107 E Chestnut St

St. Michaels, MD 21663

$1,195,000
Price
2
Beds
2,024 Sq. Ft.
$590 / Sq. Ft.
2,024
Sq. Ft.
$590
per Sq. Ft.

Description

St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820. Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions, built-ins and storage. Magnificent main level 2 story glass enclosed solarium! This home has been meticulously...St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820. Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions, built-ins and storage. Magnificent main level 2 story glass enclosed solarium! This home has been meticulously maintained and cared for. Enjoy evenings on the front porch or on the rear screen porch overlooking the gardens. The rear yard also has an old time boat house/shed which is insulated and heated and the current owners have gone through the local Historic approvals to renovate the boathouse/shed into a guest house. See documents for plans and drawings. Convenient walking distance to St. Michaels Harbor, Chesapeake Bay Maritime Museum, and numerous shops and great restaurants. This home is Gem so don't miss out on this opportunity!
  1. Listed by Robert L Fitton II • Meredith Fine Properties
    P: (703)-577-1747 rfitton@monogram-homes.com

Property Details for 107 East Chestnut Street

Tax ID Number
2102063735
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Victorian
Levels/Stories
2
Furnished
No
LISTING UPDATED: 10/28/2025 05:14 PM

Property Details for 107 East Chestnut Street

StatusActive
MLS #MDTA2011802
Days on Market94
Taxes$6,175 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1870
Lot Size0.08 AC / 3,600 SF
CountyTalbot County

Location

Listing Courtesy of Meredith Fine Properties
Add your commute

Building Information for 107 East Chestnut Street

Stories2Year Built1870Building Size-Lot Size0.08 AC / 3,600 SF

Payment Calculator

$6,420 per month

30 year fixed, 6.28% Interest

Principal and Interest

$5,905

Property Taxes

$515

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 107 East Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • 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
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $424,400
  • County Tax: $3,846
  • Improvement Assessed Value: $149,400
  • City Town Tax: $2,329
  • Land Assessed Value: $275,000
  • Land Use Code: R
  • Agricultural Tax Due: No
  • Historic: Yes
  • Zoning: R
  • Tax Page Number: 1
  • Automatically Update Tax Values Y/N: No
Lease Information
Lease Information
  • Pets Allowed: No
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 1
  • # Bathrooms Half Main Level: 0
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, Family Room, Laundry, Bathroom 1, Bathroom 2, Additional Bedroom
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Bathroom 1
  • Room Level: Main
  • Room Exists: Yes
Room 2
  • Room Type: Bedroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
Room 3
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
Room 4
  • Room Type: Family Room
  • Room Level: Main
  • Room Exists: Yes
Room 5
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
Room 6
  • Room Type: Living Room
  • Room Level: Main
  • Room Exists: Yes
Room 7
  • Room Type: Laundry
  • Room Level: Upper 1
  • Room Exists: Yes
Room 8
  • Room Type: Additional Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
Room 9
  • Room Type: Bathroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Total Finished SQFT: 2,024.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 2,024.00
  • Total SQFT: 2,024.00
  • Total SQFT Source: Assessor
  • Main Entrance Orientation: East
  • Construction Materials: Combination, Vinyl Siding, Wood Siding
  • Roof: Composite
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8041/4430/2162/804144302162_512_384_WM_9DHDxv4BGlvICkMq.jpg
  • Wall and Ceiling Types: 2 Story Ceilings, Beamed Ceilings, Dry Wall
  • Flooring Type: Solid Hardwood
  • Foundation Details: Crawl Space, Other
  • Room and Floor: Bathrooms Full-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bathrooms Full-Upper Level 1-1
  • # Bathrooms Full: 2
  • # Bathrooms Half: 0
  • Other Structure: Shed
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Lot Size Dimensions: 3600
  • Lot Dimensions Source: Estimated
  • Lot Features: Landscaping, Rear Yard
  • Fencing: Rear
  • Parcel ID: 5291553
  • Additional Parcels: No
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Driveway, Off Street, On Street
  • Parking Features: Crushed Stone
Interior Features
Interior Features
  • Interior Features: Bathroom - Stall Shower, Built-Ins, Ceiling Fan(s), Exposed Beams, Kitchen - Gourmet, Other, Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wood Floors
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Gas/Propane, Mantel(s)
  • Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer - Electric, Freezer, Instant Hot Water, Oven/Range - Electric, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
  • Accessibility Features: None
  • Security Features: Smoke Detector
  • Door Features: French, Storm
  • Laundry Type: Has Laundry, Upper Floor
  • Virtual Tour URL Unbranded: https://atlanticexposurellc.hd.pics/107-E-Chestnut-St/idx
Exterior Features
Exterior Features
  • Exterior Features: Extensive Hardscape, Exterior Lighting, Flood Lights, Other, Outbuilding(s), Secure Storage, Sidewalks, Water Fountains
  • Outdoor Living Structures: Patio(s), Porch(es), Screened
  • Pool: No Pool
Utilities
Utilities
  • Utilities: Phone Available, Propane
  • Heating: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Ceiling, Forced Air, Heat Pump(s), Zoned
  • Heating Fuel: Electric
  • Hot Water: Instant Hot Water, Propane
  • Water Source: Public
  • Sewer Septic: Public Sewer
  • Electric Service: 200+ Amp Service
Confidential Data
Listing Office
  • List Agent AOR: Northern Virginia Association of REALTORS

Property History for 107 East Chestnut Street

DateEvent & SourcePriceAppreciation
Oct 28, 2025

Price Change

BRIGHT #MDTA2011802

$1,195,000—
Sep 12, 2025

Listed (Active)

BRIGHT #MDTA2011802

$1,295,000—
Jul 15, 2022

Closed (Public Record)

Public Record #1494392209

$815,000

+6.1% / yr

Jul 15, 2022

Closed

BRIGHT #MDTA2002896

$815,000—
May 9, 2022

Pending

BRIGHT #MDTA2002896

—
May 9, 2022

Active Under Contract

BRIGHT #MDTA2002896

—
May 4, 2022

Listed (Active)

BRIGHT #MDTA2002896

$719,000—
Nov 17, 2010

Closed (Public Record)

Public Record #300084811

$410,000

+7.6% / yr

Nov 17, 2010

Closed

BRIGHT #1004758158

$410,000—
Oct 5, 2010

Pending

BRIGHT #1004758158

—
Mar 15, 2010

Listed (Active)

BRIGHT #1004758158

$525,000—
Nov 30, 2009

Withdrawn

BRIGHT #1008707100

$525,000—
Nov 30, 2009

Withdrawn

BRIGHT #1008707100

—
Dec 10, 2008

Listed (Active)

BRIGHT #1008707100

$635,000—
May 31, 2001

Closed (Public Record)

Public Record #76088569

$205,000—
May 29, 2001

Closed

BRIGHT #MDTA112280

$205,000—
Mar 30, 2001

Pending

BRIGHT #MDTA112280

—
Dec 15, 2000

Listed (Active)

BRIGHT #MDTA112280

$208,000—
Oct 7, 2000

Expired

BRIGHT #MDTA119816

$218,000—
Apr 7, 2000

Listed (Active)

BRIGHT #MDTA119816

$218,000—
DateEvent & SourcePrice
10/28/2025

Price Change

BRIGHT #MDTA2011802

$1,195,000
09/12/2025

Listed (Active)

BRIGHT #MDTA2011802

$1,295,000
07/15/2022

Closed (Public Record)

Public Record #1494392209

$815,000

+6.1% / yr

07/15/2022

Closed

BRIGHT #MDTA2002896

$815,000
05/09/2022

Pending

BRIGHT #MDTA2002896

—
05/09/2022

Active Under Contract

BRIGHT #MDTA2002896

—
05/04/2022

Listed (Active)

BRIGHT #MDTA2002896

$719,000
11/17/2010

Closed (Public Record)

Public Record #300084811

$410,000

+7.6% / yr

11/17/2010

Closed

BRIGHT #1004758158

$410,000
10/05/2010

Pending

BRIGHT #1004758158

—
03/15/2010

Listed (Active)

BRIGHT #1004758158

$525,000
11/30/2009

Withdrawn

BRIGHT #1008707100

$525,000
11/30/2009

Withdrawn

BRIGHT #1008707100

—
12/10/2008

Listed (Active)

BRIGHT #1008707100

$635,000
05/31/2001

Closed (Public Record)

Public Record #76088569

$205,000
05/29/2001

Closed

BRIGHT #MDTA112280

$205,000
03/30/2001

Pending

BRIGHT #MDTA112280

—
12/15/2000

Listed (Active)

BRIGHT #MDTA112280

$208,000
10/07/2000

Expired

BRIGHT #MDTA119816

$218,000
04/07/2000

Listed (Active)

BRIGHT #MDTA119816

$218,000

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

Public Records for 107 East Chestnut Street

Taxable ValueLand$275,000Additions$256,300Total$531,300
Tax Record2023$5,514 ($459 / month)
Home Facts
Beds0Baths2Total Finished SqFt2,024 SqFtAbove Grade Finished SqFt2,024 SqFtStories2Lot Size3,600 SqFtStyleSingle Family ResidenceYear Built1880CountyTALBOTAPN02-063735Fireplace TypeHas Fireplace

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

107 East Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on September 12, 2025 by Meredith Fine Properties, it's currently listed at $1,195,000. It has been on the market for a total of 94 days and was last sold on July 15, 2022. 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 East Chestnut Street is a 2-bed, 2-bath, 2,024 sqft single family home built in 1870.

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 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 Meredith Fine Properties

© 2025 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 10/28/2025 05:14 PM