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 Shore’s 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 backyard—the 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.
Sold for $1,225,000
$1,225,000
106 E Chestnut St, Saint Michaels, MD 21663
2beds
2,282sqft
Single Family Residence
Built in 1830
9,600 Square Feet Lot
$1,224,700 Zestimate®
$537/sqft
$2,707 Estimated rent
Home value
$1,224,700
$1.11M - $1.35M
$2,707/mo
Zestimate® history
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$2,707/mo
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$7,238/mo
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$7,238/mo
Est. payment
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Zillow last checked:
Listing updated:
Listed by:
Justin Pokrywka 443-924-0601,
Taylor Properties
Bought with:
Tom Crouch, 80097
Benson & Mangold, LLC
Source: Bright MLS,MLS#: MDTA2013108
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Primary bedroom
- Level: Upper
- Dimensions: 18 X 14
Bedroom 2
- Features: Flooring - HardWood
- Level: Upper
- Dimensions: 16 X 14
Den
- Features: Flooring - HardWood
- Level: Main
- Area: 154 Square Feet
- Dimensions: 11 X 14
Dining room
- Features: Flooring - HardWood
- Level: Main
- Area: 216 Square Feet
- Dimensions: 12 X 18
Foyer
- Features: Flooring - HardWood
- Level: Main
Kitchen
- Features: Flooring - Tile/Brick
- Level: Main
- Area: 153 Square Feet
- Dimensions: 9 X 17
Laundry
- Features: Flooring - Tile/Brick
- Level: Main
Laundry
- Level: Upper
Living room
- Features: Flooring - HardWood
- Level: Main
- Area: 224 Square Feet
- Dimensions: 14 X 16
Other
- Level: Main
- Area: 247 Square Feet
- Dimensions: 13 X 19
Other
- Features: Flooring - Tile/Brick
- Level: Main
- Area: 195 Square Feet
- Dimensions: 13 X 15
Heating
- Central, Electric, Propane
Cooling
- Geothermal
Appliances
- Included: Instant Hot Water
- Laundry: Upper Level, Laundry Room
Features
- Dry Wall
- Flooring: Carpet, Hardwood, Luxury Vinyl
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Gas/Propane
Interior area
- Total structure area: 2,282
- Total interior livable area: 2,282 sqft
- Finished area above ground: 2,282
Property
Parking
- Total spaces: 4
- Parking features: Other, Crushed Stone, Off Street, On Street, Detached
- Garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Porch
- Pool features: None
- Fencing: Partial
- Has view: Yes
- View description: Street, Garden
- Waterfront features: River
Lot
- Size: 9,600 sqft
- Features: Landscaped
Details
- Additional structures: Above Grade
- Parcel number: 2102063913
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Frame, Wood Siding
- Foundation: Crawl Space
- Roof: Shingle,Metal
Condition
- Excellent
- New construction: No
- Year built: 1830
- Major remodel year: 2003
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Multiple Phone Lines, Broadband
Community & neighborhood
Security
- Security features: Security System
Location
- Region: Saint Michaels
- Subdivision: Historic District Easton
- Municipality: ST MICHAELS
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 6/5/2026 | Sold | $1,225,000-7.5%$537/sqft |
Source:  Bright MLS #MDTA2013108 Report a problem | ||
| 5/1/2026 | Pending sale | $1,325,000$581/sqft |
Source: Bright MLS #MDTA2013108 Report a problem | ||
| 3/13/2026 | Listed for sale | $1,325,000+127.7%$581/sqft |
Source: Bright MLS #MDTA2013108 Report a problem | ||
| 8/14/2019 | Sold | $582,000-3%$255/sqft |
Source: Public Record Report a problem | ||
| 12/31/2018 | Listing removed | $599,900$263/sqft |
Source: Benson & Mangold, LLC #1000251274 Report a problem | ||
| 4/13/2018 | Listed for sale | $599,900-7.6%$263/sqft |
Source: Benson & Mangold, Llc #1000251274 Report a problem | ||
| 12/11/2016 | Listing removed | $649,000$284/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 8/3/2016 | Price change | $649,000-3.9%$284/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 7/1/2016 | Listed for sale | $675,000+266.8%$296/sqft |
Source: Benson & Mangold LLC #TA9702603 Report a problem | ||
| 6/2/1998 | Sold | $184,000$81/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $677,900 +5.7% |
| 2024 | $7,993 +10.2% | $641,467 +6% |
| 2023 | $7,251 +10.2% | $605,033 +6.4% |
| 2022 | $6,579 +0.9% | $568,600 |
| 2021 | $6,517 -2.3% | $568,600 -2.3% |
| 2020 | $6,673 -8.5% | $582,200 -8.5% |
| 2019 | $7,292 +8.7% | $636,200 +5.8% |
| 2018 | $6,707 +9.6% | $601,500 +6.1% |
| 2017 | $6,120 +19.5% | $566,800 +6.5% |
| 2016 | $5,121 | $532,100 |
| 2015 | $5,121 -23.1% | $532,100 |
| 2014 | $6,659 | $532,100 -19.5% |
| 2013 | -- | $660,600 |
| 2012 | -- | $660,600 |
| 2011 | -- | $660,600 -15.8% |
| 2010 | -- | $784,220 +12.7% |
| 2009 | -- | $695,782 +14.6% |
| 2008 | -- | $607,346 +17% |
| 2007 | -- | $518,910 +14.2% |
| 2006 | -- | $454,276 +16.6% |
| 2005 | -- | $389,643 +19.9% |
| 2004 | -- | $325,010 +13.9% |
| 2003 | -- | $285,380 +16.1% |
| 2002 | -- | $245,750 +19.2% |
| 2001 | -- | $206,120 |
Find assessor info on the county website
Neighborhood: 21663
Nearby schools
GreatSchools rating
- 5/10St. Michaels Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 0.3 mi
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,224,700
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,224,700
- Maryland
- Talbot County
- Saint Michaels
- 21663
- 106 E Chestnut St
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