USAMDSaint MichaelsSt. Michaels107 E Chestnut St

107 E Chestnut St, Saint Michaels, MD

Name: 107 E Chestnut St, For Sale in Saint Michaels - eXp Realty
Brand: TTR Sotheby's International Realty
SKU: MDTA2013968
Price: 1165000 USD

House

For Sale

Listed price in listed location currency (USD).

$1,165,000

220

MLS® MDTA2013968

Key Facts
Description
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 2024 sqft

Garage

Taxes $6,685

Days Active 22

Lot Size 0.08 Acres

Approx. Age 1880

Avg. Price Per Sqft $575

MLS® Number MDTA2013968

Property Address: 107 E Chestnut St, SAINT MICHAELS, MD, 21663

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

Description

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

MLS® NumberMDTA2013968

Laundry Level

Central VacNo

FireplaceNo

Acreage

Exterior

Garage

Approx. Age1880

Basement

DrivewayDriveway

Garage Spaces

HeatHeat Pump(s), Electric

A/CCentral A/C, Electric

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

May 29, 2026List Date

$1,165,000List Price

Home Appraisal

This property is estimated to sell between: $868,000 and $1,314,000.

Similar properties in this area sold on average for: $868,083

Expected to sell in 79 days. Similar properties sold in 101 days. This home has been on eXp Realty for 22 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.

Commute

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Starting Address

Destination Address

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