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 historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.
For sale
Price cut: $90K (6/12)
$1,195,000
114 W Chestnut St, St Michaels, MD 21663
4beds
3,528sqft
Single Family Residence
Built in 1850
7,200 Square Feet Lot
$1,161,100 Zestimate®
$339/sqft
$-- HOA
What's special
Sought-after waterfront-adjacent locationFour wood-burning fireplacesDedicated officeCustom built-insGenerous storageTimeless architectureHardwood floors throughout
- 108 days |
- 978 |
- 31 |
Zillow last checked:
Listing updated:
Listed by:
Wink Cowee 410-310-0208,
Benson & Mangold, LLC (410) 745-0415
Source: Bright MLS,MLS#: MDTA2013116
Loading...
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Great Room, Laundry, Office, Bathroom 1, Bathroom 2, Bathroom 3, Primary Bathroom, Half Bath
Primary bedroom
- Features: Flooring - HardWood, Built-in Features, Walk-In Closet(s)
- Level: Upper
- Area: 374 Square Feet
- Dimensions: 17 X 22
Bedroom 2
- Features: Flooring - HardWood, Fireplace - Wood Burning
- Level: Upper
- Area: 180 Square Feet
- Dimensions: 12 X 15
Bedroom 3
- Features: Flooring - HardWood
- Level: Upper
- Area: 132 Square Feet
- Dimensions: 11 X 12
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
- Area: 130 Square Feet
- Dimensions: 10 X 13
Primary bathroom
- Features: Flooring - Ceramic Tile, Soaking Tub, Bathroom - Walk-In Shower, Double Sink
- Level: Upper
- Area: 104 Square Feet
- Dimensions: 8 X 13
Bathroom 1
- Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
- Level: Main
- Area: 77 Square Feet
- Dimensions: 7 X 11
Bathroom 2
- Features: Flooring - Ceramic Tile
- Level: Upper
- Area: 63 Square Feet
- Dimensions: 7 X 9
Bathroom 3
- Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
- Level: Upper
- Area: 70 Square Feet
- Dimensions: 7 X 10
Dining room
- Features: Flooring - HardWood, Fireplace - Wood Burning, Built-in Features
- Level: Main
- Area: 180 Square Feet
- Dimensions: 12 X 15
Family room
- Features: Flooring - HardWood, Fireplace - Wood Burning
- Level: Main
- Area: 300 Square Feet
- Dimensions: 12 X 25
Great room
- Features: Flooring - Wood
- Level: Main
- Area: 475 Square Feet
- Dimensions: 19 X 25
Half bath
- Level: Upper
- Area: 60 Square Feet
- Dimensions: 6 X 10
Kitchen
- Features: Flooring - HardWood, Cathedral/Vaulted Ceiling, Countertop(s) - Quartz
- Level: Main
- Area: 121 Square Feet
- Dimensions: 11 X 11
Laundry
- Level: Main
- Area: 49 Square Feet
- Dimensions: 7 X 7
Living room
- Features: Flooring - HardWood, Fireplace - Wood Burning, Built-in Features
- Level: Main
- Area: 165 Square Feet
- Dimensions: 11 X 15
Mud room
- Features: Flooring - HardWood
- Level: Main
- Area: 70 Square Feet
- Dimensions: 10 X 7
Office
- Features: Flooring - HardWood
- Level: Upper
- Area: 70 Square Feet
- Dimensions: 7 X 10
Heating
- Heat Pump, Electric
Cooling
- Other, Electric
Appliances
- Included: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Washer, Tankless Water Heater, Water Heater, Refrigerator, Electric Water Heater
- Laundry: Laundry Room, Mud Room
Features
- Flooring: Hardwood, Ceramic Tile
- Has basement: No
- Number of fireplaces: 3
- Fireplace features: Wood Burning
Interior area
- Total structure area: 3,528
- Total interior livable area: 3,528 sqft
- Finished area above ground: 3,528
- Finished area below ground: 0
Property
Parking
- Parking features: Alley Access, On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Exterior features: Street Lights
- Pool features: Community
Lot
- Size: 7,200 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2102064200
- Zoning: R-1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Crawl Space
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1850
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: St Michaels
- Municipality: Saint Michaels
Financial & listing details
- Price per square foot: $339/sqft
- Tax assessed value: $850,067
- Annual tax amount: $9,815
- Date on market: 3/17/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$1,161,100
$1.10M - $1.22M
$3,971/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/12/2026 | Price change | $1,195,000-7%$339/sqft |
Source:  Bright MLS #MDTA2013116 Report a problem | ||
| 5/29/2026 | Price change | $1,285,000-4.8%$364/sqft |
Source: Bright MLS #MDTA2013116 Report a problem | ||
| 3/17/2026 | Listed for sale | $1,350,000+110.9%$383/sqft |
Source: Bright MLS #MDTA2013116 Report a problem | ||
| 7/15/2020 | Sold | $640,000-3%$181/sqft |
Source: Public Record Report a problem | ||
| 5/20/2020 | Pending sale | $660,000$187/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 3/21/2020 | Price change | $660,000-2.2%$187/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 3/13/2020 | Price change | $675,000-3.4%$191/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 2/21/2020 | Price change | $699,000-1.5%$198/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 2/7/2020 | Price change | $710,000-1.1%$201/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 1/8/2020 | Listed for sale | $718,000+19.9%$204/sqft |
Source: Chesapeake Bay Real Estate Plus, LLC #MDTA137092 Report a problem | ||
| 7/7/2017 | Sold | $599,000$170/sqft |
Source: Public Record Report a problem | ||
| 4/27/2017 | Pending sale | $599,000$170/sqft |
Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem | ||
| 4/8/2017 | Price change | $599,000-9.1%$170/sqft |
Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem | ||
| 3/10/2017 | Price change | $659,000-2.9%$187/sqft |
Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem | ||
| 3/8/2017 | Listing removed | $3,000$1/sqft |
Source: Long & Foster Real Estate, Inc. #TA9836895 Report a problem | ||
| 1/20/2017 | Listed for rent | $3,000$1/sqft |
Source: Long & Foster Real Estate, Inc. #TA9836895 Report a problem | ||
| 10/15/2016 | Price change | $679,000-2.9%$192/sqft |
Source: Long & Foster Real Estate, Inc. #TA9789211 Report a problem | ||
| 9/12/2016 | Price change | $699,000-5.5%$198/sqft |
Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem | ||
| 7/26/2016 | Price change | $739,999-3.8%$210/sqft |
Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem | ||
| 6/10/2016 | Price change | $769,000-2.5%$218/sqft |
Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem | ||
| 5/4/2016 | Price change | $789,000-2.5%$224/sqft |
Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem | ||
| 3/31/2016 | Price change | $809,000-3.6%$229/sqft |
Source: Long & Foster Real Estate, Inc. #TA9562370 Report a problem | ||
| 2/2/2016 | Listed for sale | $839,000+4.9%$238/sqft |
Source: Long & Foster Real Estate Inc. #TA9562370 Report a problem | ||
| 6/16/2013 | Listing removed | $799,950$227/sqft |
Source: Lacaze-Meredith Real Estate, A Long & Foster Company #TA7991629 Report a problem | ||
| 5/20/2013 | Listed for sale | $799,950+7.2%$227/sqft |
Source: Lacaze-Meredith Real Estate, A Long & Foster Company #TA7991629 Report a problem | ||
| 8/18/2005 | Sold | $746,000+29.7%$211/sqft |
Source: Public Record Report a problem | ||
| 11/26/2003 | Sold | $575,000+51.7%$163/sqft |
Source: Public Record Report a problem | ||
| 9/7/2000 | Sold | $379,000$107/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $780,100 +8.5% |
| 2024 | $8,961 +13.6% | $719,200 +9.3% |
| 2023 | $7,890 +14.1% | $658,300 +10.2% |
| 2022 | $6,912 +0.9% | $597,400 |
| 2021 | $6,847 | $597,400 |
| 2020 | $6,847 -11.6% | $597,400 -11.6% |
| 2019 | $7,744 +8.2% | $675,600 +5.3% |
| 2018 | $7,157 +9% | $641,833 +5.6% |
| 2017 | $6,566 +18.8% | $608,067 +5.9% |
| 2016 | $5,527 | $574,300 |
| 2015 | $5,527 -18.7% | $574,300 |
| 2014 | $6,802 | $574,300 -15.8% |
| 2013 | -- | $682,000 +0.4% |
| 2012 | -- | $679,520 +0.4% |
| 2011 | -- | $677,040 -14.7% |
| 2010 | -- | $793,610 +3.4% |
| 2009 | -- | $767,526 -2.1% |
| 2008 | -- | $784,193 +37.8% |
| 2007 | -- | $568,880 +11.7% |
| 2006 | -- | $509,252 +13.3% |
| 2005 | -- | $449,626 +15.3% |
| 2004 | -- | $390,000 +19.4% |
| 2003 | -- | $326,542 +24.1% |
| 2002 | -- | $263,086 +31.8% |
| 2001 | -- | $199,630 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 21663
Nearby schools
GreatSchools rating
- 5/10St. Michaels Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 5/10St. 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.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Maryland
- Talbot County
- Saint Michaels
- 21663
- 114 W Chestnut St
Nearby cities
Nearby zip codes
Other Saint Michaels Topics
