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106 Chestnut St E, Saint Michaels, MD 21663

Saint Michaels
Local realty services provided by:CENTURY 21 Gold
106 Chestnut St E,Saint Michaels, MD 21663
$1,325,000
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  • 2 Beds
  • 3 Baths
  • 2,282 sq. ft.
  • Single family
  • Active
Listed by: justin ryan pokrywka
Office: taylor properties
MLS#:MDTA2013108
Source:BRIGHTMLS

Price summary

  • Price:$1,325,000
  • Price per sq. ft.:$580.63

About this home

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 appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat,...

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Home facts

  • Year built:1830
  • Listing ID #:MDTA2013108
  • Added:2 day(s) ago
  • Updated:March 14, 2026 at 01:44 PM

Rooms and interior

  • Bedrooms:2
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Rooms Total:2
  • Flooring:Carpet, Hardwood, Luxury Vinyl Plank
  • Dining Description:Dining Room
  • Bedroom Description:Primary Bedroom
  • Living area:2,282 sq. ft.

Heating and cooling

  • Cooling:Geothermal
  • Heating:Central, Electric, Propane - Leased

Structure and exterior

  • Roof:Metal, Shingle
  • Year built:1830
  • Building area:2,282 sq. ft.
  • Lot area:0.22 Acres
  • Lot Features:Landscaping
  • Architectural Style:Victorian
  • Construction Materials:Frame, Wood Siding
  • Exterior Features:Patio(s), Porch(es)
  • Foundation Description:Crawl Space
  • Levels:2 Stories

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$1,325,000
  • Price per sq. ft.:$580.63
  • Tax amount:$7,276 (2026)

Features and amenities

  • Laundry features:Laundry
  • Amenities:Cable TV Available, Multiple Phone Lines, Security System

Parking

  • Parking description:Crushed Stone, Detached Garage, Off Street, On Street
  • Garage:Yes
  • Garage spaces:1

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