106 E Chestnut St

St. Michaels, MD 21663

$1,325,000
Price
2
Beds
2,282 Sq. Ft.
$581 / Sq. Ft.
2,282
Sq. Ft.
$581
per Sq. Ft.
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Description

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...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.
  1. Listed by Justin Ryan Pokrywka • Taylor Properties
    P: (443)-924-0601 eshorehomes@gmail.com

Property Details for 106 East Chestnut Street

Tax ID Number
2102063913
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Victorian
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 03/27/2026 11:12 AM

Property Details for 106 East Chestnut Street

StatusActive
MLS #MDTA2013108
Days on Market47
Taxes$7,277 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1830
Lot Size0.22 AC / 9,600 SF
CountyTalbot County
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Location

Listing Courtesy of Taylor Properties
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Building Information for 106 East Chestnut Street

Stories2Year Built1830Building Size-Lot Size0.22 AC / 9,600 SF

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$7,278 per month

30 year fixed, 6.46% Interest

Principal and Interest

$6,672

Property Taxes

$606

HOA Dues

$0

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Property Information for 106 East Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: Yes
  • Navigable Water: No
  • Tidal Water: No
  • Water Body Type: River
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2026
  • Tax Assessed Value: $636,200
  • Year Assessed: 2025
  • City Town Tax: $0
  • Clean Green Assessed: No
  • Municipal Trash: Yes
  • Loss Mitigation Fee: No
  • Agricultural Tax Due: No
  • Historic: Yes
  • Zoning: R
  • Tax Page Number: 411
  • Automatically Update Tax Values Y/N: No
Lease Information
Lease Information
  • Pets Allowed: Yes
  • Pet Restrictions: Size/Weight Restriction
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 0
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 2
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 2
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
Rooms
  • Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Kitchen, Den, Foyer, Sun/Florida Room, Laundry, Other
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Dining Room
  • Room Length: 18.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 18 X 12
  • Room Features: Flooring - HardWood
Room 2
  • Room Type: Living Room
  • Room Length: 16.0
  • Room Width: 14.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 16 X 14
  • Room Features: Flooring - HardWood
Room 3
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Tile/Brick
Room 4
  • Room Type: Bedroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Dimensions: 16 X 14
  • Room Features: Flooring - HardWood
Room 5
  • Room Type: Foyer
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 6
  • Room Type: Other
  • Room Length: 19.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 19 X 13
Room 7
  • Room Type: Den
  • Room Length: 14.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 14 X 11
  • Room Features: Flooring - HardWood
Room 8
  • Room Type: Kitchen
  • Room Length: 17.0
  • Room Width: 9.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 17 X 9
  • Room Features: Flooring - Tile/Brick
Room 9
  • Room Type: Sun/Florida Room
  • Room Length: 15.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 15 X 13
  • Room Features: Flooring - Tile/Brick
Room 10
  • Room Type: Primary Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Dimensions: 18 X 14
Room 11
  • Room Type: Laundry
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Year Major Reno Remodel: 2003
  • Building Level Count: 2
  • Total Finished SQFT: 2,282.00
  • Total Finished SQFT Source: Estimated
  • Total SQFT: 2,282.00
  • Total SQFT Source: Estimated
  • Construction Materials: Frame, Wood Siding
  • Roof: Shingle, Metal
  • Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8046/9316/7494/804693167494_512_384_WM_3t5B4FkE5xDViQVP.jpg
  • Wall and Ceiling Types: Dry Wall
  • Flooring Type: Carpet, Hardwood, Luxury Vinyl Plank
  • Foundation Details: Crawl Space
  • Room and Floor: Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2
  • # Bathrooms Full: 2
  • # Bathrooms Half: 1
  • Other Structure: Office/Studio
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Lot Features: Landscaping
  • Road Surface Type: Access - On Grade, Alley, Black Top
  • Road Responsibility: City/County
  • Fencing: Partially
  • Additional Parcels: No
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Off Street, On Street, Detached Garage
  • Num of Detached Garage Spaces: 1
  • Total Garage Spaces: 1
  • Off Street - # of Spaces: 3
  • Parking Features: Crushed Stone
  • Garage Features: Other
Interior Features
Interior Features
  • Fireplace: Yes
  • Fireplaces Count: 1
Exterior Features
Exterior Features
  • Spa: No
  • Outdoor Living Structures: Patio(s), Porch(es)
  • Pool: No Pool
Utilities
Utilities
  • Utilities: Cable TV Available, Multiple Phone Lines
  • Heating: Yes
  • Cooling Type: Geothermal
  • Cooling Fuel: Geothermal
  • Heating Type: Central
  • Heating Fuel: Central, Electric, Propane - Leased
  • Hot Water: Instant Hot Water
  • Water Source: Public
  • Sewer Septic: Public Sewer
  • Internet Services: Broadband
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS

Property History for 106 East Chestnut Street

DateEvent & SourcePriceAppreciation
Mar 13, 2026

Listed (Active)

BRIGHT #MDTA2013108

$1,325,000—
Aug 14, 2019

Closed (Public Record)

Public Record #650810572

$582,000—
Aug 14, 2019

Closed

BRIGHT #MDTA135066

$582,000—
DateEvent & SourcePrice
03/13/2026

Listed (Active)

BRIGHT #MDTA2013108

$1,325,000
08/14/2019

Closed (Public Record)

Public Record #650810572

$582,000
08/14/2019

Closed

BRIGHT #MDTA135066

$582,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 106 East Chestnut Street

Taxable ValueLand$392,400Additions$285,500Total$677,900
Tax Record2023$6,855 ($571 / month)
Home Facts
Beds0Baths2Total Finished SqFt2,135 SqFtAbove Grade Finished SqFt2,135 SqFtStories2Lot Size9,600 SqFtStyleSingle Family ResidenceYear Built1830CountyTALBOTAPN02-063913Fireplace TypeHas Fireplace

Schools near 106 East Chestnut Street

This home is within Talbot County Public Schools.
Rating
School
Type
Grades
Distance
St. Michaels Elementary School
Public - PK to 5
St. Michaels Middle/High School
Public - 6 to 12
Easton High School
Public - 9 to 12
Rating
School
Distance
St. Michaels Elementary School
PublicPK to 5

St. Michaels Middle/High School
Public6 to 12

Easton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 106 East Chestnut Street, St. Michaels, MD 21663

106 East Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on March 13, 2026 by Taylor Properties, it's currently listed at $1,325,000. It has been on the market for a total of 47 days and was last sold on August 14, 2019. This listing's school district is Talbot County Public Schools. Nearby schools include St. Michaels Elementary School, St. Michaels Middle/High School and Easton High School. 106 East Chestnut Street is a 2-bed, 3-bath, 2,282 sqft single family home built in 1830.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Taylor Properties

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 03/27/2026 11:12 AM