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Property view

14990 Winchester Boulevard, 
Los Gatos, CA 95030

$4,000,000


4

Beds


5

Baths


3,201

Sq Ft


Single Family

Sold

Listed by

Amy Mccafferty

Golden Gate Sotheby'S International Realty

MLS#

82038974

Source:

CAREIL

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About This Home

14990 Winchester Boulevard

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.

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 1946

Price Summary

4,487,000

$1,401 per Sq. Ft.

MLS #:

82038974

Sold:

May 19, 2026


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

3

Interior

Living Area:

3,201 Sq. Ft.


Structure

Structure

Building Area:

3,201 Sq. Ft.

Year Built:

1946


Lot

Lot Size (Sq. Ft):

35,837


Finances & Disclosures

Finances

Price:

$4,487,000

Price per Sq. Ft:

$1,401 per Sq. Ft.

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