✨ 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. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨
For sale
Price cut: $25.1K (6/29)
$399,900
522 High St, Chestertown, MD 21620
2beds
1,518sqft
Single Family Residence
Built in 1820
3,640 Square Feet Lot
$393,400 Zestimate®
$263/sqft
$-- HOA
What's special
Private backyard sanctuaryBrick patioPeaceful garden settingOriginal architectural detailsGenerously sized dining room
- 34 days |
- 1,747 |
- 77 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Taylor Leaverton 410-708-5775,
Benson & Mangold, LLC 4108226665
Source: Bright MLS,MLS#: MDKE2006614
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 1
Basement
- Area: 0
Heating
- Baseboard, Propane
Cooling
- None
Appliances
- Included: Tankless Water Heater
- Laundry: Dryer In Unit, Washer In Unit
Features
- Flooring: Wood
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Gas/Propane
Interior area
- Total structure area: 1,518
- Total interior livable area: 1,518 sqft
- Finished area above ground: 1,518
- Finished area below ground: 0
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: Two
- Stories: 2
- Pool features: None
Lot
- Size: 3,640 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504009584
- Zoning: R-5
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Federal
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Brick/Mortar
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1820
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Chestertown Historic District
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $263/sqft
- Tax assessed value: $302,433
- Annual tax amount: $4,636
- Date on market: 5/30/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$393,400
$374,000 - $413,000
$1,653/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/29/2026 | Price change | $399,900-5.9%$263/sqft |
Source:  Bright MLS #MDKE2006614 Report a problem | ||
| 6/13/2026 | Price change | $425,000-5.6%$280/sqft |
Source: Bright MLS #MDKE2006614 Report a problem | ||
| 5/30/2026 | Listed for sale | $450,000+38%$296/sqft |
Source: Bright MLS #MDKE2006614 Report a problem | ||
| 2/14/2006 | Sold | $326,000+214.1%$215/sqft |
Source: Public Record Report a problem | ||
| 9/16/2003 | Sold | $103,800+11%$68/sqft |
Source: Public Record Report a problem | ||
| 8/12/1999 | Sold | $93,500+49.6%$62/sqft |
Source: Public Record Report a problem | ||
| 8/31/1995 | Sold | $62,500$41/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $9,272 +108.9% | $295,800 +4.4% |
| 2024 | $4,439 +4.6% | $283,233 +4.6% |
| 2023 | $4,242 +5.5% | $270,667 +4.9% |
| 2022 | $4,019 +0.1% | $258,100 +0.7% |
| 2021 | $4,017 +0.7% | $256,300 +0.7% |
| 2020 | $3,989 +0.9% | $254,500 +0.7% |
| 2019 | $3,952 +0.6% | $252,700 |
| 2018 | $3,927 +3.3% | $252,700 |
| 2017 | $3,801 +41.7% | $252,700 |
| 2016 | $2,682 | $252,700 |
| 2015 | $2,682 | $252,700 |
| 2014 | $2,682 | $252,700 -7.4% |
| 2013 | -- | $272,800 |
| 2012 | -- | $272,800 |
| 2011 | -- | $272,800 -10.4% |
| 2010 | -- | $304,550 +18.9% |
| 2009 | -- | $256,212 +23.3% |
| 2008 | -- | $207,876 +30.3% |
| 2007 | -- | $159,540 +16.4% |
| 2006 | -- | $137,050 +19.6% |
| 2005 | -- | $114,560 +24.4% |
| 2004 | -- | $92,070 +11.9% |
| 2003 | -- | $82,300 +13.5% |
| 2002 | -- | $72,530 +15.6% |
| 2001 | -- | $62,760 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 7/10H. H. Garnett Elementary SchoolGrades: PK-5Distance: 0.1 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.6 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5.2 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Maryland
- Kent County
- Chestertown
- 21620
- 522 High St
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Chestertown Topics
