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, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.
Sold for $1,225,000
Zillow last checked:
Listing updated:
Bought with:
Tom Crouch, 80097
Benson & Mangold, LLC
Source: Bright MLS,MLS#: MDTA2013108
Price history
| Date | Event | Price |
|---|---|---|
| 6/5/2026 | Sold | $1,225,000-7.5%$537/sqft |
Source:  Bright MLS #MDTA2013108 Report a problem | ||
| 5/1/2026 | Pending sale | $1,325,000$581/sqft |
Source: Bright MLS #MDTA2013108 Report a problem | ||
| 3/13/2026 | Listed for sale | $1,325,000+127.7%$581/sqft |
Source: Bright MLS #MDTA2013108 Report a problem | ||
| 8/14/2019 | Sold | $582,000-3%$255/sqft |
Source: Public Record Report a problem | ||
| 12/31/2018 | Listing removed | $599,900$263/sqft |
Source: Benson & Mangold, LLC #1000251274 Report a problem | ||
| 4/13/2018 | Listed for sale | $599,900-7.6%$263/sqft |
Source: Benson & Mangold, Llc #1000251274 Report a problem | ||
| 12/11/2016 | Listing removed | $649,000$284/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 8/3/2016 | Price change | $649,000-3.9%$284/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 7/1/2016 | Listed for sale | $675,000+266.8%$296/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 6/2/1998 | Sold | $184,000$81/sqft |
Source: Public Record Report a problem | ||
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Estimated market value
$1,220,100
