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Back 106 E Chestnut St
Off Market

106 E Chestnut St

St. Michaels MD 21663

2
3
4
2282 sq. ft.
9600 sq. ft.
Single-Family
Last sold for $1,225,000
Justin PokrywkaJustin Pokrywka, last sold this property on 05 June 2026 after 84 days on market.

Overview

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.

Features

2 bedrooms
3 bathrooms
4 carspaces
1 garage space
2282 sq. ft. floor area
9600 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in St. Michaels over the last 12 months, the estimated median property value of 106 E Chestnut St is $825k.

Median value
$825k
Estimated value range
$155k - $1.23m
Median days on market
50
Estimated value trend
21%
increase over the last 12 months
Average days on market is based on recent, comparable sales in St. Michaels. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 106 E Chestnut St

2026
Sold
$1,225,000
05 Jun 2026 by Justin Pokrywka, of Taylor Properties
2023
Sold
$1,100,000
08 Jun 2023 by C Edwin Mangold, of Benson & Mangold, LLC
2019
Sold
$582,000
14 Aug 2019 by Thomas Crouch, of Benson & Mangold, LLC

Happy sellers in St. Michaels

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We have insufficient information to provide an overview of customer satisfaction for St. Michaels. Viewing the agent profiles, reviews and sales for St. Michaels can provide insights for this location.

Local market activity for 2 bedroom single-family properties in St. Michaels

In the last 12 months, 8 two-bedroom single-family properties similar to 106 E Chestnut St, have been sold.

This represents a 125% decrease in two-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in St. Michaels

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Cornelia C Heckenbach

Sellers who recommend Cornelia C Heckenbach have praised them for being local expert, reliable, responsive, clear communication, supportive, honest, and great negotiation

  •   5   (95 reviews)
  •  7 Reviews in St. Michaels
  •  9 Sales in St. Michaels
View profile
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Tiffany Cloud

Tiffany Cloud is a recommended agent for St. Michaels.  They have 3 local sales and collected 2 local reviews across the last 12 months.

  •   5   (4 reviews)
  •  2 Reviews in St. Michaels
  •  3 Sales in St. Michaels
View profile
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Tammy Studebaker

Tammy Studebaker is a recommended agent for St. Michaels.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (1 review)
  •  1 Review in St. Michaels
  •  1 Sale in St. Michaels
View profile
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Stacie Luhrman

Stacie Luhrman is a recommended agent for St. Michaels.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (10 reviews)
  •  1 Review in St. Michaels
  •  1 Sale in St. Michaels
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