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23444 Skyview TER, Los Gatos
$2,000,000
4 Beds ⋅ 3 Baths ⋅ ML82050576 MLS
Location is everything. Nestled within the close-knit Villa Del Monte community, this exceptional property offers peace, beauty, sunshine, clean air, and serenity with easy access to everything you need. Whether you are commuting into Silicon Valley or heading for a day in Santa Cruz, being this close to Highway 17 ensures you are never far from where you want to be. This property offers the perfect blend of privacy, sunshine, and usable land. Situated on a private and largely flat lot, you have space to relax and enjoy. The backyard and luxurious swimming pool with solar heat benefit from Southern exposure and all day sun. Outstanding floor plan. Formal living room and separate family room for both daily family life and large gatherings. The upstairs bedroom could be a home office, gym or yoga retreat. Updated kitchen with gas range, double oven, lots of storage and a bay window that looks out onto the pool and backyard. Two fireplaces. A private well means no monthly water bill. Enjoy close proximity to local, top rated schools Loma Prieta, CT English, Los Gatos High. Just minutes from the Summit Store and several local wineries for groceries, gourmet treats and drinks with friends. Enjoy the best of CA living. Mountain privacy amidst the trees and under the stars.

23444 Skyview TER, Los Gatos

Listed by Brian Bernasconi, 408-979-1400 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Kirsty Hepburn from COMPS
232/236 University AVE, Los Gatos
$2,580,000
3 Beds ⋅ 4 Baths ⋅ ML82050528 MLS
Welcome to University Avenue, a rare opportunity to own a beautifully maintained duplex in one of Los Gatos' most sought-after historic neighborhoods. Nestled among charming single-family homes, this duplex lives like a primary residence with an attached ADU, offering exceptional flexibility for owner-occupants, multigenerational living, or rental income potential. Built in 1995 and thoughtfully updated, the property features central A/C, hardwood flooring, fireplaces, attached garages, private outdoor spaces, and more. Each residence enjoys its own private entrance, garage, laundry, and yards. 236 University Avenue (approx. 1,800 sq. ft.) offers a two-story layout with 2 spacious bedrooms, an office/den, 3 bathrooms, soaring vaulted ceilings, family room, and attached garage. 232 University Avenue (approx. 700 sq. ft.) features 1 bedroom and 1 bathroom with its own private amenities and outdoor space. The location is truly exceptional. Just steps from vibrant Downtown Los Gatos, you'll enjoy easy access to renowned restaurants including Dio Deka, Telefèric Barcelona, and Los Gatos Soda Works, boutique shopping along North Santa Cruz Avenue, and nearby favorites such as Vasona Lake County Park, Oak Meadow Park, the Los Gatos Creek Trail, and Testarossa Winery.

232/236 University AVE, Los Gatos

Listed by Sammi Moser-Wingo, 408-857-2026 from The Agency
(If provided) CoList: Donald Moser from The Agency

Sold listing courtesy of Mark Vantress from SGP
18516 Skyline BLVD, Los Gatos
$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

Listed by Billy Caruso, 408-304-4872 from KW Bay Area Estates
(If provided) CoList: Danielle Davenport from KW Bay Area Estates
211 Glen Ridge AVE, Los Gatos
$4,000,000
5 Beds ⋅ 2 Baths ⋅ ML82049284 MLS
Standing proudly along one of Los Gatos most storied streets, 211 Glen Ridge is the historic George and Edith Green estate once home to the town's early pharmacist and a rare surviving 1909 Craftsman residence. This is not just a home, but a living piece of Los Gatos history, where early 20th-century craftsmanship, provenance, and enduring character converge in a way seldom found today. Meticulously restored with deep respect for its original integrity, the home preserves its authentic soul while offering an elegant solution to a complex problem, how to honor historic character while accommodating modern life. Period details remain intact: original-style hardwood floors, restored lighting, custom millwork, and finely crafted banisters that reflect true craftsmanship. Each space carries continuity, where history is genuinely retained. A gracious floor plan offers 5 bedrooms and 2 bathrooms, with light-filled living spaces anchored by a sunroom. The main level includes two bedrooms, a full bath, expansive living and dining rooms, kitchen, and sunroom; upstairs features three additional bedrooms, bath, and storage nooks. Occupying a 9,100 sq ft lot, the grounds include a rebuilt garage and a back gate to Bachman Park. This is a unique opportunity to own a piece of Los Gatos history

211 Glen Ridge AVE, Los Gatos

Listed by Michael Kenyon, 408-529-0248 from Compass
(If provided) CoList: from

Sold listing courtesy of Nicholas French from SGP
23500 Sunset DR, Los Gatos
$2,100,000
4 Beds ⋅ 3 Baths ⋅ ML82050017 MLS
Welcome Home to 23500 Sunset Dr, a Private Los Gatos Mountain Retreat in the Villa del Monte Community w/ Award-Winning Schools! Set at the End of a Cul-De-Sac on 1.52 Acres, this 4BD/3BA Home Offers 2,938 SF, Sweeping Mountain, Forest & Lower Monterey Bay Views, Pool, Hot Tub, 2-Car Garage & Outdoor Living Areas. Automatic Gate, Mature Gardens & Covered Entry Create a Peaceful Arrival. Light & Bright Living Room w/ Vaulted Exposed-Beam Ceilings, Clerestory & Picture Windows, Hardwood Floors, Built-In Speakers, Drop-Down TV System & Sitting Nook. Dining Room w/ Bay Windows, Built-In Oak Cabinetry & Murano Glass Lighting. Gourmet Chef's Kitchen w/ Granite Counters, Breakfast Bar Seating for Six, Breakfast Nook, Dual Oven + Gas Range w/ Six Burners & Griddle, Pot Filler, Vent-A-Hood & Wine Refrigerator. Primary Suite w/ Vaulted Exposed-Beam Ceiling, Sweeping Views, Pellet Stove Nook, Loft, Walk-In Closet & Skylit Ensuite. Flexible Lower Level w/ Bedroom, Office Nook, Full Bath & Exterior Access. Resort-Style Grounds w/ Upper Balcony, Trex Decking & Lush Gardens. Owned Solar, 3-Yr-Old Roof/Skylights, Whole-Home Generator, Dual-Zone HVAC, Water Tanks & Fire-Hardening Improvements. Minutes to Wineries, Summit Store, Hwy 17, Trails, Downtown Los Gatos & Santa Cruz! Truly a Must-See!

23500 Sunset DR, Los Gatos

Listed by Andy Tse, 408-807-8808 from Intero Real Estate Services
(If provided) CoList: Stephane Wimmers from Intero Real Estate Services

Sold listing courtesy of Dana Juncker from COMPS
15675 El Gato LN, Los Gatos
$4,000,000
4 Beds ⋅ 3 Baths ⋅ ML82049995 MLS
Exceptional new Craftsman-style residence on a quiet, tree-lined street in a coveted Los Gatos pocket. The main level features a dining area and spacious great room with fireplace and doors to the backyard, plus a gourmet kitchen with island, walk-in pantry, and eat-in dining. A flex room and secondary bedroom complete the first floor. Upstairs offers a laundry room, two bedrooms, and a full bath. The grand suite boasts mountain views, a walk-in closet, and a spa-like bath. Enjoy abundant natural light, top-tier schools, Alta Vista just a short walk via a nearby path, nearby parks, shopping, Good Samaritan Hospital, and easy access to Los Gatos and Cambrian. This home is approximately a short 8 minute drive to downtown Los Gatos. MOVE-IN READY! Take a tour of this completed and beautifully staged home today!

15675 El Gato LN, Los Gatos

Listed by Frances Ibay, 408-205-9858 from Thomas James Real Estate Services, Inc,
(If provided) CoList: from

Sold listing courtesy of Jackie Miano from KWLGE
14411 Shannon RD, Los Gatos
$11,600,000
7 Beds ⋅ 8 Baths ⋅ ML82049737 MLS
Welcome to this 25.5 pristine acre Los Gatos equestrian & vineyard estate w/ magnificent hillside views*Total living square feet of this one of a kind estate is over 8,935 SQFT which includes the main house custom built in 2015, the guest house, and a bedroom suite & office in the magnificent equestrian facility*This exquisite equestrian arena and garage space is 26,135 SQFT combined and has 8 equine stalls 12x24, a one bedroom studio suite, an office, a tack room, a saddle room, hay dry storage, multiple vehicle and boat garages/storage, & 3 car garage attached to the main house*This massive solar paneled world class equestrian facility could also be converted into an indoor sports facility under lights to include tennis/pickle ball, soccer, football, and lacrosse/field hockey*This rare estate includes a large office, home gym, arts & craft room, wine cellar, pool, spa, outdoor kitchen and a guest house with a separate kitchen, living room, and bedroom suite* This Los Gatos Estate is only five minutes to Downtown. There will never again be an estate in Los Gatos with 25 acres, a 25,000 SQFT equestrian arena, 9,000 SQFT contemporary home, multiple vineyards, subdivision opportunities, views, guest house, boat/RV storage, walking/riding trails, pickle ball court, & a gated estate!

14411 Shannon RD, Los Gatos

Listed by Joe Piazza, 408-410-5020 from Coldwell Banker Realty
(If provided) CoList: from

115 Belhaven DR, Los Gatos
$3,300,000
6 Beds ⋅ 3 Baths ⋅ ML82049159 MLS
Located in the highly desirable Belwood neighborhood of Los Gatos, this beautiful 6bd/3ba home is ready to welcome it's next owners. The detached 12' x 12' room offers endless possibilities, a home office, workshop, exercise room or anything your imagination can create.Step outside and enjoy the peaceful backyard retreat featuring garden boxes, a lovely garden, turf, a gazebo, and a deck off the family room. This expansive home is nestled against the foothills, providing access to scenic walking trails and beautiful views.Belwood is known for its strong sense of community. Residents enjoy gathering at Belwood Park and the active Cabana Club, which features an award-winning swim team, swimming pool, party room, pickleball courts, BBQ areas, and community events throughout the year, including summer movie nights, Halloween celebrations, and Fourth of July festivities. This friendly neighborhood feels like a step back in time, with neighbors walking their dogs, riding bikes, and hiking. The home is also conveniently located near award-winning schools, including Noddin Elementary, Union Middle School, and Leigh High School. A full bathroom and bedroom/office on the first floor provide excellent flexibility for guests, remote work, or multi-generational living.This home is a must see!

115 Belhaven DR, Los Gatos

Listed by Lori Ferrito, 408-529-6166 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Dohee Kim from KWSV
16011 Stephenie LN, Los Gatos
$3,388,800
4 Beds ⋅ 4 Baths ⋅ ML82048749 MLS
Brand-new modern farmhouse with attached ADU with kitchenette great for extended family. Located near Downtown Los Gatos and w/n the highly regarded Los Gatos school district. On the main level, open concept living and dining spaces. The chef's kitchen features slab quartz countertops, custom-crafted cabinetry, walk-in pantry, premium stainless-steel appliances and a large center island anchor the space. Luxury engineered hardwood flooring throughout with decorative wood-plank ceilings. Upstairs, a versatile loft provides the perfect setting for a secondary media lounge. An expansive laundry room. The light-filled primary suite is complete with a spa-inspired ensuite featuring dual vanities, designer finishes, and a generous walk-in closet. Two additional well-appointed bedrooms and a beautifully finished full bathroom with dual vanities complete the second floor. For that indoor outdoor living is an expansive covered veranda with wood-plank ceiling, slate tile. Rear yard includes paver patio, artificial turf, water-conscious landscaping, and modern landscape lighting. Additional amenities include Mitsubishi split-system heat pump, dual tankless water heaters, EV charging station, epoxy garage flooring, smart irrigation, alarm system, fire sprinklers, and built-in audio wiring.

16011 Stephenie LN, Los Gatos

Listed by Ralph & Rachel, 408-807-3073 from Compass
(If provided) CoList: from

20074 Beatty Ridge RD, Los Gatos
$1,225,000
3 Beds ⋅ 3 Baths ⋅ ML82048882 MLS ⋅ Las Cumbres BLDG.
Experience the ultimate in tranquil mountain living at 20074 Beatty Ridge Road, a stunning 3-bedroom, 2,450 sq. ft. retreat nestled on 1.5 acres in the highly coveted Las Cumbres community of Los Gatos. Perfectly move-in ready, the home features a light-filled open floor plan seamlessly detailed with fresh interior paint, beautiful new flooring, and abundant storage solutions throughout. Expansive large decks extend the living space outdoors, offering the perfect vantage point for soaking in panoramic mountain views and hosting effortless gatherings. Beyond the home, the unparalleled community infrastructure of Las Cumbres encompasses over 1,000 acres of shared conservation land and miles of private hiking trails. Residents enjoy access to a resort-style community center featuring a heated swimming pool, tennis and pickleball courts, bocce ball, a sports field, a playground, and a communal vegetable garden. The neighborhood thrives on a warm, active social calendar full of organized community BBQs and seasonal events. Complete with access to top-tier schools like Los Gatos High, a neighborhood volunteer fire station, and high-speed fiber internet (Madrone Broadband available), this pristine sanctuary perfectly balances peaceful privacy with a rich, connected lifestyle.

20074 Beatty Ridge RD, Los Gatos

Listed by Nicholas French, 650-773-8000 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Ed Dee from SANC
23762 Hutchinson Rd, Los Gatos
$1,250,088
3 Beds ⋅ 3 Baths ⋅ BE41136038 MLS
Experience the perfect blend of mountain serenity and Silicon Valley convenience. This beautifully updated Los Gatos home offers a rare opportunity to secure a move-in-ready residence with access to top-rated Los Gatos schools at an exceptional value. Recently remodeled, the home features a new roof, new flooring, and refreshed bathrooms - and a fully repaired and inspected septic system, so you can buy with confidence. The open-concept living areas are bathed in natural light, flowing seamlessly to a backyard deck with breathtaking skyline views and stunning sunrises. The versatile floor plan includes a flexible downstairs bedroom - perfect for a private home office, gym, or guest suite - while spacious upstairs bedrooms offer quiet privacy. Nestled in a peaceful forest setting, you are perfectly positioned for work and play: just 6 minutes from Highway 17 and only 15 minutes from the vibrant dining and shopping of Downtown Los Gatos. Whether you're hosting gatherings against a majestic mountain backdrop or enjoying a quiet morning coffee, this home delivers a lifestyle of privacy and prestige. An incredible value for those seeking the Los Gatos lifestyle without compromise.

23762 Hutchinson Rd, Los Gatos

Listed by Parul Arora, (510) 673-1238 from Compass
(If provided) CoList: from

Sold listing courtesy of Emily Baratzadeh from CBR
100 Heintz CT, Los Gatos
$4,900,000
5 Beds ⋅ 5 Baths ⋅ ML82041948 MLS
Exquisite East Los Gatos Retreat tucked away on a private cul-de-sac of 4 custom built homes in the Heritage Grove neighborhood, this 5-bed, 4.5-bath estate offers 4,195 SF of masterfully upgraded luxury. Note that 5th bedroom is used as an office and it does not have a closet. While the rest of Heritage Grove was completed five years earlier, this residence stands apart with unique craftsmanship and a sprawling 0.44-acre lot. The resort-style backyard features an infinite edge pool with an inground spa, fire pit, and BBQ island. Inside, the master suite is a sanctuary, boasting a private back deck screen room with a swing bed. The massive master bath includes 3 sinks, two toilets plus a bidet, a large jacuzzi tub, and a walk-in shower with attached his and hers walk-in closets. Enjoy expansive views of Silicon Valley, from Moffett Field to downtown and the East Bay hills. For outdoor enthusiasts, the Heintz Open Space Trailhead is literally steps away just walk out the front door and to the right. High-end upgrades include new stucco, a travertine porch, and fully owned solar. Located near top-tier schools like Alta Vista Elementary, Union Middle, and Leigh High, 100 Heintz offers the pinnacle of luxury. This home perfectly balances a private retreat with vibrant valley energy.

100 Heintz CT, Los Gatos

Listed by Ismar Maslic, 408-877-6000 from Montalvo Realty
(If provided) CoList: from

Sold listing courtesy of Anita Mohite from ATFIN
186 Lu Ray DR, Los Gatos
$3,430,000
4 Beds ⋅ 3 Baths ⋅ ML82048128 MLS
Welcome to 186 Lu Ray Dr in Los Gatos, located on a beautiful tree-lined street featuring vistas of the Los Gatos hills. Served by the highly sought-after Alta Vista Elementary School, this beautifully updated home blends convenience, style, and exceptional indoor-outdoor living. The kitchen and baths were fully remodeled in 2020 with great attention to detail. The expansive great room with soaring ceilings flows into the kitchen, the heart of the home. The kitchen features a spacious center island with bar seating and a wine fridge, quartzite counters, a Wolf gas range, and a Sub-Zero refrigerator. The home is primarily single-level, with 3 full baths and 3 beds located on the main level. The updated primary bath offers a floating vanity, large soaking tub, separate stall shower, and tile flooring. There is a separate upstairs living area and bed with built-in shelving and cozy reading nooks that create a flexible retreat, game room, or guest area. The entertainers backyard features a new pool installed in 2023 with a contemporary modern-style concrete patio, above-ground hot tub, outdoor shower, and lawn area. Additional amenities include central AC, dual pane windows, copper piping, and an EV outlet in the garage. Easy access to downtown Los Gatos, Highway 85, and Highway 17

186 Lu Ray DR, Los Gatos

Listed by Nevis and Ardizzone, 408-891-8149 from Compass
(If provided) CoList: from

Sold listing courtesy of James Ma from CBR
14380 Long Ridge RD, Los Gatos
$1,495,000
3 Beds ⋅ 3 Baths ⋅ ML82048042 MLS
NEW PRICE!!! Experience the perfect blend of refined living & mountain serenity in this immaculate Los Gatos home. Surrounded by natural beauty on 1.3 acres, mature fruit trees & a separate vegetable garden. An adorable, permitted turnkey/move-in ready 952 sq ADU is perfect for guests or rental income. The ADU features a 1 BR/1 BA with an upstairs loft, & in-unit washer & dryer, complete with outdoor space for entertaining, and its own storage space & parking. Avg. rental rates for an ADU is $2500-$3200. Just outside your front door, the property unfolds into a tranquil English garden. Delight in all the garden views from the comfort of the homes wraparound porch. This unique estate offers versatility, elegance, with plenty of room to live, work & entertain. The spacious 2,401 sq main home features 3 large BR, 3 full BA, a formal living room, formal dining, a beautiful eat-in-kitchen with breakfast bar, expansive rear deck, a separate laundry room, and a flexible bonus room which can be used as a family room, office, or hobby room. The abundant 990 sq barn is perfect for storage, cars, boats, RV, workshop or hobbies. Award winning Los Gatos Schools. A magical setting with your own storybook home for you to cherish offering lifestyle, tranquility and space.

14380 Long Ridge RD, Los Gatos

Listed by Scott Green, 408-761-2092 from Compass
(If provided) CoList: from

20100 Black RD, Los Gatos
$3,298,888
5 Beds ⋅ 4 Baths ⋅ ML82038848 MLS
Three Homes, Endless Possibilities. First time on the market ever! This extraordinary Chalet-style estate offers a true Lake Tahoe feel just 10 minutes from downtown Los Gatos with award-winning Los Gatos schools. Nestled on approximately 3.85 scenic acres surrounded by majestic redwoods and breathtaking views, this custom-built 1971 estate delivers privacy, versatility, and natural beauty. The main residence features 5 bedrooms and 4 full baths with soaring vaulted ceilings, expansive windows, formal dining room with views, oversized family room with distant views of Lexington Reservoir, and a sunroom designed to capture spectacular morning sunrises. The expansive deck & swimming pool create the perfect setting for entertaining and indoor-outdoor living. A private attached casita with a giant loft offers ideal accommodations for guests or extended family. Two detached rented ADUs provide immediate income while maintaining privacy. One unit, built in the early 2000s, is 1,200 SF with a chef inspired kitchen, while the 2nd ADU is nearly 1,000 SF. This estate is not just for horses; it's built for horsepower, featuring both a 2 car garage & oversized 4-car garage with high ceilings for large vehicles. A rare Los Gatos opportunity combining luxury, income, privacy, and lifestyle.

20100 Black RD, Los Gatos

Listed by David Conti, 408-896-4081 from KW Bay Area Estates
(If provided) CoList: from

624 Vasona AVE, Los Gatos
$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

Listed by Mark Gissler, 408-205-1729 from Intero Real Estate Services
(If provided) CoList: Caroline Anderson from Intero Real Estate Services
365 Pennsylvania AVE, Los Gatos
$3,650,000
4 Beds ⋅ 4 Baths ⋅ ML82046832 MLS
An extraordinary opportunity to own in one of the finest downtown Los Gatos locations. Built in 1991 this home's layout supports a variety of living arrangements. The primary living features 3 bedrooms, 2.5 baths w/ 2,680+/- sf. A separate second floor quarters includes 1 bedroom, 1 bath & 973+/- sf. An additional ADU of 387+/- sf is across the garden. Enjoy as is OR combine living spaces as desired. The main house highlights a stunning great room w/ open beam ceiling, bright dining & a chef's kitchen w/ SS appliances, a walk-in pantry & center island. French doors open to the rear Ipe entertainment deck creating seamless indoor-outdoor creek side living w/ privacy, views & Bocce Ball! A spacious primary suite w/ two walk-in closets, living room, study & powder room complete the main living. Downstairs, discover 2 bedrooms, family room, office, laundry & wine cellar/storage. Brazilian Cherry floors, skylights, recessed lighting, dual pane windows, AC & fresh painted interior. The expansive 11,500+/-sf grounds offer excellent space for entertaining, everyday enjoyment & incredible potential. Legal access to Wissahickon from rear of property. Great walkability to downtown & trails too. Exceptional schools complete the package. Have it all: lifestyle, flexibility & long term value!

365 Pennsylvania AVE, Los Gatos

Listed by Shelli Baker, 408-568-9412 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Erfan Modir from NTERO
140 Twin Oaks DR, Los Gatos
$7,800,000
5 Beds ⋅ 5 Baths ⋅ ML82044168 MLS
A beautifully executed, move-in ready luxury residence in the highly sought-after Surrey Farms neighborhood, this custom home by architect Gary Kohlsaat blends refined design, resort-style amenities, & a premier Los Gatos setting on a thoughtfully designed half-acre. Expansive living spaces flow into an open-concept kitchen & family room, where side-by-side La Cantina doors open to the resort-style grounds. The gourmet chefs kitchen is designed for both everyday living & entertaining, featuring premium appliances, an oversized waterfall island, designer finishes, & seamless connection to the main gathering spaces. The backyard is a true retreat with pool, spa, fire pit, turf lawn, play areas, built-in trampoline, sauna, outdoor shower, & covered loggia with fireplace, skylight, TV & outdoor kitchen with Evo grill. The primary suite offers a private deck, spa-like bath, & dual walk-in closets, while a detached ~800 sq ft pool house/ADU includes a living area, optional bedroom/dance-yoga studio & full bath for flexible living or guests. Additional features: game room, dedicated office, ground-level en-suite bedroom, smart home features, mudroom, & ~973 sq ft three-car garage with epoxy floors, home gym, & built-in storage. A truly special home with coveted Los Gatos schools.

140 Twin Oaks DR, Los Gatos

Listed by Fran Papapietro, 408-623-4155 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Lisa Radding from CBR
23054 Evergreen LN, Los Gatos
$1,620,000
3 Beds ⋅ 2 Baths ⋅ ML82046270 MLS
Mountain Serenity Meets Modern Luxury. Your Private Escape. Perched with breathtaking mountain views in the Villa Del Monte neighborhood, this 2,776 sq. ft. residence offers a masterclass in California indoor-outdoor living. Combining high-end culinary amenities with deep-rooted privacy, this property serves as a tranquil sanctuary just 16 minutes from the heart of Los Gatos. Designed for both grand entertaining and cozy family moments, the home features distinct living and family rooms anchored by gleaming hardwood floors. The back of this home is a destination in and off itself. Step out onto the durable Wood & Composite deck to find a comprehensive Outdoor Full Kitchen designed for the serious host. Experience the rare "best of both worlds" location. You are immersed in a private, nature-forward setting while remaining within the prestigious footprint of award-winning schools. Whether you are commuting to Silicon Valley or heading into Los Gatos for dinner, you are only 8.9 miles away from the city's vibrant downtown. Note: some records show 4 bedrooms; 2 bedrooms were previously combined into the current primary suite .

23054 Evergreen LN, Los Gatos

Listed by Paula L Leary, 408-425-3345 from Golden Gate Sotheby's International Realty
(If provided) CoList: Terence Leary from Golden Gate Sotheby's International Realty

Sold listing courtesy of Kirsty Hepburn from COMPS
24580 Loma Prieta AVE, Los Gatos
$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

Listed by Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty
125 Via Santa Maria, Los Gatos
$4,250,000
4 Beds ⋅ 3 Baths ⋅ ML82046035 MLS
Set on an expansive lot backing to a tranquil, tree-lined creek, this Los Gatos residence offers a rare sense of privacy and calm in one of the areas most sought-after neighborhoods. A gracious formal entry opens to beautifully proportioned living spaces, including a refined living room & a separate family room each with its own fireplace alongside a formal dining room designed for effortless entertaining. The kitchen is both functional and inviting, featuring an eat-in area, generous workspace & a full suite of appliances including a gas range, dishwasher, microwave, and oven.The primary suite is a comfortable retreat, complete with a spacious tile shower, dual vanities & a walk-in closet. The hall bathroom also offers double sinks, blending style with everyday convenience. Hardwood flooring extends through the kitchen, family room, and den (first bedroom), complemented by dual-pane windows that bring in natural light throughout the home. Outdoors, the approximately 11,840 sqft lot unfolds into a serene Creekside setting offering a sense of space and opportunity thats increasingly rare in Los Gatos. Additional highlights include a utility room, composition shingle roof, and an attached 2-car garage with attic storage. All within the highly regarded Los Gatos school district.

125 Via Santa Maria, Los Gatos

Listed by Chuck Nunnally, 408-568-1779 from KW Bay Area Estates
(If provided) CoList: from

Sold listing courtesy of George Montanari from COMPS
216 Montclair RD, Los Gatos
$3,050,000
3 Beds ⋅ 3 Baths ⋅ ML82045991 MLS
AWESOME LOCATION W/HUGE UPSIDE!! Rare Serene Sunsplashed Property, Framed by Majestic Trees Sets the Stage for Greater Expansion!FAB HIGHLY SOUGHT-AFTER N'HD! Delightful Custom will capture your heart+features awe-inspiring serene flower garden Courtyard that invites time to stand still, a place for morning coffee or just to enjoy! Rich oak flooring throughout! Spacious light-filled Living Room boasts classic fireplace and cozy hearth for those cool nights. Dining Room shares the expansive LR; perfect for gatherings and entertaining. Remodeled Kitchen+Breakfast Nook open to Superb Family Room with Cathedral beam ceilings, Fireplace+walls of glass to Picturesque Backyard. The Versatile Separate OFFICE was converted from 4th bedroom! Convenient Laundry Room offers Guest Powder Room+glass door to side yard. Bedroom Wing features the 3 Spacious Bedrooms, Hall Bath Including Primary Retreat complete with walk-in closet, Oversize vanity, Stall shower+Sliding glass door to Patio. Picturesque Private Backyard will mesmerize, Providing Endless options. Lush lawns, Trellis-covered dining patio, large sunny decks with flowering shade trees and tranquil views of majestic oaks. Detached garage includes overhead loft storage. EZ Upgrades needed:Dated baths,Re-imagine Front Patio+Renew decking!

216 Montclair RD, Los Gatos

Listed by Lucy Wedemeyer, 408-891-6861 from Christie's International Real Estate Sereno
(If provided) CoList: Keith Andry from Christie's International Real Estate Sereno

Sold listing courtesy of Greg Simpson from KWLGE
27510 Loma Prieta WAY, Los Gatos
$1,695,000
3 Beds ⋅ 3 Baths ⋅ ML82045960 MLS
Only 30 Minutes to Los Gatos or Santa Cruz * This "Top of the World" Custom Home Commands Sweeping Views of the Coastline and Unforgettable Sunsets * Designed with Both Elegance and Intention, the Upgraded Chef's Kitchen Showcases Quartz Countertops, Wolf Range, Viking Warming Drawer, Other High-End Appliances, Custom Cabinetry, Recessed Lighting, Pantry with a Glass Panel Door * Distinctive Touches * Repurposed Redwood and Walnut Accents * Freestanding Stove Lend Warmth, Character and Craftsmanship * Living Room is Defined by a Dramatic Wall of Picture Windows, Seamlessly Blending Indoor and Outdoor Beauty While Filling the Space with Natural Light * Fireplace * Rich Architectural Details Include Custom Wood Wainscoting * Hardwood and Tile Flooring * Arched Doorways * Old-World Textured Walls and Ceilings Creating a Timeless, Sophisticated Ambiance * A Few Stairs Will Direct You to a Loft-Style Game Room with Plank Floors Offers Flexible Living Space * Bonus Room Could Be 4th Bedroom * Expansive View Decks Invite Effortless Entertaining or Quiet Beautiful Sunsets * Additional Amenities Include an Automatic Water Shutoff System, Wrought Iron Fencing, Multiple View Patios, Generator Readiness for Added Security, New Septic System, and Covered Parking.

27510 Loma Prieta WAY, Los Gatos

Listed by John Espinosa, 408-309-3848 from Alta Realty Group CA
(If provided) CoList: Jennifer Espinosa from Alta Realty Group CA
19534 Montevina RD, Los Gatos
$4,499,999
6 Beds ⋅ 7 Baths ⋅ ML82041336 MLS
MOTIVATED SELLER. $1,500,000 PRICE IMPROVEMENT! Welcome to this newly constructed compound estate on over 10 private acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat features three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa offers 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step outside to your private vineyard producing your own custom-labeled wine before arriving at an impressive Auto House built for car enthusiasts. The Auto House includes five car bays for collectors, plus an office and wet bar, creating the perfect setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a barn with 8 stalls, ideal for livestock or equestrian use. Configured as a working farm, the barn includes a laundry room and bathroom downstairs, with a fully permitted 2-bedroom, 3-bathroom living space upstairs perfect for ranch hands, rental income, guests, or returning adult children. Enjoy close proximity to the El Sereno Open Space Preserve Trail, world-renowned schools, and all the incredible restaurants and entertainment Los Gatos has to offer.

19534 Montevina RD, Los Gatos

Listed by Justin Moles, 408-896-3835 from Intero Real Estate Services
(If provided) CoList: Dominic Nicoli from Intero Real Estate Services
18836 Favre Ridge RD, Los Gatos
$1,850,000
4 Beds ⋅ 3 Baths ⋅ ML82045842 MLS ⋅ Las Cumbres BLDG.
Breathtaking, unobstructed canyon & mountain views from nearly every room set the stage for this extraordinary Las Cumbras retreat. Completely rebuilt in 1995 & 2007 with permits - adding sq footage, bedrooms, living spaces & a new seismically engineered foundation - this home was architected to capture views at every turn. Soaring cathedral ceilings, a dramatic stone fireplace, hardwood floors & an open flow between living room, family room & kitchen create a space both grand & made for the way you actually live. The chef kitchen features a large center island with sink & breakfast bar, custom pecan cabinetry, granite countertops, 6-burner gas cooktop, dual wall ovens, warming oven & wine fridge. The serene primary suite includes a loft with floor-to-ceiling built-ins, glorious views, wood ceilings & walk-in closet. Main level office with full bath & closets - easily a 5th bedroom. Downstairs: 3 bedrooms, full bath & sitting area with views. Attached 2-car garage, mud room, laundry & 2nd driveway. European rolling shutters, backup generator, whole-house filtration & wildfire hardening provide peace of mind. Firewise certified community with pool, trails, sports courts & 2-gig fiber Internet. Award-winning Los Gatos schools. 25 min to downtown Los Gatos. Truly one of a kind!

18836 Favre Ridge RD, Los Gatos

Listed by Janet Souza, 408-805-3349 from Christie's International Real Estate Sereno
(If provided) CoList: from

227 Alexander AVE, Los Gatos
$6,250,000
4 Beds ⋅ 3 Baths ⋅ ML82045746 MLS
Walk to Downtown Los Gatos from this beautifully remodeled home in the premier Glen Ridge neighborhood. Extensively updated since ownership, the residence pairs classic curb appeal with a thoughtfully reimagined interior and modern systems. A lush front setting with blooming roses and a mature oak canopy creates a warm first impression. Inside, wide-plank engineered hardwood floors, vaulted ceilings, and abundant natural light define the living spaces. The living room sits just off the entry with fireplace and picture windows with plantation shutters. The kitchen is designed for everyday living and entertaining, fully updated with top of the line appliances, custom cabinetry, and under-cabinet lighting. Dining and family room areas open to the patio through French doors, enhancing indoor-outdoor flow. The main level includes 3 guest beds, 2 full baths and laundry closet. The expansive primary suite occupies the upper level with vaulted wood-plank ceilings, private balcony, soaking tub, tile shower, skylights, multiple closets, and laundry. A lower-level bonus room adds flexibility. The backyard enjoys a tile patio with built-in BBQ, mature oak and ample land to enjoy. Paved driveway lined with greenery leads to the detached 2-car garage with epoxy flooring. This home has it all!

227 Alexander AVE, Los Gatos

Listed by Amy McCafferty, 408-387-3227 from Golden Gate Sotheby's International Realty
(If provided) CoList: Eric McCafferty from Golden Gate Sotheby's International Realty

Sold listing courtesy of Greg Simpson from KWLGE
19544 Sky Oaks WAY, Los Gatos
$3,625,000
4 Beds ⋅ 3 Baths ⋅ ML82045681 MLS

19544 Sky Oaks WAY, Los Gatos

Listed by Sonia Leclerc, 408-373-6140 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Kristina Young from CBR
21420 Bear Creek RD, Los Gatos
$2,050,000
5 Beds ⋅ 3 Baths ⋅ ML82045668 MLS
For comp purposes, sold with APN 091-021-11-000 Lovely ranch style home with kitchen updates, fresh paint, new carpets. Views and small vineyard.

21420 Bear Creek RD, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: from

Sold listing courtesy of Christopher Braun from ROOM
16250 Brooke Acres DR, Los Gatos
$5,500,000
4 Beds ⋅ 4 Baths ⋅ ML82045580 MLS
Listing & Sale added For Comp purposes.

16250 Brooke Acres DR, Los Gatos

Listed by Shawn Ansari, 408-529-4574 from Compass
(If provided) CoList: from

Sold listing courtesy of Nevis and Ardizzone from COMPS
116 Regent DR, Los Gatos
$4,000,499
4 Beds ⋅ 4 Baths ⋅ ML82045562 MLS ⋅ Heritage Grove of Los Gatos BLDG.
Welcome to 116 Regent Dr in Los Gatos in the desirable Heritage Grove development and nearby to the Heintz Open Space Preserve. This home offers lovely vistas of the valley floor across to Mount Diablo. This home offers 3,320±sf of living space on a .25 acre lot. A spacious bonus room/formal office and separate living room with a gas fireplace are located off the entry. A formal dining room offers an abundance of entertainment space. The kitchen opens to a great room which offers high ceilings, a wood-burning fireplace, and large windows overlooking the verdant backyard. The kitchen features a gas cooktop, built-in double oven, island with sink, granite counters, built-in refrigerator, and dishwasher. Upstairs are 4 beds and 3 baths, including the primary suite. The primary offers a private balcony and windows overlooking beautiful valley views featuring a double-sink vanity, large jetted soaking tub, separate stall shower, and spacious walk-in closet. There is a second en-suite bed, and beds 3 and 4 conveniently share a Jack and Jill bath. The backyard has a wide variety of fruit trees, including fig, apricot, pomegranate, orange, lemon, loquat, peach, persimmon, and avocado. Conveniently located near hiking trails with easy access to Hwy 85. Alta Vista Elementary.

116 Regent DR, Los Gatos

Listed by Nevis and Ardizzone, 408-891-8149 from Compass
(If provided) CoList: from

Sold listing courtesy of Moe Baniani from COMPS

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