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$3,875,000
7 Beds ⋅ 26026897 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
Stunning, turnkey short-term rental opportunity in the heart of downtown Charleston. This exceptional two-unit property features a total of 7 bedrooms and 7 bathrooms, including a 4 bed / 4 bath Unit A and a 3 bed / 3 bath Unit B, offering immediate income potential ($375k+) with professional management already in place and a proven track record of consistent 5-star guest reviews. Originally a historic residence, the property has been completely renovated by a premier general contractor and interior design team, blending classic Charleston character with modern functionality. Each unit is professionally furnished and thoughtfully appointed, and the sale includes all appliances, fixtures, and furnishings providing a seamless, turnkey investment.The outdoor living experience sets this property apart, featuring a private backyard retreat with spa, built-in grill, expansive lounge deck, and large outdoor dining area. Blue stone patios and brick walkways are complemented by custom landscaping and iron gates, creating one of the most distinctive and upscale outdoor environments in the city. Projected 2026 revenue is estimated at $375,000+ underscoring the property's strong performance and demand. Additional financials and expense details are available upon request. Ideally located within walking and biking distance to MUSC, as well as the vibrant shops, restaurants, and nightlife of Cannonborough-Elliotborough and Upper King Street, this offering presents a rare opportunity to acquire a high-performing, fully permitted short-term rental asset in one of Charleston's most sought-after neighborhoods.

111 Cannon Street, Charleston
$1,725,000
10 Beds ⋅ 26025369 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
A 1998-built triplex in Cannonborough-Elliottborough -- newer construction on a block of 1850s stock. Two separate buildings on one parcel: a detached two-story single house fronting Smith Street (4BR/2BA, 1,486 SF), plus a two-unit building behind, each 3BR/1BA at 1,166 SF. 3,819 SF total, 10 bedrooms, off-street parking. 100% occupied at $13,100/month -- $157,200 of in-place annual rent -- with all three leases written through July 2027. Two blocks to MUSC, a short walk to the College of Charleston, King Street dining and Upper King. DR-2F zoning; two detached buildings on one parcel leave the door open to a future condominium regime. Normalized T12 operating statement, rent roll, tax bill and bound insurance policies available to qualified buyers.

183 Smith Street, Charleston
$5,300,000
9 Beds ⋅ 9 Baths ⋅ 26017628 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
A rare opportunity to own one of Charleston's most distinctive hospitality properties, The Ashley Inn seamlessly blends historic grandeur, modern luxury, and proven income-producing potential in the heart of downtown Charleston. Originally constructed in 1852 as a magnificent Greek Revival Charleston Single House by prominent machinist and industrialist William Lebby, this meticulously restored landmark showcases nearly two centuries of Charleston history while offering today's most sought-after conveniences. Following an extensive renovation and restoration, The Ashley Inn stands as a turnkey boutique lodging property featuring eight beautifully appointed guest accommodations across the main residence and carriage house. The main house offers seven ensuite guest rooms, each thoughtfullydesigned to honor the property's historic character while providing modern comfort. Rich architectural details, including original heart pine floors, intricate millwork, oversized pocket doors, soaring ceilings, and preserved period craftsmanship, create an atmosphere that is both elegant and inviting. Signature Charleston double piazzas stretch the full length of the home, offering guests the quintessential Lowcountry experience with shaded outdoor living spaces overlooking the historic streetscape. One of the property's most captivating features is the renowned Speakeasy Suite, where a historic underground cistern has been transformed into a one-of-a-kind private lounge, creating an unforgettable guest experience unlike any other in Charleston. Complementing the main inn is a separate carriage house featuring two bedrooms and two baths, operating as a legal, active short-term rental. Complete with its own living spaces and amenities, the carriage house provides exceptional flexibility for continued hospitality operations, owner occupancy, or additional rental income. The Ashley Inn's premier location places guests within walking distance of Charleston's celebrated restaurants, shopping districts, museums, medical centers, and historic attractions. Rare onsite parking further enhances the property's appeal, an increasingly valuable amenity in downtown Charleston. This is a great value add opportunity to add a pool and further increase the income. Whether envisioned as a continued boutique bed-and-breakfast operation, a luxury hospitality investment, an event venue, or a grand private residence with income-producing accommodations, The Ashley Inn represents an extraordinary opportunity to acquire a fully renovated historic property with unmatched character, exceptional versatility, and an irreplaceable presence in one of the South's most coveted destinations.

201 Ashley Avenue, Charleston
$5,300,000
26017624 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
A rare opportunity to own one of Charleston's most distinctive hospitality properties, The Ashley Inn seamlessly blends historic grandeur, modern luxury, and proven income-producing potential in the heart of downtown Charleston. Originally constructed in 1852 as a magnificent Greek Revival Charleston Single House by prominent machinist and industrialist William Lebby, this meticulously restored landmark showcases nearly two centuries of Charleston history while offering today's most sought-after conveniences. Following an extensive renovation and restoration, The Ashley Inn stands as a turnkey boutique lodging property featuring eight beautifully appointed guest accommodations across the main residence and carriage house. The main house offers seven ensuite guest rooms, each thoughtfullydesigned to honor the property's historic character while providing modern comfort. Rich architectural details, including original heart pine floors, intricate millwork, oversized pocket doors, soaring ceilings, and preserved period craftsmanship, create an atmosphere that is both elegant and inviting. Signature Charleston double piazzas stretch the full length of the home, offering guests the quintessential Lowcountry experience with shaded outdoor living spaces overlooking the historic streetscape. One of the property's most captivating features is the renowned Speakeasy Suite, where a historic underground cistern has been transformed into a one-of-a-kind private lounge, creating an unforgettable guest experience unlike any other in Charleston. Complementing the main inn is a separate carriage house featuring two bedrooms and two baths, operating as a legal, active short-term rental. Complete with its own living spaces and amenities, the carriage house provides exceptional flexibility for continued hospitality operations, owner occupancy, or additional rental income. The Ashley Inn's premier location places guests within walking distance of Charleston's celebrated restaurants, shopping districts, museums, medical centers, and historic attractions. Rare onsite parking further enhances the property's appeal, an increasingly valuable amenity in downtown Charleston. This is a great value add opportunity to add a pool and further increase the income. Whether envisioned as a continued boutique bed-and-breakfast operation, a luxury hospitality investment, an event venue, or a grand private residence with income-producing accommodations, The Ashley Inn represents an extraordinary opportunity to acquire a fully renovated historic property with unmatched character, exceptional versatility, and an irreplaceable presence in one of the South's most coveted destinations.

201 Ashley Avenue, Charleston