106 E Chestnut St Saint Michaels, MD 21663
Estimated payment $7,425/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: 03/11/2026
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
- Coming Soon on 3/13/26
- 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 |
|---|---|---|---|---|---|
| 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
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site.
The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc.
- 114 E Chew Ave
- 107 W Chestnut St
- 101 Mulberry St
- 216 E Chew Ave
- Lot 16A Meadow St
- 111 Gloria Ave
- 205 Cherry St
- 117 Chesapeake Ave
- 938 Marea Terrace
- 408 Spinnaker Ln
- 101 Brooks Ln
- 209 Webb Ln
- 912 Calvert Ave
- 926 Calvert Ave
- 216 Brooks Ln
- 320 Perry Cabin Dr
- 228 Perry Cabin Dr Unit 228 / 226
- 228 Tyler Ave
- 24390 Oakwood Park Rd
- 601 Cove Rd
- 219 E Chew Ave
- 106B Conner St
- 108 Railroad Ave
- 921 C S Talbot St Unit C
- 111 Mitchell St
- 24362 Widgeon Place Unit 2
- 24345 Widgeon Place Unit 29
- 23260 Wells Point Rd
- 10493 Miracle House Cir
- 28480 Pinehurst Cir
- 28525 Augusta Ct
- 28400 Pinehurst Cir
- 406 Bethune Dr
- 47 Clay St Unit 101
- 7410 Tour Dr
- 295 Bay St Unit 6
- 344 Ashby Commons Dr
- 102 Marlboro Ave
- 123 N Washington St Unit 201
- 123 S Washington St Unit 202
Ask me questions while you tour the home.