Curious about this home?

Ask anything — no agents, no pressure

Try asking

About This Home

This 10-bedroom, 11-bathroom single family at 49 Smith Street in Charleston, SC is listed for $5,500,000 ($731 per sqft). Built in 1860, the home offers 7,526 sqft of living space on a 0.20 acres lot.

Agent Description

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 architectura

l 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 facade.

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 ex

ceptional 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.

Key Features

  • Built in 1860
  • 0.20 acre lot
  • 3 stories
  • 1 parking spaces
  • Fireplace

Property Details

3 stories
10 full, 1 half
1 space
1860

Amenities

FireplaceA/C

Monthly Cost Estimate

$29,415/mo

20% down · 6.5% · 30 years

Principal$3,978
Interest$23,833
Insurance$1,604

Estimates only. Actual payments may vary.

Location

49 Smith Street

Charleston, SC 29401

Harleston Village

Features & Amenities

Exterior Features

Garden

Property Details

Construction

Brick Stucco

Parking

Garage

Heating

Electric (Heating)

Cooling

Central AirWindow Unit(s)

Questions & Answers

This 10-bedroom, 11-bathroom single family at 49 Smith Street is listed at $5,500,000 ($731/sqft). The estimated monthly payment is $23,833 based on 20% down at 6.5% interest.

Key features include: Built in 1860, 0.20 acre lot, 3 stories, 1 parking spaces, Fireplace. Exterior Features: Garden.

This property is listed by Harrison Bocook and can be reached at (888) 440-2798 or hjmbocook@gmail.com.

Similar Homes in Charleston

View all
HB

Harrison Bocook

Agent at EXP Realty LLC

(888) 440-2798

Listed by EXP Realty LLC

MLS# 26009115· Source: listhub· Updated 8 days ago

Copyright © 2026 CHS Regional MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

49 Smith Street, Charleston, SC 29401

Open this listing in: