49 SMITH ST Charleston SC 29401-1718

Rare Mixed-Use / Investment Opportunity | Harleston Village | Charleston, SC

Positioned in the heart of Harleston Village, one of Downtown Charleston’s most sought-after and supply-constrained neighborhoods, 49 Smith Street presents a rare opportunity to acquire a historic income-producing asset with significant long-term upside and multiple exit strategies.​

Currently configured as 8 total income-producing units consisting of 7 residential units within the main house plus a separate carriage house residence, the property is generating approximately $25,775 per month in gross scheduled rent ($309,300 annually).​

The existing unit mix offers immediate cash flow with clear rental upside through lease optimization and premium furnished / executive rental strategies, while the true value lies in the property’s exceptional optionality.​

Investors and developers will recognize the rare opportunity to reposition the main residence into a premier single-family trophy home, similar to the neighboring comparable conversion, while preserving the detached carriage house as a guest residence, luxury rental, or ancillary structure.​ Additional potential exists for a unit-by-unit condominium sell-off strategy, subject to buyer verification and approvals.​

The property has benefited from approximately $450,000 in capital improvements completed throughout 2024–2025, significantly enhancing the asset and reducing near-term capital expenditure requirements.​

Additional value-add components include permitted pool plans, premium courtyard / outdoor living space, garage and carport parking, and the inherent scarcity of large-scale historic assets in Downtown Charleston.​

This is less a traditional multifamily cap-rate acquisition and more a high-barrier-to-entry trophy asset with multiple monetization pathways:

• ​stabilized hold with rental upside
• ​luxury single-family conversion
• ​condominium sell-off
• ​live / rent hybrid strategy

Opportunities of this scale and location in Harleston Village rarely come to market.​

• ​Trophy Harleston Village location in Downtown Charleston
• ​8 total units (7 in main residence + detached carriage house)
• ​$25,775/month gross scheduled rent
• ​$309,300 annual gross income
• ​Approx. $450,000 in capital improvements completed (2024–2025)
• ​Value-add rental upside through lease optimization
• ​Rare single-family conversion opportunity
• ​Potential condo sell-off / adaptive reuse strategy
• ​Permitted Aquatica pool plans included
• ​Garage, carport, and courtyard parking components
• ​High-barrier-to-entry historic Charleston asset
• ​Multiple exit strategies: hold, convert, condo, luxury end-user

Historic European-inspired villa estate in the heart of Harleston Village. 49 Smith Street is a landmark multifamily compound featuring eight residential units across a Circa 1860 front building and an 1881 carriage house. The exterior showcases original two-color English Flemish brick, soft white mortar, and hand-poured glass windows that provide abundant natural light and views of mature Cypress trees.

The property totals approximately 7,525 sq ft with 10 bedrooms, 10.5 bathrooms, multiple verandas, a garage, carport parking, and rooftop deck access from the two-story carriage house. The property underwent significant renovations in 2024 and 2025, including updated kitchens, bathrooms, appliances, flooring, interior finishes, and selective system upgrades throughout both structures. Seven units include in-unit laundry, with an additional shared laundry room on site. Multiple future options exist, including continued multifamily operation, potential condo conversion, or conversion of the buildings back into a single-family estate.

Located half a block from the Wentworth Mansion and within walking distance to Colonial Lake, restaurants, shops, hotels, and major historic landmarks. Floor plans and additional details available upon request. Showings require 24-hour notice. Offering 3% to Buyers Agent.