$1,195,000
 $6,415 est/mo Sourced by Back At You

114 W Chestnut St,ST MICHAELS, MD 21663

ST MICHAELS, MD 21663

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Description

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

Details

MLS #MDTA2014898
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive-bright
Year1850
Days On Site25
Listing Provided ByTTR Sotheby's International Realty | Robert D Lacaze

Features

Bed(s)4
Bath(s) 4 Total
SQ Feet3,528
Story(s)3
ZoningR-1
Acreage0.17

Interior

CoolingCentral A/C
Heating Yes / NoYes
HeatingHeat Pump(s)
AppliancesDishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Refrigerator, Washer, Water Heater, Water Heater - Tankless

Exterior

Exterior FeaturesStreet Lights
RoofArchitectural Shingle
Construction MaterialsFrame
Foundation DetailsCrawl Space

Parking

Garage Yes / NoNo

Utilities

UtilitiesCable TV, Electric Available

Taxes

Tax Annual Amount9815

Area Information

StateMD
CountyTALBOT MD
CityST MICHAELS
Zip Code21663
AreaTALBOT MD
Community NameNONE AVAILABLE
School DistrictTALBOT COUNTY PUBLIC SCHOOLS
Listing VS Median (in NONE AVAILABLE)
Price:
$1,195,000
low | high
Med:
$359,900
100% of Average
sqft:
3,528
low | high
Med:
1,589
100% of Average
$ / sqft:
$339
low | high
Med:
$226
83.131955836543% of Average
On site:
25
low | high
Med:
50
50% of Average
Sourced by Back At You

Market Activity 21663

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Learn More About This Property

StateMD
CountyTALBOT MD
CityST MICHAELS
Zip Code21663
AreaTALBOT MD
Community NameNONE AVAILABLE
School DistrictTALBOT COUNTY PUBLIC SCHOOLS
Listing VS Median (in NONE AVAILABLE)
Price:
$1,195,000
low | high
Med:
$359,900
100% of Average
sqft:
3,528
low | high
Med:
1,589
100% of Average
$ / sqft:
$339
low | high
Med:
$226
83.131955836543% of Average
On site:
25
low | high
Med:
50
50% of Average
Sourced by Back At You
Nearby Listings (Within 1/2 mile)
Price: $896K - $1.493M
sqft: 2,500 - 4,000
Listing Updated: September 15, 2026 at 6:53:44 PM PDT