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.
Sold for $1,395,000
$1,395,000
121 W Chestnut St, St Michaels, MD 21663
3beds
2,540sqft
Single Family Residence
Built in 1890
7,500 Square Feet Lot
$1,388,600 Zestimate®
$549/sqft
$2,804 Estimated rent
Home value
$1,388,600
$1.22M - $1.57M
$2,804/mo
Zestimate® history
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List your homeWhat's special
Decorative fireplaceBuilt insWood flooringWood shingle sidingSitting roomAmple cabinet spaceFarm sink
Zillow last checked:
Listing updated:
Listed by:
Carolina Barksdale 443-786-0348,
Benson & Mangold, LLC
Bought with:
Wink Cowee, 16686
Benson & Mangold, LLC
Source: Bright MLS,MLS#: MDTA2013474
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Foyer, Laundry, Office, Bathroom 2, Primary Bathroom, Half Bath
Primary bedroom
- Features: Ceiling Fan(s), Attached Bathroom, Flooring - HardWood, Walk-In Closet(s)
- Level: Upper
Bedroom 2
- Features: Ceiling Fan(s), Flooring - HardWood, Window Treatments
- Level: Upper
Bedroom 3
- Features: Ceiling Fan(s), Flooring - HardWood
- Level: Upper
Primary bathroom
- Features: Bathroom - Walk-In Shower, Flooring - Ceramic Tile
- Level: Upper
Bathroom 2
- Features: Flooring - Ceramic Tile, Window Treatments, Double Sink
- Level: Upper
Dining room
- Features: Flooring - HardWood, Built-in Features, Crown Molding
- Level: Main
Foyer
- Features: Flooring - HardWood
- Level: Main
Half bath
- Level: Main
Kitchen
- Features: Granite Counters, Countertop(s) - Quartz, Flooring - Wood, Kitchen Island, Lighting - Ceiling, Kitchen - Gas Cooking, Lighting - Pendants, Recessed Lighting
- Level: Main
Laundry
- Level: Main
Living room
- Features: Fireplace - Gas, Built-in Features, Ceiling Fan(s), Crown Molding
- Level: Main
Mud room
- Level: Main
Office
- Features: Flooring - HardWood
- Level: Upper
Heating
- Heat Pump, Other, Electric
Cooling
- Central Air, Ceiling Fan(s), Ductless, Electric
Appliances
- Included: Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven, Range Hood, Refrigerator, Washer, Stainless Steel Appliance(s), Electric Water Heater
- Laundry: Main Level, Laundry Room, Mud Room
Features
- Attic, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-in Features, Ceiling Fan(s), Crown Molding, Double/Dual Staircase, Kitchen - Gourmet, Kitchen Island, Primary Bath(s), Recessed Lighting, Formal/Separate Dining Room, Additional Stairway, Walk-In Closet(s)
- Flooring: Wood
- Windows: Window Treatments
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Gas/Propane, Mantel(s)
Interior area
- Total structure area: 2,540
- Total interior livable area: 2,540 sqft
- Finished area above ground: 2,540
- Finished area below ground: 0
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Pool features: None
- Waterfront features: Canoe/Kayak, River
- Body of water: San Domingo Creek
Lot
- Size: 7,500 Square Feet
- Dimensions: 60.00 x
- Features: Landscaped
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 2102060841
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Crawl Space
Condition
- Excellent
- New construction: No
- Year built: 1890
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Historic District
HOA
- Has HOA: No
Location
- Region: St Michaels
- Municipality: Saint Michaels
Financial & listing details
- Price per square foot: $549/sqft
- Tax assessed value: $751,233
- Annual tax amount: $8,592
- Date on market: 4/14/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 6/22/2026 | Sold | $1,395,000$549/sqft |
Source:  Bright MLS #MDTA2013474 Report a problem | ||
| 4/27/2026 | Pending sale | $1,395,000$549/sqft |
Source: Bright MLS #MDTA2013474 Report a problem | ||
| 4/16/2026 | Contingent | $1,395,000$549/sqft |
Source: Bright MLS #MDTA2013474 Report a problem | ||
| 4/14/2026 | Listed for sale | $1,395,000+244.4%$549/sqft |
Source: Bright MLS #MDTA2013474 Report a problem | ||
| 1/19/2016 | Sold | $405,000-9%$159/sqft |
Source: Public Record Report a problem | ||
| 12/3/2015 | Pending sale | $445,000$175/sqft |
Source: Chesapeake Bay Real Estate Plus LLC #TA8265179 Report a problem | ||
| 8/27/2015 | Price change | $445,000-4.3%$175/sqft |
Source: Chesapeake Bay Real Estate Plus LLC #TA8265179 Report a problem | ||
| 3/13/2015 | Price change | $465,000+26471.4%$183/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8265179 Report a problem | ||
| 2/23/2015 | Price change | $1,750-99.6%$1/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8487634 Report a problem | ||
| 10/29/2014 | Price change | $465,000-4.1%$183/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8265179 Report a problem | ||
| 2/4/2014 | Listed for sale | $485,000+94%$191/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #TA8265179 Report a problem | ||
| 3/18/2011 | Sold | $250,000-33.3%$98/sqft |
Source: Public Record Report a problem | ||
| 9/26/2010 | Price change | $375,000-24.2%$148/sqft |
Source: Champion Realty #TA7441465 Report a problem | ||
| 6/25/2010 | Price change | $495,000-9.2%$195/sqft |
Source: Lacaze Meredith Real Estate #TA7349720 Report a problem | ||
| 5/30/2010 | Listed for sale | $545,000+7.9%$215/sqft |
Source: Lacaze Meredith Real Estate #TA7349720 Report a problem | ||
| 1/14/2010 | Listing removed | $505,000$199/sqft |
Source: Lacaze Meredith Real Estate #TA7220345 Report a problem | ||
| 12/31/2009 | Listed for sale | $505,000$199/sqft |
Source: Lacaze Meredith Real Estate #TA7220345 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $682,900 +6.1% |
| 2024 | $8,017 +10.8% | $643,433 +6.5% |
| 2023 | $7,239 +10.8% | $603,967 +7% |
| 2022 | $6,531 +1.5% | $564,500 +0.5% |
| 2021 | $6,435 +0.5% | $561,433 +0.5% |
| 2020 | $6,400 +0.6% | $558,367 +0.6% |
| 2019 | $6,365 +47.6% | $555,300 +43.6% |
| 2018 | $4,312 +8.5% | $386,667 +5.1% |
| 2017 | $3,973 +18.2% | $367,933 +5.4% |
| 2016 | $3,361 | $349,200 |
| 2015 | $3,361 -20.1% | $349,200 |
| 2014 | $4,205 | $349,200 -16.3% |
| 2013 | -- | $417,200 |
| 2012 | -- | $417,200 |
| 2011 | -- | $417,200 -16.5% |
| 2010 | -- | $499,500 +9.1% |
| 2009 | -- | $457,680 +10.1% |
| 2008 | -- | $415,860 +11.2% |
| 2007 | -- | $374,040 +15% |
| 2006 | -- | $325,242 +17.7% |
| 2005 | -- | $276,446 +21.4% |
| 2004 | -- | $227,650 +16.5% |
| 2003 | -- | $195,460 +19.7% |
| 2002 | -- | $163,270 +24.6% |
| 2001 | -- | $131,080 |
Find assessor info on the county website
Neighborhood: 21663
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Nearby schools
GreatSchools rating
- 8/10St. Michaels Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 6/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 0.4 mi
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,388,600
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Estimated market value
$1,388,600
- Maryland
- Talbot County
- Saint Michaels
- 21663
- 121 W Chestnut St
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