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Chestertown Maryland Commercial & Residential Property Values
View Property Records by
Street
in Chestertown, Maryland
We found
587
streets in Chestertown, Maryland.
Popular Streets in
Chestertown, Maryland
Street
Properties
Avg. Beds
Avg. Baths
Avg. Property Value
Avg. Property Size
Last Sale Date
Broad Neck Rd
98
3
2
$829,987
2,390 Sq.Ft.
11/1/2024
Cannon St
115
3
2
$381,432
1,920 Sq.Ft.
12/13/2024
Chestertown Rd
79
3
2
$378,585
1,914 Sq.Ft.
12/2/2024
Devon Dr
96
4
3
$460,323
2,638 Sq.Ft.
9/27/2024
High St
181
3
2
$395,779
4,632 Sq.Ft.
5/5/2025
Morgnec Rd
77
3
2
$542,522
8,688 Sq.Ft.
4/8/2025
Quaker Neck Rd
117
4
2
$671,656
2,481 Sq.Ft.
1/10/2025
Queen St
95
3
3
$517,989
2,315 Sq.Ft.
3/26/2025
Washington Ave
114
4
2
$450,377
6,604 Sq.Ft.
3/10/2025
Water St
79
4
3
$755,395
2,715 Sq.Ft.
3/17/2025
All Streets in
Chestertown, Maryland
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All Streets in
Chestertown, Maryland
Street
Properties
Avg. Beds
Avg. Baths
Avg. Property Value
Avg. Property Size
Last Sale Date
Pennsylvania Railroad Rd
1
N/A
N/A
N/A
N/A
N/A
Pentridge Ct
6
5
4
$1,643,000
3,600 Sq.Ft.
9/23/2024
Pentridge Ln
16
4
3
$1,611,000
3,512 Sq.Ft.
6/28/2023
Perkins Hill Rd
21
3
3
$556,857
3,095 Sq.Ft.
9/17/2021
Persimmon Dr
19
2
1
$176,421
1,271 Sq.Ft.
4/11/2025
Philosophers Ter
26
3
2
$392,895
2,811 Sq.Ft.
6/5/2024
Pine Acres Rd
7
3
1
$832,571
1,277 Sq.Ft.
6/15/2007
Pine Ave
1
N/A
1
$239,000
1,040 Sq.Ft.
3/27/2006
Pine Chip Rd
12
3
2
$364,250
1,416 Sq.Ft.
5/31/2024
Pine Cove Ln
22
3
2
$327,000
1,499 Sq.Ft.
4/29/2025
Pine St
28
3
1
$302,536
1,438 Sq.Ft.
6/26/2024
Pine Tree Rd
57
3
2
$301,111
6,984 Sq.Ft.
1/27/2025
Pintail Rd
13
2
1
$271,500
1,130 Sq.Ft.
4/10/2014
Pippin Hill Ln
3
5
3
$801,333
3,299 Sq.Ft.
7/29/2019
Point Ln
10
3
2
$637,500
1,954 Sq.Ft.
1/31/2023
Point Rd
2
N/A
4
N/A
2,688 Sq.Ft.
4/4/2002
Pomona-Ches Rd
1
N/A
N/A
N/A
1,681 Sq.Ft.
1/30/2014
Pomona-Cliff Rd
2
N/A
1
$273,000
1,266 Sq.Ft.
2/3/2022
Pomona-Cliffs Rd
1
N/A
N/A
N/A
N/A
12/21/2010
Pomona-Clif Rd
1
N/A
N/A
N/A
N/A
12/20/2006
Pomona-Langford Rd
1
N/A
N/A
N/A
N/A
N/A
Pomona-Lang Rd
1
N/A
N/A
N/A
N/A
N/A
Pomona Rd
13
4
2
$593,364
3,226 Sq.Ft.
4/15/2022
Pond Ln
1
4
2
$529,000
2,250 Sq.Ft.
N/A
Pondtown Rd
40
3
2
$292,200
1,220 Sq.Ft.
7/5/2023
Pondview Ct
8
4
3
$506,125
2,676 Sq.Ft.
5/31/2024
Poplar Ave
35
3
1
$235,714
1,111 Sq.Ft.
10/31/2024
Poplar St
45
2
1
$229,977
990 Sq.Ft.
12/6/2021
Porter Grove-Melitota Rd
1
N/A
N/A
N/A
N/A
N/A
Preston Ln
8
3
2
$431,875
2,013 Sq.Ft.
9/11/2023
Prestwick Dr
5
3
3
$459,200
2,887 Sq.Ft.
3/10/2022
Primrose Point Farm Ln
4
1
4
$725,000
2,971 Sq.Ft.
11/15/2021
Primrose Rd
11
3
2
$375,727
2,027 Sq.Ft.
2/27/2025
Princess Anne Dr
28
3
2
$397,556
1,831 Sq.Ft.
3/13/2025
Private Ln
1
N/A
1
$844,000
984 Sq.Ft.
9/29/2004
Prospect St
24
3
1
$213,333
1,312 Sq.Ft.
4/17/2025
Providence Plantation Ln
2
6
4
$3,800,500
5,420 Sq.Ft.
1/23/2006
Pyles Dr
6
N/A
N/A
$283,000
N/A
10/28/2015
Quaker Neck Landing Rd
37
3
2
$566,387
1,866 Sq.Ft.
12/2/2024
Quaker Neck Rd
117
4
2
$671,656
2,481 Sq.Ft.
1/10/2025
Queen Anne St
9
3
1
$236,000
1,468 Sq.Ft.
8/22/2023
Queen St
95
3
3
$517,989
2,315 Sq.Ft.
3/26/2025
Radcliffe Dr
22
3
2
$461,800
1,868 Sq.Ft.
8/19/2024
Radcliffe Rd
20
3
2
$561,450
2,602 Sq.Ft.
4/5/2023
Raleigh Ln
1
N/A
N/A
$221,000
N/A
N/A
Raleigh Rd
16
3
1
$268,133
1,165 Sq.Ft.
5/1/2025
Ramsey Ln
1
N/A
2
$358,000
2,412 Sq.Ft.
1/13/2004
Redfield Rd
9
N/A
N/A
$179,222
N/A
11/28/2023
Reed Ct
5
3
2
$477,200
1,939 Sq.Ft.
6/29/2024
Reward Farm Ln
2
N/A
N/A
N/A
N/A
12/2/1999
Rhea Ct
3
3
2
$217,333
1,092 Sq.Ft.
4/20/2016
Ricauds Branch Rd
15
3
2
$450,333
2,083 Sq.Ft.
2/26/2021
Richard Dr
27
3
2
$466,852
2,039 Sq.Ft.
5/23/2024
Richards Rd
7
3
2
$848,000
1,737 Sq.Ft.
10/1/2020
Rileys Mill Rd
7
3
2
$542,167
2,186 Sq.Ft.
11/15/2019
River Rd
59
4
2
$605,179
2,417 Sq.Ft.
12/20/2024
Rivershore Rd
11
3
2
$558,545
1,923 Sq.Ft.
2/16/2018
Riverside Ter
14
2
1
$397,429
1,382 Sq.Ft.
5/2/2024
Riverview Pl
3
3
2
$590,667
1,745 Sq.Ft.
5/27/2021
Riverview Point Ln
2
3
4
$996,000
3,539 Sq.Ft.
8/14/2014
Riverview Rd
13
3
2
$381,000
1,712 Sq.Ft.
3/14/2025
Rock Hall Rd
15
3
2
$440,818
3,005 Sq.Ft.
11/9/2022
Rolla Rd
3
N/A
N/A
$252,000
N/A
12/18/2006
Rolling Rd
31
3
2
$316,034
1,493 Sq.Ft.
11/8/2024
Rolphs Wharf Rd
20
4
2
$573,929
2,995 Sq.Ft.
4/15/2022
Roosevelt Dr
25
3
2
$273,600
1,240 Sq.Ft.
2/29/2024
Rosin Creek Mdws
1
4
3
$1,175,000
3,360 Sq.Ft.
11/21/2018
Rosin Dr
44
3
2
$388,091
1,589 Sq.Ft.
7/30/2024
Round Top Creek Ln
1
N/A
N/A
$831,000
N/A
5/11/2023
Round Top Landing Rd
3
3
4
$3,064,000
3,622 Sq.Ft.
6/11/2019
Round Top Rd
50
3
2
$329,604
1,447 Sq.Ft.
9/23/2024
Round Top Vw
3
N/A
2
$422,333
2,072 Sq.Ft.
1/30/2006
Round Top-Wharf Rd
6
N/A
1
$301,000
979 Sq.Ft.
2/12/2024
Royston Shores Ct
3
N/A
2
$717,333
2,151 Sq.Ft.
4/14/2006
Royston Shores Rd
21
4
2
$696,714
2,275 Sq.Ft.
3/13/2024
Rt 291 Rd
1
N/A
N/A
N/A
N/A
N/A
R W-Bayshore Rd
1
N/A
N/A
$221,000
N/A
N/A
Ryan Ct
4
2
2
$438,500
1,829 Sq.Ft.
4/1/2024
Sandpiper Rd
47
3
2
$241,766
1,377 Sq.Ft.
11/18/2024
Sandy Bottom Rd
29
3
2
$409,476
1,643 Sq.Ft.
2/16/2024
Schauber Rd
3
N/A
N/A
N/A
11,733 Sq.Ft.
9/7/2000
Scheeler Rd
15
N/A
N/A
N/A
42,562 Sq.Ft.
10/20/2023
School Rd
16
3
2
$307,133
1,374 Sq.Ft.
2/27/2024
Schooner Rd
23
3
1
$257,217
1,495 Sq.Ft.
9/23/2022
Schrader Rd
4
4
2
$466,333
2,376 Sq.Ft.
4/5/2016
Secor Rd
3
3
2
$368,667
1,573 Sq.Ft.
4/4/2025
Sheaffer Rd
20
4
2
$460,050
2,093 Sq.Ft.
4/22/2025
Sheldrake Dr
60
3
2
$232,550
1,593 Sq.Ft.
5/28/2021
Shelldrake Dr
1
N/A
N/A
$121,000
N/A
10/6/2005
Sheriff Meredith Rd
3
N/A
2
$434,000
2,260 Sq.Ft.
5/11/2021
Shine Smith Rd
4
N/A
N/A
N/A
N/A
5/31/2022
Shoals Rd
1
N/A
1
$304,000
960 Sq.Ft.
8/8/2008
Shortall St
22
3
2
$256,045
1,211 Sq.Ft.
1/31/2025
Silver Heel Rd
25
4
3
$356,920
2,131 Sq.Ft.
1/10/2025
Skipjack Rd
3
3
2
$254,333
1,329 Sq.Ft.
3/18/2019
Skippers Ct
1
N/A
3
$398,000
2,004 Sq.Ft.
N/A
Skippers Ln
5
3
1
$352,600
1,239 Sq.Ft.
8/4/2021
Smithville Rd
1
N/A
N/A
$268,000
N/A
N/A
Snyder Ln
15
3
2
$229,067
1,325 Sq.Ft.
11/4/2024
Sommers Pl
4
4
3
$488,750
2,766 Sq.Ft.
12/28/2016
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Investment Properties in
Chestertown, Maryland
626 High St
Chestertown, MD 21620
Estimated Value
$317,000
Living Area
1,855 SqFt
Beds
4
Baths
1.5
Year Built
1920
Property Type
Single Family
Ownership Type
Multiple
APN
04-026888
Neighborhood
Chestertown
School District
Kent County Public Schools
105 Holly Ct
Chestertown, MD 21620
Estimated Value
$467,000
Living Area
1,942 SqFt
Beds
3
Baths
2
Year Built
1984
Property Type
Single Family
Ownership Type
Multiple
APN
02-017830
Neighborhood
Kingstown
School District
Queen Annes County Public Schools
201 S Water St
Chestertown, MD 21620
Estimated Value
$903,000
Living Area
2,400 SqFt
Beds
4
Baths
2
Year Built
1860
Property Type
Single Family
Ownership Type
Multiple
APN
04-006011
Neighborhood
Chestertown
School District
Kent County Public Schools
300 N Water St
Chestertown, MD 21620
Estimated Value
$1,161,000
Living Area
4,274 SqFt
Beds
6
Baths
5
Year Built
1910
Property Type
Single Family
Ownership Type
Related
APN
04-008251
Neighborhood
Chestertown
School District
Kent County Public Schools
112 N Water St
Chestertown, MD 21620
Estimated Value
$836,000
Living Area
4,065 SqFt
Beds
5
Baths
3.5
Year Built
1900
Property Type
Single Family
Ownership Type
Related
APN
04-008286
Neighborhood
Chestertown
School District
Kent County Public Schools
201 Rolling Rd
Chestertown, MD 21620
Estimated Value
$381,000
Living Area
2,652 SqFt
Beds
4
Baths
2
Year Built
1975
Property Type
Single Family
Ownership Type
Individual
APN
04-012526
Neighborhood
Chestertown
School District
Kent County Public Schools
610 High St
Chestertown, MD 21620
Estimated Value
$237,000
Living Area
1,536 SqFt
Beds
3
Baths
1
Year Built
1900
Property Type
Single Family
Ownership Type
Individual
APN
04-017382
Neighborhood
Chestertown
School District
Kent County Public Schools
221 Philosophers Ter
Chestertown, MD 21620
Estimated Value
$260,000
Living Area
720 SqFt
Beds
2
Baths
1
Year Built
1939
Property Type
Single Family
Ownership Type
Related
APN
04-010353
Neighborhood
Chestertown
School District
Kent County Public Schools
225 S Water St #6
Chestertown, MD 21620
Estimated Value
$900,000
Living Area
2,800 SqFt
Beds
3
Baths
2.5
Year Built
2006
Property Type
Condominium
Ownership Type
Individual
APN
04-028716
Neighborhood
Chestertown
School District
Kent County Public Schools
120 Garland Ave
Chestertown, MD 21620
Estimated Value
$416,000
Living Area
1,980 SqFt
Beds
3
Baths
2.5
Year Built
2001
Property Type
Single Family
Ownership Type
Related
APN
02-023695
Neighborhood
Kingstown
School District
Queen Annes County Public Schools
8095 Quaker Neck Rd
Chestertown, MD 21620
Estimated Value
$415,000
Living Area
2,164 SqFt
Beds
2
Baths
4
Year Built
2011
Property Type
Condominium
Ownership Type
Corporate
APN
07-003676
Municipality
CHESTERTOWN
School District
Kent County Public Schools
106 Tamarack Rd
Chestertown, MD 21620
Estimated Value
$281,000
Living Area
992 SqFt
Beds
2
Baths
1
Year Built
1995
Property Type
Single Family
Ownership Type
Individual
APN
02-008718
Neighborhood
Kingstown
School District
Queen Annes County Public Schools
106 Manor Ave
Chestertown, MD 21620
Estimated Value
$284,000
Living Area
1,248 SqFt
Beds
3
Baths
2
Year Built
1980
Property Type
Single Family
Ownership Type
Individual
APN
04-002512
Neighborhood
Chestertown
School District
Kent County Public Schools
115 Chester Arms Dr
Chestertown, MD 21620
Estimated Value
$255,000
Living Area
1,140 SqFt
Beds
3
Baths
2
Year Built
2022
Property Type
Townhouse
Ownership Type
Related
APN
04-021371
Neighborhood
Chestertown
School District
Kent County Public Schools
310 Devon Dr
Chestertown, MD 21620
Estimated Value
$468,000
Living Area
2,444 SqFt
Beds
5
Baths
2.5
Year Built
2009
Property Type
Single Family
Ownership Type
Individual
APN
04-337549
Neighborhood
Chestertown
School District
Kent County Public Schools
7 Rolling Rd
Chestertown, MD 21620
Estimated Value
$253,000
Living Area
975 SqFt
Beds
3
Baths
1
Year Built
1961
Property Type
Single Family
Ownership Type
Individual
APN
04-009541
Neighborhood
Chestertown
School District
Kent County Public Schools
Additional Questions?
Looking for off-market properties in Chestertown, Maryland?
Traditional methods include networking with contractors, scouting neighborhoods ("driving for dollars"), or purchasing leads from wholesalers can be tedious. PropertyReach streamlines this process with predictive analytics and neighborhood benchmarks, using Chestertown, Maryland property records and MLS failed listings to refine your search. Effortlessly compare properties, access owner contact details, and secure the best off-market deals at the right price.
What is the median home value in Chestertown, Maryland?
The median home value in Chestertown, Maryland is $367,000, with an average home value of $448,955. The average price per square foot for homes in the area is $138.84.
How Can I Find Pre-foreclosures or Distressed Properties in Chestertown, Maryland?
Foreclosures and distressed properties in Chestertown, Maryland can be found through public records, foreclosure notices, and auction announcements from the county clerk or sheriff’s office. PropertyReach streamlines this by aggregating public and MLS data, making it easier to identify distressed properties and connect with owners directly.
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