107 W Chestnut St

St. Michaels, MD 21663

$1,350,000
Price
3
Beds
1,914 Sq. Ft.
$705 / Sq. Ft.
1,914
Sq. Ft.
$705
per Sq. Ft.

Description

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...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.
  1. Listed by Dawn A Lednum • Chesapeake Bay Real Estate Plus, LLC
    P: (410)-745-6702 dawnlednum@gmail.com

Property Details for 107 West Chestnut Street

Tax ID Number
02-064243
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Bungalow
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 02/12/2026 01:38 AM

Property Details for 107 West Chestnut Street

StatusActive
MLS #MDTA2012552
Days on Market53
Taxes$4,866 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1920
Lot Size0.17 AC / 7,500 SF
CountyTalbot County

Location

Listing Courtesy of Chesapeake Bay Real Estate Plus, LLC
Add your commute

Building Information for 107 West Chestnut Street

Stories2Year Built1920Building Size-Lot Size0.17 AC / 7,500 SF

Payment Calculator

$6,985 per month

30 year fixed, 6.15% Interest

Principal and Interest

$6,580

Property Taxes

$406

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 107 West Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • Elementary School: ST. MICHAELS (TALBOT MD)
  • ElementarySchoolSource: Listing Agent
  • Middle Or Junior School: ST. MICHAELS (TALBOT MD)
  • MiddleSchoolSource: Listing Agent
  • High School: ST. MICHAELS (TALBOT MD)
  • County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2019
  • Tax Assessed Value: $424,600
  • Year Assessed: 2019
  • County Tax: $2,641
  • Improvement Assessed Value: $143,400
  • City Town Tax: $2,224
  • Land Assessed Value: $281,200
  • Clean Green Assessed: No
  • Municipal Trash: Yes
  • Land Use Code: 110
  • Agricultural Tax Due: No
  • Historic: Yes
  • Zoning: RES
  • Tax Lot: 1901
  • Tax Page Number: 195
  • Automatically Update Tax Values Y/N: No
Lease Information
Lease Information
  • Pets Allowed: Yes
  • Pet Restrictions: No Pet Restrictions
Rooms
Main
  • # Bedrooms Count Main Level: 1
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 2
  • # Bathrooms Count All Upper Levels: 1
  • # Bathrooms Full All Upper Levels: 1
Upper Level 1
  • # Bedrooms Count Upper Level: 2
  • # Bathrooms Count Upper Level: 1
  • # Bathrooms Full Upper Level: 1
Rooms
  • Room List: Living Room, Dining Room, Bedroom 2, Kitchen, Basement, Bedroom 1, Other, Bathroom 1, Screened Porch
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Living Room
  • Room Length: 16.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Fireplace - Wood Burning, Flooring - Carpet
Room 2
  • Room Type: Dining Room
  • Room Length: 16.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet, Chair Rail, Built-Ins
Room 3
  • Room Type: Kitchen
  • Room Length: 15.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Vinyl, Countertop(s) - Quartz, Chair Rail, Breakfast Nook
Room 4
  • Room Type: Bedroom 1
  • Room Length: 14.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet, Ceiling Fan(s)
Room 5
  • Room Type: Bedroom 2
  • Room Length: 13.0
  • Room Width: 10.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet, Ceiling Fan(s)
Room 6
  • Room Type: Bathroom 1
  • Room Length: 9.0
  • Room Width: 9.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Vinyl, Double Sink
Room 7
  • Room Type: Screened Porch
  • Room Length: 29.0
  • Room Width: 10.0
  • Room Level: Main
  • Room Exists: Yes
Room 8
  • Room Type: Other
  • Room Length: 16.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
Room 9
  • Room Type: Basement
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Year Major Reno Remodel: 2023
  • Total Finished SQFT: 1,914.00
  • Total Finished SQFT Source: Estimated
  • Total SQFT: 1,914.00
  • Total SQFT Source: Estimated
  • Main Entrance Orientation: Southeast
  • Construction Materials: Aluminum Siding
  • Roof: Architectural Shingle
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8044/0114/3250/804401143250_512_384_WM_nQPd0J4_vQcqk42i.jpg
  • Flooring Type: Solid Hardwood
  • Basement Type: Partial
  • Foundation Details: Block
  • Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bathrooms Full-Upper Level 1-1
  • # Bathrooms Full: 2
  • Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Lot Size Dimensions: 60x125
  • Lot Dimensions Source: Estimated
  • Lot Features: Landscaping, Rear Yard, SideYard(s)
  • Road Frontage Length: 60.00
  • Fencing: Picket, Fully, Wood
  • Location Type: Middle Of Block
  • Additional Parcels: No
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: On Street, Off Street
  • Off Street - # of Spaces: 2
  • Parking Features: Private, Stone Driveway
Interior Features
Interior Features
  • Interior Features: Breakfast Area, Ceiling Fan(s), Built-Ins, Chair Railings, Crown Moldings, Entry Level Bedroom, Kitchen - Eat-In
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: 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
  • Accessibility Features: None
  • Door Features: Insulated, Storm
  • Window Features: ENERGY STAR Qualified, Energy Efficient, Double Pane, Double Hung
  • Laundry Type: Upper Floor
  • Virtual Tour URL Unbranded: https://thru-the-lens-ivuf.view.property/public/vtour/display/2366586?a=1#!/
Exterior Features
Exterior Features
  • Spa: No
  • Exterior Features: Chimney Cap(s), Exterior Lighting, Play Area, Street Lights
  • Outdoor Living Structures: Screened, Porch(es), Deck(s)
  • Pool: No Pool
  • Horse: No
Utilities
Utilities
  • Utilities: Propane
  • Heating: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Energy Star Heating System, Heat Pump(s), Central
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
  • Electric Service: 200+ Amp Service
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS
  • List Agent URL: chesapeakebayrealestateplus.co

Property History for 107 West Chestnut Street

DateEvent & SourcePriceAppreciation
Dec 29, 2025

Listed (Active)

BRIGHT #MDTA2012552

$1,350,000—
Aug 16, 2019

Closed (Public Record)

Public Record #651509630

$425,000—
Aug 16, 2019

Closed

BRIGHT #MDTA135226

$425,000—
Jun 21, 2019

Pending

BRIGHT #MDTA135226

—
May 13, 2019

Listed (Active)

BRIGHT #MDTA135226

$450,000—
DateEvent & SourcePrice
12/29/2025

Listed (Active)

BRIGHT #MDTA2012552

$1,350,000
08/16/2019

Closed (Public Record)

Public Record #651509630

$425,000
08/16/2019

Closed

BRIGHT #MDTA135226

$425,000
06/21/2019

Pending

BRIGHT #MDTA135226

—
05/13/2019

Listed (Active)

BRIGHT #MDTA135226

$450,000

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

Public Records for 107 West Chestnut Street

Taxable ValueLand$318,500Additions$244,700Total$563,200
Tax Record2023$5,665 ($472 / month)
Home Facts
Beds0Baths1.5Total Finished SqFt1,785 SqFtAbove Grade Finished SqFt1,785 SqFtStories2Lot Size7,500 SqFtStyleSingle Family ResidenceYear Built1920CountyTALBOTAPN02-064243Fireplace TypeHas Fireplace

Schools near 107 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 107 West Chestnut Street, St. Michaels, MD 21663

107 West Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on December 29, 2025 by Chesapeake Bay Real Estate Plus, LLC, it's currently listed at $1,350,000. It has been on the market for a total of 53 days and was last sold on August 16, 2019. 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. 107 West Chestnut Street is a 3-bed, 2-bath, 1,914 sqft single family home built in 1920.

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.

Listing Courtesy of Chesapeake Bay Real Estate Plus, 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 02/12/2026 01:38 AM