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A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS

A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates

Sold listing courtesy of Adam Touni from COMPS

$6,350,000

This beautifully appointed residence blends warm natural materials with abundant windows and effortless indoor/outdoor living, on one of Woodsides most desired streets/locations. Expansive decks provide multiple areas for dining, entertaining & relaxing while overlooking the Cabernet Sauvignon vineyard. Stunning living room with vaulted wood beam ceilings, wood burning fireplace & wall of glass overlooking the vineyard. Separate family room features recessed lighting & gorgeous built-ins. Kitchen features Miele built in oven, Thermador gas cooktop, dishwasher drawers, & a glass door refrigerator. The serene primary suite features custom built-ins, a window seat, walk-in closet, private deck access w/hot tub & a beautifully detailed bath with dual vanities and freestanding soaking tub.Additional bedroom features a built-in desk and a sliding glass door to the deck. Separate den, office or wine room with wet bar & sliding doors to the back deck.Terraced gardens, level side and rear lawns, and raised beds for vegetables bring forth ultimate usability throughout the grounds.Mature landscaping and a striking outdoor water feature complete this extraordinarily peaceful setting.A rare opportunity to experience the privacy & natural beauty that define Woodside living in an A+ location.

2 Beds ⋅ 2 Baths ⋅ ML82062379 MLS

This beautifully appointed residence blends warm natural materials with abundant windows and effortless indoor/outdoor living, on one of Woodsides most desired streets/locations. Expansive decks provide multiple areas for dining, entertaining & relaxing while overlooking the Cabernet Sauvignon vineyard. Stunning living room with vaulted wood beam ceilings, wood burning fireplace & wall of glass overlooking the vineyard. Separate family room features recessed lighting & gorgeous built-ins. Kitchen features Miele built in oven, Thermador gas cooktop, dishwasher drawers, & a glass door refrigerator. The serene primary suite features custom built-ins, a window seat, walk-in closet, private deck access w/hot tub & a beautifully detailed bath with dual vanities and freestanding soaking tub.Additional bedroom features a built-in desk and a sliding glass door to the deck. Separate den, office or wine room with wet bar & sliding doors to the back deck.Terraced gardens, level side and rear lawns, and raised beds for vegetables bring forth ultimate usability throughout the grounds.Mature landscaping and a striking outdoor water feature complete this extraordinarily peaceful setting.A rare opportunity to experience the privacy & natural beauty that define Woodside living in an A+ location.

1100 Mountain Home RD, Woodside

Listed by Zach Trailer, 650-906-8008 from Compass
(If provided) CoList: from

Sold listing courtesy of Jennifer Alfaro from COMPS

$4,195,000

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

4 Beds ⋅ 4 Baths ⋅ ML82037717 MLS

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

950 Espinosa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Brittany Hogan from CCEXPRNC

$3,350,000

Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

4 Beds ⋅ 3 Baths ⋅ ML82060102 MLS

Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

232 Highland TER, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Helen Miller from APR

$8,000,000

Privately positioned at the end of a gated country lane, this elegant French Country estate combines sweeping Western Hills and sunset views with the convenience of a prime Central Woodside location. Set on approximately 1.11 acres, the grounds feature expansive terraces, mature landscaping, and inviting spaces for indoor-outdoor living and entertaining. The main residence features four bedrooms, five-and-a-half bathrooms, a dedicated office/library, a main-level primary suite with an adjoining flexible-use room, and a recently updated chefs kitchen with a sunny breakfast area. Patterned oak floors, high ceilings, and abundant natural light create a warm, sophisticated atmosphere throughout. A detached one-bedroom, one-bath guest house with a full kitchen, fireplace, and high ceilings provides an ideal setting for guests, extended stays, or a private workspace. Just moments from Woodside Town Center, Woodside School, Interstate 280, Sand Hill Road, and Stanford University, this exceptional property offers a rare combination of privacy, usable acreage, inspiring views, and close-in convenience.

4 Beds ⋅ 6 Baths ⋅ ML82060993 MLS

Privately positioned at the end of a gated country lane, this elegant French Country estate combines sweeping Western Hills and sunset views with the convenience of a prime Central Woodside location. Set on approximately 1.11 acres, the grounds feature expansive terraces, mature landscaping, and inviting spaces for indoor-outdoor living and entertaining. The main residence features four bedrooms, five-and-a-half bathrooms, a dedicated office/library, a main-level primary suite with an adjoining flexible-use room, and a recently updated chefs kitchen with a sunny breakfast area. Patterned oak floors, high ceilings, and abundant natural light create a warm, sophisticated atmosphere throughout. A detached one-bedroom, one-bath guest house with a full kitchen, fireplace, and high ceilings provides an ideal setting for guests, extended stays, or a private workspace. Just moments from Woodside Town Center, Woodside School, Interstate 280, Sand Hill Road, and Stanford University, this exceptional property offers a rare combination of privacy, usable acreage, inspiring views, and close-in convenience.

55 Mission Trail RD, Woodside

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Sally Li from CBR

$3,175,000

Woodside Retreat "Beside The Woods in Woodside" Peaceful end-of-road privacy and a rustic, eclectic retreat once featured in the Almanac, cherished by one family for 50+ years. 4 sunny, wooded acres with sweeping hill and redwood views. Private gate opens directly onto the trails of 900+ acre Huddart Park. Close to town and Woodside schools. This rustic 3600+ ft 3 beds/2.5 bths home is a study in Vintage Tahoe-style craftsmanship. The living room anchors the house with wood and brick walls, an open stone fireplace, and terracotta tile underfoot. Wooden beams carry into the country kitchen with Subzero and stainless appliances, and the dining room flows onto an expansive view deck over the gardens and pool. A home office overlooks the gardens, and a skylit staircase leads down to a gallery hallway with a stained glass window and a private family room/bedroom. The showstopper: a dramatic Great Room "tavern," host to gatherings of 150, with 19' ceils and grand fireplace of original SF cobblestones. Custom bar built from salvaged San Carlos post office and pharmacy. A reclaimed-barn-siding full bath with steam shower. Large billiard room completes the tavern vibe. Decks and brick paths trace the contour of the land to the pool, framed by redwoods on all sides. Sep 2-car garage.

3 Beds ⋅ 3 Baths ⋅ ML82054634 MLS

Woodside Retreat "Beside The Woods in Woodside" Peaceful end-of-road privacy and a rustic, eclectic retreat once featured in the Almanac, cherished by one family for 50+ years. 4 sunny, wooded acres with sweeping hill and redwood views. Private gate opens directly onto the trails of 900+ acre Huddart Park. Close to town and Woodside schools. This rustic 3600+ ft 3 beds/2.5 bths home is a study in Vintage Tahoe-style craftsmanship. The living room anchors the house with wood and brick walls, an open stone fireplace, and terracotta tile underfoot. Wooden beams carry into the country kitchen with Subzero and stainless appliances, and the dining room flows onto an expansive view deck over the gardens and pool. A home office overlooks the gardens, and a skylit staircase leads down to a gallery hallway with a stained glass window and a private family room/bedroom. The showstopper: a dramatic Great Room "tavern," host to gatherings of 150, with 19' ceils and grand fireplace of original SF cobblestones. Custom bar built from salvaged San Carlos post office and pharmacy. A reclaimed-barn-siding full bath with steam shower. Large billiard room completes the tavern vibe. Decks and brick paths trace the contour of the land to the pool, framed by redwoods on all sides. Sep 2-car garage.

496 Raymundo DR, Woodside

Listed by Don DeFranco, 415-722-7259 from Compass
(If provided) CoList: Grayson Martin from Compass

Sold listing courtesy of James Horn from JHORN

$3,705,000

Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white marble countertops, a Wolf induction range, Sub-Zero refrigerator, dual Wolf ovens, a deep corner pantry with microwave, and an island with seating, plus a Dutch door to the spacious rear patio. Enjoy a cozy family room with wood-burning fireplace, large-screen TV, and articulating door to outdoor entertaining and dining. The primary suite includes an expansive sleeping area with French doors to the nearby native plant garden and majestic Redwoods, a Mitsubishi split A/C, and an upgraded and spectacular bath with marble counters, freestanding tub, new shower, and improved walk-in closet. Additional highlights: new central forced-air system with Nest controller, Level 2 EV charger, security cameras, new septic system and gated trail access to Teague Preserve.

3 Beds ⋅ 2 Baths ⋅ ML82050036 MLS

Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white marble countertops, a Wolf induction range, Sub-Zero refrigerator, dual Wolf ovens, a deep corner pantry with microwave, and an island with seating, plus a Dutch door to the spacious rear patio. Enjoy a cozy family room with wood-burning fireplace, large-screen TV, and articulating door to outdoor entertaining and dining. The primary suite includes an expansive sleeping area with French doors to the nearby native plant garden and majestic Redwoods, a Mitsubishi split A/C, and an upgraded and spectacular bath with marble counters, freestanding tub, new shower, and improved walk-in closet. Additional highlights: new central forced-air system with Nest controller, Level 2 EV charger, security cameras, new septic system and gated trail access to Teague Preserve.

855 Patrol RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Robert Luecke from SHOPI

$4,758,000

High in the Woodside hills on a rare 1.36-acre parcel, this move-in-ready home offers sweeping bay and bridge views, complete privacy, and easy access to Silicon Valley and San Francisco's Financial District. Wide frontage and an elevated setting frame the view on arrival. The east-west orientation brings morning light into the main living spaces and afternoon sun to the rear. The plan divides into three sections: a soaring-ceiling living and dining room; a kitchen with Wolf range, Sub-Zero refrigeration, beverage and wine coolers, and an oversized pantry; and three en-suite bedrooms with custom closet organizers and Toto Washlets. Two-car attached garage. The land is the opportunity. At 1.36 acres, there's room for a pool, sport court, addition, or detached ADU buyer to verify with the Town of Woodside and San Mateo County. Turnkey, private, and view-driven. And room to make it yours.

3 Beds ⋅ 4 Baths ⋅ ML82057851 MLS ⋅ Woodside Hills BLDG.

High in the Woodside hills on a rare 1.36-acre parcel, this move-in-ready home offers sweeping bay and bridge views, complete privacy, and easy access to Silicon Valley and San Francisco's Financial District. Wide frontage and an elevated setting frame the view on arrival. The east-west orientation brings morning light into the main living spaces and afternoon sun to the rear. The plan divides into three sections: a soaring-ceiling living and dining room; a kitchen with Wolf range, Sub-Zero refrigeration, beverage and wine coolers, and an oversized pantry; and three en-suite bedrooms with custom closet organizers and Toto Washlets. Two-car attached garage. The land is the opportunity. At 1.36 acres, there's room for a pool, sport court, addition, or detached ADU buyer to verify with the Town of Woodside and San Mateo County. Turnkey, private, and view-driven. And room to make it yours.

510 Woodside DR, Woodside

Listed by Yu Chih Chiang, 408-818-0046 from Casa Nova Realtors Inc.
(If provided) CoList: from

Sold listing courtesy of Un Represented from NOBUY

$4,625,000

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Joan Cattermole from APR

$1,650,000

Contemporary, eclectic, and like living in a treehouse, this home is secluded in the redwoods on 5+ acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Acclaimed Woodside Elementary School. Miles of hiking trails all around.

3 Beds ⋅ 3 Baths ⋅ ML82058172 MLS

Contemporary, eclectic, and like living in a treehouse, this home is secluded in the redwoods on 5+ acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Acclaimed Woodside Elementary School. Miles of hiking trails all around.

14 Blue Jay WAY, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Scott Dancer from APR

$3,610,800

Nestled on nearly two private acres in a coveted Woodside setting, this Mid-Century Modern home offers a rare blend of rustic charm, natural beauty, & breathtaking panoramic views. Thoughtfully designed to embrace its spectacular surroundings, the four-bedroom, two-bath residence features a sun-drenched living room framed by a dramatic wall of floor-to-ceiling windows that capture sweeping vistas & create an effortless connection to the outdoors. Adjacent to the living room, the open kitchen & dining area also flow seamlessly onto the expansive view deck which is an ideal setting for entertaining, sunset gatherings, or quiet mornings overlooking the horizon. The main level features the primary bedroom & a full bathroom, offering the ease and convenience of single-level living. Downstairs, three additional bedrooms, a full bath, dedicated laundry room, and a spacious bonus family room provides exceptional flexibility for a media lounge, home office, or recreation space. Set on 1.95 acres of serene grounds, the property offers a true sense of privacy and includes a charming barn, adding authentic Woodside character. Lots of possibilities! With access to acclaimed Woodside schools, this special property creates a lifestyle defined by tranquility, scenic beauty, and timeless appeal.

4 Beds ⋅ 2 Baths ⋅ ML82054316 MLS

Nestled on nearly two private acres in a coveted Woodside setting, this Mid-Century Modern home offers a rare blend of rustic charm, natural beauty, & breathtaking panoramic views. Thoughtfully designed to embrace its spectacular surroundings, the four-bedroom, two-bath residence features a sun-drenched living room framed by a dramatic wall of floor-to-ceiling windows that capture sweeping vistas & create an effortless connection to the outdoors. Adjacent to the living room, the open kitchen & dining area also flow seamlessly onto the expansive view deck which is an ideal setting for entertaining, sunset gatherings, or quiet mornings overlooking the horizon. The main level features the primary bedroom & a full bathroom, offering the ease and convenience of single-level living. Downstairs, three additional bedrooms, a full bath, dedicated laundry room, and a spacious bonus family room provides exceptional flexibility for a media lounge, home office, or recreation space. Set on 1.95 acres of serene grounds, the property offers a true sense of privacy and includes a charming barn, adding authentic Woodside character. Lots of possibilities! With access to acclaimed Woodside schools, this special property creates a lifestyle defined by tranquility, scenic beauty, and timeless appeal.

3635 Partition RD, Woodside

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening from Compass

Sold listing courtesy of Grayson Martin from COMPS

$2,850,000

Sunlit Sanctuary on 3.7 beautiful acres. Sky Hill Farm, a rare, retreat-like property that blends natural beauty, indoor-outdoor living & modern luxury minutes from the heart of Silicon Valley. This beautifully renovated home has been completely reimagined w/high-end finishes & exceptional craftsmanship, offering a lifestyle of comfort, privacy & effortless elegance. Seamlessly flowing open floor plan, refined aesthetics and meticulously upgraded systems that enhance comfort, efficiency and long-term peace of mind. Sun-filled living spaces open naturally to the outdoors. The heart of the home is a gourmet kitchen featuring premium appliances, custom cabinetry, expansive counter space and functional layout. Huge deck extends the living space outward. Set on 3.7 very usable acres provides endless possibilities gardens, play areas, outdoor lounges, or simply room to breathe. The primary suite feels like a private retreat, with serene views and redwood finishes, huge walk-in closet and luxurious bath. Charming 2 bed guest house w/kitchen. Historic updated carriage house can be used as 6-car garage, workshop a dream for car collectors, hobbyists, or anyone needing serious workspace. At the back of the property sits a restored barn for storage, projects ,animals. Plans show 2427 s.f.

4 Beds ⋅ 3 Baths ⋅ ML82049221 MLS

Sunlit Sanctuary on 3.7 beautiful acres. Sky Hill Farm, a rare, retreat-like property that blends natural beauty, indoor-outdoor living & modern luxury minutes from the heart of Silicon Valley. This beautifully renovated home has been completely reimagined w/high-end finishes & exceptional craftsmanship, offering a lifestyle of comfort, privacy & effortless elegance. Seamlessly flowing open floor plan, refined aesthetics and meticulously upgraded systems that enhance comfort, efficiency and long-term peace of mind. Sun-filled living spaces open naturally to the outdoors. The heart of the home is a gourmet kitchen featuring premium appliances, custom cabinetry, expansive counter space and functional layout. Huge deck extends the living space outward. Set on 3.7 very usable acres provides endless possibilities gardens, play areas, outdoor lounges, or simply room to breathe. The primary suite feels like a private retreat, with serene views and redwood finishes, huge walk-in closet and luxurious bath. Charming 2 bed guest house w/kitchen. Historic updated carriage house can be used as 6-car garage, workshop a dream for car collectors, hobbyists, or anyone needing serious workspace. At the back of the property sits a restored barn for storage, projects ,animals. Plans show 2427 s.f.

260 Grandview DR, Woodside

Listed by Karin Bird, 650-207-0940 from Compass
(If provided) CoList: from

Sold listing courtesy of Daniel Chang from COMP

$4,000,000

Central Woodside Opportunity on 1.11 Acres. Just over one mile from Woodside town center this 1.11-acre property presents an increasingly rare opportunity in a desirable Central Woodside setting. A seasonal creek at the rear of the property and stunning western hill views that may be further enhanced create a beautiful natural environment that reflects the scenic character for which Woodside is renowned. A secondary access point from Hillside Drive to the barn further enhances the property's flexibility and future potential. The mid-century ranch-style home has been recently refreshed with new paint inside and out, refinished hardwood floors, new carpet, and refreshed landscaping. Comfortable living spaces, flexible lower-level quarters with a bonus kitchen, and a detached two-stall barn with expansive upper-level space provide immediate enjoyment while offering numerous possibilities for the future. The true appeal extends beyond the home itself. Generous acreage, a close-in location, access to acclaimed Woodside Elementary School, and surrounding estate properties create an exceptional setting for renovation, expansion, or the creation of a significant new residence all while immediately enjoying the freshly updated home.

4 Beds ⋅ 3 Baths ⋅ ML82053870 MLS

Central Woodside Opportunity on 1.11 Acres. Just over one mile from Woodside town center this 1.11-acre property presents an increasingly rare opportunity in a desirable Central Woodside setting. A seasonal creek at the rear of the property and stunning western hill views that may be further enhanced create a beautiful natural environment that reflects the scenic character for which Woodside is renowned. A secondary access point from Hillside Drive to the barn further enhances the property's flexibility and future potential. The mid-century ranch-style home has been recently refreshed with new paint inside and out, refinished hardwood floors, new carpet, and refreshed landscaping. Comfortable living spaces, flexible lower-level quarters with a bonus kitchen, and a detached two-stall barn with expansive upper-level space provide immediate enjoyment while offering numerous possibilities for the future. The true appeal extends beyond the home itself. Generous acreage, a close-in location, access to acclaimed Woodside Elementary School, and surrounding estate properties create an exceptional setting for renovation, expansion, or the creation of a significant new residence all while immediately enjoying the freshly updated home.

136 Jane DR, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Jackie Walker from SGP

$4,625,000

Located in the highly desirable Woodside Hills, this exceptional gated estate offers the perfect blend of privacy, luxury, and bay views. Set on a level one-acre lot, the property features a thoughtfully designed main residence and a fully separate guest house, ideal for extended family, guests, or work-from-home flexibility. The main house offers approximately 3,247 square feet of living space with three bedrooms and two and half bathrooms, complemented by a three-car garage. Designed for both comfort and entertaining, the home opens to expansive outdoor amenities including a pool, hot tub, and sports court, all surrounded by mature landscaping and serene views. The guest house provides approximately 1,254 square feet, featuring two bedrooms, two full baths, its own one-car garage, and complete privacy from the main residence with its own private yard. Additional highlights include solar power, a gated entry, and sweeping Bay and mountain views, making this a rare opportunity to own a versatile estate property in one of Woodside's most sought-after neighborhoods.

3 Beds ⋅ 3 Baths ⋅ ML82033724 MLS

Located in the highly desirable Woodside Hills, this exceptional gated estate offers the perfect blend of privacy, luxury, and bay views. Set on a level one-acre lot, the property features a thoughtfully designed main residence and a fully separate guest house, ideal for extended family, guests, or work-from-home flexibility. The main house offers approximately 3,247 square feet of living space with three bedrooms and two and half bathrooms, complemented by a three-car garage. Designed for both comfort and entertaining, the home opens to expansive outdoor amenities including a pool, hot tub, and sports court, all surrounded by mature landscaping and serene views. The guest house provides approximately 1,254 square feet, featuring two bedrooms, two full baths, its own one-car garage, and complete privacy from the main residence with its own private yard. Additional highlights include solar power, a gated entry, and sweeping Bay and mountain views, making this a rare opportunity to own a versatile estate property in one of Woodside's most sought-after neighborhoods.

300 Ridgeway RD, Woodside

Listed by Gregory Garcia, 650-771-0656 from Sequoia Realty Services
(If provided) CoList: from

Sold listing courtesy of Anuja Krishnan from KWPEN

$12,000,000

Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Every detail reflects a designers eye, with cohesive finishes and thoughtfully selected materials creating a sophisticated yet welcoming atmosphere throughout. A well-appointed 2-bedroom, 1-bath guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the property's country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience.

6 Beds ⋅ 5 Baths ⋅ ML82046443 MLS

Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Every detail reflects a designers eye, with cohesive finishes and thoughtfully selected materials creating a sophisticated yet welcoming atmosphere throughout. A well-appointed 2-bedroom, 1-bath guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the property's country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience.

140 Dean RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Matt Zampella from SGP

$2,250,000

Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

4 Beds ⋅ 4 Baths ⋅ ML82041849 MLS

Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

12 Summit RD, Woodside

Listed by Alexander Nichols, 650-575-4069 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Susanne Bohl from RDFIN

$2,300,000

Welcome to your own private retreat where modern comfort meets the beauty of nature. Set on a picturesque property surrounded by towering trees and breathtaking valley and ocean views, this beautifully updated home offers the perfect blend of tranquility and style. Inside, you'll find light-filled living spaces and quality finishes throughout. Large windows frame the natural landscape, creating a seamless connection between indoors and out. Step outside to discover thoughtfully designed grounds featuring lush landscaping, expansive lawns, inviting patios, and multiple areas for entertaining or relaxing. Wander along a charming walking path that winds through the property to a secret garden, an enchanting sanctuary with mature trees, unique sculptures, and peaceful spaces to unwind. Whether enjoying morning coffee overlooking the hills, hosting gatherings under the stars, or exploring your own private woodland retreat, every corner of this property offers something special. A detached garage provides room for vehicles, hobbies, or future expansion. This is more than a home it's a lifestyle where privacy, nature, and refined living come together in perfect harmony. Just minutes from Highways 92 and 280, for an easy commute to Silicon Valley, SFO, San Francisco, and the Peninsula.

3 Beds ⋅ 1 Baths ⋅ ML82053963 MLS

Welcome to your own private retreat where modern comfort meets the beauty of nature. Set on a picturesque property surrounded by towering trees and breathtaking valley and ocean views, this beautifully updated home offers the perfect blend of tranquility and style. Inside, you'll find light-filled living spaces and quality finishes throughout. Large windows frame the natural landscape, creating a seamless connection between indoors and out. Step outside to discover thoughtfully designed grounds featuring lush landscaping, expansive lawns, inviting patios, and multiple areas for entertaining or relaxing. Wander along a charming walking path that winds through the property to a secret garden, an enchanting sanctuary with mature trees, unique sculptures, and peaceful spaces to unwind. Whether enjoying morning coffee overlooking the hills, hosting gatherings under the stars, or exploring your own private woodland retreat, every corner of this property offers something special. A detached garage provides room for vehicles, hobbies, or future expansion. This is more than a home it's a lifestyle where privacy, nature, and refined living come together in perfect harmony. Just minutes from Highways 92 and 280, for an easy commute to Silicon Valley, SFO, San Francisco, and the Peninsula.

12180 Skyline BLVD, Woodside

Listed by Karen C Hoffmann, 650-400-7409 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Wei-Pei Cherng from EXPN

$7,495,000

New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

4 Beds ⋅ 6 Baths ⋅ ML82044344 MLS

New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

55 Mission Trail RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: Scott Dancer from Compass

Sold listing courtesy of Victoria Yang Surles from CBR

$2,000,000

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

3 Beds ⋅ 3 Baths ⋅ ML82035391 MLS

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

13872 Silver Sky WAY, Woodside

Listed by Joakim Bye, 650-284-2080 from Ocean Element Real Estate
(If provided) CoList: from

Sold listing courtesy of Evan Walsh from EXPCA

$5,388,000

Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers privacy, scale, and resort-inspired living. Light-filled interiors feature soaring ceilings, refined millwork, and an elegant flow designed for both entertaining and everyday living. Formal living and dining rooms provide distinct gathering spaces, while the well-appointed kitchen with custom cabinetry, stone countertops, and a center island opens seamlessly to the adjacent family room and surrounding outdoor spaces for effortless indoor outdoor living. The spacious primary suite is a private retreat with a view deck and spa-inspired bath. Three additional bedrooms offer flexibility for guests, office space, fitness, or extended living. Resort-style grounds include expansive patios, a pool, covered lounge area, mature landscaping, and multiple vantage points capturing sweeping Bay views and natural beauty throughout. Conveniently located near downtown Woodside and Redwood City, Highway 280, and major Silicon Valley employers. Nearby private schools include Menlo School, Phillips Brooks School, Sacred Heart Schools, and Woodside Priory.

4 Beds ⋅ 4 Baths ⋅ ML82041471 MLS ⋅ Woodside Hills Home Association BLDG.

Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers privacy, scale, and resort-inspired living. Light-filled interiors feature soaring ceilings, refined millwork, and an elegant flow designed for both entertaining and everyday living. Formal living and dining rooms provide distinct gathering spaces, while the well-appointed kitchen with custom cabinetry, stone countertops, and a center island opens seamlessly to the adjacent family room and surrounding outdoor spaces for effortless indoor outdoor living. The spacious primary suite is a private retreat with a view deck and spa-inspired bath. Three additional bedrooms offer flexibility for guests, office space, fitness, or extended living. Resort-style grounds include expansive patios, a pool, covered lounge area, mature landscaping, and multiple vantage points capturing sweeping Bay views and natural beauty throughout. Conveniently located near downtown Woodside and Redwood City, Highway 280, and major Silicon Valley employers. Nearby private schools include Menlo School, Phillips Brooks School, Sacred Heart Schools, and Woodside Priory.

140 Ridgeway RD, Woodside

Listed by Caroline Dinsmore, 650-773-2226 from The Agency
(If provided) CoList: from

Sold listing courtesy of Jennifer Bitter from GGSIR

$4,075,000

One Acre with Sweeping Bay Views in Woodside Hills! Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

4 Beds ⋅ 4 Baths ⋅ ML82050010 MLS

One Acre with Sweeping Bay Views in Woodside Hills! Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

199 Brookwood RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$4,050,000

Nestled on a quiet, beautifully wooded lot in desirable Woodside Hills, this meticulously updated residence blends timeless elegance with modern comfort. Light-filled interiors showcase expansive windows, refined finishes, custom window coverings and seamless indoor-outdoor flow. The remodeled chef's kitchen (2019) features a quartz-topped island, custom cabinetry, and premium Thermador, Bosch, and LG appliances, while opening to inviting dining and family spaces. A gracious living room with a redesigned gas fireplace and access to a deck creates an ideal setting for entertaining. Up the grand staircase, a serene primary suite offers high ceilings, dual walk-in closets, and a spa-inspired bath with soaking tub, curb-less shower, and designer finishes. Two additional bedrooms enjoy natural light and peaceful views. Extensively renovated, the backyard presents a resort-like retreat with multiple entertaining areas, a saltwater pool, AZEK decking, stamped concrete patios, gazebo and stone retaining walls and box planters, all surrounded by majestic oaks. Smart home features throughout the home include an EV charger. This exceptional home is situated in a premier, ultra-private location while being close to the Town of Woodside, Redwood City, schools, shopping, dining and Hwy 280.

3 Beds ⋅ 3 Baths ⋅ ML82048231 MLS

Nestled on a quiet, beautifully wooded lot in desirable Woodside Hills, this meticulously updated residence blends timeless elegance with modern comfort. Light-filled interiors showcase expansive windows, refined finishes, custom window coverings and seamless indoor-outdoor flow. The remodeled chef's kitchen (2019) features a quartz-topped island, custom cabinetry, and premium Thermador, Bosch, and LG appliances, while opening to inviting dining and family spaces. A gracious living room with a redesigned gas fireplace and access to a deck creates an ideal setting for entertaining. Up the grand staircase, a serene primary suite offers high ceilings, dual walk-in closets, and a spa-inspired bath with soaking tub, curb-less shower, and designer finishes. Two additional bedrooms enjoy natural light and peaceful views. Extensively renovated, the backyard presents a resort-like retreat with multiple entertaining areas, a saltwater pool, AZEK decking, stamped concrete patios, gazebo and stone retaining walls and box planters, all surrounded by majestic oaks. Smart home features throughout the home include an EV charger. This exceptional home is situated in a premier, ultra-private location while being close to the Town of Woodside, Redwood City, schools, shopping, dining and Hwy 280.

345 Harcross RD, Woodside

Listed by Jane Dew, 650-353-8899 from The Agency
(If provided) CoList: from

Sold listing courtesy of Carol Koffel from COMP41

$4,500,000

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

4 Beds ⋅ 4 Baths ⋅ ML82041987 MLS

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

175 Alta Mesa RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Lucy Goldenshteyn from RDFIN

$2,050,000

Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La

3 Beds ⋅ 4 Baths ⋅ ML82032237 MLS

Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La

45 Ranch RD, Woodside

Listed by James Milton, 650-868-1356 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shawnna Sullivan from CBR

$3,150,000

Truly extraordinary 10+ acre retreat offers a rare combination of privacy, usability, and natural beauty. Tastefully updated home sits on an elevated, level setting surrounded by mature trees and abundant sunshine, creating a peaceful sanctuary that feels far removed from the pace of everyday life. A private road winds down through the property, crossing a seasonal creek before opening to a spectacular sunny meadow below & connects to Horse and Hiking trails. This expansive area presents endless possibilities, from horses, barns, and riding facilities to orchards, gardens, recreational uses, or simply enjoying the open space. Outdoor enthusiasts will appreciate direct access to miles of nearby trails for hiking, horseback riding, and mountain biking right from the property. Combining turnkey living with exceptional land, tremendous sun exposure, remarkable privacy, and a setting that inspires exploration and relaxation, this is a truly special opportunity to own one of Skylines most compelling lifestyle properties

4 Beds ⋅ 3 Baths ⋅ ML82049733 MLS

Truly extraordinary 10+ acre retreat offers a rare combination of privacy, usability, and natural beauty. Tastefully updated home sits on an elevated, level setting surrounded by mature trees and abundant sunshine, creating a peaceful sanctuary that feels far removed from the pace of everyday life. A private road winds down through the property, crossing a seasonal creek before opening to a spectacular sunny meadow below & connects to Horse and Hiking trails. This expansive area presents endless possibilities, from horses, barns, and riding facilities to orchards, gardens, recreational uses, or simply enjoying the open space. Outdoor enthusiasts will appreciate direct access to miles of nearby trails for hiking, horseback riding, and mountain biking right from the property. Combining turnkey living with exceptional land, tremendous sun exposure, remarkable privacy, and a setting that inspires exploration and relaxation, this is a truly special opportunity to own one of Skylines most compelling lifestyle properties

17001 Skyline, Woodside

Listed by Nino Gaetano, 650-207-1986 from The Agency
(If provided) CoList: from

Sold listing courtesy of Greg Damelio from SGP

$5,350,000

Set at the end of a private lane on more than one acre, this stylish contemporary retreat offers a rare sense of privacy just moments from downtown Woodside. Refreshed landscaping & a spacious, partially covered front deck introduce interiors defined by clean lines, hardwood floors, vaulted ceilings, & expansive walls of glass that fill the home with natural light. The flexible two-level floor plan features 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. A dramatic living room with a fossilized limestone fireplace, formal dining room, & streamlined maple kitchen with honed black granite & butcher block surfaces create a modern yet inviting backdrop for everyday living & entertaining. Sliding glass doors open to a wraparound deck for seamless indoor-outdoor flow. The lower level expands the living space with a large recreation room with a built-in workstation for two, plus 2 additional bedrooms, one with an en suite bath. Terraced rear grounds include a free-form pool, barn with potential equestrian use, zip line, & refreshed landscaping, along with additional usable outdoor areas suited for recreation, play, or future possibilities. Just one-half mile from downtown Woodside & within the acclaimed Woodside School District.

4 Beds ⋅ 4 Baths ⋅ ML82043727 MLS

Set at the end of a private lane on more than one acre, this stylish contemporary retreat offers a rare sense of privacy just moments from downtown Woodside. Refreshed landscaping & a spacious, partially covered front deck introduce interiors defined by clean lines, hardwood floors, vaulted ceilings, & expansive walls of glass that fill the home with natural light. The flexible two-level floor plan features 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. A dramatic living room with a fossilized limestone fireplace, formal dining room, & streamlined maple kitchen with honed black granite & butcher block surfaces create a modern yet inviting backdrop for everyday living & entertaining. Sliding glass doors open to a wraparound deck for seamless indoor-outdoor flow. The lower level expands the living space with a large recreation room with a built-in workstation for two, plus 2 additional bedrooms, one with an en suite bath. Terraced rear grounds include a free-form pool, barn with potential equestrian use, zip line, & refreshed landscaping, along with additional usable outdoor areas suited for recreation, play, or future possibilities. Just one-half mile from downtown Woodside & within the acclaimed Woodside School District.

35 Neuman LN, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$2,750,000

This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

4 Beds ⋅ 4 Baths ⋅ ML82041075 MLS

This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

13370 Skyline BLVD, Woodside

Listed by Jonathan Lee, 650-619-9255 from A 2 M Real Estate
(If provided) CoList: from

Sold listing courtesy of Brent Walsh from COMPS

$12,750,000

Extraordinary residence on 5 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.

4 Beds ⋅ 8 Baths ⋅ ML82041478 MLS

Extraordinary residence on 5 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.

490 Las Pulgas DR, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Scott Dancer from APR

$5,450,000

Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature

5 Beds ⋅ 4 Baths ⋅ ML82044125 MLS

Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature

200 Todo El Mundo, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Larry Liu from APR

$8,000,000

One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

6 Beds ⋅ 9 Baths ⋅ ML82034677 MLS

One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

16351 Skyline BLVD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Kavanaugh Group from CBR