09/17/2026
ACTIVE | Chestertown, MD
Built before America — and sitting right in the heart of Historic Chestertown. 🇺🇸
The Bedingfield Hands House, circa 1750, is one of those homes where the history is part of what makes it so special. With approximately 2,472 square feet, 3 bedrooms and 4 baths, it blends original character with the conveniences you’d still want for everyday living.
Inside, you’ll find original wide-plank hardwood floors, period moldings, built-in cabinetry, multiple fireplaces, 12x12 wavy-glass windows, and so many details that reflect the home’s 18th-century beginnings. The kitchen and baths have been updated, and the home also offers central heat and air.
But the outdoor space may be one of my favorite parts. A private front courtyard surrounded by mature landscaping and seasonal gardens, brick herringbone paths, a screened porch, pergola and brick patio make this feel like your own little retreat — while still being right downtown.
And there are some details you simply don’t find in newer homes. The foundation is said to contain the mast of a ship, and that beautiful red front door carries on an early-American symbol of hospitality. There’s even a garage, which is another hard-to-find feature in Chestertown’s Historic District.
The property has also operated as a successful Airbnb, with approximately $32,000 in bookings last year, giving the next owner another possibility to consider.
If you love historic homes, beautiful gardens and being able to walk out your front door and enjoy downtown Chestertown, this one is absolutely worth seeing.
📍 106 S Queen Street | Chestertown, MD 21620
I’d love to schedule a private tour for you. Reach out anytime! 📲 443-404-4332
🔗 Property Details: https://chesapeakerealestateassociates.com/properties/106-queen-street-s-chestertown-md-us-21620-mdke2006152
🏡 Listed by Maryn LeClair at Chesapeake Real Estate Associates, LLC
Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 ☎️ 443-215-HOME
