$ 865,000
-
$865,000
Price -
3
Bed -
3.5
Bath -
2,472
SqFt
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About the Listing CHEA3 - 3294297
New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots 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.
Listing Highlights
Status
Active
Days on Site
48
Property Type
Residential
MLS ®
MDKE2006152
Year Built
1750
Total Square Footage
2,472
Lot/Acreage
0.14
Interior Details
- Bedrooms: 3
- Bathrooms: 3 Full / 1 Half
- Appliances: Dishwasher, Disposal, Dryer, Instant Hot Water, Range Hood, Refrigerator, Oven/Range - Gas, Stainless Steel Appliances, Washer, Water Heater - Tankless
- Air Cond: Ductless/Mini-Split
- Heating: Baseboard - Hot Water
- Fireplaces: 1, Gas/Propane,1 Fireplace
- Floor: Wood
- Above Ground Sq Ft: 2472
- Below Ground Sq Ft: 0
- Basement:
- Other: Breakfast Area,Built-Ins,Ceiling Fan(s),Crown Moldings,Formal/Separate Dining Room,Kitchen - Island,Wood Floors,Pantry
- Water: Public
Exterior Details
- Lot Description: Front Yard,Landscaping,Rear Yard,SideYard(s),Not New Construction,Horse Property: No,In City Limits
- Garage Capacity: 1 car
- Parking Spaces: 1
- Zoning: RB
- Roof: Shingle
- Others: Excellent
- Sewer: Public Sewer
- Parking Features: Electric Vehicle Charging Station(s),Parking Space Conveys,Garage - Rear Entry,Detached Garage,Off Street,1+ Spaces
Financial Details
- Tax Amount: $11,448
- Taxes w/Assessments: N/A
- Tax/Property ID: N/A
- Tax Year: 2025
Payment Calculator
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Questions About..
106 Queen St S Chestertown, MD 21620
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