Are yards well-kept in Saint Michaels, MD?

As of early 2026, 100% of users say yards are well-kept

Are the streets well-lit in Saint Michaels, MD?

As of early 2026, 100% of users say streets are well-lit

Is Saint Michaels, MD dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is Saint Michaels, MD quiet?

As of early 2026, 92% of users say it's quiet

Is a car needed in Saint Michaels, MD?

As of early 2026, 90% of users say car is needed

Is parking easy in Saint Michaels, MD?

As of early 2026, 82% of users say parking is easy

Is there wildlife in Saint Michaels, MD?

As of early 2026, 79% of users say there's wildlife

Does Saint Michaels, MD show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Do kids play outside in Saint Michaels, MD?

As of early 2026, 73% of users say kids play outside

Would people walk alone at night in Saint Michaels, MD?

As of early 2026, 67% of users say people would walk alone at night

Is Saint Michaels, MD walkable to restaurants?

As of early 2026, 64% of users say it's walkable to restaurants

Are there community events in Saint Michaels, MD?

As of early 2026, 63% of users say there are community events

Are neighbors friendly in Saint Michaels, MD?

As of early 2026, 58% of users say neighbors are friendly

Is Saint Michaels, MD walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Does Saint Michaels, MD have sidewalks?

As of early 2026, 45% of users say there are sidewalks

Do residents of Saint Michaels, MD plan to stay at least 5 years?

As of early 2026, 40% of users say they plan to stay for at least 5 years

FOR SALE

3D VIEW

222 E Chestnut St
Saint Michaels, MD 21663

3 Beds
2.5 Baths
2,284 sqft

$1,885,000

Est. Mortgage $10,466/mo*

Get Pre-Qualified

$1,885,000

Est. Mortgage $10,466/mo*

Get Pre-Qualified

3 Beds

2.5 Baths

2,284 sqft

Local Information

-- mins to

Commute Destination

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

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

Days on Market
Days on Market: 87

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: $825
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

Media
See Virtual Tour

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

Agent Information
Listing Agent Listing ID: MDTA2013140

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 Entire Listing Display: Y

Last check for updates: about 15 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

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
Price Change $145,000 (-6%)
07/21/2025	$2,395,000	Listed For Sale	Bright MLS #MDTA2011446

05/01/2017	$1,000,000	Sold	N/A
Recording Date 05/01/2017 Contract Date 04/24/2017 County Transfer Tax $10,000 Total Transfer Tax $15,000
04/10/2017	$1,295,000	Pending	Agent Provided

03/31/2017	$1,295,000	PriceChange	Agent Provided
Price Change $495,000 (-28%)
03/07/2017	$1,790,000	PriceChange	Agent Provided
Price Change $495,000 (38%)
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
Price Change $245,000 (-19%)
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
Price Change $1,291,100 (33,105%)
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
Recording Date 09/13/2007 County Transfer Tax N/A Total Transfer Tax N/A
10/21/2002	$1,100,000	Sold	N/A
Recording Date 10/21/2002 County Transfer Tax N/A Total Transfer Tax N/A
10/19/1999	$665,000	Sold	N/A
Recording Date 10/19/1999 County Transfer Tax N/A Total Transfer Tax N/A
02/28/1996	$400,000	Sold	N/A
Recording Date 02/28/1996 County Transfer Tax N/A Total Transfer Tax N/A
09/18/1995	$145,000	Sold	N/A
Recording Date 09/18/1995 County Transfer Tax N/A Total Transfer Tax 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
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
504 Talbot St, Saint Michaels, MD	0.22	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
204 Mulberry St, Saint Michaels, MD	0.16	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
205 E Chew Ave, Saint Michaels, MD	0.08	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
203 Mulberry St, Saint Michaels, MD	0.17	Single-Family Home	$926,000	01/15/26	3	2	1,740
106 E Chestnut St, Saint Michaels, MD	0.16	Single-Family Home	$1,225,000	06/05/26	2	2.5	2,282
109 W Chew Ave, Saint Michaels, MD	0.28	Single-Family Home	$662,500	07/18/25	3	2	1,824
103 Mulberry St, Saint Michaels, MD	0.20	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
100 Grace St, Saint Michaels, MD	0.25	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
Est. $1,937,300
4 bd
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218 E Chestnut St,
Saint Michaels, MD 21663
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NOV 14, 2025
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3D VIEW
$2,538,000
5 bd
5.5 ba
4,673 sqft
203 E Chew Ave,
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Benson & Mangold, LLC
OFF MARKET
Est. $1,688,100
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
OCT 8, 2025
$995,000
3 bd
2.5 ba
1,893 sqft
408 Water St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
Est. $1,001,700
4 bd
2.5 ba
1,781 sqft
115 W Chew Ave,
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Meredith Fine Properties

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Additional Cost

Assigned Schools

These are the assigned schools for 222 E Chestnut St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
5y ago
"There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
0
Flag
Christopherbthomas24
Resident
7y ago
"Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
2
Flag
Kats0791
Resident
7y ago
"Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
0
Flag
Janet S.
11y ago
"Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
0
Flag
rctdesign
11y ago
"Wonderful town with lots to do and very walkable!"
0
Flag

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. 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

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.

222 E Chestnut St Saint Michaels, MD 21663

$1,885,000

$1,885,000

Local Information

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222 E Chestnut St
Saint Michaels, MD 21663