


102 Flying Cloud Dr, Chestertown, MD 21620
Long & Foster Real Estate, Inc.






































Est.$2,169/moCustomize payment
Just listed
On the market for 3 days
$249/sqft
Price per square foot
Built in 1960
66 years old
Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private en...
Listed by Dawn W. Kane, Redfin Corporation
843-323-9597 · dawn.kane@redfin.com · Office 484-962-0034
Source: Bright MLS · MLS #MDKE2006482
Listed May 14, 2026
Last updated May 16, 2026
Est. monthly payment
Down payment
Based on 20% down ($65,980), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.
Rates provided by Mable Loans.
| Date | Event | Price |
|---|---|---|
| May 14, 2026 | Listed for sale | $329,900 |
304 Hadaway Dr, Chestertown, MD 21620
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High School
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