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114 W Chestnut Street

SAINT MICHAELS, MD 21663
  • $1,350,000
  • STATUS: Active
  • ON SITE: 69 Days
  • ID#: MDTA2013116
$1,350,000
  • 4
    BEDS
  • 0.17
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 3,528
    SQFT
  • $383
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1850
County:

School Ratings & Info

School District:

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.

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©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or AJ Team Realty | EXP Realty. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-05-19T23:52:34.933.
www.ajteamrealty.com/homes/173974564
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114 W Chestnut Street SAINT MICHAELS, MD 21663

  • Price: $1,350,000
  • Status: Active
  • On Site: 69 Days
  • ID#: MDTA2013116
4
Beds
4
Baths
1
½ Baths
0.17
Acres
3,528
SQFT
$383
$/SQFT
1850
Built
Neighborhood:
None Available
County:
Talbot
School District:
Talbot County Public Schools
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.
Exterior Features

Architectural Style Traditional Construction Materials Frame Exterior Features Street Lights Garage YN No Other Structures Storage Barn/Shed Parking Types AlleyOn Street Pool Yes - Community Roof Architectural Shingle Water Access YN No Water View YN No Waterfront YN No

Interior Features

Above Grade Fin SQFT 3528 Appliances DishwasherDisposalDryerExhaust FanMicrowaveOven/Range - GasWasherWater Heater - TanklessWater HeaterRefrigerator Basement YN No Below Grade Finished Area 0 Below Grade Unfinished Area 0 Cooling Other Fireplace Features Wood Fireplace YN Yes Fireplaces Total 3 Flooring HardwoodCeramic Tile Heating Heat Pump(s) Heating YN Yes Levels 3 Main Level Bedrooms 0 Room List Living RoomDining RoomPrimary BedroomBedroom 2Bedroom 3Bedroom 4KitchenFamily RoomGreat RoomLaundryMud RoomOfficeBathroom 1Bathroom 2Bathroom 3Primary BathroomHalf Bath Rooms Total 17 Upper Level1 Bedrooms 3

Property Features

Accessibility Features None Association YN No Central Air YN No Condo YN No Cooling Fuel Electric Foundation Details Crawl Space Heating Fuel Electric Hot Water ElectricTankless Municipality Saint Michaels Navigable Water YN N New Construction YN No Original MLSNumber 804613870630 Ownership Interest Fee Simple Sale Type Standard Senior Community YN No Sewer Public Sewer Structure Design Type Detached Tax Annual Amount 9815.00 Vacation Rental YN No Water Source Public Zoning R-1

Listing courtesy of Benson & Mangold, LLC: .


©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or AJ Team Realty | EXP Realty. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-05-19T23:52:34.933.
 
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