14990 Winchester Boulevard, Los Gatos, CA 95030
Local realty services provided by:Better Homes and Gardens Real Estate Everything Real Estate
14990 Winchester Boulevard,Los Gatos, CA 95030
$4,487,000
- 4 Beds
- 5 Baths
- 3,201 sq. ft.
- Single family
- Active
Upcoming open houses
- Sun, Mar 2202:00 pm - 04:00 pm
Listed by: amy mccafferty
Office: golden gate sotheby's international realty
MLS#:ML82038974
Source:CRMLS
Price summary
- Price:$4,487,000
- Price per sq. ft.:$1,401.75
About this home
Hidden along a quiet stretch of Winchester Boulevard, this distinctive LG property unfolds beyond a long private drive, where mature trees, fruit plantings, and thoughtful landscaping create both a secluded and deeply connected surrounding to nature. The approach opens to a generous motor court with space for several vehicles, complemented by a three-car garage and thoughtfully designed and private outdoor areas.
Immediately beyond the entry, two inviting gathering rooms establish the home’s relaxed yet refined character. One serves as an entertainment lounge with soaring ceilings and 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 and 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 and functionality with understated style. A striking center island finished in green Marinace granite anchors the space and incorporates a Thermador cooktop, while surrounding work areas provide dual sinks, extensive cabinetry, and 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 with built-in cabinetry with exterior access. Brand new, separate upper and lower level HVAC and exterior gutters have been installed.
The formal dining room connects naturally to both the kitchen and living areas. French doors open to a wraparound wood deck and steps leading to the landscaped garden, creating an effortless transition between indoor and outdoor entertaining. A built-in bar with glass cabinetry adds a touch of sophistication for hosting and ample storage.
Two bedrooms on the main level are thoughtfully positioned along a private hallway and 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 and 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, and 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 with natural light and extensive storage and organization.
Adding to the property’s versatility is a detached cottage, offering an ideal setting for guests, extended family, or creative work. The upper and lower levels continues the continuity of the custom design style and warm hickory flooring of the main home. The upper level includes a comfortable living area with vaulted ceiling and built-in shelving, along with a kitchenette and 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 with quartz counters, marble-inspired tile, and a spa-like shower with seating.
The outdoor spaces are designed to be both functional and inviting, with paver walkways, garden areas, and artificial turf accents providing multiple places to relax or entertain. Practical amenities including 45+ solar panels with two Tesla battery power wall storage units providing excess power capacity for the entire property. A large workout or creative room and extensive storage rooms within the three-car garage support modern living while preserving the property’s calm and very private residential character....
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Home facts
- Year built:1946
- Listing ID #:ML82038974
- Added:3 day(s) ago
- Updated:March 22, 2026 at 05:27 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:5
- Full bathrooms:3
- Half bathrooms:2
- Flooring:Carpet, Tile, Wood
- Kitchen Description:Dishwasher, Disposal, Double Oven, Gas Cooktop, Refrigerator, Vented Exhaust Fan
- Living area:3,201 sq. ft.
Heating and cooling
- Cooling:Wall Window Units
Structure and exterior
- Roof:Composition
- Year built:1946
- Building area:3,201 sq. ft.
- Lot area:0.82 Acres
- Construction Materials:Stucco
- Exterior Features:Deck
Schools
- High school:Los Gatos
- Middle school:Raymond J. Fisher
- Elementary school:Daves Avenue
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$4,487,000
- Price per sq. ft.:$1,401.75
Features and amenities
- Appliances:Dishwasher, Disposal
- Amenities:Walk In Closets
Parking
- Total parking spaces:3
- Garage:Yes
- Garage spaces:3
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