114 W CHESTNUT ST, Saint Michaels, MD 21663

• 4 beds |
• 5 baths |
• 3,528 sqft

Property Description

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 Status:

Active

Date Added:

March 17, 2026

Data Last Updated:

July 6, 2026 at 8:21PM

Listing Office:

Benson & Mangold, LLC : 4107450415

Listing Agent:

Winifred C Cowee : 4103100208

MLS ID:

MDTA2013116

Interior

• Rooms: Living RoomDining RoomPrimary BedroomBedroom 2Bedroom 3Bedroom 4KitchenFamily RoomGreat RoomLaundryMud RoomOfficeBathroom 1Bathroom 2Bathroom 3Primary BathroomHalf Bath
• Appliances: DishwasherDisposalDryerExhaust FanMicrowaveOven/Range - GasWasherWater Heater - TanklessWaterHeaterRefrigerator
• Flooring: HardwoodCeramic tile
• A/C: Other
• Heating: Heat Pump(s)Electric
• Fireplace: WoodFireplaceFireplaces: 3
• Disability Feature: None

Exterior

• General: Street LightsAbove GradeBelow Grade
• Style: Traditional

Construction

• Roofing: Architectural Shingle
• General: Frame3Crawl Space

Location

• Originating MLS: BRIGHT_MAIN
• School District: TALBOT COUNTY PUBLIC SCHOOLS
• County: TALBOT-MD

Lot

• Zoning: R-12102064200

Utilities

• Water: Public
• Sewer: Public Sewer

Financial

• Source: BRIGHT_MAIN