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$1,350,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,914 Sq. Ft.
  • Updated 8 days ago
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Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners completed a full renovation in 2023. Designer finishes throughout. Attention to detail, light placement and thoughtful preservation of its original style. The screened front porch welcomes you in with it's beautiful woodwork and sets the pace for this Chic, move-in ready Shore Home. Situated on a double lot with room for a pool. Fenced rear yard for room to run. One block to the Community pier on San Domingo Creek, kayak racks and walking path. Full details on the whole renovation are in the documents file. Note...Heated square footage is 1914 sq. ft.

Full Property Details for 107 W Chestnut St

General

  • Price: $1,350,000
  • Taxes: $4,866 (2019)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2012552
  • Updated: 1/8/2026
  • Added to Site: 18 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Bedroom 2, Kitchen, Basement, Bedroom 1, Other, Bathroom 1, Screened Porch
  • Interior Features: Breakfast Area, Ceiling Fan(s), Built-Ins, Chair Railings, Crown Moldings, Entry Level Bedroom, Kitchen - Eat-In
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Brick, Gas/Propane, Mantel(s)
  • Appliances: Dishwasher, Refrigerator, Washer, Oven/Range - Gas, Built-In Microwave, Dryer - Front Loading, Energy Efficient Appliances, Extra Refrigerator/Freezer, Icemaker, Oven - Self Cleaning, Stainless Steel Appliances, Water Heater - High-Efficiency
  • Flooring: Solid Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 2
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Upper Floor

Exterior

  • Exterior Features: Chimney Cap(s), Exterior Lighting, Play Area, Street Lights
  • Porch/Patio/Deck: Screened, Porch(es), Deck(s)

Parking

  • Total Spaces: 2
  • Parking Features: Private, Stone Driveway
  • Parking Type: On Street, Off Street

Location

  • Municipality: St. Michaels
  • County: TALBOT
  • Driving Directions: Take Rt 33 to Saint Michaels, Turn left onto West Chestnut St & the destination will be the 5th house on your right.
  • Direction Faces: Southeast
  • Location Details: Middle Of Block
  • Historic District: Yes
  • City Limits: Yes

School Information

  • School District: Talbot County Public Schools
  • Elementary School: St. Michaels
  • Middle School: St. Michaels
  • High School: St. Michaels

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Propane

Structural Information

  • Architectural Style: Bungalow
  • Structure Type: Detached
  • Construction: Aluminum Siding
  • Basement: Yes
  • Basement Desc.: Partial
  • Foundation: Block
  • Roof: Architectural Shingle
  • Windows: ENERGY STAR Qualified, Energy Efficient, Double Pane, Double Hung
  • Doors: Insulated, Storm
  • Stories Description: Main, Upper 1
  • Square Feet: 1,914
  • Sq. Ft. Source: Estimated
  • Living Area: 1,914 Sq. Ft.
  • Finished Above Grnd: 1,914 Sq. Ft.
  • Year Built: 1920
  • Year Built Source: Estimated
  • Property Condition: Excellent

Lot Features

  • Property View: Garden/Lawn
  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,500
  • Lot Size Source: Estimated
  • Lot Dimensions: 60 x 125
  • Frontage Feet: 60
  • Zoning: RES
  • Lot Description: Landscaping, Rear Yard, SideYard(s)
  • Fencing (Description): Picket, Fully, Wood

Financial Considerations

  • Price Per Sq. Ft.: $705.33
  • Assessment Year: 2019
  • City/TownTax: $2,224
  • City/TownTax Freq: Annually
  • County Tax: $2,641
  • County Tax Freq: Annually
  • Tax w/Assessment: $424,600
  • Tax Amount: $4,866
  • Tax Year: 2019

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 1901

Listed by Chesapeake Bay Real Estate Plus, LLC, Dawn A Lednum

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Listing agent

— 107 W Chestnut St —

  • Dawn A Lednum

    Chesapeake Bay Real Estate Plus, LLC

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 107 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 Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 107 W Chestnut St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/29/2025
Listed
$1,350,000
217.65%
MLS
8/16/2019
Sold
$425,000
—
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 107 W Chestnut St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$5,665
—
$563,200
9%
2023
$5,665
—
$517,933
10%
2023
$5,665
15%
$472,667
11%
2022
$4,945
1%
$427,400
—
2020
$4,877
1%
$426,467
—
2021
$4,833
162%
$425,533
—
2020
$1,847
2%
$424,600
4%
2019
$1,803
4%
$409,700
4%
2018
$1,739
8%
$394,800
4%
2017
$1,605
2%
$379,900
—
2016
$1,576
1%
$379,900
—
2015
$1,564
-2%
$379,900
-18%
2014
$1,591
—
$461,700
—
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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NMLS#: 1598647

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Listed by Chesapeake Bay Real Estate Plus, LLC, Dawn A Lednum

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107 W Chestnut Street, Saint Michaels, MD 21663 (MLS# MDTA2012552) is a Single Family property with 3 bedrooms and 2 full bathrooms. 107 W Chestnut Street is currently listed for $1,350,000 and was received on December 29, 2025. Want to learn more about 107 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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