121 W Chestnut St

St. Michaels, MD 21663

$1,395,000
Price
3
Beds
2,540 Sq. Ft.
$549 / Sq. Ft.
2,540
Sq. Ft.
$549
per Sq. Ft.
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New
New

Description

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important...121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.
  1. Listed by Carolina Barksdale • Benson & Mangold, LLC
    P: (443)-786-0348 carolina@talbotrealestate.com

Property Details for 121 West Chestnut Street

Tax ID Number
2102060841
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Colonial
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 04/14/2026 10:09 AM

Property Details for 121 West Chestnut Street

StatusActive
MLS #MDTA2013474
Days on Market1
Taxes$8,592 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1890
Lot Size0.17 AC / 7,500 SF
CountyTalbot County
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Location

Listing Courtesy of Benson & Mangold, LLC
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Building Information for 121 West Chestnut Street

Stories2Year Built1890Building Size-Lot Size0.17 AC / 7,500 SF

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$7,741 per month

30 year fixed, 6.46% Interest

Principal and Interest

$7,025

Property Taxes

$716

HOA Dues

$0

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Property Information for 121 West 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: No
  • Water Access: Yes
  • Water Access Features: Canoe/Kayak
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: No
  • Water Body Name: San Domingo Creek
  • Water Body Type: River
  • Riparian Rights Y/N: No
  • Docks Count: 0
  • Mean Low Water Feet: 3.00
  • Distance To Body Of Water: 300.00
  • Distance To Body Of Water Units: Feet
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $751,233
  • Year Assessed: 2026
  • County Tax: $5,383
  • Improvement Assessed Value: $468,100
  • City Town Tax: $3,209
  • Land Assessed Value: $419,800
  • Clean Green Assessed: No
  • Municipal Trash: Yes
  • Land Use Code: R
  • Zoning: R
  • School Tax: $0
  • 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, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Foyer, Laundry, Mud Room, Office, Bathroom 2, Primary Bathroom, Half Bath
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Foyer
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 2
  • Room Type: Living Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Fireplace - Gas, Built-Ins, Ceiling Fan(s), Crown Molding
Room 3
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Built-Ins, Crown Molding
Room 4
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Countertop(s) - Granite, Countertop(s) - Quartz, Flooring - Wood, Island, Lighting - Ceiling, Kitchen - Gas Cooking, Lighting - Pendants, Lighting - Recessed
Room 5
  • Room Type: Mud Room
  • Room Level: Main
  • Room Exists: Yes
Room 6
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
Room 7
  • Room Type: Half Bath
  • Room Level: Main
  • Room Exists: Yes
Room 8
  • Room Type: Primary Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Attached Bathroom, Flooring - HardWood, Walk-In Closet(s)
Room 9
  • Room Type: Primary Bathroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Bathroom - Walk-In Shower, Flooring - Ceramic Tile
Room 10
  • Room Type: Bedroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Flooring - HardWood, Window Treatments
Room 11
  • Room Type: Bedroom 3
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Flooring - HardWood
Room 12
  • Room Type: Bathroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Ceramic Tile, Window Treatments, Double Sink
Room 13
  • Room Type: Office
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Building Info
Building Info
  • Total Finished SQFT: 2,540.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Lot Size Dimensions: 60.00 x
  • Lot Dimensions Source: Assessor
  • Lot Features: Landscaping
  • Parcel ID: 5291305
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: On Street
Interior Features
Interior Features
  • Interior Features: Attic, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Ceiling Fan(s), Crown Moldings, Double/Dual Staircase, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Recessed Lighting, Formal/Separate Dining Room, Wood Floors, Additional Stairway, Walk-in Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Gas/Propane, Mantel(s)
  • Appliances: Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Range Hood, Refrigerator, Washer, Stainless Steel Appliances
  • Accessibility Features: None
  • Laundry Type: Main Floor
Exterior Features
Exterior Features
  • Exterior Features: Outbuilding(s)
  • Pool: No Pool
  • Community Docks Count: 1
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Ductless/Mini-Split
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Other
  • 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: TalbotRealEstate.com

Property History for 121 West Chestnut Street

DateEvent & SourcePriceAppreciation
Apr 14, 2026

Listed (Active)

BRIGHT #MDTA2013474

$1,395,000—
Jan 15, 2016

Closed (Public Record)

Public Record #564773653

$405,000

+10.5% / yr

Jan 15, 2016

Closed

BRIGHT #1002821698

$405,000—
Dec 3, 2015

Pending

BRIGHT #1002821698

—
Feb 3, 2014

Listed (Active)

BRIGHT #1002821698

$485,000—
Mar 17, 2011

Closed (Public Record)

Public Record #305767400

$250,000—
Mar 17, 2011

Closed

BRIGHT #1004297038

$250,000—
Feb 7, 2011

Pending

BRIGHT #1004297038

—
Feb 7, 2011

Listed (Active)

BRIGHT #1004297038

$375,000—
Dec 7, 2010

Withdrawn

BRIGHT #1009230112

—
Sep 20, 2010

Listed (Active)

BRIGHT #1009230112

$375,000—
Sep 13, 2010

Withdrawn

BRIGHT #1009124832

—
May 28, 2010

Listed (Active)

BRIGHT #1009124832

$545,000—
Jan 11, 2010

Expired

BRIGHT #1006638994

—
Dec 11, 2009

Listed (Active)

BRIGHT #1006638994

$505,000—
Jul 30, 2004

Withdrawn

BRIGHT #MDTA131766

—
Oct 9, 2003

Listed (Active)

BRIGHT #MDTA131766

$485,000—
DateEvent & SourcePrice
04/14/2026

Listed (Active)

BRIGHT #MDTA2013474

$1,395,000
01/15/2016

Closed (Public Record)

Public Record #564773653

$405,000

+10.5% / yr

01/15/2016

Closed

BRIGHT #1002821698

$405,000
12/03/2015

Pending

BRIGHT #1002821698

—
02/03/2014

Listed (Active)

BRIGHT #1002821698

$485,000
03/17/2011

Closed (Public Record)

Public Record #305767400

$250,000
03/17/2011

Closed

BRIGHT #1004297038

$250,000
02/07/2011

Pending

BRIGHT #1004297038

—
02/07/2011

Listed (Active)

BRIGHT #1004297038

$375,000
12/07/2010

Withdrawn

BRIGHT #1009230112

—
09/20/2010

Listed (Active)

BRIGHT #1009230112

$375,000
09/13/2010

Withdrawn

BRIGHT #1009124832

—
05/28/2010

Listed (Active)

BRIGHT #1009124832

$545,000
01/11/2010

Expired

BRIGHT #1006638994

—
12/11/2009

Listed (Active)

BRIGHT #1006638994

$505,000
07/30/2004

Withdrawn

BRIGHT #MDTA131766

—
10/09/2003

Listed (Active)

BRIGHT #MDTA131766

$485,000

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

Public Records for 121 West Chestnut Street

Taxable ValueLand$318,500Additions$364,400Total$682,900
Tax Record2023$6,303 ($525 / month)
Home Facts
Beds0Baths2.5Total Finished SqFt2,540 SqFtAbove Grade Finished SqFt2,540 SqFtStories2Lot Size7,500 SqFtStyleSingle Family ResidenceYear Built1890CountyTALBOTAPN02-060841Fireplace TypeHas Fireplace

Schools near 121 West 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 121 West Chestnut Street, St. Michaels, MD 21663

121 West Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on April 14, 2026 by Benson & Mangold, LLC, it's currently listed at $1,395,000. It has been on the market for a total of 1 days and was last sold on January 15, 2016. 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. 121 West Chestnut Street is a 3-bed, 3-bath, 2,540 sqft single family home built in 1890.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Benson & Mangold, LLC

© 2026 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 04/14/2026 10:09 AM