Seller's Agent in 2026
Carolina Barksdale
Benson & Mangold, LLC
(443) 786-0348
34 Total Sales
121 W Chestnut St St. Michaels, MD 21663
Saint Michaels Area
3
Beds
2.5
Baths
2,540
Sq Ft
7,500
Sq Ft Lot
Highlights
- Home fronts navigable water
- Gourmet Kitchen
- Dual Staircase
- Canoe or Kayak Water Access
- Carriage House
- Wood Flooring
About This Home
As of June 2026121 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
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $8,592
Year Built
- Built in 1890
Lot Details
- 7,500 Sq Ft Lot
- Home fronts navigable water
- Landscaped
- Property is in excellent condition
Parking
- On-Street Parking
Home Design
- Carriage House
- Colonial Architecture
- Frame Construction
Interior Spaces
- 2,540 Sq Ft Home
- Property has 2 Levels
- Dual Staircase
- Built-In Features
- Crown Molding
- Ceiling Fan
- Recessed Lighting
- Fireplace Mantel
- Gas Fireplace
- Window Treatments
- Mud Room
- Entrance Foyer
- Living Room
- Formal Dining Room
- Home Office
- Wood Flooring
- Crawl Space
- Attic
Kitchen
- Gourmet Kitchen
- Built-In Convection Oven
- Cooktop with Range Hood
- Dishwasher
- Stainless Steel Appliances
- Kitchen Island
- Farmhouse Sink
Bedrooms and Bathrooms
- 3 Bedrooms
- En-Suite Bathroom
- Walk-In Closet
- Bathtub with Shower
- Walk-in Shower
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Outdoor Features
- Canoe or Kayak Water Access
- River Nearby
- Outbuilding
Utilities
- Ductless Heating Or Cooling System
- Central Air
- Heat Pump System
- Vented Exhaust Fan
- Electric Water Heater
- Municipal Trash
Listing and Financial Details
- Assessor Parcel Number 2102060841
Community Details
Overview
- No Home Owners Association
- Historic District Subdivision
Recreation
- 1 Community Docks
Ownership History
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
Name
Owned For
Owner Type
Purchase Details
Listed on
Apr 14, 2026
Closed on
Jun 22, 2026
Sold by
Bought by
Seller's Agent
Carolina Barksdale
Benson & Mangold, LLC
Buyer's Agent
Wink Cowee
Benson & Mangold, LLC
List Price
$1,395,000
Sold Price
$1,395,000
Views
15
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-14.91%
Purchase Details
Listed on
Feb 3, 2014
Closed on
Jan 15, 2016
Sold by
Bought by
Seller's Agent
Dawn Lednum
Chesapeake Bay Real Estate Plus, LLC
Buyer's Agent
Dawn Lednum
Chesapeake Bay Real Estate Plus, LLC
List Price
$485,000
Sold Price
$405,000
Premium/Discount to List
-$80,000
-16.49%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
12.58%
Original Mortgage
$364,500
Interest Rate
3.97%
Mortgage Type
New Conventional
Purchase Details
Closed on
Mar 17, 2011
Sold by
Bought by
Purchase Details
Closed on
Sep 16, 1991
Sold by
Bought by
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Home Values in the Area
Average Home Value in this Area
Purchase History
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 | -- |
Source: Public Records
Mortgage History
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 |
Source: Public Records
Property History
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 | -9.0% | $231 / Sq Ft | View Prior Sale |
| 12/03/2015 12/03/15 | Pending | -- | -- | -- | |
| 08/27/2015 08/27/15 | Price Changed | $445,000 | 0.0% | $254 / Sq Ft | |
| 03/28/2015 03/28/15 | Rented | $1,600 | -99.7% | -- | |
| 03/27/2015 03/27/15 | Under Contract | -- | -- | -- | |
| 10/28/2014 10/28/14 | Price Changed | $465,000 | 0.0% | $265 / Sq Ft | |
| 10/23/2014 10/23/14 | For Rent | $1,750 | 0.0% | -- | |
| 02/03/2014 02/03/14 | For Sale | $485,000 | 0.0% | $277 / Sq Ft | |
| 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 | -- | -- |
Source: Bright MLS
Tax History
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 |
|---|---|---|---|---|
| 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 |
Source: Public Records
Agents Affiliated with this Home
-
Carolina Barksdale
-
Wink Cowee
Buyer's Agent in 2026
Wink Cowee
Benson & Mangold, LLC
(410) 310-0208
51 Total Sales
-
Dawn Lednum
Seller's Agent in 2016
Dawn Lednum
Chesapeake Bay Real Estate Plus, LLC
(410) 829-3603
1 in this area
80 Total Sales
-
Kate Koeppen
Buyer's Agent in 2015
Kate Koeppen
Chesapeake Bay Real Estate Plus, LLC
(410) 829-0705
28 Total Sales
Map
Source: Bright MLS
MLS Number: MDTA2013474
APN: 02-060841
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