Under contract-accepting backup offers. Built by Silliman CitySide Homes, this Santa Barbara-inspired custom residence was the 2013 Parade of Homes Grand Award Winner! This 4 bedroom, 3-1/2 bath home offers 2,955 square feet of living area, a first-floor primary suite, upstairs bonus room, detached two-car garage, and private pool. Mediterranean architecture, a concrete tile roof, and courtyard-oriented design create a distinctive arrival. From the covered front entry, the foyer offers an open view through sliding glass doors to the lanai and pool. The kitchen, dining room, and main living area are located to the right and arranged around the rear courtyard. The spacious great room features tile flooring, 10-foot ceilings, crown molding, and a gas fireplace. Open to the living and dining areas, the kitchen is appointed with granite countertops, custom wood cabinetry, Bosch stainless steel appliances, a gas cooktop, center island, and a breakfast bar with substantial seating. Additional features include 42-inch upper cabinets, under-cabinet lighting, and a stainless undermount sink. Privately situated on the first floor and separated from the main living spaces, the primary suite features hardwood flooring, a generous walk-in closet, and views of the courtyard and pool. The primary bath includes a soaking tub, separate shower, and granite-topped vanity with dual sinks. Upstairs, three alternate bedrooms, two full baths, and a large bonus room offer flexible accommodations for guests, a home office, media room, or secondary living area. Two bedrooms share a Jack-and-Jill bath with dual sinks, a tub/shower combination, and a private water closet. The third bedroom has a dedicated bathroom. Outdoor living is central to the home's design. The addition of the pool, travertine decking, and surrounding landscaping further enhances the original courtyard concept. Deep covered and open-air spaces provide room for dining, lounging, and entertaining. The detached two-car garage is accessed from the rear motor court, preserving the privacy of the outdoor living areas. Additional improvements include exterior shutters, awnings, exterior lighting, gutters, interior shutters and blinds, and customized garage storage. Beyond the visible finishes, Silliman's original CitySide construction standards included insulated masonry walls, open-cell spray-foam insulation at the roof deck, high-performance windows, insulated sliding glass doors, and a concrete tile roof. Two newer HVAC systems were installed in 2022 and 2025. The home also features Rinnai tankless water heaters and a dedicated laundry room. Located in one of Maitland's most walkable areas, the property offers convenient access to Lake Lily Park, the farmers market, neighborhood restaurants, shopping, and community activities. Winter Park's Park Avenue, with its boutiques, restaurants, museums, and cultural attractions, is approximately a seven-minute drive away. Award-winning custom construction, a flexible floor plan, significant improvements, and a private pool courtyard come together in the heart of Maitland.