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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
Southgate Dr
4
3
2
$368,250
1,795 Sq.Ft.
7/31/2020
Speer Rd
4
N/A
N/A
$739,000
5,652 Sq.Ft.
4/11/2016
Spinnaker Rd
7
2
2
$263,429
1,281 Sq.Ft.
3/1/2023
Spring Ave
10
6
3
$791,000
4,014 Sq.Ft.
5/10/2021
Spring Hill Farm Cir
2
N/A
N/A
N/A
N/A
N/A
Spring Hill Farm Ln
2
N/A
5
N/A
6,189 Sq.Ft.
5/7/2002
Squires Ln
1
N/A
N/A
N/A
N/A
3/17/2023
Star Rd
5
N/A
2
$240,400
1,430 Sq.Ft.
10/11/2012
Step Rd
14
4
2
$308,786
1,525 Sq.Ft.
9/15/2023
Stockton Startt Rd
3
N/A
2
$1,119,667
1,998 Sq.Ft.
2/3/2006
St Paul Rd
1
N/A
N/A
N/A
N/A
4/11/2003
St Pauls Rd
1
N/A
N/A
N/A
N/A
N/A
Stryckning Rd
6
4
2
$364,200
1,722 Sq.Ft.
5/29/2020
Summerfield Ln
1
N/A
4
$1,136,000
4,416 Sq.Ft.
1/29/2003
Summerfiled Ln
1
N/A
N/A
N/A
N/A
N/A
Sunburst Ave
13
3
1
$251,308
1,211 Sq.Ft.
11/6/2024
Sutton Way
7
4
3
$457,857
2,606 Sq.Ft.
5/8/2024
Swan Creek Rd
1
N/A
2
$920,000
2,422 Sq.Ft.
5/24/1995
Talbot Blvd
34
5
N/A
N/A
6,378 Sq.Ft.
9/29/2022
Tamarack Rd
10
3
2
$328,900
1,338 Sq.Ft.
8/14/2024
Tennessee Ave
7
3
2
$238,000
1,278 Sq.Ft.
5/21/2021
Tern Rd
1
N/A
N/A
$247,000
N/A
N/A
Texas Ave
45
3
1
$256,489
1,545 Sq.Ft.
10/20/2023
Third Point Rd
1
N/A
N/A
$431,000
N/A
12/18/2020
Thrift Ln
1
N/A
1
$530,000
1,792 Sq.Ft.
9/23/1997
Tilden Ln
4
4
2
$937,000
3,178 Sq.Ft.
9/24/2024
Tintah Rd
4
3
2
$270,500
1,322 Sq.Ft.
11/21/2024
Tolchester Beach Rd
33
2
1
$284,560
2,048 Sq.Ft.
12/14/2023
Tolchester Rd
14
N/A
2
$407,778
2,124 Sq.Ft.
3/20/2023
Tolchester State Rd
6
1
N/A
$228,000
N/A
8/31/2011
Tolchester St Rd
1
N/A
N/A
$246,000
N/A
N/A
Tonopah Rd
10
4
2
$256,400
3,676 Sq.Ft.
12/20/2024
Tooey Ln
2
N/A
3
$303,500
1,848 Sq.Ft.
N/A
Top Rd
6
N/A
N/A
N/A
N/A
6/11/2019
Top Rd Round
11
N/A
2
$630,000
1,446 Sq.Ft.
8/18/2020
Towhee Rd
12
N/A
N/A
$240,833
N/A
4/30/2022
Trafford Dr
23
4
3
$429,304
2,422 Sq.Ft.
3/5/2025
Truslow Farm Ln
5
4
2
$781,000
2,691 Sq.Ft.
2/6/2025
Truslow Rd
33
3
2
$412,704
2,052 Sq.Ft.
12/20/2024
Truslow Run
2
N/A
5
$774,000
3,510 Sq.Ft.
8/24/1984
Turnberry Ct
1
N/A
4
$848,000
2,645 Sq.Ft.
2/17/2017
Tuxedo Rd
12
3
1
$302,583
1,293 Sq.Ft.
1/26/2023
Twin Ct
14
3
2
$357,786
1,891 Sq.Ft.
12/10/2024
Twin Ct At Northgate Dr
1
N/A
N/A
N/A
N/A
11/27/1995
Twin Oaks Farm Ln
3
N/A
2
$333,000
1,565 Sq.Ft.
N/A
Union Church Rd
16
4
3
$524,533
2,519 Sq.Ft.
3/7/2025
Upper Creek Ln
6
4
3
$618,167
2,861 Sq.Ft.
8/9/2013
Valley Rd
9
3
2
$389,667
2,182 Sq.Ft.
10/29/2020
Van Land Farm Ln
2
N/A
4
$737,000
5,346 Sq.Ft.
12/13/2018
Venaringham Ln
5
5
3
$1,171,000
3,300 Sq.Ft.
5/8/2017
Vermont Ave
4
N/A
2
$1,053,333
1,648 Sq.Ft.
7/14/2023
Vickers Dr
1
N/A
N/A
N/A
20,244 Sq.Ft.
7/14/2023
Vireo Rd
4
3
2
$249,500
1,392 Sq.Ft.
1/22/2025
Virginia Ave
6
N/A
2
$233,000
1,568 Sq.Ft.
3/9/2016
Vogeler Dr
6
2
3
$680,000
2,377 Sq.Ft.
1/26/2024
Waldo Dr
13
3
2
$356,154
1,636 Sq.Ft.
3/3/2021
Wallis Brothers Rd
2
N/A
N/A
N/A
N/A
N/A
Wallis Rd
1
N/A
2
$483,000
2,067 Sq.Ft.
5/5/1994
Walls Ln
1
N/A
2
$488,000
1,792 Sq.Ft.
N/A
Walnut Point Rd
22
4
3
$1,450,833
3,259 Sq.Ft.
2/16/2022
Ward Oaks Ln
5
N/A
4
$616,500
3,004 Sq.Ft.
3/9/2004
Warner Dr
2
N/A
N/A
N/A
59,975 Sq.Ft.
2/19/2019
Warwick Rd
19
3
2
$307,211
1,348 Sq.Ft.
7/5/2023
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
Waterview Ln
23
3
3
$627,696
3,033 Sq.Ft.
12/30/2024
Waterview Rd
1
N/A
N/A
$193,000
N/A
4/29/2002
Watonga Rd
14
3
2
$295,857
1,429 Sq.Ft.
4/1/2025
Westwood Ln
3
3
2
$633,333
2,352 Sq.Ft.
5/22/2024
Whispering Pines Ln
3
N/A
2
$409,500
1,788 Sq.Ft.
11/27/2002
White Swan Ct
7
5
4
$979,667
3,492 Sq.Ft.
4/25/2024
Whitworth Ct
4
3
3
$565,500
2,695 Sq.Ft.
7/22/2020
Wilkens Ln
3
N/A
N/A
N/A
N/A
N/A
Wilkins Ln
24
4
2
$570,611
2,847 Sq.Ft.
3/26/2022
Willow Oak Ln
3
2
2
$235,667
1,156 Sq.Ft.
5/8/2024
Wilton Rd
11
3
2
$326,818
1,414 Sq.Ft.
7/3/2024
Windy Maples Ln
1
N/A
3
$829,000
1,680 Sq.Ft.
N/A
Wood Duck Ln
13
3
2
$233,615
1,243 Sq.Ft.
5/31/2023
Woodsedge Dr
1
N/A
N/A
N/A
2,264 Sq.Ft.
N/A
Woods Rd
14
N/A
N/A
$211,333
1,036 Sq.Ft.
2/13/2025
Woodstock Rd
20
3
1
$306,300
1,292 Sq.Ft.
12/12/2022
Woodsview Ct
4
3
2
$436,250
2,153 Sq.Ft.
7/20/2018
Woodsview Ln
1
4
4
$1,806,000
3,402 Sq.Ft.
12/12/2013
Wood Yard Ln
3
N/A
1
$278,333
843 Sq.Ft.
3/31/2025
Worton Rd
11
4
2
$394,571
5,334 Sq.Ft.
10/5/2023
Wykoff Rd
1
N/A
N/A
$263,000
N/A
2/7/2007
Wyoming Ave
13
4
2
$296,615
1,768 Sq.Ft.
7/30/2024
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Investment Properties in
Chestertown, Maryland
328 Devon Dr
Chestertown, MD 21620
Estimated Value
$452,000
Living Area
2,504 SqFt
Beds
4
Baths
2.5
Year Built
2008
Property Type
Single Family
Ownership Type
Related
APN
04-337506
Neighborhood
Chestertown
School District
Kent County Public Schools
1017 Twin Ct
Chestertown, MD 21620
Estimated Value
$468,000
Living Area
3,176 SqFt
Beds
4
Baths
2.5
Year Built
1991
Property Type
Single Family
Ownership Type
Related
APN
04-023307
Subdivision
Crestview
School District
Kent County Public Schools
207 Longfellow Dr
Chestertown, MD 21620
Estimated Value
$345,000
Living Area
2,024 SqFt
Beds
3
Baths
2
Year Built
1969
Property Type
Single Family
Ownership Type
Individual
APN
02-007681
Neighborhood
Kingstown
School District
Queen Annes County Public Schools
100 Adela Way
Chestertown, MD 21620
Estimated Value
$509,000
Living Area
2,492 SqFt
Beds
4
Baths
3.5
Year Built
2008
Property Type
Single Family
Ownership Type
Related
APN
04-336674
Neighborhood
Chestertown
School District
Kent County Public Schools
26741 Mallard Rd
Chestertown, MD 21620
Estimated Value
$1,037,000
Living Area
1,752 SqFt
Beds
3
Baths
2
Year Built
1970
Property Type
Single Family
Ownership Type
Related
APN
04-003691
Subdivision
Chesmar
School District
Kent County Public Schools
528 Cannon St
Chestertown, MD 21620
Estimated Value
$282,000
Living Area
1,176 SqFt
Beds
3
Baths
1
Year Built
1922
Property Type
Single Family
Ownership Type
Individual
APN
04-015886
Neighborhood
Chestertown
School District
Kent County Public Schools
120 Washington Ave
Chestertown, MD 21620
Estimated Value
$459,000
Living Area
2,579 SqFt
Beds
4
Baths
3
Year Built
1900
Property Type
Single Family
Ownership Type
Related
APN
04-017269
Neighborhood
Chestertown
School District
Kent County Public Schools
254 Round Top Rd
Chestertown, MD 21620
Estimated Value
$376,000
Living Area
1,564 SqFt
Beds
3
Baths
2
Year Built
2000
Property Type
Single Family
Ownership Type
Individual
APN
02-024063
Subdivision
John A Burris Lands
School District
Queen Annes County Public Schools
208 Barroll Dr
Chestertown, MD 21620
Estimated Value
$407,000
Living Area
1,564 SqFt
Beds
3
Baths
3
Year Built
1985
Property Type
Single Family
Ownership Type
Corporate
APN
04-005201
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
104 Riverview Pl
Chestertown, MD 21620
Estimated Value
$814,000
Living Area
2,196 SqFt
Beds
3
Baths
2
Year Built
2015
Property Type
Single Family
Ownership Type
Related
APN
02-004607
Neighborhood
Kingstown
School District
Queen Annes County Public Schools
10617 Worton Rd
Worton, MD 21678
Estimated Value
$281,000
Living Area
2,230 SqFt
Beds
3
Baths
2
Year Built
1966
Property Type
Single Family
Ownership Type
Multiple
APN
03-021637
Neighborhood
N/A
School District
Kent County Public Schools
205 N Lynchburg St
Chestertown, MD 21620
Estimated Value
$157,000
Living Area
945 SqFt
Beds
3
Baths
1
Year Built
1979
Property Type
Single Family
Ownership Type
Individual
APN
04-015789
Neighborhood
Chestertown
School District
Kent County Public Schools
10656 Worton Rd
Worton, MD 21678
Estimated Value
$219,000
Living Area
1,296 SqFt
Beds
2
Baths
1
Year Built
1946
Property Type
Single Family
Ownership Type
Individual
APN
03-004597
Subdivision
Pauline C Stavely Subdivision
School District
Kent County Public Schools
113 Trafford Dr
Chestertown, MD 21620
Estimated Value
$469,000
Living Area
2,490 SqFt
Beds
4
Baths
2.5
Year Built
2010
Property Type
Single Family
Ownership Type
Related
APN
04-336402
Neighborhood
Chestertown
School District
Kent County Public Schools
209 Philosophers Ter
Chestertown, MD 21620
Estimated Value
$355,000
Living Area
1,188 SqFt
Beds
3
Baths
1.5
Year Built
1924
Property Type
Single Family
Ownership Type
Individual
APN
04-007506
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 $139.05.
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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