222 E Chestnut St, Saint Michaels, MD 21663
SOLD
AUG 10, 2026

$1,818,800

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,284 sqft

222 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $10,755/mo*
Refinance Your Home
Currently Off Market - Sold Aug 10, 2026 for $1,825,000 (3% below list price)

Home Value

Trulia Estimate
$1.82M
Since last month
Increased$49K (+2.7%)
Since last year
Decreased$306K (-14.4%)
Since last sale
Decreased$6K (-0.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +93% in the last 10 years
MonthEstimated value
2026
September 2026$1.82M
August 2026$1.82M
July 2026$1.77M
June 2026$1.78M
May 2026$1.79M
April 2026$1.8M
March 2026$1.85M
February 2026$2.1M
January 2026$2.09M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
204 Mulberry St, Saint Michaels, MD
0.16
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
114 E Chew Ave, Saint Michaels, MD
0.13
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
408 Water St, Saint Michaels, MD
0.12
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
205 E Chew Ave, Saint Michaels, MD
0.08
Single-Family Home
$1,175,000
11/14/25
2
1.5
1,780
121 W Chestnut St, St Michaels, MD
0.34
Single-Family Home
$1,395,000
06/22/26
3
2.5
2,540
106 E Chestnut St, Saint Michaels, MD
0.16
Single-Family Home
$1,225,000
06/05/26
2
2.5
2,282
203 Mulberry St, Saint Michaels, MD
0.17
Single-Family Home
$926,000
01/15/26
3
2
1,740
504 Seymour Ave, Saint Michaels, MD
0.31
Single-Family Home
$969,000
09/09/26
3
2.5
2,200
216 E Chew Ave, Saint Michaels, MD
0.05
Single-Family Home
$1,522,000
08/28/26
4
3.5
3,575

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
218 E Chestnut St, Saint Michaels, MD 21663
0.03
$1,925,400
4
4
2,639
Off Market
216 E Chew Ave, Saint Michaels, MD 21663
0.05
$1,522,000
4
3.5
3,575
Recently Sold
103 N Harbor Rd, St Michaels, MD 21663
0.12
$2,216,500
4
4.5
3,732
Off Market
417 Water St, Saint Michaels, MD 21663
0.08
$1,794,600
3
3.5
2,579
Off Market
205 E Chew Ave, Saint Michaels, MD 21663
0.08
$1,133,300
2
1.5
1,780
Off Market
303 Manor St, Saint Michaels, MD 21663
0.10
$1,950,000
3
3
2,622
For Sale
202 E Chestnut St, Saint Michaels, MD 21663
0.09
$1,250,000
3
3
2,052
For Sale
203 E Chew Ave, Saint Michaels, MD 21663
0.09
$2,125,000
5
5.5
4,673
Recently Sold
408 Water St, Saint Michaels, MD 21663
0.12
$956,400
3
2.5
1,893
Off Market
204 E Marengo St, Saint Michaels, MD 21663
0.13
$539,900
2
1
1,200
For Sale
114 E Chew Ave, Saint Michaels, MD 21663
0.13
$1,152,500
3
2.5
2,336
Recently Sold

Local Information

  • Map ViewExplore the area around 222 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
2,284 sqft
$799/sqft
2 Open Spaces

About this House

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.
222 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 3 bathroom, 2,284 sqft single-family home built in 1996. It last sold for $1,825,000 on Aug 10, 2026 (3% below the $1,885,000 asking price). More recently, it was listed as a rental in October 2013 with an asking price of $3,900 per month. That rental listing was removed on April 8, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,818,800, with a rent estimate of $2,940/month.
Last check for updates: about 12 hours ago
Listed by Cornelia C Heckenbach, (410) 310-1229
Long & Foster Real Estate, Inc.
Bought with: Unrepresented, (844) 552-7444, Unrepresented
Source: Bright MLS, MLS#MDTA2013140

Home Details for 222 E Chestnut St

Interior Features

Interior Details
Number of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Family Room, Foyer, Full Bath, Half Bath, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2284 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Oven/Range - Gas, Washer, Electric Water HeaterDishwasherDryerLaundry: Washer/Dryer Hookups Only,Laundry RoomWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Other,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Hardwood, Wood
View
Has a ViewView: Water, Garden

Exterior Features

Exterior Home Features
Roof: Architectural ShingleOther Structures: Above Grade, Below GradeExterior: SidewalksFoundation: Block, Brick/Mortar, Crawl SpaceNo Private Pool
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Driveway
Pool
Pool: None
Frontage
WaterfrontWaterfront: Private Dock Site, River, Boat - Powered, Sail, Canoe/KayakOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: St. Michaels Harbor - Miles River
Farm & Range
Frontage Length: Water Frontage Ft: 180
Finished Area
Finished Area (above surface): 2284 Square Feet

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 2102062836

Price & Status

Price
List Price: $1,885,000Price Per Sqft: $799/sqft
Status Change & Dates
Off Market Date: Mon Aug 10 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: SAINT MICHAELSCommunity: St. Michaels
School Information
Elementary School District: Talbot County Public SchoolsJr High / Middle School District: Talbot County Public SchoolsHigh School District: Talbot County Public Schools

Building

Building Area
Building Area: 2284 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 7292 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDTA2013140Municipality: Saint MichaelsWater ViewWater View: WaterAbove Grade Unfinished Area: 2284

Additional Information

Source Internet Consumer Comment: YSource Internet Automated Valuation Display: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Aug 10, 2026
Source: Bright MLS #MDTA2013140
Sold
$1,825,000
Jul 8, 2026
Source: Bright MLS #MDTA2013140
Pending
$1,885,000
Mar 19, 2026
Source: Bright MLS #MDTA2013140
Listed For Sale
$1,885,000
Dec 16, 2025
Source: Bright MLS #MDTA2011446
ListingRemoved
$2,250,000
Aug 27, 2025
Source: Bright MLS #MDTA2011446
PriceChange
$2,250,000
Price decreased by 6%

Market trends in Saint Michaels

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
6MoM

Around this home

What Locals Say about Saint Michaels

At least 2 Trulia users voted on each feature.

  • 100 % Say yards are well-kept

  • 100 % Say streets are well-lit

  • 92 % Say it's dog friendly

  • 92 % Say it's quiet

  • 90 % Say car is needed

  • 82 % Say parking is easy

  • 79 % Say there's wildlife

  • 75 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 67 % Say people would walk alone at night

  • 64 % Say it's walkable to restaurants

  • 63 % Say there are community events

  • 58 % Say neighbors are friendly

  • 50 % Say it's walkable to grocery stores

  • 45 % Say there are sidewalks

  • 40 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Kgialo
    "There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
    0
    Flag
  • Christopherbthomas24
    "Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
    2
    Flag
  • Kats0791
    "Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
    0
    Flag
  • Janet S.
    "Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
    0
    Flag
  • rctdesign
    "Wonderful town with lots to do and very walkable!"
    0
    Flag

LGBTQ Local Legal Protections

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. Click here for more information

Frequently asked questions about 222 E Chestnut St

  • What is 222 E Chestnut St estimated to be worth?
    Trulia's estimated value for 222 E Chestnut St in Saint Michaels, MD is $1,818,800.
  • What is the price history for 222 E Chestnut St?
    222 E Chestnut St in Saint Michaels, MD last sold for $1,825,000 in August 2026.
  • Is Saint Michaels a buyer's or seller's market?
    Saint Michaels is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 222 E Chestnut St?
    The closest schools to 222 E Chestnut St in Saint Michaels, MD are St. Michaels Elementary School (Pre-K, rated 8/10), St. Michaels Middle/High School (rated 6/10).
  • Does 222 E Chestnut St have air conditioning?
    Yes, 222 E Chestnut St in Saint Michaels, MD has air conditioning.
  • Does 222 E Chestnut St have laundry facilities?
    Yes, 222 E Chestnut St in Saint Michaels, MD has in-unit laundry.

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