188 properties for sale in Woodside Highlands

Some homes are simply built. Others are cared for, collected, and shaped over time. Set among mature trees and thoughtfully designed gardens, this distinctive Portola Valley farmhouse reflects years of careful stewardship. Reclaimed wide-plank North Carolina pine floors, plaster walls and ceilings, painted millwork, marble, handmade tile, exposed beams and French doors give the home its character. The kitchen features a La Cornue range, original farmhouse sink, marble countertops, generous island, butler's pantry and cozy dining nook. The dining room is suited to everyday meals and larger gatherings, while the living room centers on a marble wood-burning fireplace and opens through two sets of French doors to a covered porch overlooking the gardens. The primary suite includes a walk-in closet and marble bath with mosaic tile and imported European brass fixtures. Upstairs are two additional bedrooms, a claw-foot bath and flexible spaces for study, work, hobbies or storage. A spacious fa

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded in 2002 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.

One-of-a-Kind Mountain Oasis on Spacious Sunny Lot! Charming 1930s log cabin cottage getaway with impeccable newer construction master suite addition, on fenced 1u002F3 acre of natural, drought resistant landscaping among dozens of majestic redwoods. Open kitchen with granite counters and new six-burner gas range. High ceilings, radiant heated hardwood and tile floors throughout. High quality finishes and attention to detail should not be overlooked. Expansive south facing deck with morning and afternoon sun provide stunning views. Large detached single car garage with EV charger, storage and attic, plus parking for multiple vehicles. Walking distance to Alice's Restaurant, Skywood Trading Post Grocery, and endless hikingu002Fbiking trails. Easy access to HWY 35 Skyline Blvd and HWY 84 Woodside Road to Silicon Valley or the coast. A welcoming neighborhood and close knit community are the inherent benefits of ownership. Old world character meets modern day amenities in an idyllic settin

Welcome to 320 Center Street, a meticulously re-imagined Redwood City home offering an unparalleled combination of state-of-the-art construction and flexible living. This pristine property features two independent, turn-key homes. The primary home is 1446 sq. Ft. The ADU over the garage is 645 sq. Ft. for a total of 2091 sq ft. Both are powered by full, grid-tied solar systems. The three bed, two and a half bath home has designer finishes throughout. Including: nine foot ceilings, gorgeous wide-plank hardwood flooring that flow seamlessly under modern recessed lighting. A spectacular open-concept gourmet kitchen with custom light oak flat-panel cabinetry, stainless steel appliances, and brilliant skylights. The centerpiece is a gold veined quartz waterfall island. The tranquil primary suite offers peaceful backyard views and a spa-inspired bathroom with walk-in shower The hall bath has a beautiful shower combo and matching light wood cabinetry. There are high end double paned windows t

A+ Location half block to Stanford in the College Terrace Neighborhood, backing up to a 1+ acre park with direct access. Convert the carport into up to 4 new ADU units to make this an 8 Unit property for HUGE income and property value increases! This property is offered individually, or conjunction with our listing of the neighboring property at 2120. 2122 Williams St (duplex). Strong in-place income, attractive floor plans, private outdoor spaces, covered parking, and direct gated access to Cameron Park. Located just steps from Stanford University, Stanford Research Park, California Avenue, Caltrain, shopping, dining, and major employment centers, the property benefits from exceptional tenant demand

Rare opportunity to own a beautifully remodeled townhouse-style condo in a gated community just blocks from vibrant downtown Redwood City and the exciting Elco Yards development. Thoughtfully redesigned with designer finishes throughout, this light-filled home blends style, comfort, and convenience. The main level features European hardwood floors, an updated powder room, in-unit laundry with a full-size washer and dryer, and a stunning kitchen with modern white cabinetry, quartz countertops, premium stainless-steel appliances, a gas cooktop, and a spacious eat-in area overlooking the living room. The inviting living room features a cozy, decorative fireplace with ambient lighting and opens to a private yard, perfect for relaxing or entertaining. Upstairs are two well-appointed bedrooms, including a spacious primary suite with dual closets, a private balcony, and a convenient laundry chute. The beautifully remodeled bathroom showcases elegant tile and heated floors. Additional highligh

This classic Spanish bungalow with three iconic arches. At the foyer, dining room and kitchen, has been expanded, updated and modernized with features including skylights, a sun tunnel, and dual-pane windows. Living room has wide windows looking to the covered porch and and a rustic brick fireplace. The dining room was enlarged to includes bench seating (with storage), a wide skylight, and a French door to a large deck. Remodeled kitchen boasts an efficient layout, abundant storage, a cozy breakfast nook, a wide laundry closet and door to deck for outdoor dining and entertaining. The primary suite bathroom has a stall shower, skylight and rustic tile floors. Oak floors are in most of the house. The detached garage boasts a cozy office, wall of storage cabinets and room for one car. Located in the peaceful College Terrace neighborhood, close to Stanford University & medical facilities. This home is about 1.6 miles from Town & Country Center, 8/10 mile from Caltrain, 7/10 mile from Molli

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 acre

The grass is greener on Fernside! This home was expanded to 2,030 sqft during a'down-to-the-studs' renovation. Enjoy peace of mind with all-new plumbing and electrical systems, not a single original pipe or wire remains. A new high-efficiency heat pump HVAC system, a new roof, new windows, new solid core doors, and custom moldings add both style and substance. The expansive living space showcases soaring ceilings, thoughtfully selected finishes, oak cabinetry, and KitchenAid appliances. French doors lead to a peaceful yard with fresh landscaping and all new stamped concrete, perfect for family and friends! Situated on a peaceful tree lined street this generous lot backs up to Hetch Hetchy open space giving added privacy with no rear neighbors and access to the greenbelt walking path. The highly sought after Farm Hill Estates neighborhood offers a tranquil retreat while remaining just minutes from shopping, dining, parks, and major commuter routes. Don't miss your chance to make it all

Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in dappled sunlight, the home exudes warmth and charm throughout. The well-appointed floor plan includes 4 bedrooms and 2.5 bathrooms, with inviting living spaces that seamlessly connect to the outdoors perfect for both relaxed everyday living and elegant entertaining. Step outside to your own private oasis, complete with a pool, lush lawns, barn and meandering brick walkways. Whether enjoying quiet mornings or hosting gatherings, the setting offers unmatched serenity and beauty. Located within the boundaries of the highly acclaimed Woodside Elementary School, this exceptional property combines rural

Situated in the highly sought-after College Terrace neighborhood, this charming 1904 Craftsman home offers a rare blend of historic character, generous outdoor space, and an unbeatable location. Just moments from Stanford University, vibrant California Ave restaurants, farmers market, major tech campuses and award-winning schools, this inviting 2-story home places you at the heart of one of Palo Alto's most desirable neighborhoods. With approximately 1,807 square feet of living space, the home is filled with warmth and timeless details, including original oak hardwood floors, leaded windows, and classic period craftsmanship. A covered front porch welcomes you into a charming sitting area that flows into the living room and dining room. Upstairs, the home has 3 bedrooms, 2 bathrooms, and a spacious family room. Set on a generous, level lot over 10,000 square feet, the property is surrounded by mature trees and thoughtfully defined yard areas with room to relax, entertain, garden, or sim

An inviting front porch swing welcomes you to this classic Farm Hill Neighborhood home. Open the door and feel the comfort of a home well loved. An eat-in kitchen has a vintage wall oven. A mid century antique that still cooks a perfect meal. Imagine the 70 thanksgiving meals prepared here! The kitchen opens to dining and living areas with a slider to the bckyrd. Main level has 2 beds and full bath. Upstairs has primary suite with his/hers closets and bath, and an additional 2 lrg beds and a 3rd bath. 2 car garage with high overhead space. Interior: Recently painted, several newer light fixtures added. Newer carpeting, newer flooring in 2 baths. Main level bath has newer vanity, sink, medicine cabinet and toilet. Rich hardwd floors throughout, all refinished. Set on a 8434 sf lot featuring: newer interlocking driveway pavers; newer fencing and landscaping; sod area with gopher wire; automatic sprinklers front and rear; BBQ & party patio area; garden shed, stunning views from upstairs b

A+ Location half block to Stanford in the College Terrace Neighborhood, backing up to a 1+ acre park with direct access. Convert the carport into 2 new ADU units to make this a 4-plex property for HUGE income and property value increases! This property is offered individually, or also find our listing of the neighboring property at 2106. 2112 Williams St. Strong in-place income, attractive floor plans, private outdoor spaces, covered parking, and direct gated access to Cameron Park. Located just steps from Stanford University, Stanford Research Park, California Avenue, Caltrain, shopping, dining, and major employment centers, the property benefits from exceptional tenant demand

More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal for guests or office use. The primary suite is privately located and features a steam shower and jetted tub. Outdoor living is equally inviting with an arbor-covered deck, newly planted lawns, terraced gardens, play area, and raised vegetable beds. Located on a cul-de-sac street less than one mile from the Woodside town center and served by renowned Woodside Elementary School (TK-8). Additional highlights include abundant storage, optional RV parking with hookups, and refreshed landscaping throughout

Set upon an extraordinary 3.25-acre setting, and just west of Palo Alto sits this charming one-story home which offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks this serene landscape, creating a seamless connection between indoor comfort and outdoor living. The property is graced with mature fruit trees, including pear, cherry and peach trees that add both charm and seasonal delight. Inside, the living room is a striking centerpiece, featuring a grand stone fireplace with a wood stove insert, complemented by soaring redwood-beam ceilings that add warmth and character to the space. A generously sized family room offers flexibility for relaxation, entertaining, or extended living. Modern convenience meets country tranquility with reliable high-speed intern

227 Madrone St is a stunning 3-unit apartment community with one single-family home located in the thriving city of Redwood City, California. Situated on a 7,500 square foot parcel of land, the subject property was originally constructed in 1950 and has a gross building area of approximately 4,268 square feet, offering its tenants beautifully designed three-bedroom and two-bedroom floor plans. 227 Madrone St has undergone significant capital improvements and updates in the past few years, including extensive interior renovations featuring updated kitchens, stainless steel appliances, renovated bathrooms, in-unit washers and dryers, and an updated electrical system. The subject property is located within walking distance to lively Downtown Redwood City, which offers tenants a myriad of high-end shopping, dining, and entertainment options. The Redwood City Caltrain Station, offering Baby Bullet service, is also within walking distance and provides an inexpensive, hassle-free commute to m

Enter this sun-drenched single-level home to find an expansive great room anchored by a skylight that fills the space with natural light. The open-concept layout, featuring a gourmet kitchen with a Miele range, flows effortlessly into the living and dining areas. Thoughtful renovations over the years touch nearly every corner of the home, from hardwood floors to updated bathrooms, complemented by clever storage throughout. The dining area opens onto a pergola-covered patio and flagstone terrace, a true outdoor living room perfect for summer entertaining, before giving way to a backyard sanctuary of mature fruit trees, blueberry bushes, and a raised garden box. High-end upgrades abound: owned solar panels and a Tesla Powerwall battery system, central AC and a high-efficiency furnace, a ventless Miele heat-pump dryer, a newer (2019) 'cool roof, and a voluntary seismic retrofit with automatic gas shut-off for real peace of mind. Smart home features round out the package, including a Nest

One-of-a-Kind Mountain Oasis on Spacious Sunny Lot! Charming 1930s log cabin cottage getaway with impeccable newer construction master suite addition, on fenced 1/3 acre of natural, drought resistant landscaping among dozens of majestic redwoods. Open kitchen with granite counters and new six-burner gas range. High ceilings, radiant heated hardwood and tile floors throughout. High quality finishes and attention to detail should not be overlooked. Expansive south facing deck with morning and afternoon sun provide stunning views. Large detached single car garage with EV charger, storage and attic, plus parking for multiple vehicles. Walking distance to Alice's Restaurant, Skywood Trading Post Grocery, and endless hiking/biking trails. Easy access to HWY 35 Skyline Blvd and HWY 84 Woodside Road to Silicon Valley or the coast. A welcoming neighborhood and close knit community are the inherent benefits of ownership. Old world character meets modern day amenities in an idyllic setting!

Elevated Perspective. Everyday Calm. Discover a calmer side of Silicon Valley living in this updated Farm Hill townhome with breathtaking elevated views across surrounding greenery, the community greenbelt, layered hillside vistas, and glimpses of the Bay beyond, an inspiring backdrop for everyday living. The inviting living room opens to a view balcony. Luxury upgrades include hardwood flooring, quartz countertops, updated cabinets, recessed lights, upgraded electrical panel, and innovative SMART thermostat-controlled hydronic baseboard heating. The kitchen offers generous pantry storage and adjacent dining with sliding doors to the rear patio in a tranquil greenbelt setting. Upstairs, the primary bedroom features vaulted ceilings, abundant natural light, wall-to-wall mirrored closets, and direct access to a 2nd balcony where the panoramic views truly shine. Versatile 2nd bedroom ideal for guests, home office, or evolving lifestyle needs. In-home laundry and covered parking add everyd

Rare SB9 dual-home opportunity featuring 2 detached single-family homes on 1 expansive 10,600 SF lot in the heart of Redwood City. Newly built in 2026, 214B Sequoia is a stunning 2-story residence offering 4 bedrooms, 2.5 baths, approximately 1,970 SF of thoughtfully designed living space, and an attached 2-car garage. Sophisticated modern finishes include wide-plank oak hardwood floors, black-frame windows, designer two-tone cabinetry, marble-look backsplash, and a dramatic staircase with black iron balusters and oak handrail. Luxurious primary suite features tray ceiling, walk-in closet, and spa-inspired bath with frameless glass shower. 214 Sequoia is a fully remodeled single-story home completed in 2023, offering 2 bedrooms, 1 bathroom, and approximately 777 SF of living space. Ideal for rental income, extended family, guest use, or a private office. Combined, the property offers approximately 2,747 SF of habitable living space across two fully independent homes on one parcel a rar

Situated on a picturesque tree-lined street and located down a private lane, in one of Redwood City's most desirable neighborhoods, this beautifully updated single-level home combines timeless charm with modern upgrades and a flexible layout. Experience a designer kitchen that flows perfectly to a sun-filled breakfast room, large living room, and dedicated formal dining room. Details adorn the home including rich hardwood floors, and two cozy fireplaces. The primary suite features a walk-in closet and a sleek spa-like bathroom with stall shower, separate soaking tub, and dual vanities. Two additional spacious bedrooms also benefit from their own dedicated en-suite baths, plus a 4th bright bedroom, and a dedicated hall bath. A convenient attached two-car garage with built-in storage, laundry, and epoxy-style paint allow for even more flexibility in uses. The private backyard is a peaceful retreat with mature landscaping, inviting patios. With a prominent location known for being a cross

Perched on a picturesque Emerald Hills street, this beautifully maintained Redwood City home captures sweeping panoramic views of the San Francisco Bay, Mount Diablo, and the Peninsula. Thoughtfully designed across multiple levels the light-filled interior features soaring ceilings, rich hardwood flooring with decorative inlay, crown molding, skylights, and expansive windows that showcase breathtaking scenery. The dramatic living room flows to a formal dining room with direct backyard access for effortless indoor-outdoor living, while a dedicated office or den provides flexible space. The kitchen features freshly stained cabinetry, granite countertops, Viking gas range and two ovens, plus a skylight and outdoor access. Upstairs, the primary suite offers a view balcony, and bathroom with jet tub, and walk-in closet. Three additional bedrooms provide comfortable accommodations across two levels. Outside, enjoy beautifully terraced gardens from composite decking to a paver patio with buil