106 CHESTNUT ST E Saint Michaels, MD 21663
2 Beds
3 Baths
2,282 SqFt
UPDATED:
Key Details
Property Type Single Family Home
Sub Type Detached
Listing Status Active
Purchase Type For Sale
Square Footage 2,282 sqft
Price per Sqft $580
Subdivision Historic District Easton
MLS Listing ID MDTA2013108
Style Victorian
Bedrooms 2
Full Baths 2
Half Baths 1
HOA Y/N N
Abv Grd Liv Area 2,282
Year Built 1830
Available Date 2026-03-13
Annual Tax Amount $7,276
Tax Year 2026
Lot Size 9,600 Sqft
Acres 0.22
Property Sub-Type Detached
Source BRIGHT
Property Description
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.
Location
State MD
County Talbot
Zoning R
Rooms
Other Rooms Living Room, Dining Room, Primary Bedroom, Bedroom 2, Kitchen, Den, Foyer, Sun/Florida Room, Laundry, Other
Interior
Hot Water Instant Hot Water
Heating Central
Cooling Geothermal
Flooring Carpet, Hardwood, Luxury Vinyl Plank
Fireplaces Number 1
Fireplaces Type Gas/Propane
Fireplace Y
Heat Source Central, Electric, Propane - Leased
Laundry Upper Floor
Exterior
Exterior Feature Patio(s), Porch(es)
Parking Features Other
Garage Spaces 4.0
Fence Partially
Utilities Available Cable TV Available, Multiple Phone Lines
Water Access N
View Street, Garden/Lawn
Roof Type Shingle,Metal
Street Surface Access - On Grade,Alley,Black Top
Accessibility None
Porch Patio(s), Porch(es)
Road Frontage City/County
Total Parking Spaces 4
Garage Y
Building
Lot Description Landscaping
Story 2
Foundation Crawl Space
Above Ground Finished SqFt 2282
Sewer Public Sewer
Water Public
Architectural Style Victorian
Level or Stories 2
Additional Building Above Grade
Structure Type Dry Wall
New Construction N
Schools
School District Talbot County Public Schools
Others
Pets Allowed Y
Senior Community No
Tax ID 2102063913
Ownership Fee Simple
SqFt Source 2282
Security Features Security System
Acceptable Financing Cash, Conventional
Listing Terms Cash, Conventional
Financing Cash,Conventional
Special Listing Condition Standard
Pets Allowed Size/Weight Restriction
Virtual Tour https://mls.truplace.com/property/1051/141985/
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