222 E Chestnut St

St. Michaels, MD 21663

$2,250,000
Price
3
Beds
2,284 Sq. Ft.
$985 / Sq. Ft.
2,284
Sq. Ft.
$985
per Sq. Ft.
Virtual Tour
Virtual Tour
a front view of a house with a yard
a living room with furniture and a table
a bathroom with a sink and a mirror
a spacious bathroom with a double vanity sink toilet and a tub
a bedroom with a bed and a night stand
a bedroom with a bed and wooden floor
a bed sitting in a bedroom next to a window
a bedroom with a bed and window
a view of a workspace with furniture and a window
a bedroom with a bed chair and window
a view of a hallway with wooden floor
a view of a lake from a balcony
a living room with fireplace furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a wooden floor
a kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances a stove and cabinets
a kitchen with granite countertop a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a kitchen with granite countertop a sink a stove and wooden floor
a bathroom with a toilet a sink and a mirror
a living room with furniture and wooden floor next to a window
a living room with furniture and a book shelf
a living room with furniture a flat screen tv and a fireplace
a living room with furniture wooden floor and a potted plant
a living room with furniture a window and a flat screen tv
a view of a hallway with wooden floor and staircase
a bathroom with a toilet sink and mirror
a view of a lake with a city view
a view of a lake with sitting area
a view of a lake with boats and trees in the background
a view of a building with swimming pool and a chairs
a view of swimming pool from a balcony
a view of a house with swimming pool and sitting area
a view of a house and a yard with a fountain
a front view of a house with a garden
a front view of a house with garden
a front view of a house with garden

Description

A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom, 2.5-bath home inside and out, showcasing coastal décor by a local designer. The home lives comfortably and is...A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom, 2.5-bath home inside and out, showcasing coastal décor by a local designer. The home lives comfortably and is designed for both relaxed everyday living and effortless entertaining. Enjoy a covered front porch and balconies off the bedrooms, all with breathtaking views of the harbor. Additional highlights include a fenced-in yard, beautiful professional landscaping, and a rebuilt bulkhead. Ideally located just a short walk to the town’s restaurants, bars, museums, and shops—this home allows you to fully enjoy the charm and lifestyle of historic St. Michaels. Offered completely turnkey .

Property Details for 222 East Chestnut Street

Tax ID Number
2102062836
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Colonial
Levels/Stories
2
Furnished
Yes
LISTING UPDATED: 11/19/2025 01:01 AM

Property Details for 222 East Chestnut Street

StatusActive
MLS #MDTA2011446
Days on Market145
Taxes$13,297 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1996
Lot Size0.17 AC / 7,292 SF
CountyTalbot County

Location

Listing Courtesy of Benson & Mangold, LLC
Add your commute

Virtual Tour

Building Information for 222 East Chestnut Street

Stories2Year Built1996Building Size-Lot Size0.17 AC / 7,292 SF

Payment Calculator

$12,226 per month

30 year fixed, 6.28% Interest

Principal and Interest

$11,118

Property Taxes

$1,108

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 222 East Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: Yes
  • Water Access: Yes
  • Water Access Features: Boat - Powered, Sail, Canoe/Kayak
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: Yes
  • Water Body Name: ST. MICHAELS HARBOR
  • Water Body Type: River
  • Water Frontage In Feet: 70.0
  • Riparian Rights Y/N: Yes
  • Docks Count: 4
  • Dock Type and Features: Pier (Perpendicular), Multiple Slip
  • Dock/Slip Conveys Y/N: true
  • Dock/Slip Conveyance: Deeded
  • Slips Count: 4
  • Boats Power Count: 3-5
  • Boats Nonpower Count: 3-5
  • Mean Low Water Feet: 4.00
  • Distance To Body Of Water: .00
  • Distance To Body Of Water Units: Blocks
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $1,094,000
  • Year Assessed: 2025
  • County Tax: $8,281
  • Improvement Assessed Value: $402,000
  • City Town Tax: $5,015
  • Land Assessed Value: $692,000
  • Special Assessment Pymnt: Annually
  • Clean Green Assessed: No
  • Land Use Code: R
  • Zoning: RES
  • Tax Lot: 1
  • School Tax: $0
  • Tax Page Number: 582
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 0
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 3
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
  • # Bathrooms Half All Upper Levels: 0
Upper Level 1
  • # Bedrooms Count Upper Level: 3
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
  • # Bathrooms Half Upper Level: 0
Rooms
  • Room List: Living Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Foyer, Laundry, Primary Bathroom, Full Bath, Half Bath
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Family Room
  • Room Length: 23.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
Room 2
  • Room Type: Kitchen
  • Room Length: 13.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Island
Room 3
  • Room Type: Living Room
  • Room Length: 15.0
  • Room Width: 29.0
  • Room Level: Main
  • Room Exists: Yes
Room 4
  • Room Type: Laundry
  • Room Length: 6.0
  • Room Width: 8.0
  • Room Level: Main
  • Room Exists: Yes
Room 5
  • Room Type: Half Bath
  • Room Length: 5.0
  • Room Width: 6.0
  • Room Level: Main
  • Room Exists: Yes
Room 6
  • Room Type: Foyer
  • Room Length: 10.0
  • Room Width: 4.0
  • Room Level: Main
  • Room Exists: Yes
Room 7
  • Room Type: Primary Bedroom
  • Room Length: 15.0
  • Room Width: 23.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Balcony Access
Room 8
  • Room Type: Primary Bathroom
  • Room Length: 17.0
  • Room Width: 7.0
  • Room Level: Upper 1
  • Room Exists: Yes
Room 9
  • Room Type: Bedroom 2
  • Room Length: 10.0
  • Room Width: 14.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Balcony Access
Room 10
  • Room Type: Bedroom 3
  • Room Length: 9.0
  • Room Width: 23.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Balcony Access
Room 11
  • Room Type: Full Bath
  • Room Length: 13.0
  • Room Width: 4.0
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Total Finished SQFT: 2,284.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 2,284.00
  • Total SQFT: 2,284.00
  • Total SQFT Source: Assessor
  • Construction Materials: Vinyl Siding
  • Roof: Architectural Shingle
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8040/2682/7182/804026827182_512_384_WM_pJnG3UD9bZiAc8Vz.jpg
  • Flooring Type: Hardwood
  • Foundation Details: Block, Brick/Mortar, Crawl Space
  • Room and Floor: Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2
  • # Bathrooms Full: 2
  • # Bathrooms Half: 1
  • Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Lot Features: Bulkheaded
  • Location Type: River
  • Parcel ID: 5291475
Parking
Parking
  • Type Of Parking: Driveway
  • Driveway - # of Spaces: 2
  • Parking Features: Circular Driveway
Interior Features
Interior Features
  • Interior Features: Attic, Dining Area, Chair Railings, Upgraded Countertops, Crown Moldings, Primary Bath(s), Window Treatments, Wood Floors, Floor Plan - Traditional
  • Fireplace: Yes
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS
  • List Agent URL: www.ChesapeakeBayProperties.com

Property History for 222 East Chestnut Street

DateEvent & SourcePriceAppreciation
Nov 10, 2025

Listed (Active)

BRIGHT #MDTA2011446

—
Nov 7, 2025

Expired

BRIGHT #MDTA2011446

—
Aug 27, 2025

Price Change

BRIGHT #MDTA2011446

$2,250,000—
Jul 21, 2025

Listed (Active)

BRIGHT #MDTA2011446

$2,395,000—
Apr 28, 2017

Closed

BRIGHT #1002360078

$1,000,000—
Apr 24, 2017

Closed (Public Record)

Public Record #602135649

$1,000,000—
Apr 10, 2017

Withdrawn

BRIGHT #1008293976

—
Apr 8, 2017

Pending

BRIGHT #1002360078

—
Feb 20, 2017

Listed (Active)

BRIGHT #1008293976

$1,790,000—
Feb 20, 2017

Listed (Active)

BRIGHT #1002360078

$1,295,000—
Nov 20, 2016

Expired

BRIGHT #1007234226

—
May 20, 2016

Listed (Active)

BRIGHT #1007234226

$1,295,000—
Nov 17, 2014

Withdrawn

BRIGHT #1007657082

—
May 28, 2014

Withdrawn

BRIGHT #1007577502

—
May 21, 2014

Listed (Active)

BRIGHT #1007657082

$1,295,000—
Feb 5, 2014

Listed (Active)

BRIGHT #1007577502

$1,695,000—
Nov 4, 2013

Expired

BRIGHT #1006992982

—
Apr 22, 2013

Withdrawn

BRIGHT #1009620756

$1,500,000—
Apr 22, 2013

Withdrawn

BRIGHT #1009620756

—
Apr 22, 2013

Listed (Active)

BRIGHT #1006992982

$1,497,000—
Jun 18, 2012

Listed (Active)

BRIGHT #1009620756

$2,175,000—
Jan 31, 2007

Expired

BRIGHT #MDTA124586

$1,495,000—
Sep 10, 2006

Listed (Active)

BRIGHT #MDTA124586

$1,495,000—
Oct 18, 2002

Closed

BRIGHT #MDTA108316

$1,100,000—
Sep 6, 2002

Pending

BRIGHT #MDTA108316

—
Aug 29, 2002

Listed (Active)

BRIGHT #MDTA108316

$1,100,000—
Oct 15, 1999

Closed

BRIGHT #MDTA114732

$665,000—
Sep 12, 1999

Pending

BRIGHT #MDTA114732

—
Sep 2, 1999

Listed (Active)

BRIGHT #MDTA114732

$750,000—
Nov 2, 1998

Expired

BRIGHT #MDTA121438

$495,000—
Jul 2, 1998

Listed (Active)

BRIGHT #MDTA121438

$495,000—
Jun 30, 1998

Expired

BRIGHT #MDTA123030

—
Mar 23, 1998

Listed (Active)

BRIGHT #MDTA123030

$750,000—
Feb 28, 1996

Closed

BRIGHT #MDTA119394

$400,000—
Jan 24, 1996

Pending

BRIGHT #MDTA119394

—
Jan 22, 1996

Listed (Active)

BRIGHT #MDTA119394

$425,000—
DateEvent & SourcePrice
11/10/2025

Listed (Active)

BRIGHT #MDTA2011446

—
11/07/2025

Expired

BRIGHT #MDTA2011446

—
08/27/2025

Price Change

BRIGHT #MDTA2011446

$2,250,000
07/21/2025

Listed (Active)

BRIGHT #MDTA2011446

$2,395,000
04/28/2017

Closed

BRIGHT #1002360078

$1,000,000
04/24/2017

Closed (Public Record)

Public Record #602135649

$1,000,000
04/10/2017

Withdrawn

BRIGHT #1008293976

—
04/08/2017

Pending

BRIGHT #1002360078

—
02/20/2017

Listed (Active)

BRIGHT #1008293976

$1,790,000
02/20/2017

Listed (Active)

BRIGHT #1002360078

$1,295,000
11/20/2016

Expired

BRIGHT #1007234226

—
05/20/2016

Listed (Active)

BRIGHT #1007234226

$1,295,000
11/17/2014

Withdrawn

BRIGHT #1007657082

—
05/28/2014

Withdrawn

BRIGHT #1007577502

—
05/21/2014

Listed (Active)

BRIGHT #1007657082

$1,295,000
02/05/2014

Listed (Active)

BRIGHT #1007577502

$1,695,000
11/04/2013

Expired

BRIGHT #1006992982

—
04/22/2013

Withdrawn

BRIGHT #1009620756

$1,500,000
04/22/2013

Withdrawn

BRIGHT #1009620756

—
04/22/2013

Listed (Active)

BRIGHT #1006992982

$1,497,000
06/18/2012

Listed (Active)

BRIGHT #1009620756

$2,175,000
01/31/2007

Expired

BRIGHT #MDTA124586

$1,495,000
09/10/2006

Listed (Active)

BRIGHT #MDTA124586

$1,495,000
10/18/2002

Closed

BRIGHT #MDTA108316

$1,100,000
09/06/2002

Pending

BRIGHT #MDTA108316

—
08/29/2002

Listed (Active)

BRIGHT #MDTA108316

$1,100,000
10/15/1999

Closed

BRIGHT #MDTA114732

$665,000
09/12/1999

Pending

BRIGHT #MDTA114732

—
09/02/1999

Listed (Active)

BRIGHT #MDTA114732

$750,000
11/02/1998

Expired

BRIGHT #MDTA121438

$495,000
07/02/1998

Listed (Active)

BRIGHT #MDTA121438

$495,000
06/30/1998

Expired

BRIGHT #MDTA123030

—
03/23/1998

Listed (Active)

BRIGHT #MDTA123030

$750,000
02/28/1996

Closed

BRIGHT #MDTA119394

$400,000
01/24/1996

Pending

BRIGHT #MDTA119394

—
01/22/1996

Listed (Active)

BRIGHT #MDTA119394

$425,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 222 East Chestnut Street

Taxable ValueLand$692,000Additions$402,000Total$1,094,000
Tax Record2023$12,469 ($1,039 / month)
Home Facts
Beds0Baths2.5Total Finished SqFt2,284 SqFtAbove Grade Finished SqFt2,284 SqFtStories2Lot Size7,292 SqFtStyleSingle Family ResidenceYear Built1996CountyTALBOTAPN02-062836Fireplace TypeHas Fireplace

Schools near 222 East Chestnut Street

This home is within Talbot County Public Schools.
Rating
School
Type
Grades
Distance
St. Michaels Elementary School
Public - PK to 5
St. Michaels Middle/High School
Public - 6 to 12
Easton High School
Public - 9 to 12
Rating
School
Distance
St. Michaels Elementary School
PublicPK to 5

St. Michaels Middle/High School
Public6 to 12

Easton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 222 East Chestnut Street, St. Michaels, MD 21663

222 East Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on July 21, 2025 by Benson & Mangold, LLC, it's currently listed at $2,250,000. It has been on the market for a total of 145 days and was last sold on April 28, 2017. This listing's school district is Talbot County Public Schools. Nearby schools include St. Michaels Elementary School, St. Michaels Middle/High School and Easton High School. 222 East Chestnut Street is a 3-bed, 3-bath, 2,284 sqft single family home built in 1996.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Benson & Mangold, LLC

© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 11/19/2025 01:01 AM