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18 Pinckney Street, Charleston
$1,780,000
4 Beds ⋅ 1.5 Baths ⋅ 26027741 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
Rare opportunity to renovate and restore a historic Charleston residence in the heart of downtown. Situated on the corner of Pinckney Street and Motley Lane, 18 Pinckney offers classic Charleston character with its traditional two-story facade, tall windows, side piazza and commanding corner presence. Just a short walk from Market Street, restaurants, shopping and the many attractions of the Historic District, the location is exceptional.Currently configured with separate entrances to the first and second floors, the property offers tremendous flexibility for a buyer looking to create a distinctive single-family residence, two residential units, an owner-occupied home with rental income, or a live/work arrangement.The first floor provides approximately 1,280 square feet, with an additional 1,118 square feet upstairs. The property is being offered as a fixer-upper, allowing the next owner to thoughtfully renovate while preserving its historic charm and tailoring the interiors to their own vision. Its Limited Business zoning provides additional possibilities, while residential rental use is permitted. A former commercial kitchen, including a hood and grease trap, remains in place. For a buyer looking for historic architecture, renovation potential and a highly walkable downtown location, 18 Pinckney Street is an opportunity to create a truly one-of-a-kind Charleston home.

18 Pinckney Street, Charleston
46 Pinckney Street, Charleston
$3,735,000
4 Beds ⋅ 3.5 Baths ⋅ 26024446 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
A rare opportunity to own both a distinguished Historic Charleston residence and an established income-producing property in the heart of the Historic District. The Jacob Rabb House, circa 1851, offers exceptional versatility as a full-time residence, Charleston pied-a-terre or investment property(licensed short term rental) . Located in coveted Ansonborough, the home is just steps from the City Market and within an easy stroll of King Street, Waterfront Park, world-class dining, galleries and many of Charleston's most celebrated landmarks.Offering approximately 2,770 square feet, this beautifully appointed three-story residence features four bedrooms, three and a half baths and the architectural character of a classic Charleston home, thoughtfully complemented by sophisticatedmodern updates while preserving its historic charm and storied past. Gracious living spaces extend outdoors to a private walled garden, expansive courtyard and patio, along with two classic Charleston piazzas--ideal for entertaining, dining al fresco or simply enjoying Charleston's year-round lifestyle. Off-street parking for 2 to 3 cars adds a rare convenience in this location. Inside, a welcoming foyer and staircase set the tone for the residence. The chef-inspired kitchen features a La Cornue range, Carrara marble countertops and center island and flows naturally into the dining room, while a sunlit living room is anchored by an original fireplace. The upper floors provide four well-appointed bedrooms and flexible accommodations for family and guests, with a classic Charleston piazza offering an inviting outdoor retreat. Beyond its appeal as a private residence, 46 Pinckney Street presents a compelling investment opportunity. The property is an established, licensed short-term rental under professional management, with $268K in gross rental revenue currently on the books for 2026, a year-end projection of $274K and a 2027 target of approximately $299K. For a second-home owner, the existing rental operation also provides the opportunity to generate income during periods of non-use while retaining the property for personal enjoyment. Few properties combine historic provenance, residential livability, walkability, private outdoor space, coveted off-street parking and income-producing potential in such a desirable downtown Charleston location. The Jacob Rabb House offers the opportunity to own not simply a piece of Charleston history, but a remarkable property positioned for both personal enjoyment and investment. Financial information available upon request. Booked revenue may be subject to cancellations or adjustments; projections and targets are estimates provided by ownership/management and are not guarantees of future performance.

46 Pinckney Street, Charleston
58 Laurens Street, Charleston
$3,275,000
4 Beds ⋅ 4.5 Baths ⋅ 26024387 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
Tucked on a quiet, tree-lined street in the heart of Ansonborough, this reimagined four-bedroom home pairs 1940s character with a meticulous renovation and thoughtful nods to midcentury design.Built in 1940 and taken down to the studs in 2022, this turnkey home offers four bedrooms and 4.5 baths with custom finishes and discerning details throughout. High-end features include top-of-the-line Thermador appliances (including a built-in coffee and espresso maker), Farrow & Ball paint, and Buster + Punch switches and hardware. The home is also wired for sound with built-in speakers.On the first floor, a bedroom with an ensuite bath overlooks the tree-lined street. The dining room features a gas fireplace, while the kitchen offers custom cabinetry and a perfectly situated breakfast nookAt the rear of the home, the living room includes remote-controlled shades and opens onto the back porch and an off-street parking spot. The second floor holds three additional bedrooms, three full bathrooms, and a den with a second gas fireplace that opens to the second-floor balcony. The primary suite enjoys lovely views of the Mary Smith House garden and includes a walk-in closet with custom cabinetry and a shoe carousel, maximizing every inch of space. The sun-filled primary bath features a steam shower and a freestanding Victoria + Albert soaking tub. The third floor adds 460 square feet of flexible living space (not included in the home's total square footage) -- ideal for a home office or children's playroom. Storage is thoughtfully integrated throughout, including under-stairs storage concealed behind built-in bookcases and wall panels. The full 2022 renovation included an encapsulated crawlspace and all-new major systems -- plumbing, electrical, HVAC, and a Rinnai tankless water heater. Located in Zone X, no flood insurance is required.

58 Laurens Street, Charleston
44 Wentworth Street, Charleston
$3,750,000
4 Beds ⋅ 4.5 Baths ⋅ 26023394 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
Beautifully built in the Charleston Single style, this elegant home offers the grace and scale of nearby historic properties without the usual maintenance expense. Located in convenient and desirable Ansonborough, featuring solid masonry construction, ample parking and a charming walled garden are just a few of the key features.Tall ceilings with well proportioned rooms echo the past including an open staircase to all three levels. Luxurious finishes in the well crafted kitchen and four full baths, even in a private terrace off the primary suite. Meticulous owners recently replaced all three HVAC systems, allowing for a turnkey ownership experience.

44 Wentworth Street, Charleston
59 Society Street, Charleston
$3,900,000
7 Beds ⋅ 5.5 Baths ⋅ 26023257 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
A rare opportunity to own a distinguished masonry Charleston Single House in the heart of historic Ansonborough. The Jonah M. Venning House, circa 1839, is an elegant residence featuring classic copper-clad piazzas, a private courtyard, and deep off-street parking, all within one of Charleston's most sought-after historic neighborhoods. The main residence offers 4 bedrooms and 31/2 baths, including true third-floor bedrooms, providing exceptional space and flexibility. Behind the main house are two separately metered residential units: a 2-bedroom, 1-bath apartment and a 1-bedroom, 1-bath apartment, creating opportunities for guest accommodations, multigenerational living, rental income, or future integration into a larger single-family estate.As part of the celebrated Ansonborough Rehabilitation Project, the property was carefully preserved as part of Charleston's ongoing commitment to protecting its architectural heritage. A conservation easement held by the Historic Charleston Foundation further ensures the stewardship of this important historic resource. Lovingly maintained by the current owner since 1991, the home underwent a thoughtful restoration by renowned Charleston craftsman Richard Marks Restorations, Inc. in 2003, reflecting a deep respect for its historic character and enduring quality. Additional highlights include: - X Flood Zone designation, with no flood insurance currently required. - Three electric meters serving the property. - Recently vacated apartments with prior rental income of approximately $3,200 per month. - Offers ability to combine main house and carriage apartments into one extraordinary residence. The seller's preference is to convey the home fully furnished including the antiques that were selected for this home via separate bill of sale. This offers a truly turnkey opportunity to enjoy one of Charleston's treasured historic properties.

59 Society Street, Charleston
36 Society Street, Charleston
$7,200,000
7 Beds ⋅ 7.5 Baths ⋅ 26007985 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
An extraordinary offering in the heart of historic Ansonborough -- where Charleston's past is not only preserved, but beautifully reimagined.Constructed in 1840 by Henry Street in the years following the Great Fire, this rare double-front Greek Revival residence stands as a lasting expression of resilience, craftsmanship, and architectural significance. Its stately masonry facade and iconic piazzas set the tone before you ever step inside -- a quiet reminder that this is something far beyond the expected.Inside, the home unfolds with intention. Grand double parlors, rich in detail and proportion, create a sense of understated elegance -- where historic character is honored and thoughtfully layered with modern refinement. Every space feels curated yet livable, designed to...accommodate both intimate moments and elevated entertaining with ease. At the center of the home, a chef's kitchen of exceptional caliber anchors daily living -- seamlessly blending performance, design, and gathering. Throughout, the residence offers a level of scale and flexibility rarely found downtown, with multiple living areas, private quarters, and opportunities for multi-generational living or discreet guest accommodations. Beyond the interiors, a private courtyard retreat introduces an entirely different rhythm -- complete with a saltwater pool, outdoor kitchen, and thoughtfully designed gathering spaces that feel worlds away while remaining in the heart of the city. Positioned just steps from Charleston's most celebrated dining, cultural landmarks, and waterfront views, this is a residence defined not by square footage, but by lifestyle -- walkable, storied, and deeply rooted in place. A rare opportunity to own a piece of Charleston history, reimagined for today.

36 Society Street, Charleston
17 Anson Street, Charleston
$2,050,000
3 Beds ⋅ 2.5 Baths ⋅ 26007859 MLS ⋅ Ansonborough SubDv. ⋅ Active Status
This 1890s Charleston single, steeped in history and character while offering modern conveniences, is perfectly placed in the heart of downtown Charleston, steps from restaurants, cultural venues, and a full-service grocery. The owners' meticulous maintenance and renovation of the interior, exterior, and garden make it a turnkey property for anyone looking to move right in. The kitchen, renovated in late 2025, features top-of-the line appliances such as a Wolf oven and range and built-in Subzero refrigerator, complemented by custom cabinetry and counters and full-height backsplashes crafted from Italian marble. An eat-in dining area and sitting room niche overlook the private garden. Parking for golf cart available.The formal dining room and living room retain many of the original historic details of the home, such as crown moldings, hardwood floors, and working fireplaces. All elements of the ground level, inside and out, make for easy and joyful entertaining. The living room could also be used as a bedroom. The original staircase leads to the second floor bedrooms and two full baths. The primary suite is generously sized, featuring a walk-in closet and additional compact home office fitted with soundproofing material. The beautifully updated primary bath is bright and spacious, with dappled sunlight often brightening the herringbone tile floor, double-wide vanity, and custom-built shower. A second full bath, also bright and fully updated, is fitted with a tub. Light fills the home through the day, beginning with sunrises over the second bedroom and traditional double piazzas, continuing with afternoon light and natural shade from a Japanese maple in the kitchen and garden, and ending with quintessentially Charleston sunsets over Ansonborough roofscapes in the primary bedroom. True to the home's original design, the owners have used a sitting room adjoining the primary bedroom as a bedroom, with the first-floor living room also available for use as a bedroom.

17 Anson Street, Charleston