Karla Wieland-Cherry
Meredith Fine Properties
(410) 339-8350
31 Total Sales
3 in Saint Michaels
$220K - $575K Price Range
121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.
Last Agent to Sell the Property
(410) 745-0415 info@bensonandmangold.com Benson & Mangold, LLC Brokerage Phone: 4107450415 License #575707 Listed on: 04/14/2026
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Karla Wieland-Cherry
Meredith Fine Properties
(410) 339-8350
31 Total Sales
3 in Saint Michaels
$220K - $575K Price Range
Charlotte Savoy
The KW Collective
(667) 771-4326
670 Total Sales
1 in Saint Michaels
$815,000 Price
Brian Gearhart
Benson & Mangold, LLC
(667) 243-8199
301 Total Sales
30 in Saint Michaels
$301K - $3.7M Price Range
Amy Juras
Long & Foster Real Estate, Inc.
(443) 214-3318
78 Total Sales
1 in Saint Michaels
$350,000 Price
Christopher Clinton
Coldwell Banker Chesapeake Real Estate Company
(410) 339-8206
7 Total Sales
7 in Saint Michaels
$193K - $1.5M Price Range
Christopher Coppola
Compass
(781) 463-5340
48 Total Sales
2 in Saint Michaels
$777K - $865K Price Range
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $1,395,000 | Chicago Title | |
| Deed | $405,000 | Venture Title Company Llc | |
| Deed | $250,000 | Eastern Shore Title Company | |
| Deed | $92,000 | -- |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $320,000 | New Conventional | |
| Previous Owner | $364,500 | New Conventional | |
| Previous Owner | $30,000 | Credit Line Revolving | |
| Previous Owner | $105,000 | Unknown |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/22/2026 06/22/26 | Sold | $1,395,000 | 0.0% | $549 / Sq Ft | |
| 04/15/2026 04/15/26 | Pending | -- | -- | -- | |
| 04/14/2026 04/14/26 | For Sale | $1,395,000 | +244.4% | $549 / Sq Ft | |
| 01/15/2016 01/15/16 | Sold | $405,000 | 0.0% | $231 / Sq Ft | View Prior Sale |
| 03/28/2015 03/28/15 | Rented | $1,600 | -8.6% | -- | |
| 03/27/2015 03/27/15 | Under Contract | -- | -- | -- | |
| 10/23/2014 10/23/14 | For Rent | $1,750 | +16.7% | -- | |
| 02/18/2012 02/18/12 | Rented | $1,500 | -6.3% | -- | |
| 02/03/2012 02/03/12 | Under Contract | -- | -- | -- | |
| 11/14/2011 11/14/11 | For Rent | $1,600 | -- | -- |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $6,641 | $751,233 | $0 | $0 |
| 2025 | $6,641 | $682,900 | $318,500 | $364,400 |
| 2024 | $6,534 | $643,433 | $0 | $0 |
| 2023 | $6,246 | $603,967 | $0 | $0 |
| 2022 | $5,989 | $564,500 | $304,000 | $260,500 |
| 2021 | $5,927 | $561,433 | $0 | $0 |
| 2020 | $5,927 | $558,367 | $0 | $0 |
| 2019 | $5,924 | $555,300 | $281,200 | $274,100 |
| 2018 | $4,124 | $386,667 | $0 | $0 |
| 2017 | $3,973 | $367,933 | $0 | $0 |
| 2016 | $3,361 | $349,200 | $0 | $0 |
| 2015 | $4,205 | $349,200 | $0 | $0 |
| 2014 | $4,205 | $349,200 | $0 | $0 |
Seller's Agent in 2026
Carolina Barksdale
Benson & Mangold, LLC
(443) 786-0348
33 Total Sales
Buyer's Agent in 2026
Wink Cowee
Benson & Mangold, LLC
(410) 310-0208
50 Total Sales
Seller's Agent in 2016
Dawn Lednum
Chesapeake Bay Real Estate Plus, LLC
(410) 829-3603
79 Total Sales
Buyer's Agent in 2015
Kate Koeppen
Chesapeake Bay Real Estate Plus, LLC
(410) 829-0705
28 Total Sales
Source: Bright MLS
MLS Number: MDTA2013474
APN: 02-060841
Ask me questions while you tour the home.