222 E Chestnut St

Off Market

222 E Chestnut St

St. Michaels MD 21663

2284 sq. ft.

7292 sq. ft.

Single-Family

Last sold for $1,825,000

Cornelia C Heckenbach, last sold this property on 10 August 2026 after 384 days on market.

Overview

Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come By Chance’s, design team. Across living spaces, you’ll enjoy quiet refinement of the original 1996 construction as hand-scraped hardwoods, tailored millwork, crisp coastal hues, and light-filled windows frame seasonal harbor moments. Host visiting guests near your wood-burning hearth where built-ins hold favorite reads, collected shells, and travel mementos. Here, both curated and comfortably lived-in personality mirror mornings with coffee and dinner aromas from your breezy kitchen of high-end appliances, stone surfaces, and a central island. While everything from simple breakfasts to generous crab feasts overlook nautical views from your sunlit sitting room, you’re sure to linger long after meals from either of the double balconies. Here, let casual conversation entertain, then settle within either of your three serene bedrooms letting two full and one half baths refresh. Outside, toss yard toys for a four legged friend, cast off kayaks towards quiet coves, or set sail into the open expanse of the Chesapeake Bay. Closer to home, afternoons unfold, just a stroll’s-distance away toward daily discoveries within nearby St. Michaels shops, cafés, museums, and the yacht club.

Features

3 bedrooms

3 bathrooms

2 carspaces

2284 sq. ft. floor area

7292 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in St. Michaels over the last 12 months, the estimated median property value of 222 E Chestnut St is $719.5k.

Median value

$719.5k

Estimated value range

$426k - $2.7m

Median days on market

Estimated value trend

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 222 E Chestnut St

2026

Sold

$1,825,000

10 Aug 2026 by Cornelia C Heckenbach, of Long & Foster Real Estate, Inc.

2017

Sold

$1,000,000

28 Apr 2017 by Kathy Christensen

Happy sellers in St. Michaels

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 3 bedroom single-family properties in St. Michaels

In the last 12 months, 32 three-bedroom single-family properties similar to 222 E Chestnut St, have been sold.

This represents a 3% decrease in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in St. Michaels for a market analysis.

Cornelia C Heckenbach

at Cornelia C Heckenbach - St Michaels Real Estate

(95 reviews)

Get a market analysis

Tiffany Cloud

at Meredith Fine Properties

(4 reviews)

Get a market analysis

Tammy Studebaker

(1 review)

Get a market analysis

Stacie Luhrman

at Benson & Mangold, LLC

(10 reviews)

Get a market analysis

Nearby agents

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

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