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114 W Chestnut Street photo 1
for sale
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$1,195,000

4beds
|
5baths
|
3,528sqft
|
1850built
114 W Chestnut Street,Saint Michaels, MD 21663

Est.$7,858/moCustomize payment

What's special

$339/sqft

Price per square foot

Built in 1850

176 years old

Overview

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 ...

Listing updated: June 12, 2026 at 3:51 PM

Listed by:

Winifred C Cowee 4103100208, Benson & Mangold, LLC

Source: Bright MLS · MLS #MDTA2013116Bright MLS

Property details

Cost estimate

Est. monthly payment

$7,481/mo
Principal & interest
$6,264
Property tax
$818
Home insurance (est.)
$398

Down payment

$239,00020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($239,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
Jun 12, 2026Price reduced$1,195,000($90,000)
May 29, 2026Price reduced$1,285,000($65,000)
Mar 17, 2026Listed for sale$1,350,000

Location

114 W Chestnut Street, Saint Michaels, MD 21663

Recently sold nearby

Similar homes sold within 0.5 miles in the last 90 days.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Nearby homes

$1,195,000

4 beds · 5 baths · 3,528 sqft

Bright MLS

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated: 7/2/2026.