Located in the heart of Harleston Village, 89 Ashley Avenue beautifully blends historic Charleston character with thoughtful modern updates and a large saltwater pool. Built in 1838, this classic brick Charleston single showcases Federal Period architecture with Flemish bond brickwork, a slate roof, high ceilings, detailed moldings, and original heart pine floors. The home also received a Carolopolis Award in 1974, recognizing its historic preservation and architectural significance.Spanning approximately 4,298 square feet across four levels, the home features five bedrooms, five full bathrooms, and one half bathroom. Light-filled interiors and generously scaled rooms offer both comfort and flexibility, while a grand central staircase with decorative millwork connects each level.Along the south side of the home, the iconic three-tiered piazzas provide inviting outdoor living spaces accessible from multiple rooms. The garden level is designed for seamless indoor-outdoor living, opening to a private courtyard and pool area. Recently renovated, the heated and chilled saltwater pool features lunar quartz tile, an ivory travertine deck, professionally landscaped grounds, and a tall Charleston-style privacy fence. Additional pool upgrades include a Hayward HeatPro heater/chiller system, new salt system, automatic autofill system, updated pool light controls, upgraded plumbing infrastructure, and enhanced equipment for easier maintenance and year-round enjoyment. Inside, the kitchen has been thoughtfully updated with Sub-Zero and Wolf appliances, Haier refrigerator drawers, custom cabinetry, and a quartzite waterfall island. Kitchen lighting improvements, including relocated fixtures, updated recessed lighting, and improved switch functionality, enhance both form and function. French doors open directly to the pool terrace, creating an ideal setting for entertaining. The main living area has been enhanced with custom built-in shelving, lower cabinetry, updated trim work, fresh paint, a mounted TV, and integrated electrical improvements. The powder room has also been renovated with a new sink, custom Sandberg Swedish wallpaper, finish carpentry, drywall repair, and fresh paint, creating a refined guest space. Additional improvements throughout the home include drywall and finish repairs, fireplace patching and painting, shelving enhancements, new doors, trim refinements, updated plumbing fixtures, interior painting, and replacement of many light fixtures to improve both presentation and functionality. The home is also equipped with a Moen Flo smart water monitoring and automatic shutoff system, providing real-time leak detection, automatic shutoff protection, and an estimated 8% homeowners insurance savings through eligible carrier discounts. On the second floor, you'll find a generous secondary living space and an expansive primary suite with a luxurious bath featuring a soaking tub, marble shower, and walk-in closet. Both rooms open onto the piazza overlooking the courtyard and large pool. The third floor offers two additional large bedrooms with custom closets, a flexible bonus room, and access to another wide piazza. Two fourth-floor bedrooms, each with private en-suite baths and built-in storage, complete the home. Extensive exterior and structural improvements further enhance the property. In 2024, the covered porch roof was fully replaced with a new standing seam aluminum roof in medium bronze, complete with updated flashing, high-temperature ice and water shield protection, and detailed copper work. The front knee wall was also replaced with new copper detailing to elevate both durability and curb appeal. In 2025, comprehensive brick cleaning and repointing were completed on the front, side, and rear elevations, followed by full chimney repointing to preserve the integrity of the historic masonry. In 2026, all porch decking was replaced using historically appropriate wood and fully painted to maintain the architectural character of the home. The exterior has also undergone a full paint project, including shutters, windows, siding, porch ceilings, railings, posts, and foundation areas. Approximately half of the shutters were replaced, while the remaining shutters were restored to full functionality. Additional weatherproofing improvements, caulking, and sealing have been completed throughout the property. The rear grounds have been thoughtfully improved with new Old Carolina brick pavers in a 45-degree herringbone pattern, upgraded driveway and courtyard hardscaping, artificial turf installation, refreshed landscaping, and enhanced exterior presentation. A Tesla Gen 3 Wall Connector EV charger was also installed in the rear parking area. Additional system upgrades include extensive servicing and improvements to the home's four-system Trane heat pump HVAC system, including duct replacement, airflow enhancements, dehumidifier support, surge protection, condenser repairs, evaporator coil cleaning, anti-fungal treatment, vibration dampening, refrigerant servicing, and crawlspace insulation improvements. The Trane systems include registered limited warranty coverage, with functional parts coverage generally extending to June 2028 and compressor coverage on the heat pumps extending to June 2030. A rare highlight is the .10-acre rear lot, accessed by a shared driveway, offering parking for six or more vehicles, additional garden space, and the potential for a future garage or accessory structure. Just a short distance from Colonial Lake, Moultrie Playground, and nearby tennis and pickleball courts, 89 Ashley Avenue presents a rare opportunity to own a thoughtfully updated historic residence in one of Charleston's most desirable neighborhoods.