Change Real Estate Presents:

114 W Chestnut Street
Saint Michaels MD 21663

For Sale: $1,285,000.00 Active

List Date: 2026-03-17

Saint Michaels
4 bedrooms
5 bathrooms
3,528 build ft2
7,200 land ft2

About This Property

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.

Listing Agent: Winifred C Cowee. Benson & Mangold, LLC 410-310-0208 winkcowee@gmail.com

Property Features

Location Information
County:
Subdivision: NONE AVAILABLE
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Interior Features
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Washer, Water Heater - Tankless, WaterHeater, Refrigerator
Interior:
Laundry:
Furnished: None
Flooring: Hardwood, CeramicTile
Water: Public
Cooling: Other
Heating: Heat Pump(s)
Fireplaces: 3
Windows:
Utilities:
Sewer: Public Sewer
Rooms
Room Type: Bedroom 4
Features: Flooring - Carpet
Level: Upper 2
Room Type: Half Bath
Level: Upper 2
Room Type: Primary Bedroom
Features: Flooring - HardWood, Built-Ins, Walk-In Closet(s)
Level: Upper 1
Room Type: Primary Bathroom
Features: Flooring - Ceramic Tile, Bathroom - Soaking Tub, Bathroom - Walk-In Shower, Double Sink
Level: Upper 1
Room Type: Bedroom 2
Features: Flooring - HardWood, Fireplace - Wood Burning
Level: Upper 1
Room Type: Bathroom 2
Features: Flooring - Ceramic Tile
Level: Upper 1
Room Type: Bedroom 3
Features: Flooring - HardWood
Level: Upper 1
Room Type: Bathroom 3
Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Level: Upper 1
Room Type: Office
Features: Flooring - HardWood
Level: Upper 1
Room Type: Living Room
Features: Flooring - HardWood, Fireplace - Wood Burning, Built-Ins
Level: Main
Room Type: Dining Room
Features: Flooring - HardWood, Fireplace - Wood Burning, Built-Ins
Level: Main
Room Type: Kitchen
Features: Flooring - HardWood, Cathedral/Vaulted Ceiling, Countertop(s) - Quartz
Level: Main
Room Type: Family Room
Features: Flooring - HardWood, Fireplace - Wood Burning
Level: Main
Room Type: Great Room
Features: Flooring - Wood
Level: Main
Room Type: Bathroom 1
Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
Level: Main
Room Type: Laundry
Level: Main
Room Type: Mud Room
Features: Flooring - HardWood
Level: Main
Exterior Features
Year Built: 1850
Legal Subdivision: *
Subdivision Name: None Available
Exterior Features: Street Lights
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Winifred C Cowee. Benson & Mangold, LLC 410-310-0208 winkcowee@gmail.com

Property Photos [Click to enlarge]

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