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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

$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

$3,800,000

A Six-Bedroom Modern Masterpiece in Woodside Glens. Discover a stunning 2024 reimagined home where modern design meets family functionality just one mile from Woodside Town Center. This 6-bedroom, 3-bath smart home offers 3,087 sq. ft. of beautifully expanded and remodeled living space on a ~7,000 sq. ft. flat lot. The dramatic entry with custom iron and glass doors opens to airy, vaulted living spaces and a great room with a sleek all-white kitchen featuring quartz counters and Bosch appliances. The flexible layout includes a lower-level wing with two bedrooms, an office, laundry, and a rec room opening to the terrace ideal for guests, work, or play. Upstairs, the private primary suite offers skylit ceilings, a spa-like bath, and a balcony with western hill views. Smart-home systems, whole-home audio, three-zone heat pump climate control, and full fire sprinklers ensure comfort and peace of mind. Outdoor living shines with an expansive terrace, full outdoor kitchen, and RV hookups. Located in the acclaimed Woodside Elementary School District.

6 Beds ⋅ 3 Baths ⋅ ML82022347 MLS

A Six-Bedroom Modern Masterpiece in Woodside Glens. Discover a stunning 2024 reimagined home where modern design meets family functionality just one mile from Woodside Town Center. This 6-bedroom, 3-bath smart home offers 3,087 sq. ft. of beautifully expanded and remodeled living space on a ~7,000 sq. ft. flat lot. The dramatic entry with custom iron and glass doors opens to airy, vaulted living spaces and a great room with a sleek all-white kitchen featuring quartz counters and Bosch appliances. The flexible layout includes a lower-level wing with two bedrooms, an office, laundry, and a rec room opening to the terrace ideal for guests, work, or play. Upstairs, the private primary suite offers skylit ceilings, a spa-like bath, and a balcony with western hill views. Smart-home systems, whole-home audio, three-zone heat pump climate control, and full fire sprinklers ensure comfort and peace of mind. Outdoor living shines with an expansive terrace, full outdoor kitchen, and RV hookups. Located in the acclaimed Woodside Elementary School District.

118 Hillside DR, Woodside

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

Sold listing courtesy of Michael R. Perrelli from CBR

$3,500,000

Custom built in 1992 on one of the largest parcels in the area. Over 14,000 sq. foot lot. On the market for the first time! Sweeping western hill views, close-in convenience, plus pool and spa. A dramatic great room with soaring two-story ceiling, arched clerestory windows, and skylights highlights the open floor plan that connects living, dining, and kitchen areas to a spacious view deck. 4 bedrooms and an office are arranged across 3 levels, including a main-level primary bedroom with adjoining bath and bedroom ideal for office or nursery. The upper level has a office and skylit loft lounge, while the lower level has two bedrooms, a full bath, and recreation room with refreshment bar opening to the pool deck. Outdoor amenities include a large above-ground pool surrounded with vast decking for entertaining space plus a separate spa. All just minutes to Town Center, hiking trails, and acclaimed Woodside School. Room to add an ADU.

4 Beds ⋅ 3 Baths ⋅ ML82020106 MLS

Custom built in 1992 on one of the largest parcels in the area. Over 14,000 sq. foot lot. On the market for the first time! Sweeping western hill views, close-in convenience, plus pool and spa. A dramatic great room with soaring two-story ceiling, arched clerestory windows, and skylights highlights the open floor plan that connects living, dining, and kitchen areas to a spacious view deck. 4 bedrooms and an office are arranged across 3 levels, including a main-level primary bedroom with adjoining bath and bedroom ideal for office or nursery. The upper level has a office and skylit loft lounge, while the lower level has two bedrooms, a full bath, and recreation room with refreshment bar opening to the pool deck. Outdoor amenities include a large above-ground pool surrounded with vast decking for entertaining space plus a separate spa. All just minutes to Town Center, hiking trails, and acclaimed Woodside School. Room to add an ADU.

129 Hillside DR, Woodside

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

Sold listing courtesy of Cliff Whearley from WRLY

$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

$2,925,000

Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living and entertaining. Natural light pours through skylights and a large sliding door that opens to a private patio, seamlessly connecting indoor and outdoor spaces. The dining room showcases a wall of windows framing views of the lush yard and filtered sunlight through the surrounding oaks. A private primary retreat, completed in 2017 with foundation and seismic retrofitting, offers a peaceful sanctuary with luxurious appointments and imported stone floors. A standout feature is the fully equipped guest house with its own kitchen and full bathroom, perfect for extended family, guests, a home office, or rental income potential. Located in the desirable Woodside Glens neighborhood, this home offers exceptional proximity to downtown Woodside and Woodside Elementary School. Roberts Market, charming cafés, and local favorites are just a short stroll away.

3 Beds ⋅ 2 Baths ⋅ ML82032025 MLS

Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living and entertaining. Natural light pours through skylights and a large sliding door that opens to a private patio, seamlessly connecting indoor and outdoor spaces. The dining room showcases a wall of windows framing views of the lush yard and filtered sunlight through the surrounding oaks. A private primary retreat, completed in 2017 with foundation and seismic retrofitting, offers a peaceful sanctuary with luxurious appointments and imported stone floors. A standout feature is the fully equipped guest house with its own kitchen and full bathroom, perfect for extended family, guests, a home office, or rental income potential. Located in the desirable Woodside Glens neighborhood, this home offers exceptional proximity to downtown Woodside and Woodside Elementary School. Roberts Market, charming cafés, and local favorites are just a short stroll away.

240 Glenwood AVE, Woodside

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of John Shroyer from TODAY

$2,750,000

APPROVED PLANS AND PERMITS PULLED. Providing over one-third acre of level double-wide land, this expansive parcel is an exceptional opportunity to build your dream home in the heart of Woodside. Over 4,415 total square feet with pre-approved architectural plans, by Simpson Design Group, with ADU, pool and all landscaping, are available saving years of time in the building process. Offering gorgeous views of the Kite Hill Wildflower Preserve and just steps from its beautiful hiking trails, it is the rare combination of a tranquil country setting located just minutes from the town center. Listing photos of the home are renderings only, there is not currently a home on this lot. Potential for approximately 4,415 total sq ft || main house : 3 bd, 2.5 ba, 3,475 sq ft | adu 500 sf | 440 sq ft 2 car garage. This property is also ideally situated with access to the acclaimed Woodside Elementary School (K8), making it a highly desirable address for those seeking a premier Peninsula lifestyle. Offering wonderful views and outstanding location, this lot presents the perfect canvas to create the home ready for permit issue, or to create your own dream home, in one of Silicon Valleys most sought-after communities.

ML82020559 MLS

APPROVED PLANS AND PERMITS PULLED. Providing over one-third acre of level double-wide land, this expansive parcel is an exceptional opportunity to build your dream home in the heart of Woodside. Over 4,415 total square feet with pre-approved architectural plans, by Simpson Design Group, with ADU, pool and all landscaping, are available saving years of time in the building process. Offering gorgeous views of the Kite Hill Wildflower Preserve and just steps from its beautiful hiking trails, it is the rare combination of a tranquil country setting located just minutes from the town center. Listing photos of the home are renderings only, there is not currently a home on this lot. Potential for approximately 4,415 total sq ft || main house : 3 bd, 2.5 ba, 3,475 sq ft | adu 500 sf | 440 sq ft 2 car garage. This property is also ideally situated with access to the acclaimed Woodside Elementary School (K8), making it a highly desirable address for those seeking a premier Peninsula lifestyle. Offering wonderful views and outstanding location, this lot presents the perfect canvas to create the home ready for permit issue, or to create your own dream home, in one of Silicon Valleys most sought-after communities.

152 Alta Mesa RD, Woodside

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

Sold listing courtesy of Glenn Sennett from CBR

$2,718,000

Set on a rare 3-parcel, 0.43-acre lot, this one-of-a-kind Woodside property blends timeless character with modern updates in one of the areas most coveted neighborhoods. Surrounded by mature oaks and breathtaking foothill views, it offers the perfect balance of privacy, nature, and conveniencejust minutes from scenic trails, open space preserves, major freeways, and vibrant downtown Woodside. Originally built in the 1920s, the home exudes classic charm while showcasing thoughtful renovations, including a beautifully updated kitchen, fresh interior paint, and a versatile lower-level guest or bonus suite. Vaulted wood-beamed ceilings add warmth and character to the main living areas, complemented by a formal dining room and multiple flex-use rooms that can serve as offices, guest quarters, or creative spaces. On the first floor, you'll find a full bathroom, bonus living or guest area, plus a bonus room ideal for storage, a home workshop, or future expansion. With over 2,400 sq. ft. of living space, this flexible layout offers endless potential for customization and growth. Offering an exceptional opportunity, this property is perfect for builders, investors, or those dreaming of creating their own Woodside retreat.

3 Beds ⋅ 2 Baths ⋅ ML82026774 MLS

Set on a rare 3-parcel, 0.43-acre lot, this one-of-a-kind Woodside property blends timeless character with modern updates in one of the areas most coveted neighborhoods. Surrounded by mature oaks and breathtaking foothill views, it offers the perfect balance of privacy, nature, and conveniencejust minutes from scenic trails, open space preserves, major freeways, and vibrant downtown Woodside. Originally built in the 1920s, the home exudes classic charm while showcasing thoughtful renovations, including a beautifully updated kitchen, fresh interior paint, and a versatile lower-level guest or bonus suite. Vaulted wood-beamed ceilings add warmth and character to the main living areas, complemented by a formal dining room and multiple flex-use rooms that can serve as offices, guest quarters, or creative spaces. On the first floor, you'll find a full bathroom, bonus living or guest area, plus a bonus room ideal for storage, a home workshop, or future expansion. With over 2,400 sq. ft. of living space, this flexible layout offers endless potential for customization and growth. Offering an exceptional opportunity, this property is perfect for builders, investors, or those dreaming of creating their own Woodside retreat.

112 Highland TER, Woodside

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

Sold listing courtesy of Lilly Tamayo from NTERO

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