MLS: #MDKE2006614, Listed By: Taylor Leaverton, Benson & Mangold, LLC, Source:Bright MLS
522 High Street
CHESTERTOWN, MD 21620
2
Bed
3
Bath
1,518Sqft
0.08Acre(Lot)
✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project.
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 2Bathroom Information
Total Baths: 3 Full Baths: 3 -
Flooring Information
Wood -
Roofing Information
Shingle -
Interior Features
Roof: Shingle Appliances: Washer, Tankless Water Heater, Dryer -
Heating & Cooling
Has Heating: Yes Heating: Propane, Baseboard Cooling: None
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Building Information
Year Built: 1820 Building Area Total: 1518 Construction Materials: Brick Pool Features: None Private Pool: No
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Lot Information
Lot Size Acres: 0.08 Lot Size Source: Assessor Lot Size Square Feet: 3640Property Information
Subdivision: CHESTERTOWN HISTORIC DISTRICT Source Property Type: Residential Postal Code Plus 4: 1314 Property SubType: Single Family Residence Levels: Two Property Age: 206
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Listing Price Information
Listing Price: $425000
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Tax Information
Parcel Number: 1504009584 Tax Year: 2025 Annual Tax: $4636
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Parking Information
On Street
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Location Information
Direction: West on High St, property will be on the left side, - East on High St, property is on the right side WaterSource: Public
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 1904 Pondtown Road, Chestertown, MD, 21620 | $265,000 | 3 | 1 | 1,967 | 1,967 SqFt |
| 204 Double Creek Road, Chestertown, MD, 21620 | $565,000 | 3 | 3 | 2,927 | 2,927 SqFt |
| 240 Merganser Drive, Chestertown, MD, 21620 | $399,000 | 3 | 2 | 1,120 | 1,120 SqFt |
| 118 Grant Court, Chestertown, MD, 21620 | $457,500 | 3 | 2 | 1,664 | 1,664 SqFt |
| 109 Wilton Road, Chestertown, MD, 21620 | $344,900 | 3 | 2 | 1,392 | 1,392 SqFt |
| 215 Fairview Drive, Chestertown, MD, 21620 | $425,000 | 3 | 3 | 1,784 | 1,784 SqFt |
| 208 Central Drive, Chestertown, MD, 21620 | $299,000 | 3 | 1 | 1,120 | 1,120 SqFt |
| 704 Truslow Road, Chestertown, MD, 21620 | $440,000 | 3 | 3 | 2,060 | 2,060 SqFt |
| 101 Coleman Drive, Chestertown, MD, 21620 | $524,900 | 3 | 3 | 2,268 | 2,268 SqFt |
| 231 Richard Drive, Chestertown, MD, 21620 | $1,150,000 | 5 | 3 | 2,956 | 2,956 SqFt |
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Nearby For Sale
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.
ByOwner last updated this listing 06/16/2026 @ 01:01
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