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107 E Chestnut, Saint Michaels, MD 21663

$1,165,000
  • 107 E Chestnut, Saint Michaels, MD 21663 Main Photo

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BEDS2 BATHS2 full SQUARE FEET2,024 MLS#MDTA2013968
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONST MICHAELS SCHOOLTALBOT COUNTY PUBLIC SCHOOLS

Property 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.

107 E Chestnut | MLS# MDTA2013968

This single family home located at 107 E Chestnut, Saint Michaels, MD 21663 is currently listed for sale with an asking price of $1,165,000. This property was built in 1880 and has 2 bedrooms and 2 full baths with 2024 sq. ft. E Chestnut is located in the ST MICHAELS subdivision within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search ST MICHAELS real estate on alanmoose.homesale.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C
Fireplaces: 1
Fuel Type: Electric
Heating: Heat Pump(s)
Home Style: Victorian
Lot Size: 0.08 Acres
Stories: 2.0
Taxes: $6,685
Year Built: 1880

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Exterior: Aluminum Siding, Wood Siding
Flooring: Hardwood
Interior: Bathroom - Walk-In Shower, Combination Dining/Living, Exposed Beams, Family Room Off Kitchen, Kitchen - Gourmet
Lot Dimensions: 0.08 Acre(S)
Municipality: Saint Michaels
Sewer: Public Sewer
SQFT Above Finished: 2024
SQFT Total Finished: 2024
Structure Type: Detached
Water: Public

Local Schools

School District: TALBOT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 4107452596

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Estimated Payment

$ 3,489.66 per month $2,592.78 Principal & Interest $557.08 Property Tax $339.79 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/12/2026. The listing information on this page last changed on 06/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 06/12/2026 9:48:17 AM EST) or Bright MLS (last updated Fri 06/12/2026 9:29:26 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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