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$5,750,000
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
$5,750,000
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
$3,980,000
7 Beds ⋅ 26016384 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 $367,000, with over $200,000 already booked, 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
$5,200,000
12 Beds ⋅ 10 Baths ⋅ 26014869 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
Looking for that perfect investment property? Look no further than 162 Spring Street: a turnkey investment asset featuring twelve bedrooms, ten bathrooms, seven off-street parking spaces, and a triple-net-leased restaurant in the heart of Charleston's STR overlay. On pace for over $400,000 in gross revenue! Approximately 5,881 square feet across three separate buildings. All furniture and fixtures included in the sale . The property transfers with a proven rental revenue history and a sitting commercial tenant.The front building includes two, 2BR/2BA STR-licensed condos positioned behind a fully leased NNN commercial space. (Three units total)The middle building is a 4BR/3BA single-family home built in 2018.The perfect house to own downtown, that doesn't come with the deferred maintenance of a 100 year old historic home.The last building on the property is another 4BR/3BA home of matching construction vintage, equally equipped for short-term rental performance. Cannonborough-Elliotborough is the most-watched submarket on the peninsula -- Michelin-starred operators (Vern's, Chez Nous), independent retail along Spring and Upper King, and a guest demographic that skews higher-income and longer-stay than the City Market tourist corridor. The opportunity to acquire four fully licensed and operating short-term-rentals PLUS a restaurant space is a rare find here in Charleston.

162 Spring Street, Charleston
$5,200,000
12 Beds ⋅ 26014816 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
On pace for over $400,000 in gross revenue! Introducing 162 Spring Street: a turnkey investment asset featuring twelve bedrooms, ten bathrooms, seven off-street parking spaces, and a triple-net-leased restaurant in the heart of Charleston's STR overlay. Approximately 5,881 square feet across three separate buildings. All furniture and fixtures included in the sale . The property transfers with a proven rental revenue history and a sitting commercial tenant.The front building includes two, 2BR/2BA STR-licensed condos positioned behind a fully leased NNN commercial space. (Three units total)The middle building is a 4BR/3BA single-family home built in 2018. The perfect house to own downtown, that doesn't come with the deferred maintenance of a 100 year old historic home.The last building on the property is another 4BR/3BA home of matching construction vintage, equally equipped for short-term rental performance. Cannonborough-Elliotborough is the most-watched submarket on the peninsula -- Michelin-starred operators (Vern's, Chez Nous), independent retail along Spring and Upper King, and a guest demographic that skews higher-income and longer-stay than the City Market tourist corridor. The opportunity to acquire four fully licensed and operating short-term-rentals PLUS a restaurant space is a rare find here in Charleston.

162 Spring Street Unit #A, B, C, D, E, Charleston
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 26010215 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
Tucked within the charming Catfiddle Street enclave in the heart of Cannonborough-Elliottborough, 26 Catfiddle Street offers a thoughtful blend of classic Charleston character and modern functionality. This three-bedroom, three-bath residence is designed with flexibility in mind, making it equally appealing as a primary home, investment property, or combination of both.The ground level features a private studio space with its own full bath, ideal for use as a guest suite, home office, or income-producing rental.Upstairs, the main level is centered around an open-concept living and kitchen space, complete with a fireplace and natural flow for everyday living and entertaining. A well-appointed bedroom and full bath are also located on this floor. The top level offers an additional bedroom and bath, along with a lofted area that overlooks the living space below, adding architectural interest and a sense of openness throughout. Recent updates include beautifully refreshed bathrooms in 2023 and a newly painted exterior, enhancing both the interior comfort and curb appeal. With its stucco exterior, efficient layout, and prime downtown location just moments from local dining, shopping, and neighborhood favorites, 26 Catfiddle Street presents a unique opportunity to enjoy the best of Charleston living in one of its most vibrant communities.

26 Catfiddle Street, Charleston
$1,850,000
3 Beds ⋅ 3 Baths ⋅ 25030360 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
This beautifully restored 3-bedroom, 3-bath single family detached home is an active, legal short term rental. This property has been thoughtfully renovated, blending original character with high-end finishes & contemporary comfort. Inside, you'll find gorgeous hardwood floors, exposed wooden beam ceilings, & luxury designer touches throughout. The bright, elegant kitchen features white cabinetry w/ gold hardware, striking quartz countertops with dramatic blue & gray veining, & warm hardwood flooring. A sleek peninsula with bar seating, gold faucet, & open layout make this kitchen both functional and beautiful, perfect for gathering & entertaining. Each bedroom offers its own refined style & comfort, along with an en-suite bathroom. Step outside to your private fenced pool deck where asplash pool with soothing waterfall feature creates an oasis of tranquility, ideal for cooling off or relaxing in total privacy. This home also includes one off-street parking space, accessible via the driveway to the left of 65 Spring Street. Pedestrian access is available through the charming brick walkway between 65 and 67 Spring, adding to the home's classic Charleston appeal. Currently operating as an active, legal short-term rental, this property offers exceptional investment potential or a turn-key option for a primary or secondary residence in one of the city's most sought-after neighborhoods. Experience the best of Charleston living, historic charm, modern luxury, and a private retreat, all in one beautifully restored home.

67 Spring Street Unit #A, Charleston
$3,197,000
6 Beds ⋅ 25007619 MLS ⋅ Cannonborough-Elliotborough SubDv. ⋅ Active Status
SEE ATTACHED BROCHURE. To qualify for B&B/STR, must be primary residence. 194-196 Rutledge Ave, ''The Rutledge Ave Inn'', is a 5 unit existing & operating Bed and Breakfast located in the Short-Term Rental Overlay. The main house (196 Rutledge), built in 1910, was renovated down to the studs in 2008 and includes four spacious rental units; two 2BR/2.5BA units A&B, and two 1BR/1BA units C&D. The units are in great condition with modern luxury finishes coupled with historic charm. The Cottage (194 Rutledge) which was built in 2008, is a two level 2BR/2.5BA detached house with it's own private fenced in yard and back porch. The Cottage is setback off the street providing a peaceful and unique oasis. The property exudes modern amenities with historical charm. (continued)

194-196 Rutledge Avenue, Charleston