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… Read More 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. Read Less
Courtesy of Justin Ryan Pokrywka, Taylor Properties 301-970-2447
Listing Snapshot
Days Online
5
Last Updated
Property Type
Single Family Residential
Beds
2
Full Baths
2
Partial Baths
1
Square Ft.
2,282
Lot Size
0.22 Acres
Year Built
1830
MLS Number
MDTA2013108
Additional Details
Property Access
Road Responsibility: City/County, Road Surface: Access - On Grade, Alley, Black Top
Building
Built in 1830, Built in 2003 (effective), Living area: 2282, 2 stories, Levels: 2, Construction Materials: Frame, Wood Siding
Cooling
Geothermal
Accessibility Features
None
Exterior Features
Patio/Porch Features: Patio(s), Porch(es)
Fence
Partially
Fireplaces
1 fireplace, Gas/Propane
Floors
Carpet, Hardwood, Luxury Vinyl Plank
Foundation
Crawl Space
Garage
1 spaces
Heating
Central
Lot
0.22 acres, Landscaping
Parking
Crushed Stone
Pets Policy
Allowed: Size/Weight Restriction
Property
Excellent, Other structures: Above Grade, Street, Garden/Lawn
Roof
Shingle, Metal
Security Features
Security System
Sewer
Public Sewer
Taxes
Additional parcels description:, Annual Amount: $7,276.54, Year: 2026, Zoning: R
Utilities
Cable TV Available, Multiple Phone Lines, Water Source: Public
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