High St, Chestertown Property Records
High St, Chestertown property records offer valuable insights into the street’s history, zoning regulations, market trends, and development patterns. These records detail ownership history, tax assessments, property values, and building permits, helping homeowners track changes, buyers evaluate opportunities, and investors assess market potential. Legal professionals rely on them for ownership verification and dispute resolution. Whether restoring a historic home, planning a purchase, or analyzing future developments, property data on High St provides crucial information. Understanding these records ensures informed decisions, helping all stakeholders navigate Chestertown’s dynamic real estate landscape with confidence and strategic foresight.
Properties on High St, Chestertown
This section provides property records for the 60 properties on High St in Chestertown. Each entry lists the street address, city and ZIP code, property type, assessed value and tax, market value, owner occupancy status, year built, living area, bathrooms, lot size, last sale date, building permits, owner records, loans, and listings.
Select an address below to uncover more details about the property
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100 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$632,800
Assessed Tax:
$9,917.26
Market Value:
$942,321
Owner Status:
Not Owner Occupied
Year Built:
1900
Living Area:
1,998 Sq. Ft.
Bathrooms:
3
Area Lot:
50.96 Acres
Last Sale Date:
10/04/2017
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
2
102 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$1,730,700
Assessed Tax:
$27,123.52
Market Value:
$2,624,192
Owner Status:
Not Owner Occupied
Year Built:
1769
Living Area:
5,334 Sq. Ft.
Bathrooms:
4
Area Lot:
389.78 Acres
Building Permits:
0
Owner Records:
1
Listings:
1
105 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$1,290,100
Assessed Tax:
$20,218.44
Market Value:
$973,788
Owner Status:
Not Owner Occupied
Year Built:
1900
Living Area:
3,243 Sq. Ft.
Bathrooms:
3
Area Lot:
61.71 Acres
Last Sale Date:
05/23/2025
Building Permits:
0
Owner Records:
1
Loans:
3
Listings:
3
106 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$557,300
Assessed Tax:
$8,734.02
Market Value:
$836,068
Owner Status:
Owner Occupied
Year Built:
1800
Living Area:
3,060 Sq. Ft.
Bathrooms:
4
Area Lot:
82.64 Acres
Last Sale Date:
05/14/2024
Building Permits:
0
Owner Records:
2
Loans:
0
Listings:
1
108 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$594,300
Assessed Tax:
$9,313.88
Market Value:
$898,710
Owner Status:
Not Owner Occupied
Year Built:
1800
Living Area:
2,367 Sq. Ft.
Bathrooms:
2
Area Lot:
107.85 Acres
Last Sale Date:
11/25/2024
Building Permits:
0
Owner Records:
2
Loans:
1
Listings:
2
109 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$445,300
Assessed Tax:
$6,978.76
Market Value:
$531,249
Owner Status:
Owner Occupied
Year Built:
1753
Living Area:
2,087 Sq. Ft.
Bathrooms:
3
Area Lot:
91.99 Acres
Last Sale Date:
07/09/2021
Building Permits:
0
Owner Records:
3
Loans:
1
Listings:
13
110 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$514,100
Assessed Tax:
$8,056.98
Market Value:
$690,410
Owner Status:
Owner Occupied
Year Built:
1835
Living Area:
2,624 Sq. Ft.
Bathrooms:
3
Area Lot:
130.17 Acres
Last Sale Date:
04/01/2020
Building Permits:
0
Owner Records:
1
Loans:
3
Listings:
5
111 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$352,200
Assessed Tax:
$5,519.67
Market Value:
$525,404
Owner Status:
Not Owner Occupied
Year Built:
1800
Living Area:
2,061 Sq. Ft.
Bathrooms:
2
Area Lot:
39.14 Acres
Building Permits:
0
Owner Records:
1
Listings:
0
112 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$646,800
Assessed Tax:
$10,136.66
Market Value:
$970,338
Owner Status:
Owner Occupied
Year Built:
1870
Living Area:
3,127 Sq. Ft.
Bathrooms:
4
Area Lot:
125 Acres
Last Sale Date:
08/17/2023
Building Permits:
0
Owner Records:
3
Loans:
0
Listings:
1
113 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$326,600
Assessed Tax:
$5,065.78
Market Value:
$487,214
Owner Status:
Owner Occupied
Year Built:
1800
Living Area:
2,070 Sq. Ft.
Bathrooms:
2
Area Lot:
39.14 Acres
Last Sale Date:
06/02/2021
Building Permits:
0
Owner Records:
2
Loans:
3
Listings:
6
114 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$500,733
Assessed Tax:
$7,847.50
Market Value:
$620,953
Owner Status:
Not Owner Occupied
Year Built:
1800
Living Area:
2,530 Sq. Ft.
Bathrooms:
2
Area Lot:
51.24 Acres
Last Sale Date:
08/05/2024
Building Permits:
0
Owner Records:
1
Loans:
2
Listings:
10
115 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$309,700
Assessed Tax:
$4,853.61
Market Value:
$462,003
Owner Status:
Not Owner Occupied
Year Built:
1900
Living Area:
1,284 Sq. Ft.
Bathrooms:
2
Area Lot:
41.78 Acres
Last Sale Date:
06/19/2019
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
9
116 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$537,600
Assessed Tax:
$8,425.28
Market Value:
$752,741
Owner Status:
Owner Occupied
Year Built:
1800
Living Area:
2,496 Sq. Ft.
Bathrooms:
2
Area Lot:
33.56 Acres
Last Sale Date:
02/18/2022
Building Permits:
0
Owner Records:
2
Loans:
1
Listings:
10
117 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$729,100
Assessed Tax:
$11,032.56
Market Value:
$1,087,654
Owner Status:
Owner Occupied
Year Built:
1790
Living Area:
3,226 Sq. Ft.
Bathrooms:
4
Area Lot:
89.99 Acres
Last Sale Date:
07/29/2022
Building Permits:
0
Owner Records:
2
Loans:
2
Listings:
5
119 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$509,100
Assessed Tax:
$7,978.62
Market Value:
$683,695
Owner Status:
Owner Occupied
Year Built:
1900
Living Area:
3,247 Sq. Ft.
Bathrooms:
6
Area Lot:
252 Acres
Last Sale Date:
11/09/2021
Building Permits:
0
Owner Records:
1
Loans:
1
Listings:
0
121 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$410,500
Assessed Tax:
$6,433.38
Market Value:
$658,630
Owner Status:
Owner Occupied
Year Built:
1900
Living Area:
2,312 Sq. Ft.
Bathrooms:
2
Area Lot:
137.74 Acres
Last Sale Date:
02/07/2019
Building Permits:
0
Owner Records:
2
Loans:
0
Listings:
0
123 High St
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$325,000
Assessed Tax:
$5,093.40
Market Value:
$898,043
Owner Status:
Not Owner Occupied
Year Built:
1870
Living Area:
2,908 Sq. Ft.
Bathrooms:
3
Area Lot:
83.77 Acres
Last Sale Date:
08/30/2024
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
5
125 High St # 2 123
Chestertown, MD 21620
Type:
Residential
Assessed Value:
$325,000
Assessed Tax:
$5,093.40
Owner Status:
Not Owner Occupied
Bathrooms:
0
Area Lot:
0 Acres
Last Sale Date:
10/07/2024
Building Permits:
0
Owner Records:
2
Loans:
0
Listings:
0
127 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$383,600
Assessed Tax:
$6,011.80
Market Value:
$619,800
Owner Status:
Owner Occupied
Year Built:
1900
Living Area:
1,643 Sq. Ft.
Bathrooms:
2
Area Lot:
44.47 Acres
Last Sale Date:
03/29/2022
Building Permits:
0
Owner Records:
1
Loans:
2
Listings:
3
200 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$829,900
Assessed Tax:
$8,348.38
Owner Status:
Not Owner Occupied
Year Built:
1900
Living Area:
6,918 Sq. Ft.
Bathrooms:
0
Area Lot:
137.74 Acres
Last Sale Date:
03/07/2022
Building Permits:
0
Owner Records:
1
Loans:
1
Listings:
2
201 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$276,733
Assessed Tax:
$4,336.98
Owner Status:
Not Owner Occupied
Year Built:
1880
Living Area:
4,950 Sq. Ft.
Bathrooms:
0
Area Lot:
97.11 Acres
Last Sale Date:
03/10/2025
Building Permits:
0
Owner Records:
1
Loans:
2
Listings:
1
205 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$191,600
Assessed Tax:
$3,002.78
Owner Status:
Not Owner Occupied
Year Built:
1880
Living Area:
2,864 Sq. Ft.
Bathrooms:
0
Area Lot:
107.58 Acres
Building Permits:
0
Owner Records:
2
Listings:
0
208 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$971,567
Assessed Tax:
$15,226.42
Owner Status:
Owner Occupied
Year Built:
1902
Living Area:
8,190 Sq. Ft.
Bathrooms:
0
Area Lot:
147.98 Acres
Last Sale Date:
05/20/2014
Building Permits:
0
Owner Records:
1
Loans:
1
Listings:
0
210 High St
Chestertown, MD 21620
Type:
Other / Unknown
Assessed Value:
$196,733
Owner Status:
Owner Occupied
Bathrooms:
0
Area Lot:
284 Acres
Building Permits:
0
Owner Records:
1
Listings:
0
210 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$335,733
Owner Status:
Owner Occupied
Year Built:
1932
Living Area:
4,261 Sq. Ft.
Bathrooms:
0
Area Lot:
124.56 Acres
Last Sale Date:
03/27/2025
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
0
211 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$949,400
Assessed Tax:
$14,879.02
Owner Status:
Not Owner Occupied
Year Built:
1849
Living Area:
11,148 Sq. Ft.
Bathrooms:
0
Area Lot:
542.4 Acres
Last Sale Date:
05/01/2017
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
1
215 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$600,267
Assessed Tax:
$6,815.20
Owner Status:
Not Owner Occupied
Year Built:
1880
Living Area:
2,120 Sq. Ft.
Bathrooms:
0
Area Lot:
64.99 Acres
Last Sale Date:
06/07/2017
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
3
217 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$833,267
Assessed Tax:
$13,058.98
Owner Status:
Owner Occupied
Year Built:
1963
Living Area:
8,950 Sq. Ft.
Bathrooms:
0
Area Lot:
337.24 Acres
Last Sale Date:
05/30/2023
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
3
220 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$654,967
Assessed Tax:
$10,264.64
Owner Status:
Owner Occupied
Year Built:
1886
Living Area:
11,548 Sq. Ft.
Bathrooms:
0
Area Lot:
91.14 Acres
Last Sale Date:
06/21/2022
Building Permits:
0
Owner Records:
1
Loans:
0
Listings:
1
227 High St
Chestertown, MD 21620
Type:
Commercial
Assessed Value:
$462,633
Assessed Tax:
$7,250.42
Owner Status:
Owner Occupied
Year Built:
1952
Living Area:
4,824 Sq. Ft.
Bathrooms:
0
Area Lot:
141.99 Acres
Last Sale Date:
01/09/2015
Building Permits:
0
Owner Records:
1
Loans:
1
Listings:
1
Streets Near High St
The three major streets in Chestertown were selected by the number of properties located on each. Property records for these streets may include property values, ownership information, mortgage transactions, tax assessments, and other property details.
| Street Name | # Of Properties | # Of Residents | Avg. Property Value |
|---|---|---|---|
| Montgomery, Chestertown | 18 | 20 | $327,775 |
| Gander, Chestertown | 7 | 12 | $466,752 |
| Creekwood, Chestertown | 2 | 3 | $1,088,688 |