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114 W Chestnut Street, Saint Michaels, MD 21663

$1,350,000
  • 114 W Chestnut Street, Saint Michaels, MD 21663 Main Photo

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New to the Market
BEDS4 BATHS4 full 1 partial SQUARE FEET3,528 MLS#MDTA2013116
STATUSACTIVE PROPERTY TYPEResidential - Single Family SCHOOLTALBOT COUNTY PUBLIC SCHOOLS

Property Description

Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting interior with hardwood floors, multiple comfortable living areas, and four wood-burning fireplaces that add warmth and character throughout. The spacious layout includes four bedrooms and four and one-half baths, providing flexibility for everyday living and hosting guests, along with a dedicated office, custom built-ins, and abundant storage. Outside, the beautifully landscaped and fenced yard offers privacy and space for outdoor enjoyment, complemented by a detached studio/workshop ideal for creative pursuits or hobbies. Off-street parking adds convenience in this prime in-town setting. With a prime location, generous living and storage space, and historic charm, this distinctive property represents exceptional value in the heart of St. Michaels.

114 W Chestnut Street | MLS# MDTA2013116

This single family home located at 114 W Chestnut Street, Saint Michaels, MD 21663 is currently listed for sale with an asking price of $1,350,000. This property was built in 1850 and has 4 bedrooms and 4 full and 1 partial baths with 3528 sq. ft. W Chestnut Street is located within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search Saint Michaels real estate on www.lynseybennettrealtor.com today.

Property Features

Property Type: Residential - Single Family
Fireplaces: 3
Fuel Type: Electric
Heating: Heat Pump(s)
Home Style: Traditional
Lot Size: 0.17 Acres
Roof Type: Architectural Shingle
Stories: 3.0
Taxes: $9,815
Year Built: 1850

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Washer, Water Heater - Tankless, Water Heater, Refrigerator
Exterior: Street Lights
Exterior: Frame
Fireplace: Wood
Flooring: Hardwood, Ceramic Tile
Lot Dimensions: 0.17 Acre(S)
Municipality: Saint Michaels
Number of Rooms: 17
Rooms: 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
Sewer: Public Sewer
SQFT Above Finished: 3528
SQFT Total Finished: 3528
Structure Type: Detached
Water: Public

Room Sizes

Living Room: 15 x 11 Level - Main
Dining Room: 15 x 12 Level - Main
Kitchen: 11 x 11 Level - Main
Family Room: 25 x 12 Level - Main
Great Room: 25 x 19 Level - Main
Bathroom 1: 11 x 7 Level - Main
Laundry: 7 x 7 Level - Main
Mud Room: 7 x 10 Level - Main
Primary Bedroom: 22 x 17 Level - Upper 1
Primary Bathroom: 13 x 8 Level - Upper 1
Bedroom 2: 15 x 12 Level - Upper 1
Bedroom 3: 12 x 11 Level - Upper 1
Bathroom 2: 9 x 7 Level - Upper 1
Bathroom 3: 10 x 7 Level - Upper 1
Office: 10 x 7 Level - Upper 1
Bedroom 4: 13 x 10 Level - Upper 2
Half Bath: 10 x 6 Level - Upper 2

Local Schools

School District: TALBOT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Benson & Mangold, LLC
Agency Phone: 4107450415

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Estimated Payment

$ 4,216.18 per month $3,004.51 Principal & Interest $817.92 Property Tax $393.75 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/18/2026. The listing information on this page last changed on 03/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/18/2026 12:01:02 AM EST) or Bright MLS (last updated Tue 03/17/2026 11:50:02 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Lynsey Bennett 

16 Greenmeadow Drive, Suite 300, Timonium, MD 21093
410-561-0044

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