Under Contract

49 Smith Street

Charleston, SC 29401
Mark as Favorite
Bed 10

Bed

Bath 10.5

Bath

SqFt7,526

Sqft

Acres0.20

Acre(Lot)

Tucked within the heart of Harleston Village, 49 Smith Street presents an extraordinarily rare opportunity to own one of downtown Charleston's most distinctive historic compounds. Originally anchored by a circa 1860 main residence and complemented by a separate circa 1880 carriage house, this landmark European villa-style estate blends architectural pedigree, private compound living, and exceptional long-term potential across approximately 7,525 square feet. Behind its striking two-tone English Flemish brick facade, the property unfolds as a true multi-structure estate--an offering seldom found in one of Charleston's most sought-after neighborhoods. The sprawling three-story main residence encompasses over 5,000 square feet. It is currently configured as seven independent residences, many of which feature original fireplaces, stately wood interiors, hand-poured glass windows, and an abundance of natural light that pours through the historic façade. Complementing the main house is a fully private two-story carriage house exceeding 2,000 square feet, accessed through its own gated entry and complete with a garage, expansive porch, and elevated rooftop terrace. This secluded secondary residence offers an extraordinary living experience--ideal as a luxurious guest residence, private office, studio, or boutique retreat. What sets 49 Smith apart is the extraordinary balance of immediate utility and future vision. The opportunity to thoughtfully reimagine the main residence into one of Harleston Village's most compelling private homes has already been carefully explored, with preliminary architectural and construction guidance reinforcing the extraordinary potential of the estate. For the right buyer, this presents a rare chance to create a grand three-story historic residence while preserving the carriage house as a private, design-forward complement--an offering that would be exceptionally rare within the downtown Charleston market. Equally compelling is the lifestyle this property affords today. Morning light filters through the hand-poured glass windows, illuminating preserved historic interiors and rich architectural details. Evenings unfold across the veranda patios and rooftop terrace, creating a layered indoor-outdoor living experience that feels both private and deeply connected to the rhythm of downtown Charleston. Just moments from Colonial Lake, King Street, Broad Street, and the iconic Wentworth Mansion, the location offers a walkable lifestyle surrounded by Charleston's most celebrated architecture, dining, shopping, and cultural landmarks. Whether envisioned as a legacy private residence, a multi-generational compound, or an income-producing hold with exceptional upside, 49 Smith Street offers a level of scale, flexibility, and architectural significance that is rarely available. This is more than a property--it is a once-in-a-generation opportunity to steward one of Harleston Village's most remarkable estates into its next chapter.

Read More Expand

Detail Ic Property Details

Property Type : Residential

Price : $5,500,000

AD Id : 76681151

MLS Id : 26009115

Beds : 10

Lot Size : 0.20 Acre

Living Area Size : 7,526

Year Built : 1860

Garage : 1

County : Charleston

Subdivision: Harleston Village

  • Map Map

Map

Map What's Nearby

Map Nearby Areas

Feature Features

  • Bathroom Information

    Full Baths: 10 Half Baths: 1
  • Flooring Information

    Other
  • Roofing Information

    Built-Up, Metal
  • Interior Features

    See Remarks, Other Roof: Built-Up, Metal
  • Heating & Cooling

    Heating: Electric Cooling: Central Air, Window Unit(s) WaterSource: Public

  • Building Information

    Year Built: 1860 Construction Materials: Brick, See Remarks, Stucco
  • Exterior Features

    Garden
    Foundation Details: Other
    Porch: Covered

  • Lot Information

    Lot Description: 0 - .5 Acre, Other Lot Size Area: 0.2 Lot Size Units: Acres Lot Square Feet: 8,712 Lot Acres: 0.2 Stories: 3 Main Square Feet: 0.2

    Property Information

    Property Type: Residential Sub Type: Single Family DetachedStyle: Villa Subdivision: Harleston Village

  • Elementary School: Memminger
    Junior High School: Simmons Pinckney
    Senior High School: Burke
  • Utility Information

    Charleston Water Service, Dominion Energy
  • Location Information

    Direction: Located On Smith Between Wentworth And Montagu. Steps Away From The Wentworth Mansion.
Sell a home like this and save $329,501 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
4 S Adgers Wharf, Charleston, SC, 29401 $5,850,000 4 3.5 4,022 4,022 SqFt
18 Boyces Wharf, Charleston, SC, 29401 $5,450,000 3 4.5 3,363 3,363 SqFt
4 Tradd Street, Charleston, SC, 29401 $1,999,000 3 2 1,366 1,366 SqFt
87 East Bay Street #D, Charleston, SC, 29401 $1,195,000 1 1 745 745 SqFt
2 Water Street, Charleston, SC, 29401 $13,750,000 6 6.5 7,183 7,183 SqFt
2 Laurens Street #4F, Charleston, SC, 29401 $3,550,000 3 3.5 3,790 3,790 SqFt
25 East Battery Street, Charleston, SC, 29401 $28,000,000 6 6.5 11,367 11,367 SqFt
15 Broad Street, Charleston, SC, 29401 $2,995,000 -- -- 7,024 7,024 SqFt
4 Bedons Alley, Charleston, SC, 29401 $4,950,000 3 2.5 2,702 2,702 SqFt
12 A Bedons Alley, Charleston, SC, 29401 $2,575,000 2 2.0 1,670 1,670 SqFt

Copyright © 2026 by the Multiple Listing Service of the Charleston Trident Association of Realtors® (CTAR). This information is believed to be accurate but is not guaranteed. Subject to verification by all parties. This data is copyrighted and may not be transmitted, retransmitted, copied, framed, repurposed, or altered in any way for any other site, individual and/or purpose without the express written permission of the Multiple Listing Service of the Charleston Trident Association of Realtors® (CTAR). Information Deemed Reliable But Not Guaranteed. Any use of search facilities of data on this site, other than by a consumer looking to purchase real estate, is prohibited.

ByOwner last updated this listing 06/10/2026 @ 19:25

MLS: 26009115 LISTED BY: Harrison Bocook, EXP Realty LLC SOURCE: CHS Regional MLS

Selling? Save $329,501 when you sell a home like this

Tour with a ByOwner Agent