222 E Chestnut St
Saint Michaels, MD 21663
3 Beds
2.5 Baths
2,284 sqft
3 Beds
2.5 Baths
2,284 sqft
Local Information
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Description
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.
Home Highlights
Parking
2 Open Spaces
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$825
Listed
87 days ago
Home Details for 222 E Chestnut St
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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 |
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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 |
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Days on Market: 87 |
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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 |
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Price List Price: $1,885,000Price Per Sqft: $825 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: ACTIVE |
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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 |
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Listing Agent Listing ID: MDTA2013140 |
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Building Area Building Area: 2284 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 7292 sqft |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Right To Sell |
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Business Information Ownership: Fee Simple |
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Mls Number: MDTA2013140Municipality: Saint MichaelsWater ViewWater View: WaterAbove Grade Unfinished Area: 2284 |
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Source Internet Entire Listing Display: Y |
Last check for updates: about 14 hours ago
Listing courtesy of Cornelia C Heckenbach, (410) 310-1229
Long & Foster Real Estate, Inc., (410) 745-0283
Source: Bright MLS, MLS#MDTA2013140
Also Listed on Long & Foster Broker Feed, Bright MLS.
Market trends in Saint Michaels
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
8MoM
Price History for 222 E Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 03/19/2026 | $1,885,000 | Listed For Sale | Bright MLS #MDTA2013140 |
| 12/16/2025 | $2,250,000 | ListingRemoved | Bright MLS #MDTA2011446 |
| 08/27/2025 | $2,250,000 | PriceChange | Bright MLS #MDTA2011446 |
| 07/21/2025 | $2,395,000 | Listed For Sale | Bright MLS #MDTA2011446 |
| 05/01/2017 | $1,000,000 | Sold | N/A |
| 04/10/2017 | $1,295,000 | Pending | Agent Provided |
| 03/31/2017 | $1,295,000 | PriceChange | Agent Provided |
| 03/07/2017 | $1,790,000 | PriceChange | Agent Provided |
| 02/20/2017 | $1,295,000 | Listed For Sale | Agent Provided |
| 11/22/2016 | $1,050,000 | ListingRemoved | Agent Provided |
| 09/10/2016 | $1,050,000 | PriceChange | Agent Provided |
| 05/20/2016 | $1,295,000 | Listed For Sale | Agent Provided |
| 11/17/2014 | $1,295,000 | ListingRemoved | Agent Provided |
| 05/22/2014 | $1,295,000 | PriceChange | Agent Provided |
| 04/08/2014 | $3,900 | ListingRemoved | Agent Provided |
| 02/06/2014 | $1,695,000 | Listed For Sale | Agent Provided |
| 10/30/2013 | $3,900 | Listed For Rent | Agent Provided |
| 10/25/2013 | $1,497,000 | ListingRemoved | Agent Provided |
| 04/23/2013 | $1,497,000 | Listed For Sale | Agent Provided |
| 06/22/2012 | $2,175,000 | ListingRemoved | Agent Provided |
| 06/19/2012 | $2,175,000 | Listed For Sale | Agent Provided |
| 09/13/2007 | $1,850,000 | Sold | N/A |
| 10/21/2002 | $1,100,000 | Sold | N/A |
| 10/19/1999 | $665,000 | Sold | N/A |
| 02/28/1996 | $400,000 | Sold | N/A |
| 09/18/1995 | $145,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $1,094,000 |
Home facts updated by county records
Comparable Sales for 222 E Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.13 | Single-Family Home | $1,152,500 | 06/10/26 | 3 | 2.5 | 2,336 | |
0.12 | Single-Family Home | $995,000 | 10/08/25 | 3 | 2.5 | 1,893 | |
0.22 | Single-Family Home | $850,000 | 07/31/25 | 3 | 2.5 | 2,072 | |
0.16 | Single-Family Home | $1,350,000 | 10/27/25 | 3 | 2.5 | 2,320 | |
0.08 | Single-Family Home | $1,175,000 | 11/14/25 | 2 | 1.5 | 1,780 | |
0.17 | Single-Family Home | $926,000 | 01/15/26 | 3 | 2 | 1,740 | |
0.16 | Single-Family Home | $1,225,000 | 06/05/26 | 2 | 2.5 | 2,282 | |
0.28 | Single-Family Home | $662,500 | 07/18/25 | 3 | 2 | 1,824 | |
0.20 | Single-Family Home | $800,000 | 08/15/25 | 4 | 1.5 | 1,596 | |
0.25 | Single-Family Home | $1,000,000 | 02/13/26 | 2 | 2.5 | 1,445 |
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Assigned Schools
These are the assigned schools for 222 E Chestnut St.
- St. Michaels Elementary School
- PK-5
- Public
- 333 Students
5/10GreatSchools RatingParent Rating AverageThis USED to be a good school. I have had 3 children at this school and now they are in private school. We moved here so I could be a stay at home mom. Because of the lack of accountability at this school I had to go back to work to pay for private school. The dream of living in a small town with a small school and being able to get my kids off the bus in the afternoon is gone. Teachers that have had children in this school are sending their own kids to private school. This should tell you enough right there. Also, this school only goes up to 5th grade and the student to teacher ratio is not accurate. They have eliminated teachers/classes so they have larger class sizes.Parent Review8y ago - St. Michaels Middle/High School
- 6-12
- Public
- 443 Students
5/10GreatSchools RatingParent Rating AverageN/ATeacher Review18y ago 
Check out schools near 222 E Chestnut St.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Cornelia C Heckenbach, Long & Foster Real Estate, Inc., (410) 745-0283
Agent Phone: (410) 310-1229
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.
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Copyright 2026 Bright MLS, Inc. Click here for more information
222 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 3 bathroom, 2,284 sqft single-family home built in 1996. This property is currently available for sale and was listed by Bright MLS on Mar 18, 2026. The MLS # for this home is MLS# MDTA2013140.