Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.
Sold for $370,000
$370,000
217 Philosophers Ter, Chestertown, MD 21620
3beds
1,404sqft
Single Family Residence
Built in 1950
10,688 Square Feet Lot
$372,500 Zestimate®
$264/sqft
$2,037 Estimated rent
Home value
$372,500
Estimated sales range
Not available
$2,037/mo
Zestimate® history
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List your homeWhat's special
Wood-burning fireplacePrivate backyardDetached garageHardwood floorsSizable drivewayAmple off-street parkingAbundant natural light
Zillow last checked:
Listing updated:
Listed by:
Courtney Chipouras 410-200-1224,
TTR Sotheby's International Realty
Bought with:
Sarah King, 645887
Cross Street Realtors LLC
Source: Bright MLS,MLS#: MDKE2006332
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 1
Rooms
- Room types: Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Basement, Bedroom 1, Sun/Florida Room, Bathroom 1, Half Bath
Bedroom 1
- Features: Flooring - HardWood
- Level: Main
Bedroom 2
- Features: Flooring - Carpet
- Level: Upper
Bedroom 3
- Features: Flooring - Carpet
- Level: Upper
Bathroom 1
- Features: Bathroom - Tub Shower
- Level: Main
Basement
- Features: Basement - Unfinished
- Level: Lower
Dining room
- Features: Flooring - HardWood
- Level: Main
Half bath
- Level: Upper
Kitchen
- Level: Main
Living room
- Features: Flooring - HardWood, Fireplace - Wood Burning
- Level: Main
Other
- Features: Flooring - Tile/Brick
- Level: Main
Heating
- Heat Pump, Oil
Cooling
- Heat Pump, Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Electric Water Heater
- Laundry: In Basement
Features
- Bathroom - Tub Shower, Ceiling Fan(s), Entry Level Bedroom, Floor Plan - Traditional, Formal/Separate Dining Room
- Flooring: Carpet, Wood
- Basement: Unfinished
- Number of fireplaces: 1
Interior area
- Total structure area: 1,404
- Total interior livable area: 1,404 sqft
- Finished area above ground: 1,404
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Garage Faces Front, Garage Door Opener, Asphalt, Detached, Driveway, On Street
- Garage spaces: 1
- Uncovered spaces: 2
Accessibility
- Accessibility features: Accessible Approach with Ramp
Features
- Levels: Two
- Stories: 2
- Patio & porch: Enclosed
- Exterior features: Flood Lights
- Pool features: None
Lot
- Size: 10,688 Square Feet
- Features: Rear Yard, Backs to Trees
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504016734
- Zoning: R-3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Block
Condition
- New construction: No
- Year built: 1950
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $264/sqft
- Tax assessed value: $214,600
- Annual tax amount: $3,352
- Date on market: 4/1/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/1/2026 | Sold | $370,000+13.8%$264/sqft |
Source:  Bright MLS #MDKE2006332 Report a problem | ||
| 4/18/2026 | Pending sale | $325,000$231/sqft |
Source: Bright MLS #MDKE2006332 Report a problem | ||
| 4/4/2026 | Contingent | $325,000$231/sqft |
Source: Bright MLS #MDKE2006332 Report a problem | ||
| 4/1/2026 | Listed for sale | $325,000+58.5%$231/sqft |
Source: Bright MLS #MDKE2006332 Report a problem | ||
| 11/3/2011 | Sold | $205,000-6.6%$146/sqft |
Source: Public Record Report a problem | ||
| 7/8/2011 | Price change | $219,500-4.4%$156/sqft |
Source: Cross Street Realtors LLC #KE7594438 Report a problem | ||
| 5/7/2011 | Listed for sale | $229,500$163/sqft |
Source: Cross Street Realtors LLC #KE7594438 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,704 +105.4% | $213,900 +2.7% |
| 2024 | $3,263 +2.8% | $208,233 +2.8% |
| 2023 | $3,175 +3.5% | $202,567 +2.9% |
| 2022 | $3,066 -0.5% | $196,900 +0.2% |
| 2021 | $3,081 +0.2% | $196,600 +0.2% |
| 2020 | $3,076 +0.4% | $196,300 +0.2% |
| 2019 | $3,065 +0.6% | $196,000 |
| 2018 | $3,046 +3.3% | $196,000 |
| 2017 | $2,948 +20.8% | $196,000 -0.9% |
| 2016 | $2,440 | $197,800 |
| 2015 | $2,440 | $197,800 |
| 2014 | $2,440 | $197,800 -9.1% |
| 2013 | -- | $217,500 |
| 2012 | -- | $217,500 |
| 2011 | -- | $217,500 -11.8% |
| 2010 | -- | $246,660 +10.1% |
| 2009 | -- | $224,026 +11.2% |
| 2008 | -- | $201,393 +12.7% |
| 2007 | -- | $178,760 +14.8% |
| 2006 | -- | $155,686 +17.4% |
| 2005 | -- | $132,613 +21.1% |
| 2004 | -- | $109,540 +1.2% |
| 2003 | -- | $108,210 +1.2% |
| 2002 | -- | $106,880 +1.3% |
| 2001 | -- | $105,550 |
Find assessor info on the county website
Neighborhood: 21620
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Nearby schools
GreatSchools rating
- 7/10H. H. Garnett Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.2 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5.1 mi
Schools provided by the listing agent
- Elementary: Garnett
- Middle: Kent County
- High: Kent County
- 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.
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Estimated market value
$372,500
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$372,500
- Maryland
- Kent County
- Chestertown
- 21620
- 217 Philosophers Ter
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