Los Gatos CA Historical Real Estate, Homes for Sale

4 Beds ⋅ 3 Baths ⋅ ML82050572 MLS

Extensively remodeled in 2024 to 2025, this beautifully upgraded home is nestled in one of the areas most sought-after neighborhoods. Recent major improvements include a brand-new ROOF, HVAC, and water heater, along with elegant engineered hardwood flooring, updated lighting, a stunning remodeled kitchen, and a luxurious primary bathroom. The home was also fumigated in 2024 and includes a 3-year termite-free warranty for added peace of mind. A grand formal foyer welcomes you into the sophisticated living room, highlighted by a warm fireplace. The redesigned kitchen features sleek SS appliances and a peninsula that seamlessly connects to the dining area. This flexible space can also serve as a family room, with direct access to the side yard. The spacious primary suite is a true retreat, opening to a large private deck, perfect for relaxing mornings or evening unwinding. Additional upgrades include an extended driveway with new paving and redwood gate, as well as a beautifully landscaped backyard complete with mature fruit trees, including a fig tree.Located within a top-rated school district and just a short stroll to vibrant downtown Los Gatos, this home also offers convenient access to major commute routes and nearby open spaces. A rare, turnkey opportunity not to be missed.

321 Johnson AVE, Los Gatos

Listing courtesy of Serena Zhang, 510-272-7777 from Shè Homes
(If provided) CoList: from

$5,000,000

2 Beds ⋅ 2 Baths ⋅ ML82050479 MLS

Set across approximately 30.9 gently rolling acres at approximately 2,400 feet in elevation within the prestigious Santa Cruz Mountains AVA, Ascona Vineyards is a distinguished wine country estate that seamlessly blends agricultural functionality with timeless architectural elegance. Sweeping vineyard and countryside views frame approximately 16 acres of organically farmed vines planted with a curated collection of premium grape varietals, presenting a rare opportunity for boutique wine production, lifestyle ownership, or long-term legacy investment. **Accepting BackUp offers** At the heart of the estate, the Tuscany Revival farmhouse evokes the warmth and character of a refined European vineyard retreat. Thoughtfully positioned to capture the surrounding natural beauty and tranquil setting, the residence features luxurious finishes, inviting living spaces, and an effortless connection to the landscape. Designed for both private enjoyment and commercial vineyard operations, the property is fully fenced and extensively improved with a professionally designed winery facility, utility and storage buildings, and infrastructure supporting ongoing production and future expansion.

18516 Skyline BLVD, Los Gatos

Listing courtesy of Billy Caruso, 408-304-4872 from KW Bay Area Estates
(If provided) CoList: Danielle Davenport from KW Bay Area Estates

$448,000

1 Beds ⋅ 1 Baths ⋅ ML82049682 MLS

Connected Silicon Valley Living | Welcome home to this bright and updated ground floor residence nested in a magnolia-lined Los Gatos community. Fresh paint throughout, new light fixtures, a new stove, and updated finishes create a home that feels considered from the first step in. The open layout flows naturally from living to dining to kitchen, bright, uncluttered, and easy to make your own. An enclosed patio extends the living space further, ideal as a home office or a quiet retreat. Step through the patio door and you arrive at a gentle community lawn anchored by a mature magnolia tree, the kind of restorative corner that Silicon Valley rarely offers. Here, the world slows down just enough. Tucked at the end of a residential drive, Wedgewood Manor community is defined by its graceful magnolia trees, lush landscaping, and an unhurried sense of arrival. Los Gatos carries a reputation earned over decades, a vibrant downtown, tree-lined streets, and a character that has only deepened with time. Highways 17 and 85 are minutes away, with Netflix headquartered right in town. The Santa Cruz Mountains and miles of hiking trails are within easy reach. A life as connected as it is grounded. Move-in ready. Your Silicon Valley story starts here.

14225 Lora 21, Los Gatos

Listing courtesy of Haiyan Fu, 650-201-7338 from KW Bay Area Estates
(If provided) CoList: from

$1,499,000

2 Beds ⋅ 1 Baths ⋅ ML82048729 MLS

APN 562-31-014 & APN 562-31-013. Mountaintop Privacy & Panoramic OCEAN & City Lights Views at 15880 Soda Springs Road, Los Gatos. Perched high above Silicon Valley on nearly eight acres of pristine hilltop land, Two lots of record, 15880 Soda Springs Rd offers a rare combination of seclusion, scale, & truly sweeping views, while remaining just 20 minutes from the heart of Los Gatos. The property sits adjacent to the 19,000 acre Sierra Azul Open Space Preserve, protected by Santa Clara County's High Scenic zoning. This not only safeguards long-term views and value, but also provides direct access to miles of scenic trails for hiking or horseback riding. This is a property designed for those who value privacy, nature, and the freedom to create a legacy estate in one of Northern California's most desirable mountain settings. On this property is a charming English style home that blends comfort with character. Featuring high ceilings, large casement windows flooding the interior with natural light, wood flooring throughout, a spacious attic for storage or future living space, and an expansive deck ideal for enjoying sunsets, coastal breezes, and starlit evenings. Opportunity to live in the existing home while creating your dream custom home and/or luxury equestrian estate.

15880 Soda Springs RD, Los Gatos

Listing courtesy of Monterey Peninsula Home Team, 831-601-3284 from KW Coastal Estates
(If provided) CoList: from

$899,000

2 Beds ⋅ 2 Baths ⋅ ML82048722 MLS ⋅ Chemeketa Park BLDG.

Retreat in the Hills of Los Gatos, charming Mountain Home with Custom-Built Cabin Escape to this peaceful, wooded Los Gatos hills home mountain living with Silicon Valley convenience. The living room features new windows opening to a sunny deck with forest views. The gourmet kitchen boasts custom cabinetry, center island, new LG appliances with double oven, gas range, and walk-in pantry with washer/dryer. Primary suite offers walk-in closet and tiled shower. One additional bedroom and a flex for family, guests, or office. Outside, a restored 121 sq ft custom cabin suits guests, studio, gym, or home office. Deck overlooks Los Gatos Creek with under-deck storage. Recent Improvements: New flooring, Expanded windows, New roof, Kitchen remodel, Furnace, Water heater, Electrical panel & gateway, 2 Tesla Powerwalls, 220V EV charger, Landscape lighting, Retention walls, Refurbished cabin Community: playground, garden & clubhouse with hikes and events. Location 6 min to Lexington Elementary (IB World School) Feeds Fisher Middle & Los Gatos High, Hwy 17 access, Minutes to downtown, Lexington Reservoir & redwood trails, 2 fire stations nearby (incl. S-70i Firehawk) Ideal for families, remote workers, or anyone craving mountain charm near the Bay Area. Book a showing today.

20851 Assiniboine TRL, Los Gatos

Listing courtesy of Dan Hunnicutt, 650-704-5628 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

$949,000

2 Beds ⋅ 2 Baths ⋅ ML82048081 MLS ⋅ Laurel Community League- Water BLDG.

**Santa Cruz Mountains Retreat with Privacy, Redwoods & Easy Highway 17 Access** Escape to the peaceful beauty of the Santa Cruz Mountains with this charming rural retreat located in Santa Cruz County with a desirable Los Gatos address. Situated on approximately 6.9 acres surrounded by majestic redwood trees, this property offers privacy, tranquility, and convenient access just minutes from Highway 17. Ideally located halfway between Santa Cruz and Silicon Valley and within the sought-after Scotts Valley School District. This inviting home features approximately 1,700 sq ft with 2 bedrooms, 1 1/2 bathrooms, a loft, and a basement. Enjoy an expanded front porch deck with a new overhang porch, perfect for relaxing and taking in the serene mountain setting. The remodeled kitchen includes new cabinets, laminate countertops, an R/O water system, and whole-house water softener. The updated bathroom features a luxurious steam shower, while new vinyl flooring enhances the interior. Additional highlights include a basement, workshop, multiple outbuildings and sheds, ample parking, and a 500-gallon reserve water tank. Whether you are seeking a full-time residence or peaceful getaway, this unique mountain property offers the perfect blend of comfort, nature, and convenience.

16730 Laurel RD, Los Gatos

Listing courtesy of Debbie P. Marino, 408-210-2400 from Pellego
(If provided) CoList: from

$2,198,000

5 Beds ⋅ ML82027892 MLS

Welcome to 228 Union Ave, an exceptional duplex opportunity in the heart of Los Gatos. Each unit offers an inviting blend of comfort, functionality, and outdoor living, making this a perfect property for both investors and owner-occupants alike. Both residences feature well designed layouts, abundant natural light, and generous living spaces. Each unit enjoys its own large private backyard, ideal for entertaining, gardening, relaxing, or creating the outdoor space of your dreams. Properties with this level of outdoor usability are truly rare in Los Gatos. With its prime location just minutes from top rated Los Gatos schools, shopping, dining, and major commute routes, this duplex delivers convenience and long term value. Whether you're looking to live in one unit and rent the other, expand your portfolio, or add additional income potential, the possibilities are endless. Dont miss the chance to own a versatile duplex with fantastic outdoor amenities in one of Silicon Valleys most desirable communities.

228 Union AVE, Los Gatos

Listing courtesy of Dominic Gluhaich, 408-710-4538 from Intero Real Estate Services
(If provided) CoList: from

$1,928,000

6 Beds ⋅ ML82047225 MLS

Rare opportunity to own a well-maintained duplex in a prime Los Gatos location! One unit features 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1.5 bathrooms. With approximately 2,397 total square feet of living space, this property offers flexibility for owner-occupants, investors, or multi-generational living. Desirable floor plans, and a highly sought-after location make this a standout property. Convenient commute access near major employers, shopping, dining, and top-rated schools.

624 Vasona AVE, Los Gatos

Listing courtesy of Mark Gissler, 408-205-1729 from Intero Real Estate Services
(If provided) CoList: Caroline Anderson from Intero Real Estate Services

$2,548,000

5 Beds ⋅ 3 Baths ⋅ ML82042111 MLS

Offered by the Kennedy Estate as part of a multiparcel disposition, this 3,378 sq ft residence along with APN 562-01-038 will be sold together making approximately 79 total acres, presenting a rare large acreage opportunity in the Los Gatos mountains. Built in 1925, the home features five bedrooms, three bathrooms, an attached garage, and a detached garage. The land highlights the properties long history in the region, with natural terrain, established improvements, and a mature apple orchard that has been part of the landscape for many years. The location reflects a largescale ownership footprint within the Loma Prieta community, offering notable acreage, enduring character, and a setting that showcases the scale and presence of this mountain property.

24580 Loma Prieta AVE, Los Gatos

Listing courtesy of Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty

$1,250,000

3 Beds ⋅ 3 Baths ⋅ ML82041703 MLS ⋅ BIG REDWOOD PARK BLDG.

Redwood Canyon Retreat, Mountain Living, Convenience and Lifestyle! Tucked among towering redwoods, 15 min to Los Gatos, 20 min to Santa Cruz, easy Hwy 17 access via the Glenwood cutoff. This beautifully remodeled 3-bed, 3-bath mountain home delivers serenity without sacrificing convenience. With 2,744 sq ft of permitted living space across two renovated structures - Premium Wolf appliances, quartz countertops, hardwood floors and three gas fireplaces set the tone inside, while sweeping redwood decks and forest views complete the picture outside. The primary suite features a stone fireplace, hardwood floors, private deck access and redwood forest views. A second fully remodeled bathroom stuns with marble tile, backlit LED mirror, vessel sink, rain-head shower and matte-black fixtures - a spa-level finish rarely found at this price. The lower level functions as a self-contained 1-bed/1-bath unit and with a permitted guest cottage they EACH could generate ~ $1.8k-2.2k/month, offsetting ~ $4k of a monthly mortgage. Live in the main home and earn income from two units. 2-car garage, workshop, spacious parking, auto sprinklers and BBQ area. Top-rated Scotts Valley schools. Mountain escape. City access. Income potential. Rarely does one property deliver all three.

18485 Main BLVD, Los Gatos

Listing courtesy of Daniil Gorkov, 408-444-1093 from Beverly & Company
(If provided) CoList: from

$2,598,000

3 Beds ⋅ 2 Baths ⋅ ML82040247 MLS

Rare Opportunity in the Beautiful and Prestigious town of Los Gatos This classic fixer-upper sits on a spacious, highly desirable lot that offers incredible potential. Perfect for contractors, visionaries, or anyone ready to build their dream home from the ground up. Tear down or renovate to create a custom residence in one of Silicon Valleys most sought-after communities, surrounded by luxury homes and excellent schools in the Los Gatos Union School District. The true value here is the generous lot size and prime location a blank canvas in an elite neighborhood where land opportunities are increasingly scarce.

16001 Stephenie LN, Los Gatos

Listing courtesy of Ralph & Rachel, 408-807-3073 from Compass
(If provided) CoList: from

$13,800,000

6 Beds ⋅ 6 Baths ⋅ ML82039880 MLS

Discover extraordinary luxury in the heart of Los Gatos. This breathtaking 20.5-acre estate offers unmatched privacy, mountain views, and a natural flowing stream crossed by your own private bridge. Inside the main residence, enjoy a gourmet chef's kitchen, elegant wet bar, private theater room, steam room, full gym, and dedicated yoga studio. Two laundry areas and a custom dog wash add everyday convenience. Step outside to a resort-style swimming pool surrounded by serene landscape. Plus, a separate two-bedroom guest house features its own laundry room, garage, and private backyard perfect for extended family or guests. Luxury, nature, and sophistication all in one extraordinary property.

130 Wood RD, Los Gatos

Listing courtesy of Rick Alva, 408-472-3999 from Windermere Valley Properties
(If provided) CoList: from

$399,950

1 Beds ⋅ 1 Baths ⋅ ML82038606 MLS ⋅ Wedgewood Manor BLDG.

Rare "end-unit" studio in the coveted Wedgewood Manor, perfectly positioned as a private nature oasis. This 2026 remodel defines Los Gatos luxury, featuring massive windows that frame stunning views of a serene, babbling stream and lush greenery. The interior transformation boasts new German-engineered waterproof plank floors, elegant slab quartz counters, and brand-new stainless steel appliances. Bathed in natural light and enhanced by new recessed lighting and designer paint, the open layout includes a remodeled modern bath and a charming eat-in dining area. Located in a premier geographic hub, you are steps from the prestigious La Rinconada Country Club and the world-class tennis/fitness facilities at Bay Club Courtside. Enjoy a sophisticated lifestyle with effortless access to the Michelin-rated dining of Downtown Los Gatos and the vibrant shops of Downtown Campbell. Community amenities include elevator access, a welcoming clubhouse, BBQ areas, and an assigned carport with dedicated storage. With direct access to scenic hiking trails and proximity to major Silicon Valley tech hubs via Hwys 85 and 17, this is a rare opportunity for high-end, low-maintenance living in an unparalleled creekside setting. Sophistication meets tranquility at 14225 Lora Drive #51.

14225 Lora DR 51, Los Gatos

Listing courtesy of JR McKee, 408-406-7777 from Home In Silicon Valley
(If provided) CoList: from

$3,988,000

4 Beds ⋅ 5 Baths ⋅ ML82036838 MLS

Classic home in Los Gatos, reimagined by renowned local architect Gary Schloh, to blend historic character with modern livability AND A RARE OPPORTUNITY TO CREATE A FAMILY COMPOUND because an adjacent lot with approved plans is also available. Buyer to verify plans with town. See FAQs and plans among disclosures. Set on approximately 12,000 sq ft, the property unfolds into a private, resort-like retreat. The rear grounds evoke an Italian villa with lush landscaping, mature trees, and multiple spaces for entertaining and relaxation. Inside, warm, sophisticated interiors offer seamless indoor-outdoor flow. The living room with fireplace anchors the home, while formal and informal spaces connect to the gardens. Flexible layout includes a separate dining room, media room/4th bedroom and a great room with patio access that could serve as a 5th bedroom, guest suite, or office. The gourmet kitchen features custom cabinetry and premium appliances and adjoining den and laundry room. The primary suite offers tree-filled views, fireplace, walk-in closet, and spa-like bath with soaking tub and shower. Additional features include wine cellar, 2-car garage, and underground utilities. Near Los Gatos Creek Trail, Vasona Lake Park, and downtown.

120 Oak Meadow DR, Los Gatos

Listing courtesy of Robin Sedgwick, 408-355-5374 from Coldwell Banker Realty
(If provided) CoList: Donald Knight from Coldwell Banker Realty

$1,698,000

4 Beds ⋅ 4 Baths ⋅ ML82035012 MLS

Offered through the Kennedy Estate. Set on 21.37 acres in the Los Gatos mountains, this property features a 2,559 square foot home built in 1952 with five bedrooms and three and a half bathrooms. The residence has been held by the Kennedy family for many years and remains in original condition, offering a rare opportunity for buyers seeking a large acreage setting with long established improvements. The land includes natural terrain, mature trees, and areas used for pear cultivation. A unique chance to own a substantial mountain property with privacy and space. Buyers are advised to verify all property details, including utilities, access, zoning, permits, square footage, with the appropriate county agencies.

24733 Loma Prieta AVE, Los Gatos

Listing courtesy of Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty

$698,000

1 Beds ⋅ 1 Baths ⋅ ML82034137 MLS

This property is part of the Kennedy Estate. A rare 26.8-acres Los Gatos mountain property featuring a natural spring, mature trees, and exceptional privacy. This property includes an older home situated within a serene, wooded setting, offering a unique opportunity for those seeking substantial acreage and a natural water source. Buyers should verify zoning, access, utilities, square footage, septic, water rights, and all permitted uses with Santa Clara County. A peaceful retreat ideal for those looking to secure significant land in a desirable mountain location.

24733 Loma Prieta AVE, Los Gatos

Listing courtesy of Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty

$1,572,000

2 Beds ⋅ 1 Baths ⋅ ML82034135 MLS

This property is part of the Kennedy Estate. Two adjoining parcels (APN 098 011 22 and 098 011 23) totaling 44.61 acres in a peaceful, private mountain setting. These parcels include a small home, an additional structure suitable for storage, and an established orchard, offering a blend of existing improvements and expansive natural landscape. The property features open space, mature trees, and long-term land holding appeal. Buyers should verify zoning, utilities, access, septic, water sources, and all permitted uses with Santa Cruz County. A substantial acreage offering in a desirable rural location.

24580 Loma Prieta AVE, Los Gatos

Listing courtesy of Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty

$5,995,000

5 Beds ⋅ 7 Baths ⋅ ML82033361 MLS

Legendary Chateau Liberte' is a landmark property at the Summit of Old Santa Cruz Highway, presiding over seventy-two pristine acres of towering Redwood forests. Main residence is restored with milled Redwood from the property. The income producing multiple rental dwellings include two cottages, a magical treehouse, and a secluded Cavco cedar cabin home. There is a large swimming pool, ponds, creeks, waterfalls with an underground prolific Artesian fed cistern supplying water to all the houses, pool, and ponds. Multiple fruit and nut trees with ten acres or arable land for vineyards of Pinot Noir and Chardonnay grapes. There is incredible horse property potential with manicured trails encompassing all 72 acres. The Williamson Act encompasses all parcels.Two RV sites with full utility hook-ups. 5,240 feet of security fencing with a security gate. Six-tenths of a mile private paved driveway. Your own private world awaits with rolling meadows, Koi and Turtles in the 360,000 gallon pond with it's own idyllic dock. Top Los Gatos Schools. APN# 558-04-045, 16 acres, SCC Cert. of Compliance included, 3 parcels total. Helicopter landing area. Only eight miles to the charming Los Gatos village. Majestic property. Lifetime opportunity for the next steward of the legendary Chateau Liberte'.

22700 Old Santa Cruz HWY, Los Gatos

Listing courtesy of George Rabe, 408-234-8238 from Intero Real Estate Services
(If provided) CoList: from

$1,100,000

3 Beds ⋅ 2 Baths ⋅ ML82026468 MLS

A stunning Los Gatos sanctuary where peace, beauty and convenience harmonize perfectly with breathtaking views for miles. This inviting home offers 3 beds,2 baths with 1,706 SF, nestled on 4.766 acres of abundant bliss. Soothing sounds of nature create a true sense of escape just minutes from downtown Los Gatos. Wake up to panoramic vistas and gentle morning light streaming through the trees. Experience balance with restorative fresh mountain air inviting you to slow down and breathe deeply. The open living spaces feature large windows that frame the surrounding landscape, blending indoor comfort with the natural splendor outside. Whether you're enjoying dining on the deck at sunset or hosting friends under a canopy of stars, this property embodies the essence of California mountain living, peaceful, private, and profoundly beautiful. This well located property offers an easy commute to Silicon Valleys major employers and top-rated Los Gatos schools (8/8/10 Great Schools ratings). You're close enough to downtown to enjoy world-class restaurants, wineries, concerts, boutique shopping, and weekend farmers markets, yet far enough to truly unwind and recharge. Don't miss this rare opportunity to own a piece of paradise, where convenience meets calm and every day feels like a getaway.

15245 Stetson RD, Los Gatos

Listing courtesy of Lisa Provenzano, 408-386-0467 from KW Bay Area Estates
(If provided) CoList: Mario Ramirez from KW Bay Area Estates

$4,888,000

21 Beds ⋅ 14 Baths ⋅ ML81991766 MLS

Take advantage of this opportunity to own this private 34-acre property with the ultra rare zoning of Private Campground. Perfect for a private retreat center or high-end family getaway. The Lodge is a spacious 4,413 sq ft main building featuring seven bedrooms, a large Grand room, a commercial kitchen, offices, & more. Additionally, there are eight cozy 192 sq ft half bath cabins equipped with electric fireplaces, kitchenettes, sofa beds, & loft beds for extra guests. Six dorm-style A-frames, totaling 768 sq ft, also provide additional accommodations. A highlight of the property is the Grand room, which showcases a stunning handcrafted redwood table. This artistic centerpiece seats 20 comfortably & can be lifted to the ceiling, offering a flexible space for various activities. Additional work spaces in the Grand room look out over the grounds. Nature lovers will appreciate the open-air amphitheater, a tranquil meadow, a network of winding trails, & more. A flowing creek with a small dam and a private beach area add to the magic. The campground is equipped with high-speed internet, making it suitable for a family compound, a serene retreat center, or an off-site coding facility. Pricing includes all 4 parcels. Price per sq ft is $728 across 6,717 total sq ft of living space.

16770 Redwood Lodge RD, Los Gatos

Listing courtesy of Cassandra Maas, 408-472-7988 from Anderson Christie, Inc.
(If provided) CoList: from

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Los Gatos Historical Real Estate

Jim Matzen

Hauslley Silva