BEDS2
BATHS2 full 1 partial
SQUARE FEET2,282
MLS#MDTA2013108
STATUSACTIVE
PROPERTY TYPEResidential - Single Family
SUBDIVISIONHISTORIC DISTRICT EASTON
SCHOOLTALBOT COUNTY PUBLIC SCHOOLS
Property Description
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.
Property Features
Property Type: Residential - Single Family
Cooling: Geothermal
Fireplaces: 1
Fuel Type: Central, Electric, Propane - Leased
Garage: 1
Heating: Central
Home Style: Victorian
Lot Size: 0.22 Acres
Roof Type: Shingle, Metal
Stories: 2.0
Taxes: $7,276
Year Built: 1830
Feature Descriptions
Additional Structures: Above Grade
Exterior: Frame, Wood Siding
Fencing: Partially
Fireplace: Gas/Propane
Flooring: Carpet, Hardwood, Luxury Vinyl Plank
Lot: Landscaping
Lot Dimensions: 0.22 Acre(S)
Municipality: ST MICHAELS
Number of Rooms: 2
Parking Features: Crushed Stone
Parking Notes: 4 Total Parking Spaces
Pet Restrictions: Size/Weight Restriction
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Kitchen, Den, Foyer, Sun/Florida Room, Laundry, Other
Sewer: Public Sewer
Special View Info: Street, Garden/Lawn
SQFT Above Finished: 2282
SQFT Total Finished: 2282
Structure Type: Detached
Total Garage/Parking Spaces: 4
Utilities: Cable TV Available, Multiple Phone Lines
Water: Public
Room Sizes
Dining Room: 18 x 12 Level - Main
Living Room: 16 x 14 Level - Main
Other: 19 x 13 Level - Main
Den: 14 x 11 Level - Main
Kitchen: 17 x 9 Level - Main
Sun/Florida Room: 15 x 13 Level - Main
Local Schools
School District: TALBOT COUNTY PUBLIC SCHOOLS
Listed By / Shown By
Listed By
Agency Name: Taylor Properties
Agency Phone: 3019702447
Shown By
Agent Name: Lynsey Bennett
Agent Phone: Cell: (410) 935-2009
Agency Title: Berkshire Hathaway HomeServices Homesale Realty
First AmericanEstimate Your Payment
Estimated Payment
$ 3,941.67 per month $2,948.88 Principal & Interest $606.33 Property Tax $386.46 Homeowner's Insurance
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
106 Chestnut Street E | MLS# MDTA2013108
This single family home located at 106 Chestnut Street E, Saint Michaels, MD 21663 is currently listed for sale with an asking price of $1,325,000. This property was built in 1830 and has 2 bedrooms and 2 full and 1 partial baths with 2282 sq. ft. Chestnut Street E is located in the HISTORIC DISTRICT EASTON subdivision within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search HISTORIC DISTRICT EASTON real estate on www.lynseybennettrealtor.com today.