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114 W Chestnut Street Saint Michaels, MD $ 1,350,000
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$ 1,350,000 Get more info
114 W Chestnut Street
$ 1,350,000
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114 W Chestnut Street

Saint Michaels, MD, 21663
$ 1,350,000
Bedrooms4 Baths4.1 Sq 3,528

Monthly Estimate*

$ 8,312

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Single Family Home for sale in Saint Michaels, MD

for $1,350,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,528 square foot home was built in 1850 on a lot size of 0.17.

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 towns 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 homes 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 Marylands most desirable waterfront communities.

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Single Family Active

Price

$ 1,350,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 9,815

Style

Traditional

Lot Size

0.17

Year Built

1850

Town/City

Saint Michaels

County/Region

Talbot

MLS | Web ID

MDTA2013116
Features
General
Living Area 3528
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Other
Possession Settlement
Roof Architectural Shingle
Appliances Dishwasher Disposal Dryer Exhaust Fan Microwave Oven/Range - Gas Washer Water Heater - Tankless Water Heater Refrigerator
Zoning R-1
Architectural Style Traditional
Construction Materials Frame
School District TALBOT COUNTY PUBLIC SCHOOLS
Year Built 1850
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Municipality Saint Michaels
Accessibility None
County TALBOT
New Construction N
Property Type Residential
HOA N
Subdivision Name NONE AVAILABLE
Garage Y/N N
Water Access Y/N N
Other Structures Above Grade Below Grade
Total Rooms 17
Full Baths 4
Status ACTIVE
Directions From Easton: Rt. 33 to St. Michaels. Left on W. Chestnut. House on left. Sign posted.
City SAINT MICHAELS
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 7200.00
Tax Annual Amount 9815.0
Home Warranty Y/N N
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 1
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 382.65
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
Legal Subdivision *
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Interior
Heating Fuel Electric
Flooring Hardwood Ceramic Tile
Total Fireplaces 3
Fireplace Features Wood
Hot Water Electric Tankless
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 3528
Half Baths 1
Central Air Y/N N
Total Bedrooms 4
Below Grade Finished Area 0
Room Type Living Room Dining Room Primary Bedroom Bedroom 2 Bedroom 3 Bedroom 4 Kitchen Family Room Great Room Laundry Mud Room Office Bathroom 1 Bathroom 2 Bathroom 3 Primary Bathroom Half Bath
Main Level Bedrooms 0
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 5
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Exterior
Exterior Amenities Street Lights
Pool Yes - Community
Water Source Public
Type of Parking Alley On Street
Foundation Details Crawl Space
Water View Y/N N
Lot Size Acres 0.17
Lot Size Source Assessor
Waterfront Y/N N
Land Assessed Value 417300.00
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 114
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* Excluded Features
List By
Benson & Mangold, Llc

Broker

winkcowee@gmail.com

Email

Affordability Calculator

$9,130
Per Month
91%
9%
0%
Monthly Principal & Interest
$8,312
Monthly Property Taxes
$818
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3533924 Elementary School
3534231 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
3/12/2026$1,350,000 Listed Price

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114 W Chestnut Street, Saint Michaels, MD, 21663 is a Single Family Home for sale at $1,350,000 with 3,528 sqft and a lot size of 0.17. 114 W Chestnut Street has 4 bedrooms, 4.1 baths, and was built in 1850. The property's zip code is 21663 which is in Saint Michaels, MD

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