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Welcome to 14950 Gypsy Hill Road, a custom executive home built in 1995 located on a cul-de-sac offering thoughtfully designed indoor outdoor living and access to award winning Saratoga schools. Set on nearly two acres with professionally landscaped grounds, a sparkling pool, sport court, pergola covered conversation area with fireplace and large putting green, this property blends privacy, tranquility and convenience. Interior highlights include fresh paint, high ceilings, recessed lighting, plush new carpeting, hardwood and tile flooring. The main level features a primary suite, two en-suite bedrooms, a private office and a powder bathroom near common living areas. Spacious, light filled living and dining rooms are ideal for everyday comfort and entertaining. Downstairs, an entertainment area, guest bedroom and full bath offer flexibility for visitors. The private backyard features pergola-covered patios, an outdoor kitchen and inviting spaces for dining, relaxing and entertaining. Minutes from downtown Saratoga, major tech campuses, renowned wineries, fine dining, boutique shopping, outdoor recreation and Mountain Winery, this exceptional property offers beautiful grounds, outstanding schools and a premier Silicon Valley location, with lasting appeal and sophistication.

4 Beds ⋅ 5 Baths ⋅ ML82060194 MLS

Welcome to 14950 Gypsy Hill Road, a custom executive home built in 1995 located on a cul-de-sac offering thoughtfully designed indoor outdoor living and access to award winning Saratoga schools. Set on nearly two acres with professionally landscaped grounds, a sparkling pool, sport court, pergola covered conversation area with fireplace and large putting green, this property blends privacy, tranquility and convenience. Interior highlights include fresh paint, high ceilings, recessed lighting, plush new carpeting, hardwood and tile flooring. The main level features a primary suite, two en-suite bedrooms, a private office and a powder bathroom near common living areas. Spacious, light filled living and dining rooms are ideal for everyday comfort and entertaining. Downstairs, an entertainment area, guest bedroom and full bath offer flexibility for visitors. The private backyard features pergola-covered patios, an outdoor kitchen and inviting spaces for dining, relaxing and entertaining. Minutes from downtown Saratoga, major tech campuses, renowned wineries, fine dining, boutique shopping, outdoor recreation and Mountain Winery, this exceptional property offers beautiful grounds, outstanding schools and a premier Silicon Valley location, with lasting appeal and sophistication.

14950 Gypsy Hill RD, Saratoga

Welcome Home to 14275 Hilltop Way a Private Saratoga Retreat w/ Mountain Views & Award-Winning Schools! East-Facing Double Door Entry, Fresh Paint, Recessed Lighting & Huge Picture Windows! Light & Bright w/ Multiple Skylights! Elegant Interior w/ Hardwood Floors, Formal Dining Room w/ Chandelier, Breakfast Nook & Motorized Window Treatments. Living Room w/ Vaulted Cathedral Ceiling, Chandeliers, Wood-Burning Fireplace, Built-Ins & Display Shelving. Double Sliding Glass Doors to Front Courtyard! Family Room w/ Double Sliding Doors to Courtyard & Fireplace. Kitchen w/ Stone Counters, Designer Tile Backsplash, Custom Wood Cabinetry & Stainless Steel Appliances. Primary Suite w/ Mountain Views, French Doors to Freshly Stained Ipe Deck & Dual Walk-In Closets. Spa-Like Ensuite w/ Natural Stone Tile, Dual Vanity, Skylight, Oversized Shower, Sunken Tub & Smart Toilet. Attached Possible ADU w/ Secondary Kitchen, Laundry & Stainless Steel Appliances. Owned Solar, EV Charger, Dual-Zone HVAC & Tankless Water Heater. Travertine Patio, Covered Pergola, Outdoor Kitchen, PebbleTec Pool, New Pool Filter & Heater, Waterfall, Lush Gardens, Fruit Orchard & Wide Driveway. Minutes to Saratoga Farmers Market, Hwy 85, Downtown LG, Downtown Saratoga, Apple & NVIDIA. Truly Exceptional Saratoga Estate!

5 Beds ⋅ 4 Baths ⋅ ML82053919 MLS

Welcome Home to 14275 Hilltop Way a Private Saratoga Retreat w/ Mountain Views & Award-Winning Schools! East-Facing Double Door Entry, Fresh Paint, Recessed Lighting & Huge Picture Windows! Light & Bright w/ Multiple Skylights! Elegant Interior w/ Hardwood Floors, Formal Dining Room w/ Chandelier, Breakfast Nook & Motorized Window Treatments. Living Room w/ Vaulted Cathedral Ceiling, Chandeliers, Wood-Burning Fireplace, Built-Ins & Display Shelving. Double Sliding Glass Doors to Front Courtyard! Family Room w/ Double Sliding Doors to Courtyard & Fireplace. Kitchen w/ Stone Counters, Designer Tile Backsplash, Custom Wood Cabinetry & Stainless Steel Appliances. Primary Suite w/ Mountain Views, French Doors to Freshly Stained Ipe Deck & Dual Walk-In Closets. Spa-Like Ensuite w/ Natural Stone Tile, Dual Vanity, Skylight, Oversized Shower, Sunken Tub & Smart Toilet. Attached Possible ADU w/ Secondary Kitchen, Laundry & Stainless Steel Appliances. Owned Solar, EV Charger, Dual-Zone HVAC & Tankless Water Heater. Travertine Patio, Covered Pergola, Outdoor Kitchen, PebbleTec Pool, New Pool Filter & Heater, Waterfall, Lush Gardens, Fruit Orchard & Wide Driveway. Minutes to Saratoga Farmers Market, Hwy 85, Downtown LG, Downtown Saratoga, Apple & NVIDIA. Truly Exceptional Saratoga Estate!

14275 Hilltop WAY, Saratoga

Knoll top estate boasts panoramic views! Wheelchair accessibility includes entry ramp, 3 floor elevator & walk-in bathtub/shower. Hardwood floors, custom mill work, & high ceilings. Large windows & glass doors invite abundance of natural light. Formal living & dining rooms & well appointed office. Luxury primary w/ fireplace, Jacuzzi, double sinks & oversized shower. Craft/sewing/art room. Flexible as a 4th bedrm, play- hobby room, or creative workspace. Industrial workshop w/ 240 three phase power, air compressor plumbed throughout, storage, sink & ventilation perfect for wood workers, machinists, welders, auto enthusiasts etc. Or transform into a game room, gym, theatre or extension of garage. Space for oversized vehicles. Gourmet kitchen: 2 Thermador convection ovens, Thermador 5-burner cooktop, Kohler cook sink, & Grohe faucets. Sub Zero refrigerator/ freezer, Thermador warming drawer, 2 Fisher & Paykel dishwashers, 2 GE Profile microwaves. Butlers pantry w/ additional counter & cabinet space, sink & beverage fridge. Finished attic used as playroom, storage, extended pantry. Built-in speakers throughout. 20 KVA Winco Generator. 600 amp, 240 volt, 3 phase electrical service & 5 - 100 amp sub panels. 3 HVAC systems. Garage w/built-in workbench & exhaust hood. 30 foot flag pole.

4 Beds ⋅ 4 Baths ⋅ ML82055490 MLS

Knoll top estate boasts panoramic views! Wheelchair accessibility includes entry ramp, 3 floor elevator & walk-in bathtub/shower. Hardwood floors, custom mill work, & high ceilings. Large windows & glass doors invite abundance of natural light. Formal living & dining rooms & well appointed office. Luxury primary w/ fireplace, Jacuzzi, double sinks & oversized shower. Craft/sewing/art room. Flexible as a 4th bedrm, play- hobby room, or creative workspace. Industrial workshop w/ 240 three phase power, air compressor plumbed throughout, storage, sink & ventilation perfect for wood workers, machinists, welders, auto enthusiasts etc. Or transform into a game room, gym, theatre or extension of garage. Space for oversized vehicles. Gourmet kitchen: 2 Thermador convection ovens, Thermador 5-burner cooktop, Kohler cook sink, & Grohe faucets. Sub Zero refrigerator/ freezer, Thermador warming drawer, 2 Fisher & Paykel dishwashers, 2 GE Profile microwaves. Butlers pantry w/ additional counter & cabinet space, sink & beverage fridge. Finished attic used as playroom, storage, extended pantry. Built-in speakers throughout. 20 KVA Winco Generator. 600 amp, 240 volt, 3 phase electrical service & 5 - 100 amp sub panels. 3 HVAC systems. Garage w/built-in workbench & exhaust hood. 30 foot flag pole.

15217 Sobey RD, Saratoga

Are you tired of waiting for your dream home? Then why not build it exactly the way you envision? Welcome to a rare opportunity to create your custom dream home on a private and peaceful 16,878-square-foot vacant lot in a highly desirable setting surrounded by beautiful luxury residences. This exceptional parcel offers picturesque mountain views, abundant natural sunlight, nearby access to utilities, and convenient proximity to award-winning schools. Design a home tailored to your lifestyle, preferences, and future needs-all in a quiet, established neighborhood offering privacy, natural beauty, and tremendous potential. Bring your architect, builder, and imagination to transform this remarkable property into the home you have always dreamed of.

Are you tired of waiting for your dream home? Then why not build it exactly the way you envision? Welcome to a rare opportunity to create your custom dream home on a private and peaceful 16,878-square-foot vacant lot in a highly desirable setting surrounded by beautiful luxury residences. This exceptional parcel offers picturesque mountain views, abundant natural sunlight, nearby access to utilities, and convenient proximity to award-winning schools. Design a home tailored to your lifestyle, preferences, and future needs-all in a quiet, established neighborhood offering privacy, natural beauty, and tremendous potential. Bring your architect, builder, and imagination to transform this remarkable property into the home you have always dreamed of.

14171 Chester AVE, Saratoga

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All measurements and all calculations of area (i.e., Sq Ft and Acreage) are approximate. Broker has represented to MetroList that Broker has a valid listing signed by seller authorizing placement in the MLS. Above information is provided by Seller and/or other sources and has not been verified by Broker. Copyright 2026 MetroList Services, Inc. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of MetroList® MLS. All information has been provided by seller/other sources and has not been verified by broker. All interested persons should independently verify the accuracy of all information. Last updated .