107 E Chestnut, Saint Michaels, MD 21663 | For Sale

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For Sale $1,165,000 ($575.59 per Sq Ft)

$1,165,000 ($575.59 per Sq Ft)
  • (0)
  • 2 Bedrooms
  • 2 Bathrooms
  • 2,024 Sq Ft
  • 3,600 Sq Ft

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.

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Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Upcoming Open House

Saturday June 20th, 2026
from 11:00 am - 1:00 pm

View Event

Income

Rental Units


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Expenses

Property Details

List Price $1,165,000
Property Type Single Family Homes
Usable Sqft 2,024
Number of Stories 0 stories
Parking Spots 0 spots
Year Built 1880
Last Sold Unknown
Sold Price Unknown
APN # 2102063735
MLS # MDTA2013968
Property ID 322889889
Lot Sqft 3,600
Zoning R
Days on Market 7
Original List Price Unknown
Date Updated June 17, 2026
Date Created June 10, 2026

Listing Provided By

Monica S Penwell an agent of . Lic #591461


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Data last updated: June 17, 2026.
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