Change Real Estate Presents:

106 Chestnut Street
Saint Michaels MD 21663

For Sale: $1,325,000.00 Active

List Date: 2026-03-13

Saint Michaels
2 bedrooms
3 bathrooms
2,282 build ft2
9,600 land ft2

About This Property

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.

Listing Agent: Justin Ryan Pokrywka. Taylor Properties 443-924-0601 eshorehomes@gmail.com

Virtual Tours / Videos

https://mls.truplace.com/property/1051/141985/

Property Features

Location Information
County:
Subdivision: HISTORIC DISTRICT EASTON
click to open map in a new window
Interior Features
Appliances:
Interior:
Laundry:
Furnished: None
Flooring: Carpet, Hardwood, Luxury Vinyl Plank
Water: Public
Cooling: Geothermal
Heating: Central
Fireplaces: 1
Windows:
Utilities: Cable TV Available, Multiple Phone Lines
Sewer: Public Sewer
Rooms
Room Type: Primary Bedroom
Dimensions: 18 X 14
Level: Upper 1
Room Type: Bedroom 2
Dimensions: 16 X 14
Features: Flooring - HardWood
Level: Upper 1
Room Type: Laundry
Level: Upper 1
Room Type: Foyer
Features: Flooring - HardWood
Level: Main
Room Type: Kitchen
Dimensions: 17 X 9
Features: Flooring - Tile/Brick
Level: Main
Room Type: Dining Room
Dimensions: 18 X 12
Features: Flooring - HardWood
Level: Main
Room Type: Living Room
Dimensions: 16 X 14
Features: Flooring - HardWood
Level: Main
Room Type: Sun/Florida Room
Dimensions: 15 X 13
Features: Flooring - Tile/Brick
Level: Main
Room Type: Laundry
Features: Flooring - Tile/Brick
Level: Main
Room Type: Den
Dimensions: 14 X 11
Features: Flooring - HardWood
Level: Main
Room Type: Other
Dimensions: 19 X 13
Level: Main
Exterior Features
Year Built: 1830
Subdivision Name: Historic District Easton
Parking: Crushed Stone
Garage Spaces: 1.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Justin Ryan Pokrywka. Taylor Properties 443-924-0601 eshorehomes@gmail.com

Property Photos [Click to enlarge]

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