This stunning c. 1785 four-story masonry home has been carefully preserved, exhibiting significant historical integrity. It has undergone a meticulous 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 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.
Active
$9,600,000
55 E Bay St, Charleston, SC 29401
5beds
7,343sqft
Est.:
Single Family Residence
Built in 1785
8,276.4 Square Feet Lot
$9,171,600 Zestimate®
$1,307/sqft
$-- HOA
What's special
Cypress panelingPalmetto treesPrivate porchQuarter of an acreSpacious second-floor guest suiteElliptical fan lightCantilevered marble balcony
- 5 days
- on Zillow |
- 2,045 |
- 138 |
Zillow last checked: 7 hours ago
Listing updated: June 10, 2025 at 07:41am
Listed by:
The Boulevard Company
Source: CTMLS,MLS#: 25016001

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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Family Room, Office, Dining Room
Cooling
- Central Air
Appliances
- Laundry: Laundry Room
Features
- Ceiling - Cathedral/Vaulted, High Ceilings, Garden Tub/Shower, Walk-In Closet(s), Eat-in Kitchen, Formal Living, Pantry
- Windows: Window Treatments
- Has basement: Yes
- Has fireplace: Yes
- Fireplace features: Three +
Interior area
- Total structure area: 7,343
- Total interior livable area: 7,343 sqft
Property
Parking
- Parking features: Off Street, Other
Features
- Stories: 4
- Entry location: Ground Level
- Patio & porch: Screened
- Fencing: Wrought Iron
Lot
- Size: 8,276.4 Square Feet
Details
- Parcel number: 4581301068
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Roof: Slate
Condition
- New construction: No
- Year built: 1785
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Charleston Water Service, Dominion Energy
Community & HOA
Community
- Subdivision: South of Broad
Location
- Region: Charleston
Financial & listing details
- Price per square foot: $1,307/sqft
- Tax assessed value: $3,770,000
- Annual tax amount: $16,672
- Date on market: 6/9/2025
- Listing terms: Cash,Conventional
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