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$1,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,540 Sq. Ft.
  • Updated 7 hours ago
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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.

Full Property Details for 121 W Chestnut

General

  • Price: $1,395,000
  • Taxes: $8,592 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2013474
  • Updated: Today (4/14/2026)
  • Added to Site: Today

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Foyer, Laundry, Mud Room, Office, Bathroom 2, Primary Bathroom, Half Bath
  • Interior Features: Attic, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Ceiling Fan(s), Crown Moldings, Double/Dual Staircase, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Recessed Lighting, Formal/Separate Dining Room, Wood Floors, Additional Stairway, Walk-in Closet(s), Window Treatments
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane, Mantel(s)
  • Appliances: Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Range Hood, Refrigerator, Washer, Stainless Steel Appliances

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Other Rooms

  • Laundry: Main Floor

Exterior

  • Exterior Features: Outbuilding(s)

Parking

  • Parking Type: On Street

Location

  • Municipality: Saint Michaels
  • County: TALBOT
  • Subdivision: HISTORIC DISTRICT
  • Driving Directions: Talbot Street to left on West Chestnut, property on right towards end, no sign
  • City Limits: Yes

School Information

  • School District: Talbot County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Ductless/Mini-Split
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Other
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 300 Feet

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Crawl Space
  • Stories Description: Main, Upper 1
  • Square Feet: 2,540
  • Sq. Ft. Source: Assessor
  • Living Area: 2,540 Sq. Ft.
  • Finished Above Grnd: 2,540 Sq. Ft.
  • Year Built: 1890
  • Year Built Source: Assessor
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Carriage House

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,500
  • Lot Size Source: Assessor
  • Lot Dimensions: 60.00 x
  • Zoning: R
  • Lot Description: Landscaping

Water Features

  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Canoe/Kayak
  • Water Front Type: River
  • Water Front Name: San Domingo Creek

Financial Considerations

  • Price Per Sq. Ft.: $549.21
  • Assessment Year: 2026
  • City/TownTax: $3,209
  • City/TownTax Freq: Annually
  • County Tax: $5,383
  • County Tax Freq: Annually
  • Tax w/Assessment: $751,233
  • Tax Amount: $8,592
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2540

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Benson & Mangold, LLC, Carolina Barksdale

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Listing agent

— 121 W Chestnut —

  • Carolina Barksdale

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 121 W Chestnut

School District:Talbot County Public Schools
NameGradesDistance
St. Michaels Elementary School
100 Seymour Avenue, Saint Michaels, MD 21663
PK-60.5 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-120.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 121 W Chestnut Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/14/2026
Listed
$1,395,000
244.44%
MLS
1/15/2016
Sold
$405,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 121 W Chestnut

Year
Property Taxes
Change
Tax Assessment
Change
2023
$6,303
—
$682,900
6%
2023
$6,303
—
$643,433
7%
2023
$6,303
-3%
$603,967
7%
2022
$6,531
9%
$564,500
1%
2020
$5,981
1%
$561,433
1%
2021
$5,927
—
$558,367
1%
2020
$5,924
44%
$555,300
44%
2019
$4,124
4%
$386,667
5%
2018
$3,973
15%
$367,933
5%
2017
$3,465
2%
$349,200
—
2016
$3,391
1%
$349,200
—
2015
$3,359
-15%
$349,200
-16%
2014
$3,955
—
$417,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Carolina Barksdale

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121 W Chestnut, Saint Michaels, MD 21663 (MLS# MDTA2013474) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 121 W Chestnut is currently listed for $1,395,000 and was received on April 14, 2026. Want to learn more about 121 W Chestnut? Do you have questions about finding other Single Family real estate for sale in Saint Michaels? You can browse all Saint Michaels real estate or contact a Coldwell Banker agent to request more information.

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