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106 Chestnut Street E Saint Michaels, MD $ 1,325,000
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106 Chestnut Street E
$ 1,325,000
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106 Chestnut Street E

Saint Michaels, MD, 21663
$ 1,325,000
Bedrooms2 Baths2.1 Sq 2,282

Monthly Estimate*

$ 8,158

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Single Family Home for sale in Saint Michaels, MD

for $1,325,000 with 2 bedrooms and 2 full baths, 1 half bath. This 2,282 square foot home was built in 1830 on a lot size of 0.22.

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 Shores 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 backyardthe 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.

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Single Family Active

Price

$ 1,325,000

Bedrooms

2

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 7,276

Style

Victorian

Lot Size

0.22

Year Built

1830

Town/City

Saint Michaels

County/Region

Talbot

MLS | Web ID

MDTA2013108
Features
General
Living Area 2282
Sewer Public Sewer
Heating Central
Cooling Geothermal
Utilities Cable TV Available Multiple Phone Lines
Possession Settlement
Roof Shingle Metal
Zoning R
Garage Spaces 1.00
Patio/Porch Features Patio(s) Porch(es)
Architectural Style Victorian
Security Features Security System
Construction Materials Frame Wood Siding
School District TALBOT COUNTY PUBLIC SCHOOLS
Year Built 1830
View Street Garden/Lawn
Levels 2
Tax Year 2026
Ownership Fee Simple
Cool Fuel Geothermal
Municipality ST MICHAELS
Accessibility None
County TALBOT
New Construction N
Property Type Residential
HOA N
Subdivision Name HISTORIC DISTRICT EASTON
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade
Total Rooms 2
Full Baths 2
Status ACTIVE
Directions GPS
City SAINT MICHAELS
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 9600.00
Tax Annual Amount 7276.54
Home Warranty Y/N N
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 0
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 580.63
Acceptable Financing Cash Conventional
Additional Parcels Y/N N
Historic Y/N Y
Lease Considered Y/N N
Vacation Rental Y/N N
Virtual Tour https://mls.truplace.com/property/1051/141985/
Standard Status Active
Year Built Source Estimated
Association Recreation Fee N
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Interior
Heating Fuel Central Electric Propane - Leased
Flooring Carpet Hardwood Luxury Vinyl Plank
Total Fireplaces 1
Fireplace Features Gas/Propane
Hot Water Instant Hot Water
Total Stories 2
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 2282
Half Baths 1
Central Air Y/N N
Total Bedrooms 2
Room Type Living Room Dining Room Primary Bedroom Bedroom 2 Kitchen Den Foyer Sun/Florida Room Laundry Other
Main Level Bedrooms 0
Laundry Type Upper Floor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 3
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Exterior
Pool No Pool
Fencing Partially
Parking Features Crushed Stone
Lot Features Landscaping
Water Source Public
Garage Features Other
Type of Parking Off Street On Street Detached Garage
Foundation Details Crawl Space
Spa N
Water View Y/N N
Lot Size Acres 0.22
Road Surface Type Access - On Grade Alley Black Top
Water Body Type River
Lot Size Source Estimated
Waterfront Y/N N
Road Responsibility City/County
Navigable Water Y/N N
Water Oriented Y/N Y
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Internal Only
Street Number 1 106
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* Excluded Features
List By
Taylor Properties

Broker

eshorehomes@gmail.com

Email

Affordability Calculator

$8,765
Per Month
93%
7%
0%
Monthly Principal & Interest
$8,158
Monthly Property Taxes
$606
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3533924 Elementary School
3534231 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
3/11/2026$1,325,000 Listed Price

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106 Chestnut Street E, Saint Michaels, MD, 21663 is a Single Family Home for sale at $1,325,000 with 2,282 sqft and a lot size of 0.22. 106 Chestnut Street E has 2 bedrooms, 2.1 baths, and was built in 1830. The property's zip code is 21663 which is in Saint Michaels, MD

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