Rare offerings demand attention, and this property delivers a combination seldom found in Winchester. Originally established before Red Fox Run was developed, this .53-acre property offers the privacy, space, and flexibility that newer subdivision homes simply cannot replicate. A fully fenced concrete pool, expansive outdoor entertaining space, mature setting, and oversized homesite create a standout opportunity for buyers seeking multigenerational living, income-producing potential, or a high-functioning primary residence with amazing flexibility. The main level offers one-level living with three spacious bedrooms and three full bathrooms, including a private ensuite primary bedroom thoughtfully positioned opposite the secondary bedrooms for separation and privacy. Recently refinished hardwood floors, fresh interior paint, freshly painted pool decking, and refreshed exterior elements create a move-in ready presentation with immediate appeal. Natural light pours through the oversized picture window into the large family room, while the dining room and dedicated laundry room are conveniently situated. The fully finished basement dramatically expands the home's value proposition with a separate entrance, full kitchen, full bath, bedroom, family room, and additional flex space ideal for short-term rental opportunities, college event lodging, in-law accommodations, extended guest stays, or supplemental income potential. Few properties in Winchester offer this level of versatility combined with a private pool and oversized lot within an established neighborhood setting. Positioned approximately $60,000 below assessment value, this property presents a compelling opportunity for buyers searching for house hacking potential, multigenerational layouts, STR flexibility, pool homes, finished basements with kitchens, or homes suited for Shenandoah University events and regional festivals. Properties with this combination of land, flexibility, privacy, pool amenities, and income-producing capability rarely reach the market.