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106 W Chestnut St photo 1
for sale
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$1,325,000

2beds
|
3baths
|
2,282sqft
|
1830built
106 W Chestnut St,St Michaels, MD 21663

Est.$8,712/moCustomize payment

What's special

$581/sqft

Price per square foot

Built in 1830

196 years old

1 parking spaces

Garage

Overview

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore's most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new applianc...

Listed on March 13, 2026 · Source: MLS #MDTA2013108

Property details

Cost estimate

Est. monthly payment

$7,994/mo
Principal & interest
$6,946
Property tax
$606
Home insurance (est.)
$442

Down payment

$265,00020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($265,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Customize scenario

Price history

DateEventPrice
Mar 13, 2026Listed for sale$1,325,000

Location

106 W Chestnut St, St Michaels, MD 21663

Nearby homes

$1,325,000

2 beds · 3 baths · 2,282 sqft