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Chestertown, MD, 21620 • 21620 • Kent County
$350/sqft
Down payment assistance available
3Beds
4Baths
2,472Sqft
0.14 acLot
1750Built
Scenic Views
Street · Garden
Colonial,Georgian Style
Built 1750 · 276 years of history
Historic Chestertown
21620
Outdoor Living
Patio · Screened
1 Fireplace
Gas/Propane
Special Features
Above Grade · Below Grade
1-Car Garage
Garage Faces Rear · Electric Vehicle Charging Station(s) · Parking Space Conveys · Detached · Off Street
Premium Finishes
Crown Molding
This home is in high demand
Listed 8 days ago · 626 views · 18 saves · Top 1% likely to sell soon
Demand and pricing signals for this listing
626 views
People checking out this listing
18 saves
Buyers have saved this home
8 days on market
Recently listed
$350/sqft
Price per square foot
This home ranks in the top 1% of listings most likely to go under contract soon, based on market activity and demand signals.
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Single Family · Built 1750 · Historic
*Open House Friday April 3rd 5-7pm and Saturday April 4th 10am-12pm *The Bedingfield Hands House, circa 1750, traces its routes back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large front courtyard, the property features beautifully landscaped gardens and a mature magnolia tree creating a private and welcoming outdoor retreat. Offering approximately 2,472 square feet, the home includes three generously sized bedrooms and three-and-a-half updated bathrooms with elegant details throughout, including crown moulding, original wide-plank hardwood floors, and timeless architectural charm. Major renovations completed in the 1950s —include a kitchen, laundry room, and baths—while preserving the home’s historic integrity. Central heating and air conditioning provide comfortable modern living within this classic setting. The property is also one of the few downtown homes to include a garage. Currently operating as one of the most successful Airbnbs in the area with a strong rental history ($32K in bookings last year!), this property offers the best of both worlds—an ideal vacation home and a turn-key income-producing investment. Furniture is negotiable. Ideally located in the heart of Chestertown’s historic district, the home is just steps from art galleries, gift shops, the local farmers market, and beloved annual events like the Chestertown Tea Party Festival, Downrigging Weekend, and the Dickens of a Christmas. The Chester River located just down the street offers endless opportunities for boating and waterfront recreation, while the town itself maintains a relaxed pace of life where history, culture, and community come together. A rare and remarkable offering, the Bedingfield Hands House now stands ready for its next owner to continue its story—preserving its past, enjoying its present, and carrying its legacy forward for generations to come.
Standout features identified
Our analysis highlights mature magnolia tree, timeless architectural charm, and beautifully landscaped gardens as key attractions of this home.
Based on current rates
Est. 6.10% rate · 30yr fixed · $692,000 loan
Full calculator →Key facts and listing details
18 categories of property features
14 rooms detailed
Bedroom1
UpperBedroom2
UpperBedroom3
UpperBathroom1
MainBathroom2
UpperBathroom3
UpperMarket data and value estimates
3 schools rated nearby
Chestertown, MD, 21620
11 events
25 years of records
Local context around this listing
Chestertown, MD • Kent County
Nearby neighborhoods
Nearby cities
Nearby zip codes
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