106 E Chestnut St Saint Michaels, MD 21663
Estimated payment $7,583/month
Highlights
- Water Oriented
- Garden View
- Sun or Florida Room
- Wood Flooring
- Victorian Architecture
- 3-minute walk to Saint Marys Square
About This Home
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.
Listing Agent
(301) 970-2447 eshorehomes@gmail.com Taylor Properties Brokerage Phone: 3019702447 License #RS-0038270 Listed on: 03/13/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $7,277
Year Built
- Built in 1830 | Remodeled in 2003
Lot Details
- 9,600 Sq Ft Lot
- Partially Fenced Property
- Landscaped
- Historic Home
- Property is in excellent condition
Parking
- 1 Car Detached Garage
- Gravel Driveway
- On-Street Parking
Home Design
- Victorian Architecture
- Frame Construction
- Shingle Roof
- Metal Roof
- Wood Siding
Interior Spaces
- 2,282 Sq Ft Home
- Property has 2 Levels
- Gas Fireplace
- Entrance Foyer
- Living Room
- Dining Room
- Office or Studio
- Sun or Florida Room
- Garden Views
- Crawl Space
- Home Security System
- Instant Hot Water
Flooring
- Wood
- Carpet
- Luxury Vinyl Plank Tile
Bedrooms and Bathrooms
- 2 Bedrooms
Laundry
- Laundry Room
- Laundry on upper level
Outdoor Features
- Water Oriented
- River Nearby
- Patio
- Porch
Utilities
- Central Heating
- Heating System Powered By Leased Propane
- Geothermal Heating and Cooling
- Municipal Trash
- Multiple Phone Lines
- Cable TV Available
Community Details
- No Home Owners Association
- Historic District Easton Subdivision
Listing and Financial Details
- Assessor Parcel Number 2102063913
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $7,211 | $677,900 | $392,400 | $285,500 |
| 2024 | $7,102 | $641,467 | $0 | $0 |
| 2023 | $6,794 | $605,033 | $0 | $0 |
| 2022 | $6,519 | $568,600 | $392,400 | $176,200 |
| 2021 | $12,752 | $568,600 | $392,400 | $176,200 |
| 2020 | $6,613 | $582,200 | $392,400 | $189,800 |
| 2019 | $6,161 | $636,200 | $401,500 | $234,700 |
| 2018 | $5,783 | $601,500 | $0 | $0 |
| 2017 | $5,279 | $566,800 | $0 | $0 |
| 2016 | $5,121 | $532,100 | $0 | $0 |
| 2015 | $6,659 | $532,100 | $0 | $0 |
| 2014 | $6,659 | $532,100 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 03/13/2026 03/13/26 | For Sale | $1,325,000 | +127.7% | $581 / Sq Ft | |
| 08/14/2019 08/14/19 | Sold | $582,000 | -3.0% | $255 / Sq Ft | View Prior Sale |
| 07/11/2019 07/11/19 | Pending | -- | -- | -- | |
| 04/25/2019 04/25/19 | For Sale | $599,900 | -- | $263 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | -- | None Listed On Document | |
| Deed | $582,000 | Eastern Shore Title Company | |
| Deed | $184,000 | -- | |
| Deed | -- | -- | |
| Deed | $108,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $60,000 | No Value Available |
Source: Bright MLS
MLS Number: MDTA2013108
APN: 02-063913
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