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$1,165,000
22 Days On Site

107 E CHESTNUT
SAINT MICHAELS, MD21663

For Sale|Single Family Residence|Active
2
Beds
2
Total Baths
2
Full Baths
2,024
SqFt
$576
/SqFt
1880
Built
Subdivision:
ST. MICHAELS
County:
TALBOT
Listing courtesy of TTR Sotheby's International Realty
Call Now: 443.632.3000
Is this the listing for you? We can help make it yours.
443.632.3000
107 E CHESTNUT107 E CHESTNUT107 E CHESTNUT107 E CHESTNUT
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Monthly Payment (Est.)

$5,315
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$1,165,000
Days On Site 
22 Days
Bedrooms 
2
Inside Area (SqFt) 
2,024 sqft
Total Baths 
2
Full Baths 
2
Partial Baths 
N/A
Lot Size 
0.08 Acres
Year Built 
1880
MLS® Number 
MDTA2013968
Status 
Active
Property Tax 
$6,685
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Assessor
Friends & Family
Recent Activity
a week agoStatus changed to Active
a week agoListing updated with changes from the MLS®
3 weeks agoListing first seen on site
General Features
Acres 
0.08
Levels 
Two
Parking 
Driveway
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Special Circumstances 
Standard
SqFt Above 
2024
SqFt Total 
2024
Style 
Victorian
Water Source 
Public
Zoning 
R
Interior Features
Appliances 
Gas Water Heater
Basement 
Crawl Space
Cooling 
Central AirElectric
Fireplace 
Yes
Fireplaces 
1
Flooring 
Hardwood
Heating 
ElectricHeat Pump
Interior 
Beamed Ceilings
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Exterior Features
Construction Details 
Aluminum SidingWood Siding
Pool Features 
None
Community Features
School District 
TALBOT COUNTY PUBLIC SCHOOLS
Schools
School District
TALBOT COUNTY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of TTR Sotheby's International Realty



The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.

Neighborhood & Commute
Source: Walkscore
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