Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything. Most homes in this price range make you choose: updated systems or a great location. This one delivers both. Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the Eastern Shore's most walkable town right outside your front door — without the noise or traffic. The home has been completely overhauled from the outside in. New metal roof, gutters, downspouts, vinyl siding, and windows protect your investment from the elements before you ever step inside. Inside, a new HVAC system, updated 200-amp electrical panel, new hot water heater, and fully replaced water main and plumbing mean zero deferred maintenance — just move in and live. Refinished hardwood floors and new vinyl flooring run throughout open, light-filled spaces. The updated bathroom features a new vanity, and the laundry room comes equipped with a brand-new washer and dryer. The kitchen opens directly into the dining area and flows into the family room — a layout that makes everyday living easy and entertaining effortless. Start your mornings on the enclosed porch. Host friends on a generous corner lot with room to breathe. Park conveniently on the private gravel pad with direct kitchen access. This is what move-in ready actually looks like. Schedule your tour today.
Under contract
$215,000
100 Prospect St, Chestertown, MD 21620
3beds
1,373sqft
Single Family Residence
Built in 1953
3,475 Square Feet Lot
$216,700 Zestimate®
$157/sqft
$-- HOA
What's special
Refinished hardwood floorsOpen light-filled spacesNew hot water heaterNew metal roofNew hvac systemEnclosed porchNew vinyl flooring
- 29 days |
- 590 |
- 52 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Mr. David J Moore 410-777-5848,
Real Broker, LLC 8554500442,
Listing Team: David J. Moore & Associates
Source: Bright MLS,MLS#: MDKE2006544
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 1
- Full bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 3
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Heat Pump, Electric
Appliances
- Included: Dryer, Washer, Oven/Range - Electric, Electric Water Heater
- Laundry: Has Laundry
Features
- Attic, Breakfast Area, Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Open Floorplan, Eat-in Kitchen
- Flooring: Hardwood, Laminate, Wood
- Doors: Storm Door(s)
- Windows: Double Pane Windows, Energy Efficient
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,373
- Total interior livable area: 1,373 sqft
- Finished area above ground: 1,373
- Finished area below ground: 0
Property
Parking
- Parking features: Crushed Stone, Driveway, Off Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: One
- Stories: 1
- Exterior features: Play Area, Sidewalks
- Pool features: None
- Has view: Yes
- View description: Street, Trees/Woods
- Waterfront features: Bay
- Body of water: Chester River
Lot
- Size: 3,475 Square Feet
- Features: Level, Corner Lot, Corner Lot/Unit
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504017234
- Zoning: R-5
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Vinyl Siding, Frame
- Foundation: Crawl Space
- Roof: Metal
Condition
- New construction: No
- Year built: 1953
- Major remodel year: 2021
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Available
Community & HOA
Community
- Security: Carbon Monoxide Detector(s), Smoke Detector(s)
- Subdivision: Chestertown
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $157/sqft
- Tax assessed value: $177,567
- Annual tax amount: $2,744
- Date on market: 6/4/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,FHA,Rural Development,USDA Loan,VA Loan
- Ownership: Fee Simple
- Road surface type: Black Top
Estimated market value
$216,700
$206,000 - $228,000
$1,620/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/9/2026 | Contingent | $215,000$157/sqft |
Source:  Bright MLS #MDKE2006544 Report a problem | ||
| 6/4/2026 | Listed for sale | $215,000+17.9%$157/sqft |
Source: Bright MLS #MDKE2006544 Report a problem | ||
| 9/30/2021 | Sold | $182,400+305.3%$133/sqft |
Source: Bright MLS #MDKE2000284 Report a problem | ||
| 4/2/2021 | Sold | $45,000$33/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,488 +135.6% | $175,100 +17.8% |
| 2024 | $2,330 +21.6% | $148,667 +21.6% |
| 2023 | $1,916 +28.4% | $122,233 +27.6% |
| 2022 | $1,492 -0.4% | $95,800 +0.2% |
| 2021 | $1,498 +0.2% | $95,567 +0.2% |
| 2020 | $1,494 +0.5% | $95,333 +0.2% |
| 2019 | $1,487 +0.6% | $95,100 |
| 2018 | $1,478 +3.3% | $95,100 |
| 2017 | $1,430 | $95,100 -1.2% |
| 2016 | -- | $96,300 |
| 2015 | -- | $96,300 |
| 2014 | -- | $96,300 -0.7% |
| 2013 | -- | $97,000 +0% |
| 2012 | -- | $96,973 +0% |
| 2011 | -- | $96,947 +0% |
| 2010 | -- | $96,920 +11.5% |
| 2009 | -- | $86,942 +13% |
| 2008 | -- | $76,966 +14.9% |
| 2007 | -- | $66,990 +12.8% |
| 2006 | -- | $59,386 +14.7% |
| 2005 | -- | $51,783 +17.2% |
| 2004 | -- | $44,180 +12.1% |
| 2003 | -- | $39,420 +13.7% |
| 2002 | -- | $34,660 +15.9% |
| 2001 | -- | $29,900 |
Find assessor info on the county website
Monthly payment
Est. payment$--/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.
See how much you could borrow to make a competitive offer.
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: 0.5 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5 mi
Schools provided by the listing agent
- 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.
A local agent can set up tours, give advice and negotiate with sellers.
- Maryland
- Kent County
- Chestertown
- 21620
- 100 Prospect St
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Chestertown Topics
