55 Bay Street : The Brennaman Group

The Brennaman Group > Charleston > South Of Broad > 55 Bay Street

55 Bay Street, Charleston, SC 29401 $8,995,000

At just $8,995,000, 55 Bay Street is the least expensive 5 bedroom home for sale in the South Of Broad neighborhood of Charleston.

Bedrooms 5

Full Bathrooms 5

SqFt 7,343

Updated 11/14/2025

Half Bathrooms 1

Price/SqFt $1,225

General Features

Category Residential

Style Charleston Single

Stories 4

Lot Description 0 - .5 Acre

County Charleston

City Charleston

Subdivision South Of Broad

MLS number 25024554 (Active)

Address 55 Bay Street, Charleston, SC 29401 US

Listing Provided by The Boulevard Company

Sale Type Not an Auction

MLS Area 51 - Peninsula Charleston Inside of Crosstown

Description : This stunning c.

This stunning c. 1785 four-story masonry home has been carefully preserved, exhibiting significant historical integrity. It has undergone an extensive renovation, elegantly updated to accommodate modern living and entertaining. Book-ended by Rainbow Row and High Battery, the Jonathan Simpson House was built within the original walled city by a wealthy merchant. Twelve-foot ceilings and grand rooms allow the house to be filled with light. The pine floors run the full extent of the house (28'). Much of the original molding, cypress paneling, doors, and interior shutters remain. The current owners created a hyphen to connect the original home and kitchen house under the direction of renowned Charleston architects Dufford Young, with construction by Artis, winning a 2019 Carolopolis Award.The project allowed for a new side garden design by Sheila Wertimer. The gourmet kitchen features a butler's pantry, mudroom, and floor-to-ceiling steel doors overlooking the side garden. The former kitchen house now features a spacious second-floor guest suite or office and a large secondary living room flanked by original fireplaces, as well as access to the screened porch overlooking the magnificent backyard that encompasses nearly a quarter of an acre of peace and tranquility. Plans were created for a 10' x 30' swimming pool and have been approved by the city. The existing custom-built "shed" could be easily converted to a pool house with bathroom. The original staircase remains, rising eloquently for all four flights, one of the tallest in the city. The second floor of the home has a 21x25 drawing room with five floor-to-ceiling windows. Across the hall, a primary suite with a fireplace and a private porch overlooking historic rooftops and palmetto trees. The third floor includes two spacious bedrooms, both with en-suite bathrooms, as well as a laundry room. The front bedroom offers clear views of Charleston Harbor. The back bedroom offers a private porch that's perched in the palmetto trees. The fourth floor is laid out as a two-room guest suite with a full bathroom and a living room, incredible historic and water views from every window. Of significant architectural interest is the cantilevered marble balcony, which projects from the second floor and is the only one in Charleston constructed in this manner. The elliptical fan light and the use of tall, glazed windows typify the work of the Adam period. Also of notable distinction is the detailed woodwork and roping around the door frame, which makes this one of the more attractive entrances in historic Charleston. The home retains architectural features of the late Georgian period, also embracing the ornamentation that more closely resembles the Adam style or the Federal period of architectural development.

Exterior Features

Exterior Block,Stucco

Foundation Basement

Roof Slate

Water / Sewer Public Sewer

Misc. Exterior Lawn Irrigation

Interior Features

Fireplace Three +

Master Bedroom Garden Tub/Shower Combo,Multiple Closets,Walk-In Closet(s)

Cooling Central Air

Schools

Elementary School
Memminger

Middle School
Courtenay

High School
Burke

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Properties marked with the Broker Reciprocity logo are provided courtesy of Charleston Trident Multiple Listing Service, Inc. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Charleston Trident Multiple Listing Service. Real estate listings held by brokerage firms other than the website owner are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. The broker providing this data believes it to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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