USAMDSaint MichaelsHistoric District Easton106 E Chestnut St

New

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$1,325,000

For Sale

4 days ago

106 E Chestnut St, Saint Michaels, MD

House

MLS® MDTA2013108

2 Bed

3 Bath

2282 sqft

Key Facts
Description
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 2282 sqft

Garage Yes

Taxes $7,277

Days Active 3

Lot Size 0.22 acres

Approx. Age 1830

Avg. Price Per Sqft $580

MLS® Number MDTA2013108

Property Address: 106 E Chestnut St, Saint Michaels, MD, 21663

Average square foot calculated using Size range provided by listing agent.

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.

MLS® NumberMDTA2013108

Laundry LevelUpper Floor

Central VacNo

FireplaceNo

Acreage0.22

Exterior

GarageYes

Approx. Age1830

Basement

DrivewayCrushed Stone, Off Street, On Street, Detached Garage

Garage Spaces1

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Mar 11, 2026List Date

$1,325,000List Price

Home Appraisal

This property is estimated to sell between: $1,094,000 and $1,441,000.

Similar properties in this area sold on average for: $1,094,600

Expected to sell in 67 days. Similar properties sold in 70 days. This home has been on eXp Realty for 3 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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