MLS: #MDKE2005890, Listed By: Michael ONeill, Coldwell Banker Chesapeake Real Estate Company, Source:Bright MLS
105 High Street
CHESTERTOWN, MD 21620
5
Bed
5
Bath
3,243Sqft
0.06Acre(Lot)
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 5Bathroom Information
Total Baths: 5 Full Baths: 4 Half Baths: 1Room Information
Rooms Total: 10 Has Basement: Yes Basement: Interior Entry -
Interior Features
Appliances: Gas Water Heater -
Heating & Cooling
Has Heating: Yes Heating: Electric, Propane, Heat Pump Has Cooling: Yes Cooling: Central Air, Electric
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Building Information
Year Built: 1863 Building Area Total: 4235 Construction Materials: Frame Patio And Porch Features: Porch, Patio Pool Features: None Private Pool: No Water front Features: River Front View: Water, River, Scenic
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Lot Information
Lot Size Acres: 0.06 Lot Size Source: Assessor Lot Size Square Feet: 2688Property Information
Subdivision: CHESTERTOWN HISTORIC DISTRICT Source Property Type: Residential Postal Code Plus 4: 1515 Property SubType: Single Family Residence Levels: Three Or More Property Age: 163
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Listing Price Information
Listing Price: $1295500
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Tax Information
Parcel Number: 1504018273 Tax Year: 2025 Annual Tax: $20218
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Parking Information
Parking Total: 1 Garage, DetachedGarage Information
Has Garage: Yes Garage Space: 1
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Location Information
Direction: From Chestertown's waterfront at the end of High Street, walk past the Customs House (one of the original British Ports of Entry) then it will be the next house on your left. WaterSource: Public
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 1904 Pondtown Road, Chestertown, MD, 21620 | $265,000 | 3 | 1 | 1,967 | 1,967 SqFt |
| 204 Double Creek Road, Chestertown, MD, 21620 | $565,000 | 3 | 3 | 2,927 | 2,927 SqFt |
| 240 Merganser Drive, Chestertown, MD, 21620 | $399,000 | 3 | 2 | 1,120 | 1,120 SqFt |
| 118 Grant Court, Chestertown, MD, 21620 | $457,500 | 3 | 2 | 1,664 | 1,664 SqFt |
| 109 Wilton Road, Chestertown, MD, 21620 | $344,900 | 3 | 2 | 1,392 | 1,392 SqFt |
| 215 Fairview Drive, Chestertown, MD, 21620 | $425,000 | 3 | 3 | 1,784 | 1,784 SqFt |
| 208 Central Drive, Chestertown, MD, 21620 | $299,000 | 3 | 1 | 1,120 | 1,120 SqFt |
| 202 Royston Shores Road, Chestertown, MD, 21620 | $1,200,000 | 4 | 3 | 2,292 | 2,292 SqFt |
| 704 Truslow Road, Chestertown, MD, 21620 | $440,000 | 3 | 3 | 2,060 | 2,060 SqFt |
| 101 Coleman Drive, Chestertown, MD, 21620 | $524,900 | 3 | 3 | 2,268 | 2,268 SqFt |
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Nearby For Sale
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ByOwner last updated this listing 06/15/2026 @ 12:23
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