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$4,648,000

Nestled among majestic trees just 15 minutes from downtown Saratoga, this architecturally significant modern retreat offers a rare blend of design, privacy, & connection to nature. Showcased in DWELL & thoughtfully integrated into its spectacular 2.9-acre setting, the residence unfolds through walls of glass, soaring ceilings, & extraordinary indoor-outdoor living. Light pours through endless windows, framing meadow & forest views while valley lights shimmer at night. Endless space to build a pool/pool house, ADU, large garages, or keep it as a fenced in pasture for horses. Built in 2018, the home features dramatic living spaces with 20-foot ceilings, a stunning chefs kitchen anchored by an oversized marble island & premium appliances, & a spectacular primary retreat with private terrace and spa-like bath. Designed for both sophisticated entertaining & everyday sanctuary, the flexible floor plan includes multiple guest accommodations, media & recreation spaces, a roof deck & a detached 400-square-foot guest retreat or executive office. Bordered by Castle Rock State Park with direct access to nature, yet remarkably close to downtown dining, shopping, & commuter routes, this is a home for those seeking something truly unforgettable architectural, private, & impossible to replicate.

6 Beds ⋅ 5 Baths ⋅ ML82055683 MLS

Nestled among majestic trees just 15 minutes from downtown Saratoga, this architecturally significant modern retreat offers a rare blend of design, privacy, & connection to nature. Showcased in DWELL & thoughtfully integrated into its spectacular 2.9-acre setting, the residence unfolds through walls of glass, soaring ceilings, & extraordinary indoor-outdoor living. Light pours through endless windows, framing meadow & forest views while valley lights shimmer at night. Endless space to build a pool/pool house, ADU, large garages, or keep it as a fenced in pasture for horses. Built in 2018, the home features dramatic living spaces with 20-foot ceilings, a stunning chefs kitchen anchored by an oversized marble island & premium appliances, & a spectacular primary retreat with private terrace and spa-like bath. Designed for both sophisticated entertaining & everyday sanctuary, the flexible floor plan includes multiple guest accommodations, media & recreation spaces, a roof deck & a detached 400-square-foot guest retreat or executive office. Bordered by Castle Rock State Park with direct access to nature, yet remarkably close to downtown dining, shopping, & commuter routes, this is a home for those seeking something truly unforgettable architectural, private, & impossible to replicate.

13755 Skyline BLVD, Los Gatos

Listed by Tiger Teerlink, 408-828-9614 from Compass
(If provided) CoList: from

$3,800,000

Exceptional opportunity located at the corner of Shannon and Short Rd, this spacious 3,480 sq ft home on a 1 acre lot offers 5+ bedrooms and 5 full bathrooms in the main house plus a 1 bed/1 bath 792 Sq Ft guest house. The main level benefits from stunning views over Los Gatos and exceptional natural light. You'll find 2 full bedroom suites on this floor as well as formal living/dining with gorgeous views, large modern kitchen, breakfast nook, and office/family room. A spacious family rm (optional third bedroom) completes the upper level. A fully finished 1175 SqFt walkout basement conversion offers a potential 3 further bedrooms (currently 2 bedrooms are combined), 2 bathrooms and a recreation room. The property sits on a private 1 acre lot and includes a two-car garage, ample parking, an expansive terrace and a resort style pool, spa and beach area. Amenities include whole house on-grid solar power with battery backup. All buildings, pool, spa and terraces are located on the upper half acre leaving the lower half ready for your imagination. SB9 lot split may be possible (buyer to investigate) or simply enjoy the rural feel of your own private acre. A rural paradise with the convenience of a popular in-town neighborhood. Truly a unique opportunity.

6 Beds ⋅ 6 Baths ⋅ ML82051259 MLS

Exceptional opportunity located at the corner of Shannon and Short Rd, this spacious 3,480 sq ft home on a 1 acre lot offers 5+ bedrooms and 5 full bathrooms in the main house plus a 1 bed/1 bath 792 Sq Ft guest house. The main level benefits from stunning views over Los Gatos and exceptional natural light. You'll find 2 full bedroom suites on this floor as well as formal living/dining with gorgeous views, large modern kitchen, breakfast nook, and office/family room. A spacious family rm (optional third bedroom) completes the upper level. A fully finished 1175 SqFt walkout basement conversion offers a potential 3 further bedrooms (currently 2 bedrooms are combined), 2 bathrooms and a recreation room. The property sits on a private 1 acre lot and includes a two-car garage, ample parking, an expansive terrace and a resort style pool, spa and beach area. Amenities include whole house on-grid solar power with battery backup. All buildings, pool, spa and terraces are located on the upper half acre leaving the lower half ready for your imagination. SB9 lot split may be possible (buyer to investigate) or simply enjoy the rural feel of your own private acre. A rural paradise with the convenience of a popular in-town neighborhood. Truly a unique opportunity.

16057 Shannon RD, Los Gatos

Listed by Slater Thomson Team, 408-205-3758 from Intero Real Estate Services
(If provided) CoList: from

$12,498,000

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!

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

$1,928,000

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.

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

$4,998,000

$1,000,000 PRICE IMPROVEMENT! BEST VALUE IN LOS GATOS Welcome to this newly constructed compound estate on over 10 acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat offers three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa features 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step into your private vineyard, which produces your own privatelabeled wine, and you are greeted by an impressive AutoHouse for car enthusiasts. The Auto House offers five car bays for collectors, plus an office and wet bar, creating an ideal setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a live barn with 8 stalls for livestock or equestrian use. Configured as a working farm, the barn includes laundry and a bathroom downstairs, with a fully permitted 2-bedroom, 2 bathroom living space upstairs. Perfect for ranch hands, rental income, guests, or returning adult children. Approximately 3 miles from Downtown Los Gatos, you enjoy privacy while still close to shops, dining, and amenities. Award winning schools, hiking trails and scenic views this is a property you don't want to miss!

6 Beds ⋅ 7 Baths ⋅ ML82041336 MLS

$1,000,000 PRICE IMPROVEMENT! BEST VALUE IN LOS GATOS Welcome to this newly constructed compound estate on over 10 acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat offers three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa features 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step into your private vineyard, which produces your own privatelabeled wine, and you are greeted by an impressive AutoHouse for car enthusiasts. The Auto House offers five car bays for collectors, plus an office and wet bar, creating an ideal setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a live barn with 8 stalls for livestock or equestrian use. Configured as a working farm, the barn includes laundry and a bathroom downstairs, with a fully permitted 2-bedroom, 2 bathroom living space upstairs. Perfect for ranch hands, rental income, guests, or returning adult children. Approximately 3 miles from Downtown Los Gatos, you enjoy privacy while still close to shops, dining, and amenities. Award winning schools, hiking trails and scenic views this is a property you don't want to miss!

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

$9,850,000

This newly constructed estate is a testament to masterful craftsmanship and contemporary design. Unique architectural elements and bespoke finishes create light-filled spaces with seamless indoor-outdoor flow. Offering 5566± SF on a 1-acre+ lot, the home is tucked behind a shared private gate for ultimate seclusion. The residence features 5 en-suite bedrooms, 5.5 baths, a private office, and an attached in-law suite with a kitchen and laundry. A detached 999 SF ADU offers 2 bedrooms, 2 baths, and a 1-car garage ideal for guests or multi-generational living. A grand pivot entry reveals soaring 15 ceilings, floor-to-ceiling windows, European oak floors, imported stone, and Hi-Fi audio. A marble rotunda staircase, elevator, and spa-inspired baths with steam showers enhance the home scale. The chefs kitchen boasts Miele appliances, a steam oven, espresso station, wine fridge, and touch-latch cabinetry. Resort-style grounds include multiple balconies, fountains, an outdoor kitchen, a fire pit, & space for a pool or tennis court. High-tech amenities include Tesla solar/Powerwalls, EV charging, smart home integration, and a 3-car attached garage. Ideally located minutes from downtown Saratoga and Los Gatos, with easy access to Highways 17 & 85 and served by top-tier local schools.

7 Beds ⋅ 8 Baths ⋅ ML82044544 MLS

This newly constructed estate is a testament to masterful craftsmanship and contemporary design. Unique architectural elements and bespoke finishes create light-filled spaces with seamless indoor-outdoor flow. Offering 5566± SF on a 1-acre+ lot, the home is tucked behind a shared private gate for ultimate seclusion. The residence features 5 en-suite bedrooms, 5.5 baths, a private office, and an attached in-law suite with a kitchen and laundry. A detached 999 SF ADU offers 2 bedrooms, 2 baths, and a 1-car garage ideal for guests or multi-generational living. A grand pivot entry reveals soaring 15 ceilings, floor-to-ceiling windows, European oak floors, imported stone, and Hi-Fi audio. A marble rotunda staircase, elevator, and spa-inspired baths with steam showers enhance the home scale. The chefs kitchen boasts Miele appliances, a steam oven, espresso station, wine fridge, and touch-latch cabinetry. Resort-style grounds include multiple balconies, fountains, an outdoor kitchen, a fire pit, & space for a pool or tennis court. High-tech amenities include Tesla solar/Powerwalls, EV charging, smart home integration, and a 3-car attached garage. Ideally located minutes from downtown Saratoga and Los Gatos, with easy access to Highways 17 & 85 and served by top-tier local schools.

18800 Saratoga Los Gatos RD, Los Gatos

Listed by Parrin Jalali, 408-497-7797 from Intero Real Estate Services
(If provided) CoList: from

$8,950,000

Welcome to La Estancia, a rare historic estate in Glenridge, one of Los Gatos most sought-after neighborhoods and just moments from exciting downtown Los Gatos. Originally crafted in the late 1800s and refined in 1901 by architect Willis Polk, whose work includes the famed Filoli estate in Woodside, California. This Mission Revival residence blends timeless character with exceptional privacy. Set behind gates on over 1.55 FLAT acres, the property features a grand main home, a guest house, a pool, a cabana, a detached oversized two-car garage, a 1,687 sq ft walkout basement with office and storage, and a tranquil pond with a water feature framed by mature trees. Expansive living spaces highlight rich architectural details, arched openings, and hillside views. Multiple indoor-outdoor areas create an ideal setting for entertaining or a quiet retreat. The offering includes two parcels a 56,102 sq ft (APN 51040159) plus an additional 11,416 sq ft lot with Overlook Road frontage (APN 51040160), providing flexibility for future possibilities, including a potential additional residence. Buyers should verify all options with the Town of Los Gatos. Widely regarded as one of the region's most iconic estates, La Estancia offers history, beauty, and the essence of California estate living.

7 Beds ⋅ 5 Baths ⋅ ML82042840 MLS

Welcome to La Estancia, a rare historic estate in Glenridge, one of Los Gatos most sought-after neighborhoods and just moments from exciting downtown Los Gatos. Originally crafted in the late 1800s and refined in 1901 by architect Willis Polk, whose work includes the famed Filoli estate in Woodside, California. This Mission Revival residence blends timeless character with exceptional privacy. Set behind gates on over 1.55 FLAT acres, the property features a grand main home, a guest house, a pool, a cabana, a detached oversized two-car garage, a 1,687 sq ft walkout basement with office and storage, and a tranquil pond with a water feature framed by mature trees. Expansive living spaces highlight rich architectural details, arched openings, and hillside views. Multiple indoor-outdoor areas create an ideal setting for entertaining or a quiet retreat. The offering includes two parcels a 56,102 sq ft (APN 51040159) plus an additional 11,416 sq ft lot with Overlook Road frontage (APN 51040160), providing flexibility for future possibilities, including a potential additional residence. Buyers should verify all options with the Town of Los Gatos. Widely regarded as one of the region's most iconic estates, La Estancia offers history, beauty, and the essence of California estate living.

18000 Overlook RD, Los Gatos

Listed by Donald Knight, 408-313-2191 from Coldwell Banker Realty
(If provided) CoList: Robin Sedgwick from Coldwell Banker Realty

$13,800,000

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.

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

Listed by Rick Alva, 408-472-3999 from Windermere Valley Properties
(If provided) CoList: from

$4,888,000

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.

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

Listed by Cassandra Maas, 408-472-7988 from Anderson Christie, Inc.
(If provided) CoList: from

$16,000,000

EXCELLENT OPPORTUNITY! PRIME LOCATION! VALUE IS IN THE LAND Perfect Estate property or Subdivision. One of the last large and close-in properties in Los Gatos. Located in the prestigious neighborhood of Surrey Farms, this was the original developer's home and land. The property offers sweeping valley and mountain views with gently rolling hills studded with majestic oak trees but still offers an abundance of level acreage. This special property offers an endless array of possibilities... Grand Estate, Development Opportunity, Vineyard, Equestrian...

6 Beds ⋅ 5 Baths ⋅ ML81937235 MLS

EXCELLENT OPPORTUNITY! PRIME LOCATION! VALUE IS IN THE LAND Perfect Estate property or Subdivision. One of the last large and close-in properties in Los Gatos. Located in the prestigious neighborhood of Surrey Farms, this was the original developer's home and land. The property offers sweeping valley and mountain views with gently rolling hills studded with majestic oak trees but still offers an abundance of level acreage. This special property offers an endless array of possibilities... Grand Estate, Development Opportunity, Vineyard, Equestrian...

170 Twin Oaks DR, Los Gatos

Listed by Gaylene Wyatt, 408-832-6922 from Christie's International Real Estate Sereno
(If provided) CoList: from

Rodda Realty Team

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