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$1,195,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 3,528 Sq. Ft.
  • Updated 50 minutes ago

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Open House: 1:00 PM - 3:00 PM

Sunday 8/30 1:00 PM - 3:00 PM

114 W Chestnut Street,Saint Michaels, MD 21663

114 W Chestnut StreetSaint MichaelsMD21663

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Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

Full Property Details for 114 W Chestnut St

General

  • Price: $1,195,000
  • Taxes: $9,815 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2014898
  • Updated: Today (8/28/2026)
  • Added to Site: Today

Interior

  • Rooms/Areas: Living Room, Dining Room, Kitchen, Family Room, Foyer, Laundry, Office
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Fireplace(s): Wood
  • Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Refrigerator, Washer, Water Heater, Water Heater - Tankless
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 4

Additional Information

  • Shared Pool: Yes
  • Pool: Yes

Exterior

  • Exterior Features: Street Lights

Parking

  • Total Spaces: 2
  • Parking Type: Alley, On Street, Off Street, Driveway

Location

  • Municipality: St Michaels
  • County: TALBOT
  • Driving Directions: From Easton, Rt 33 to St Michaels, left on W Chestnut, home will be on the left
  • Historic District: Yes
  • City Limits: Yes

School Information

  • School District: Talbot County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric, Tankless

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV, Electric Available

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Crawl Space
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1
  • 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: Estimated
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Shed

Lot Features

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

Water Features

  • Water Front Type: Cove

Financial Considerations

  • Price Per Sq. Ft.: $338.72
  • 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: 2026
  • Tax Total Finished Sq. Ft.: 3528

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Shelving in shed

Listed by TTR Sotheby's International Realty, Robert D Lacaze

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Listing agent

— 114 W Chestnut St —

  • Robert D Lacaze

    TTR Sotheby's International Realty

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
8/28/2026
Listed
$1,195,000
86.72%
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
2025
$9,726
—
$850,067
9%
2025
$9,726
23%
$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.

Estimate the Cost for 114 W Chestnut St

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NMLS#: 1598647

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Listed by TTR Sotheby's International Realty, Robert D Lacaze

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114 W Chestnut Street, Saint Michaels, MD 21663 (MLS# MDTA2014898) is a Single Family property with 4 bedrooms and 4 full bathrooms. 114 W Chestnut Street is currently listed for $1,195,000 and was received on August 28, 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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