CHARIS REALTY GROUP

Victorian

106 CHESTNUT STREET E

SAINT MICHAELS , MD 21663

MLS#: MDTA2013108

$1,325,000

Status: Active
Listing number: MDTA2013108
Listing provided by: Taylor Properties
Listing agent phone: None
Last update: an hour ago
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HISTORIC DISTRICT EASTON - Residential

Property

Beds

2

Full Baths

2

1/2 Baths

1

Year Built

1830

Sq.Footage

2,282

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.

Features & Amenities

Interior

  • Total Bedrooms

    2

  • Bathrooms

    2

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    2282.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Geothermal

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central, Electric, Propane

  • Pet friendly

    Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    1

  • Construction Materials

    Frame, Wood Siding

  • Parking

    Off Street, On Street, Gravel, Garage, Other, Detached

  • Patio and Porch Features

    Patio, Porch

  • Pool

    Yes

  • Pool Features

    None

  • Waterfront YN

    NO

  • View

    Street, Garden

Area & Lot

  • Lot Size(acres)

    0.22

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Victorian

Price

  • Sales Price

    $1,325,000

  • Tax Amount

    $7,276.54

  • Sq. Footage

    2, 282

  • Price/SqFt

    $580

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Stories

    2

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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Listing Courtesy of Justin Ryan Pokrywka , Taylor Properties

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Agent Amy Dudrow

AGENT

Amy Dudrow

Call Amy today to schedule a private showing.

(240) 772-7866

amydudrowproperties@gmail.com


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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.

106 CHESTNUT STREET E

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