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$1,350,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,528 Sq. Ft.
  • Updated 11 hours ago
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Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting interior with hardwood floors, multiple comfortable living areas, and four wood-burning fireplaces that add warmth and character throughout. The spacious layout includes four bedrooms and four and one-half baths, providing flexibility for everyday living and hosting guests, along with a dedicated office, custom built-ins, and abundant storage. Outside, the beautifully landscaped and fenced yard offers privacy and space for outdoor enjoyment, complemented by a detached studio/workshop ideal for creative pursuits or hobbies. Off-street parking adds convenience in this prime in-town setting. With a prime location, generous living and storage space, and historic charm, this distinctive property represents exceptional value in the heart of St. Michaels.

Full Property Details for 114 W Chestnut St

General

  • Price: $1,350,000
  • Taxes: $9,815 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2013116
  • Updated: Today (3/17/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 17
  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Great Room, Laundry, Mud Room, Office, Bathroom 1, Bathroom 2, Bathroom 3, Primary Bathroom, Half Bath
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Fireplace(s): Wood
  • Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Washer, Water Heater - Tankless, Water Heater, Refrigerator
  • Flooring: Hardwood, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper 2 - 1/2 Baths: 1
  • Upper Floor Baths: 4
  • Upper - Full Baths: 3
  • Upper - 1/2 Baths: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 4
  • Bedrooms-Up2: 1

Additional Information

  • Shared Pool: Yes
  • Pool: Yes

Exterior

  • Exterior Features: Street Lights

Parking

  • Parking Type: Alley, On Street

Location

  • Municipality: Saint Michaels
  • County: TALBOT
  • Driving Directions: From Easton: Rt. 33 to St. Michaels. Left on W. Chestnut. House on left. Sign posted.
  • City Limits: Yes

School Information

  • School District: Talbot County Public Schools

Heating & Cooling

  • Cooling Type: Other
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric, Tankless

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Crawl Space
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 3,528
  • Sq. Ft. Source: Assessor
  • Living Area: 3,528 Sq. Ft.
  • Finished Above Grnd: 3,528 Sq. Ft.
  • Year Built: 1850
  • Year Built Source: Assessor

Additional Structures

  • Other Structures: Storage Barn/Shed

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,200
  • Lot Size Source: Assessor
  • Zoning: R-1

Financial Considerations

  • Price Per Sq. Ft.: $382.65
  • Assessment Year: 2026
  • City/TownTax: $3,666
  • City/TownTax Freq: Annually
  • County Tax: $6,149
  • County Tax Freq: Annually
  • Tax w/Assessment: $850,067
  • Tax Amount: $9,815
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 3528

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Benson & Mangold, LLC, Winifred C Cowee

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Listing agent

— 114 W Chestnut St —

  • Winifred C Cowee

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 114 W Chestnut St

School District:Talbot County Public Schools
NameGradesDistance
St. Michaels Elementary School
100 Seymour Avenue, Saint Michaels, MD 21663
PK-60.4 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-120.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 114 W Chestnut St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/17/2026
Listed
$1,350,000
110.94%
MLS
7/14/2020
Sold
$640,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 114 W Chestnut St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$7,890
—
$780,100
8%
2023
$7,890
—
$719,200
9%
2023
$7,890
14%
$658,300
10%
2022
$6,912
1%
$597,400
—
2020
$6,847
1%
$597,400
—
2021
$6,786
-7%
$597,400
-12%
2020
$7,328
2%
$675,600
5%
2019
$7,157
9%
$641,833
6%
2018
$6,566
15%
$608,067
6%
2017
$5,698
2%
$574,300
—
2016
$5,576
1%
$574,300
—
2015
$5,525
-14%
$574,300
-16%
2014
$6,403
—
$682,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Winifred C Cowee

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114 W Chestnut Street, Saint Michaels, MD 21663 (MLS# MDTA2013116) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 114 W Chestnut Street is currently listed for $1,350,000 and was received on March 17, 2026. Want to learn more about 114 W Chestnut Street? Do you have questions about finding other Single Family real estate for sale in Saint Michaels? You can browse all Saint Michaels real estate or contact a Coldwell Banker agent to request more information.

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