Hidden along a quiet stretch of Winchester Blvd, this distinctive LG property unfolds beyond a long private drive, where mature trees, fruit plantings, & thoughtful landscaping create both a secluded & deeply connected surrounding to nature. The approach opens to a generous motor court w/ space for several vehicles, complemented by a 3-car garage & thoughtfully designed and private outdoor areas.Immediately beyond the entry, 2 inviting gathering rooms establish the home’s relaxed yet refined character. One serves as an entertainment lounge w/ soaring ceilings & a substantial built-in media center crafted in rich wood cabinetry, while the adjoining living room offers a quieter atmosphere centered around a gas-log fireplace & a full wall of built-in shelving. Large picture windows frame views of the surrounding greenery.At the heart of the home, the kitchen blends scale & functionality w/ understated style. A striking center island finished in green Marinace granite anchors the space & incorporates a Thermador cooktop, while surrounding work areas provide dual sinks, extensive cabinetry, & a generous walk-in pantry. A sunlit breakfast area framed by wide windows creates a comfortable place to gather while overlooking the gardens. Off the kitchen, a separate laundry room w/ built-in cabinetry w/ exterior access. Brand new, separate upper & lower level HVAC & exterior gutters have been installed. The formal dining room connects naturally to both the kitchen & living areas. French doors open to a wrap-around wood deck & steps leading to the landscaped garden, creating an effortless transition between indoor & outdoor entertaining. A built-in bar w/ glass cabinetry adds a touch of sophistication for hosting & ample storage.2 bedrooms on the main level are thoughtfully positioned along a private hallway & share a well-appointed full bath while offering generous additional storage too. Upstairs, the primary suite occupies its own level, creating a tranquil retreat within the home. The expansive bedroom offers vaulted ceilings & generous proportions that allow for multiple seating areas or workspace arrangements. French doors open to a Juliet balcony overlooking the surrounding trees.The suite’s bathroom features a soaking tub, glass-enclosed shower, double vanity, & private water closet, while an adjacent space functions beautifully as a home office or dressing area. Beyond it, a large walk-in closet provides a luxurious dressing area w/ natural light & extensive storage & organization.Adding to the property’s versatility is a detached cottage, offering an ideal setting for guests, extended family, or creative work. The upper & lower levels continues the continuity of the custom design style & warm hickory flooring of the main home. The upper level includes a comfortable living area w/ vaulted ceiling & built-in shelving, along w/ a kitchenette & dining nook. Downstairs, a spacious, private bedroom opens through glass doors to a quiet paver patio surrounded by mature trees, creating a peaceful garden-level retreat. The accompanying bathroom has been stylishly updated w/ quartz counters, marble-inspired tile, & a spa-like shower w/ seating.The outdoor spaces are designed to be both functional & inviting, with paver walkways, garden areas, & artificial turf accents providing multiple places to relax or entertain. Practical amenities including 45+ solar panels w/ 2 Tesla battery power wall storage units providing excess power capacity for the entire property. A large workout or creative room & extensive storage rooms within the 3-car garage support modern living while preserving the property’s calm & very private residential character.Private, flexible, & quietly distinctive, 14990 Winchester Boulevard offers a rare combination of main residence & guest cottage in a setting that feels removed from the pace of Silicon Valley, yet remains just minutes from the shops, dining, & charm of downtown Los Gatos.