Eastside Charleston SC Homes For Sale | James Schiller & Associates

Explore the charm of 21 America Street, a beautifully renovated Charleston Single home dating back to the 1880s, ideally situated for those who appreciate walkability to all that downtown Charleston has to offer. This residence features three spacious bedrooms, three full baths, an additional home office, and a generous walk-in closet. The updated kitchen and bathrooms harmoniously blend modern convenience with the home's original character, highlighted by original hardwood floors and four elegant fireplaces. Recent enhancements include a brand-new metal standing seam roof, complete with new sheathing beneath, ensuring peace of mind for years to come. The pride of ownership is evident throughout, as the current owners have meticulously maintained the property. Enjoy the convenience of off-street parking, a newly constructed deck overlooking a fully fenced backyard, and a beautifully painted exterior that adds to the home's curb appeal. Located moments away from downtown Charleston's finest amenities, 21 America Street offers a lifestyle where you can easily stroll to charming shops, delightful restaurants, and vibrant cultural attractions. Come experience the timeless elegance of this historic gem.

Excellent development opportunity located adjacent the Upper Meeting Street Corridor and nestled in the heart of Charleston's vibrant and rapidly growing Eastside. This 8 unit entitled project features full TRC approval and all necessary permits for land disturbance, including secured DRB and MS4 approvals. The project includes six charming church units located at 52 Cooper, each offering two bedrooms and two to two-and-a-half bathrooms. Additionally, there are two spacious three-bedroom, three-bathroom townhomes located at 56 and 58 Cooper, which are fully entitled with building permits in place. The Cooper Street Development represents a thoughtful blend of restoration and new construction, focusing on preserving the distinct historical elements of the existing Sanctuary.With its prime location, comprehensive approvals, and a clear path to development, this is a rare chance to capitalize on an attractive, ready-to-build project in a neighborhood poised for continued growth and appreciation. The property is also located within short walking distance to Martin Park/MLK indoor pool & pickleball courts, City Lights Coffee, and the Cigar Factory.

Excellent development opportunity located adjacent the Upper Meeting Street Corridor and nestled in the heart of Charleston's vibrant and rapidly growing Eastside. This entitled project features full TRC approval and all necessary permits for land disturbance, including secured DRB and MS4 approvals. The project includes six charming church units located at 52 Cooper, each offering two bedrooms and two to two-and-a-half bathrooms. Additionally, there are two spacious three-bedroom, three-bathroom townhomes located at 56 and 58 Cooper, which are fully entitled with building permits in place. The Cooper Street Development represents a thoughtful blend of restoration and new construction, focusing on preserving the distinct historical elements of the existing Sanctuary.With its prime location, comprehensive approvals, and a clear path to development, this is a rare chance to capitalize on an attractive, ready-to-build project in a neighborhood poised for continued growth and appreciation. The property is also located within short walking distance to Martin Park/MLK indoor pool & pickleball courts, City Lights Coffee, and the Cigar Factory.

12 Sheppard A & B is an up and down duplex in the Eastside neighborhood of Downtown Charleston. Each unit is 3 bedrooms, 1 bathroom. This home is conveniently located across the street from a neighborhood market, the City of Charleston public swimming pool and a variety of F&B options. It's also just a short walk to the Cigar Factory or the Upper Meeting/Upper King area. This is a great opportunity for an investor or an owner occupant who would like to live in 1 unit and rent out the other.

RARE DOUBLE LOT now available in Eastside! Nestled in the heart of downtown Charleston, this beautifully remodeled 1870 Charleston Single seamlessly blends historic charm with modern convenience. Ideally located next to a lovely community park, this five-bedroom, three-bathroom home exudes classic Lowcountry elegance, featuring a striking metal roof, full-length double piazzas, and dedicated off-street parking.Renovated down to the studs in 2012, this home retains its rich character--original heart pine flooring, soaring 10-foot ceilings, and exposed brick fireplaces--while offering the comfort of contemporary living.Step inside to a bright and airy first floor, where an expansive living room leads to the kitchen, featuring stainless steel appliances and granite counter tops.with seamless access to both the front piazza and private backyard perfect for entertaining. The first floor also features a spacious living room, two generously sized bedrooms (one with a stunning brick fireplace that could serve as a first-floor owners' suite), and a full bathroom with a walk-in shower and updated vanity. Upstairs, the second floor opens to a light and bright landing leading to the upper piazza, an ideal spot to enjoy Charleston's gentle breezes. The owner's suite is a true retreat, complete with a brick fireplace, walk-in closet, and private ensuite bath. Down the hall, an additional cozy living room with a fireplace offers extra space to unwind, along with a laundry area, dual-vanity full bath, and two additional bedrooms. Outside, the private, fenced-in backyard provides plenty of space for gatherings and relaxing under the gorgeous Lowcountry skies. The current owners purchased an adjacent lot making this home one of Eastside's largest lots! The driveway easily accommodates three or more vehicles, a rare find in downtown Charleston! Just steps from a beautiful community park and within walking distance to King Street's renowned shopping, dining, and entertainment, this location is unbeatable. Whether you're looking for a primary residence or an investment property with a strong rental history, this property has it all! Schedule a showing today.

Conveniently located close to historical sites, shopping, restaurants & water views, 169 Jackson Street offers a lovely, updated housing option. The property greets you with steps guiding you to the front door entry. Downstairs you'll find an aptly appointed kitchen with an island, a guest bathroom & spacious living room with a gas fireplace. The beautiful windows & blinds provide natural light through the downstairs space. Upstairs there are 2 bedrooms with their own heating/cooling systems, closets & full bathrooms. These rooms share an upstairs laundry area. The crawlspace of this beautiful property has been encapsulated and can be used for additional storage. No off-street parking needed as this home has its own concrete driveway. Don't miss your opportunity to see this one!

Quadplex investment opportunity situated on a large .19 acre lot and located directly across from Hampstead Square. This attractive 4 unit property features 9 bedrooms/4 baths and $127,020 in gross annual income. There is potential that this property can qualify as a Category 2 (owner-occupied) short-term rental pending Zoning approval. Each unit features an open floor plan with large kitchen/living/dining areas, spacious bedrooms and updated baths. The huge fenced-in backyard is large enough to accommodate the construction of a 5th, detached single family unit (pending Zoning/BAR/TRC approval) making it ideal for continued use as an owner-occupied/investment property. All 4 units have access to newly re-built piazzas and there is plenty of off-street parking on-site.Additional recent updates include a new roof, which was installed in 2022 and updated kitchens/baths. The property is located within short walking distance to numerous shopping and dining destinations on Upper King & Meeting St as well as the Cigar Factory.

Historic 'Charleston Single' in a PRIME location surrounded by new- and re-development. WalkScore of 89 - ''Very Walkable'' with myriad options for shopping, dining, recreation like Martins Park, the City Pool, King Street, and many new local hotspots in close proximity. The home sits on a low traffic cul-de-sac and features a brand new central HVAC installed in 2025. Off-street parking for two vehicles. Fenced-in rear garden. Screened front porch. Large kitchen. Primary bedroom on the main floor. Two BRs and full bath with laundry on the second floor. Less than 10 minute bike ride to MUSC, College of Charleston. Low traffic location on a cul-de-sac. Termite warranty in place.

In the shadow of the Aiken-Rhett house museum, which is in downtown Charleston's favorite neighborhood, Wraggborough; this three (3) unit development was designed as condominiums and essentially built in 2020 for high-efficiency and low maintenance. Providing eleven (11) bedrooms, nine (9) bathrooms and three (3) half-baths currently leased through July 2025, as long-term, un-furnished rentals for a total of $16,025/mo., net operating income in 2024 was $153,078. This unique property provides many options for a discerning new owner to manage or occupy. Site plan, floor plans and photos available in media.