Discover winter luxury at 15 Shepherd Road, a custom luxury bungalow set on a premium 102.48 ft x 352.51 ft lot backing onto the peaceful winter landscape of Heber Down Conservation Area. This beautifully updated home features four main-floor bedrooms, each with its own en-suite and walk-in closet, 10-foot ceilings, new engineered hardwood floors, fresh paint (2025), and a stunning great room with a 16-foot cathedral ceiling and gas fireplace. The brand-new kitchen includes stainless steel appliances, crown moulding, large baseboards, and California shutters. The primary suite offers a custom ceiling with pot lights, a spacious walk-in dressing room, and a 5-piece spa-like en-suite with views of the pool and conservation area. The finished walk-out basement adds exceptional versatility with three additional bedrooms, a gym, two recreation rooms, a gas fireplace, and a rough-in kitchen ideal for multi-generational living. The attached workshop with 60 Amp service provides space for hobbies, a golf simulator, or storage. With its brick, stone, and stucco exterior, updated pool system (new liner, heater, UV system Aug 2025), and no rental items, this is a rare opportunity in prestigious Macedonian Village-luxury, privacy, and comfort in every season.