114 W Chestnut St

St. Michaels, MD 21663

$1,350,000
Price
4
Beds
3,528 Sq. Ft.
$383 / Sq. Ft.
3,528
Sq. Ft.
$383
per Sq. Ft.
Get preapproved with Rocket Mortgage1
a front view of a house with a garden
a view of a house with a yard and flower plants
an aerial view of multiple houses with yard
a view of livingroom with furniture and windows
a living room with furniture or fireplace and a large window
a dining room with furniture a fireplace and wooden floor
a view of a dining room with furniture window and wooden floor
a living room with furniture and a flat screen tv
a view of a dining room with furniture window and wooden floor
a bathroom with a sink mirror and tub
a bedroom with a bed and a chandelier
a spacious bathroom with a granite countertop sink toilet and shower
a view of hallway with wooden floor and stairs
a spacious bedroom with a bed and a fireplace
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
a bathroom with a sink and a mirror
a bedroom with a bed and a lamp
a spacious bedroom with a bed and dresser
a view of a house with a yard and garden
a picture of a room with a white wall and a large mirror
a picture of floor plan
a view of a lake with a park
an aerial view of multiple house
an aerial view of multiple house
a swimming pool view with a lake view
a view of a street with a big yard
a view of a pathway and a yard
a view of a lake with a outdoor space
a backyard of a house with table and chairs
a view of a street with potted plants and a large tree
a view of street with cars
an outdoor space with furniture and umbrella
an aerial view of multiple house
an aerial view of a house with a lake view
an aerial view of multiple house

Description

Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors...Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.
  1. Listed by Winifred C Cowee • Benson & Mangold, LLC
    P: (410)-310-0208 winkcowee@gmail.com

Property Details for 114 West Chestnut Street

Tax ID Number
2102064200
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Traditional
Levels/Stories
3
Waterfront
No
LISTING UPDATED: 05/18/2026 09:03 AM

Property Details for 114 West Chestnut Street

StatusActive
MLS #MDTA2013116
Days on Market71
Taxes$9,815 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1850
Lot Size0.17 AC / 7,200 SF
CountyTalbot County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Benson & Mangold, LLC
Add your commute

Building Information for 114 West Chestnut Street

Stories3Year Built1850Building Size-Lot Size0.17 AC / 7,200 SF

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage1

$7,545 per month

30 year fixed, 6.36% Interest

Principal and Interest

$6,727

Property Taxes

$818

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 114 West Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • 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
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $850,067
  • Year Assessed: 2026
  • County Tax: $6,149
  • Improvement Assessed Value: $572,700
  • City Town Tax: $3,666
  • Land Assessed Value: $417,300
  • Clean Green Assessed: No
  • Municipal Trash: Yes
  • Land Use Code: R
  • Zoning: R-1
  • School Tax: $0
  • Automatically Update Tax Values Y/N: 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: 4
  • # Bathrooms Count All Upper Levels: 4
  • # Bathrooms Full All Upper Levels: 3
  • # Bathrooms Half All Upper Levels: 1
Upper Level 1
  • # Bedrooms Count Upper Level: 3
  • # Bathrooms Count Upper Level: 3
  • # Bathrooms Full Upper Level: 3
  • # Bathrooms Half Upper Level: 0
Upper Level 2
  • # Bedrooms Count Upper Level: 1
  • # Bathrooms Count Upper Level: 1
  • # Bathrooms Full Upper Level: 0
  • # Bathrooms Half Upper Level: 1
Rooms
  • Room List: 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
  • Stories: Main, Upper 1, Upper 2
Rooms Information
Room 1
  • Room Type: Mud Room
  • Room Length: 7.0
  • Room Width: 10.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 2
  • Room Type: Primary Bedroom
  • Room Length: 22.0
  • Room Width: 17.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Built-Ins, Walk-In Closet(s)
Room 3
  • Room Type: Primary Bathroom
  • Room Length: 13.0
  • Room Width: 8.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Ceramic Tile, Bathroom - Soaking Tub, Bathroom - Walk-In Shower, Double Sink
Room 4
  • Room Type: Bedroom 2
  • Room Length: 15.0
  • Room Width: 12.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Fireplace - Wood Burning
Room 5
  • Room Type: Bedroom 3
  • Room Length: 12.0
  • Room Width: 11.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 6
  • Room Type: Bathroom 2
  • Room Length: 9.0
  • Room Width: 7.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Ceramic Tile
Room 7
  • Room Type: Bathroom 3
  • Room Length: 10.0
  • Room Width: 7.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Room 8
  • Room Type: Office
  • Room Length: 10.0
  • Room Width: 7.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 9
  • Room Type: Dining Room
  • Room Length: 15.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Fireplace - Wood Burning, Built-Ins
Room 10
  • Room Type: Great Room
  • Room Length: 25.0
  • Room Width: 19.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Room 11
  • Room Type: Bathroom 1
  • Room Length: 11.0
  • Room Width: 7.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Room 12
  • Room Type: Laundry
  • Room Length: 7.0
  • Room Width: 7.0
  • Room Level: Main
  • Room Exists: Yes
Room 13
  • Room Type: Bedroom 4
  • Room Length: 13.0
  • Room Width: 10.0
  • Room Level: Upper 2
  • Room Exists: Yes
  • Room Features: Flooring - Carpet
Room 14
  • Room Type: Half Bath
  • Room Length: 10.0
  • Room Width: 6.0
  • Room Level: Upper 2
  • Room Exists: Yes
Room 15
  • Room Type: Kitchen
  • Room Length: 11.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Cathedral/Vaulted Ceiling, Countertop(s) - Quartz
Room 16
  • Room Type: Living Room
  • Room Length: 15.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Fireplace - Wood Burning, Built-Ins
Room 17
  • Room Type: Family Room
  • Room Length: 25.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood, Fireplace - Wood Burning
Building Info
Building Info
  • Total Finished SQFT: 3,528.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 3,528.00
  • Total SQFT: 3,528.00
  • Total SQFT Source: Assessor
  • Construction Materials: Frame
  • Roof: Architectural Shingle
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8046/2659/9432/804626599432_512_384_WM_j8pzzZRmMRJic4TK.jpg
  • Flooring Type: Hardwood, Ceramic Tile
  • Foundation Details: Crawl Space
  • Room and Floor: Bathrooms Full-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Upper Level 1-3, Bedrooms-Upper Level 2-1, Bathrooms Half-Upper Level 2-1
  • # Bathrooms Full: 4
  • # Bathrooms Half: 1
  • Other Structure: Storage Barn/Shed
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 5291594
Parking
Parking
  • Type Of Parking: Alley, On Street
Interior Features
Interior Features
  • Fireplace: Yes
  • Fireplaces Count: 3
  • Fireplace Features: Wood
  • Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Washer, Water Heater - Tankless, Water Heater, Refrigerator
  • Accessibility Features: None
Exterior Features
Exterior Features
  • Exterior Features: Street Lights
  • Pool: Yes - Community
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Other
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric, Tankless
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS
  • List Agent URL: www.buythechesapeake.com

Property History for 114 West Chestnut Street

DateEvent & SourcePriceAppreciation
Mar 17, 2026

Listed (Active)

BRIGHT #MDTA2013116

$1,350,000—
Jul 14, 2020

Closed (Public Record)

Public Record #674063522

$164,000

-34.7% / yr

Jul 14, 2020

Closed

BRIGHT #MDTA137092

$640,000—
DateEvent & SourcePrice
03/17/2026

Listed (Active)

BRIGHT #MDTA2013116

$1,350,000
07/14/2020

Closed (Public Record)

Public Record #674063522

$164,000

-34.7% / yr

07/14/2020

Closed

BRIGHT #MDTA137092

$640,000

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

Public Records for 114 West Chestnut Street

Taxable ValueLand$316,600Additions$463,500Total$780,100
Tax Record2023$7,890 ($657 / month)
Home Facts
Beds0Baths4.5Total Finished SqFt3,528 SqFtAbove Grade Finished SqFt3,528 SqFtStories3Lot Size7,200 SqFtStyleSingle Family ResidenceYear Built1850CountyTALBOTAPN02-064200Fireplace TypeHas Fireplace

Schools near 114 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.

Similar Homes

Explore Nearby Homes

More information about 114 West Chestnut Street, St. Michaels, MD 21663

114 West Chestnut Street is a single family home for sale in St. Michaels, MD 21663. This property was listed for sale on March 17, 2026 by Benson & Mangold, LLC, it's currently listed at $1,350,000. It has been on the market for a total of 71 days and was last sold on July 14, 2020. 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. 114 West Chestnut Street is a 4-bed, 5-bath, 3,528 sqft single family home built in 1850.

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 Benson & Mangold, 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 05/18/2026 09:03 AM