTERTOWN MD 21620
Price Change - a week ago
1 / 1
$135,000
LandFor Sale
Active
1.8
ACRES
QUEEN ANNES
COUNTY
109 2ND STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Cross Street Realtors LLC
110 S QUEEN STREET CHESTERTOWN MD 21620
1 / 30
$525,000
Single Family Residence
Pending
3
BEDS
2
TOTAL BATHS
1,785
SQFT
110 S QUEEN STREET
CHESTERTOWN, MD21620
HISTORIC DISTRICT Subdivision
Listing courtesy of Cross Street Realtors LLC
1014 TWIN COURT CHESTERTOWN MD 21620
1 / 29
$499,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,817
SQFT
1014 TWIN COURT
CHESTERTOWN, MD21620
CRESTVIEW Subdivision
Listing courtesy of Cross Street Realtors LLC
107 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
Price Change - 4 hours ago
1 / 51
$385,000
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
2,534
SQFT
107 FLYING CLOUD DRIVE
CHESTERTOWN, MD21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of CENTURY 21 New Millennium
214 SILVER HEEL ROAD CHESTERTOWN MD 21620
Price Change - 4 days ago
1 / 26
$340,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
1,972
SQFT
214 SILVER HEEL ROAD
CHESTERTOWN, MD21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of Cross Street Realtors LLC
407 HIGH STREET CHESTERTOWN MD 21620
Price Change - 6 days ago
1 / 57
$798,000
Single Family ResidenceFor Sale
Active
3
BEDS
5
TOTAL BATHS
3,047
SQFT
407 HIGH STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
144 PROSPECT STREET CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 18
$159,000
Single Family ResidenceFor Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,082
SQFT
144 PROSPECT STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Doug Ashley Realtors, LLC
215 FAIRVIEW DRIVE CHESTERTOWN MD 21620
1 / 57
$425,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
1,784
SQFT
215 FAIRVIEW DRIVE
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Long & Foster Real Estate, Inc.
9816 FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 48
$535,000
Single Family Residence
Pending
3
BEDS
3
TOTAL BATHS
1,624
SQFT
9816 FAIRLEE ROAD
CHESTERTOWN, MD21620
FAIRLEE Subdivision
Listing courtesy of Long & Foster Real Estate, Inc.
23416 CLOQUET ROAD CHESTERTOWN MD 21620
1 / 34
$384,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,512
SQFT
23416 CLOQUET ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
116 CROSS STREET CHESTERTOWN MD 21620
1 / 9
$109,999
LandFor Sale
Active
0.18
ACRES
KENT
COUNTY
116 CROSS STREET
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
24581 WILLOW OAK LANE CHESTERTOWN MD 21620
1 / 29
$229,990
Manufactured HomeFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,352
SQFT
24581 WILLOW OAK LANE
CHESTERTOWN, MD21620
 
Listing courtesy of Doug Ashley Realtors, LLC
103 METCALF RD CHESTERTOWN MD 21620
Open House Wed, Jun 10, 5 PM
1 / 22
$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 - Chester
103 TRAFFORD DRIVE CHESTERTOWN MD 21620
Price Change - yesterday
1 / 65
$399,900
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
1,944
SQFT
103 TRAFFORD DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
104 MAPLE AVENUE CHESTERTOWN MD 21620
1 / 67
$1,469,900
Commercial SaleFor Sale
Active
7,296
SQFT
104 MAPLE AVENUE
CHESTERTOWN, MD21620
 
Listing courtesy of Real Broker, LLC - Annapolis
8706 ELM ROAD CHESTERTOWN MD 21620
1 / 7
$320,000
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,232
SQFT
8706 ELM ROAD
CHESTERTOWN, MD21620
TOLCHESTER ESTATES Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
208 CENTRAL DRIVE CHESTERTOWN MD 21620
1 / 16
$299,000
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,120
SQFT
208 CENTRAL DRIVE
CHESTERTOWN, MD21620
CHESTER HARBOR Subdivision
Listing courtesy of Redfin Corp
240 MERGANSER DRIVE CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 51
$399,000
Single Family ResidenceFor Sale
Active
3
BEDS
2
TOTAL BATHS
1,120
SQFT
240 MERGANSER DRIVE
CHESTERTOWN, MD21620
DUCKS NECK Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
24295 LANGFORD ROAD CHESTERTOWN MD 21620
1 / 73
$445,000
Single Family ResidenceFor Sale
Active
2
BEDS
3
TOTAL BATHS
1,857
SQFT
24295 LANGFORD ROAD
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
21217 TEXAS AVENUE CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 20
$244,500
Single Family ResidenceFor Sale
Active
2
BEDS
1
TOTAL BATH
912
SQFT
21217 TEXAS AVENUE
CHESTERTOWN, MD21620
TOLCHESTER ESTATES Subdivision
Listing courtesy of RE/MAX Leading Edge
226 S WATER STREET CHESTERTOWN MD 21620
1 / 31
$898,000
TownhouseFor Sale
Active
3
BEDS
4
TOTAL BATHS
2,172
SQFT
226 S WATER STREET
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Gunther-McClary Real Estate
327 CANNON STREET CHESTERTOWN MD 21620
1 / 39
$1,300,000
Mixed UseFor Sale
Active
3
TOTAL BATHS
3,740
SQFT
327 CANNON STREET
CHESTERTOWN, MD21620
HISTORIC CHESTERTOWN Subdivision
Listing courtesy of Gunther-McClary Real Estate
103 SUTTON WAY CHESTERTOWN MD 21620
1 / 53
$550,000
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
3,816
SQFT
103 SUTTON WAY
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of TTR Sotheby's International Realty
720 DEEP LANDING ROAD CHESTERTOWN MD 21620
1 / 42
$369,999
Single Family Residence
Pending
3
BEDS
2
TOTAL BATHS
1,271
SQFT
720 DEEP LANDING ROAD
CHESTERTOWN, MD21620
PINE COVE Subdivision
Listing courtesy of Coldwell Banker Waterman Realty
10584 KLAMATH ROAD CHESTERTOWN MD 21620
1 / 20
$319,900
Residential
Pending
3
BEDS
2
TOTAL BATHS
10584 KLAMATH ROAD
CHESTERTOWN, MD21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Real Broker, LLC - Chester
108 PINE STREET CHESTERTOWN MD 21620
1 / 1
$115,000
ResidentialFor Sale
Active
3
BEDS
1
TOTAL BATH
910
SQFT
108 PINE STREET
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Real Broker, LLC - Chester
COGAR ROAD CHESTERTOWN MD 21620
1 / 3
$3,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
COGAR ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
HAACKE DRIVE LOT 3 CHESTERTOWN MD 21620
1 / 4
$225,000
Commercial SaleFor Sale
Active
0.0
SQFT
HAACKE DRIVE LOT 3
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
704 TRUSLOW ROAD CHESTERTOWN MD 21620
1 / 43
$440,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
2,060
SQFT
704 TRUSLOW ROAD
CHESTERTOWN, MD21620
KINGS COURT Subdivision
Listing courtesy of RE/MAX Executive
SCHEELER ROAD LOT 2 CHESTERTOWN MD 21620
1 / 4
$250,000
Commercial SaleFor Sale
Active
0.0
SQFT
SCHEELER ROAD LOT 2
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
SCHEELER ROAD LOT 2 CHESTERTOWN MD 21620
1 / 4
$250,000
LandFor Sale
Active
0.85
ACRES
KENT
COUNTY
SCHEELER ROAD LOT 2
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
HAACKE DRIVE LOT 3 CHESTERTOWN MD 21620
1 / 7
$225,000
LandFor Sale
Active
0.87
ACRES
KENT
COUNTY
HAACKE DRIVE LOT 3
CHESTERTOWN, MD21620
 
Listing courtesy of Select Land & Homes, LLC
139 PROSPECT STREET CHESTERTOWN MD 21620
1 / 28
$225,000
Single Family ResidenceFor Sale
Active
3
BEDS
1
TOTAL BATH
1,200
SQFT
139 PROSPECT STREET
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Redfin Corp
101 COLEMAN DRIVE CHESTERTOWN MD 21620
1 / 56
$524,900
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
2,268
SQFT
101 COLEMAN DRIVE
CHESTERTOWN, MD21620
KINGS COURT Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
TONOPAH ROAD CHESTERTOWN MD 21620
1 / 3
$3,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
TONOPAH ROAD
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of Ashland Auction Group LLC
LENAPAH RD CHESTERTOWN MD 21620
1 / 3
$3,000
LandFor Sale
Active
0.34
ACRES
KENT
COUNTY
LENAPAH RD
CHESTERTOWN, MD21620
 
Listing courtesy of Ashland Auction Group LLC
202 WALDO DRIVE CHESTERTOWN MD 21620
1 / 28
$340,000
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,055
SQFT
202 WALDO DRIVE
CHESTERTOWN, MD21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
0 ROUND TOP ROAD CHESTERTOWN MD 21620
1 / 23
$200,000
LandFor Sale
Active
5.81
ACRES
QUEEN ANNES
COUNTY
0 ROUND TOP ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
109 S COLLEGE AVENUE CHESTERTOWN MD 21620
1 / 24
$419,900
Single Family Residence
Pending
3
BEDS
3
TOTAL BATHS
1,216
SQFT
109 S COLLEGE AVENUE
CHESTERTOWN, MD21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Taylor Properties
106 QUEEN STREET S CHESTERTOWN MD 21620
1 / 92
$865,000
Single Family ResidenceFor Sale
Active
3
BEDS
4
TOTAL BATHS
2,472
SQFT
106 QUEEN STREET S
CHESTERTOWN, MD21620
HISTORIC CHESTERTOWN Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
206 BURCHARD SAWMILL ROAD CHESTERTOWN MD 21620
1 / 2
$29,000
LandFor Sale
Active
1.05
ACRES
QUEEN ANNES
COUNTY
206 BURCHARD SAWMILL ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of XRealty.NET LLC
8276 BROAD NECK ROAD CHESTERTOWN MD 21620
1 / 82
$1,495,000
Single Family ResidenceFor Sale
Active
4
BEDS
4
TOTAL BATHS
3,383
SQFT
8276 BROAD NECK ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
104 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 30
$394,900
Single Family ResidenceFor Sale
Active
5
BEDS
4
TOTAL BATHS
2,535
SQFT
104 FLYING CLOUD DRIVE
CHESTERTOWN, MD21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of Real Broker, LLC - Chester
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
112 ELM STREET CHESTERTOWN MD 21620
1 / 19
$269,900
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,356
SQFT
112 ELM STREET
CHESTERTOWN, MD21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Coldwell Banker Waterman Realty
21324 PERSIMMON DRIVE CHESTERTOWN MD 21620
Real Estate Owned
1 / 17
$124,900
Townhouse
Pending
2
BEDS
1
TOTAL BATH
1,232
SQFT
21324 PERSIMMON DRIVE
CHESTERTOWN, MD21620
 
Listing courtesy of Coldwell Banker Realty - Washington
231 RICHARD DRIVE CHESTERTOWN MD 21620
1 / 51
$1,150,000
Single Family ResidenceFor Sale
Active Under Contract
5
BEDS
3
TOTAL BATHS
2,956
SQFT
231 RICHARD DRIVE
CHESTERTOWN, MD21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of TTR Sotheby's International Realty
117 WATER STREET N 2B CHESTERTOWN MD 21620
1 / 23
$350,000
CondominiumFor Sale
Active
1
BED
1
TOTAL BATH
850
SQFT
117 WATER STREET N 2B
CHESTERTOWN, MD21620
 
Listing courtesy of TTR Sotheby's International Realty
117 WATER STREET N 2A CHESTERTOWN MD 21620
1 / 24
$375,000
CondominiumFor Sale
Active
2
BEDS
1
TOTAL BATH
787
SQFT
117 WATER STREET N 2A
CHESTERTOWN, MD21620
 
Listing courtesy of TTR Sotheby's International Realty
117 WATER STREET N 1B CHESTERTOWN MD 21620
1 / 20
$200,000
CondominiumFor Sale
Active
1
BED
1
TOTAL BATH
700
SQFT
117 WATER STREET N 1B
CHESTERTOWN, MD21620
 
Listing courtesy of TTR Sotheby's International Realty
117 WATER STREET N 1A CHESTERTOWN MD 21620
1 / 46
$685,000
CondominiumFor Sale
Active
3
BEDS
3
TOTAL BATHS
3,000
SQFT
117 WATER STREET N 1A
CHESTERTOWN, MD21620
 
Listing courtesy of TTR Sotheby's International Realty
117 WATER STREET N 1A, 1B, 2A, & 2B CHESTERTOWN MD 21620
1 / 73
$1,600,000
CondominiumFor Sale
Active
7
BEDS
5
TOTAL BATHS
5,400
SQFT
117 WATER STREET N 1A, 1B, 2A, & 2B
CHESTERTOWN, MD21620
 
Listing courtesy of TTR Sotheby's International Realty
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 3
$750,000
LandFor Sale
Active
0.1
ACRES
KENT
COUNTY
201 N LYNCHBURG STREET
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of RE/MAX Associates-Hockessin
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 13
$750,000
Single Family ResidenceFor Sale
Active
2
TOTAL BATHS
2,045
SQFT
201 N LYNCHBURG STREET
CHESTERTOWN, MD21620
CHESTERTOWN Subdivision
Listing courtesy of RE/MAX Associates-Hockessin
204 DOUBLE CREEK ROAD CHESTERTOWN MD 21620
Price Change - 2 weeks ago
1 / 46
$565,000
Single Family ResidenceFor Sale
Active
3
BEDS
3
TOTAL BATHS
2,927
SQFT
204 DOUBLE CREEK ROAD
CHESTERTOWN, MD21620
DOUBLE CREEK WOODS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 13
$750,000
Commercial SaleFor Sale
Active
3,527
SQFT
201 N LYNCHBURG STREET
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Associates-Hockessin
22681 WOOD YARD LANE CHESTERTOWN MD 21620
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
6746 QUAKER ROAD CHESTERTOWN MD 21620
1 / 49
$384,000
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
1 / 50
$384,000
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
24775 LANGFORD ROAD CHESTERTOWN MD 21620
1 / 37
$319,900
Single Family ResidenceFor Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,008
SQFT
24775 LANGFORD ROAD
CHESTERTOWN, MD21620
 
Listing courtesy of RE/MAX Advantage Realty
218 CAMELOT DRIVE CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 45
$499,999
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
110 TRAFFORD DRIVE CHESTERTOWN MD 21620
1 / 22
$450,000
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
311 DEVON DRIVE CHESTERTOWN MD 21620
1 / 41
$499,000
Single Family ResidenceFor Sale
Active
4
BEDS
3
TOTAL BATHS
3,504
SQFT
311 DEVON DRIVE
CHESTERTOWN, MD21620
COVENTRY FARMS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
1 - 100of144 listings (144 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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    ExecuHome Realty Accessibility Statement

    Accessibility Statement

    • execuhome.com
    • June 9, 2026

    Compliance status

    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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    Our website implements the ARIA attributes (Accessible Rich Internet Applications) technique, alongside various different behavioral changes, to ensure blind users visiting with screen-readers are able to read, comprehend, and enjoy the website’s functions. As soon as a user with a screen-reader enters your site, they immediately receive a prompt to enter the Screen-Reader Profile so they can browse and operate your site effectively. Here’s how our website covers some of the most important screen-reader requirements, alongside console screenshots of code examples:
    1. Screen-reader optimization: we run a background process that learns the website’s components from top to bottom, to ensure ongoing compliance even when updating the website. In this process, we provide screen-readers with meaningful data using the ARIA set of attributes. For example, we provide accurate form labels; descriptions for actionable icons (social media icons, search icons, cart icons, etc.); validation guidance for form inputs; element roles such as buttons, menus, modal dialogues (popups), and others. Additionally, the background process scans all of the website’s images and provides an accurate and meaningful image-object-recognition-based description as an ALT (alternate text) tag for images that are not described. It will also extract texts that are embedded within the image, using an OCR (optical character recognition) technology. To turn on screen-reader adjustments at any time, users need only to press the Alt+1 keyboard combination. Screen-reader users also get automatic announcements to turn the Screen-reader mode on as soon as they enter the website.These adjustments are compatible with all popular screen readers, including JAWS and NVDA.
    2. Keyboard navigation optimization: The background process also adjusts the website’s HTML, and adds various behaviors using JavaScript code to make the website operable by the keyboard. This includes the ability to navigate the website using the Tab and Shift+Tab keys, operate dropdowns with the arrow keys, close them with Esc, trigger buttons and links using the Enter key, navigate between radio and checkbox elements using the arrow keys, and fill them in with the Spacebar or Enter key.Additionally, keyboard users will find quick-navigation and content-skip menus, available at any time by clicking Alt+1, or as the first elements of the site while navigating with the keyboard. The background process also handles triggered popups by moving the keyboard focus towards them as soon as they appear, and not allow the focus drift outside of it.Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

    Disability profiles supported in our website

    • Epilepsy Safe Mode: this profile enables people with epilepsy to use the website safely by eliminating the risk of seizures that result from flashing or blinking animations and risky color combinations.
    • Visually Impaired Mode: this mode adjusts the website for the convenience of users with visual impairments such as Degrading Eyesight, Tunnel Vision, Cataract, Glaucoma, and others.
    • Cognitive Disability Mode: this mode provides different assistive options to help users with cognitive impairments such as Dyslexia, Autism, CVA, and others, to focus on the essential elements of the website more easily.
    • ADHD Friendly Mode: this mode helps users with ADHD and Neurodevelopmental disorders to read, browse, and focus on the main website elements more easily while significantly reducing distractions.
    • Blindness Mode: this mode configures the website to be compatible with screen-readers such as JAWS, NVDA, VoiceOver, and TalkBack. A screen-reader is software for blind users that is installed on a computer and smartphone, and websites must be compatible with it.
    • Keyboard Navigation Profile (Motor-Impaired): this profile enables motor-impaired persons to operate the website using the keyboard Tab, Shift+Tab, and the Enter keys. Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

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    6. Cognitive disorders – we utilize a search engine that is linked to Wikipedia and Wiktionary, allowing people with cognitive disorders to decipher meanings of phrases, initials, slang, and others.
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    Browser and assistive technology compatibility

    We aim to support the widest array of browsers and assistive technologies as possible, so our users can choose the best fitting tools for them, with as few limitations as possible. Therefore, we have worked very hard to be able to support all major systems that comprise over 95% of the user market share including Google Chrome, Mozilla Firefox, Apple Safari, Opera and Microsoft Edge, JAWS and NVDA (screen readers), both for Windows and for MAC users.

    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]