190 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

Feel at home on Fernside! Thoughtfully expanded to 2,088 sqft during a'down-to-the-studs' renovation you'll 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 quiet tree lined street this generous lot backs up to Hetch Hetchy open space giving added privacy with no direct rear neighbors. The highly sought after Fram 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 yours!

Welcome to a beautiful home with huge 19,500 SF creek-front lot on quiet court near Cornelis Bol Park with top Palo Alto schools. Exceptional privacy and yard views throughout. Kitchen with Viking refrigerator, built in double ovens and 4 burner gas cooktop. Beautiful floors. Open beam vaulted ceilings throughout. Wonderful light throughout the home. All of the bedrooms are spacious. Large primary suite with two walk-in closets, fireplace, private balcony and ensuite bathroom with dual sinks, tub and walk-in shower with dual shower-heads. Inside laundry room. Two car garage and oversized driveway. Charming and peaceful yards with majestic oak trees, mature landscaping, sauna and shed. Cherish an amazing Palo Alto lifestyle in a picturesque Palo Alto neighborhood. Incredibly walkable and bikeable location near parks, trails, all 3 schools and shops. Convenient proximity to El Camino Real, Caltrain, Stanford University, Highway 280 and I-101. Award-winning Palo Alto schools: Barron Park

Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility)

There is a particular quiet at 411 Glenwood Avenue. Stand on the main level and look through walls of glass. The first thing you notice is the treetops. The second is what you do not see: neighbors. The Oak canopy and the open expanse of the Joan Olson Preserve fill the windows instead. Friends who visit call it the Treehouse. Built in 1959, the home keeps its mid-century bones: mahogany paneling, a brick fireplace, and warm cork and hardwood floors. The kitchen opens to the great room, with stone counters and a gas cooktop. Walls of glass open onto a broad deck for slow dinners, the preserve as backdrop. Upstairs, the bedrooms share that same treetop view. Downstairs adds real flexibility: an open room with a slider to a flat, green yard, suited to an office or playroom, an en suite bedroom with its own patio, plus laundry and storage. Cross the street and you are on a trailhead into the preserve, a shortcut into downtown Woodside on foot, coffee in hand, oaks the whole way. Downtown,

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

Welcome to 3705 Red Oak Way, offering turnkey modern living with sweeping hillside views in Redwood City. This light-filled 5-bedroom 3-bathroom home features brand-new interior paint, refinished hardwood flooring, and a cozy brick fireplace in the main living space. The renovated kitchen boasts gleaming quartz countertops, abundant white cabinetry, and stainless steel appliances. Both upstairs bathrooms have been upgraded with modern vanities and custom tile work. Outside, enjoy a private patio venue framed by mature landscaping, perfect for relaxed outdoor living and taking in the surrounding views of the Bay Area. Positioned close to vibrant downtown Redwood City, local parks, tech hubs, and major commute routes via Hwy 101 and 280, this home offers a turnkey Bay Area lifestyle. All electrical wiring was replaced in August 2026 and connected to a new 200 amp panel in preparation for the sale

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

Welcome to this inviting first-floor condo in Redwood City, offering comfortable living in a convenient and advantageous location. This well-maintained home features brand new flooring throughout, as well as functional living spaces, making it an excellent opportunity for first-time buyers, downsizers, or anyone looking for a low-maintenance home in a highly desirable Peninsula location. Enjoy easy access to 280, making commuting to San Francisco or Silicon Valley dually convenient. The property is also located near highly regarded local schools, shopping, dining, parks, and other everyday amenities, with Downtown Redwood City just down the hill. An in-unit washer and dryer, a spacious walk-in closet, and a private patio all enhance this lovely space. With its convenient first-floor location, desirable setting, and easy freeway access, this condo offers a great combination of comfort, convenience, and value

Welcome to 2139 Alameda De Las Pulgas! This beautifully remodeled property offers approximately 2,147 sq. Ft. of combined living space, including a 1,650 sq. Ft. main residence with 3 bedrooms and 1.5 baths and a detached 497 sq. Ft. ADU, plus a detached two-car garage, ample parking, large pool, and nearly 14,000 sq. Ft. lot. Freshly painted inside and out, the main home features a remodeled kitchen with white cabinetry, Quartz counter top, island, brand-new stainless-steel appliances, professional-style hood, skylight, new lighting, warm parquet floors, and a beautiful white-stone fireplace. The ADU offers brand-new laminate flooring and fresh paint, ideal for guests, extended family, office, or potential rental use. Move-in ready and centrally located near Woodside, Menlo Park, and Palo Alto. The expansive lot may offer future residential development possibilities, subject to zoning and city approval. Buyer to verify all development potential and requirements with the City of Redwoo

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

Welcome to this inviting and updated 1-bedroom, 1-bathroom condo ideally located on the desirable Westside of Redwood City. Situated on the 3rd floor, this bright and functional home offers comfort, convenience, and a peaceful living environment. Natural light fills the well-designed layout, creating a warm and welcoming atmosphere. Conveniently located near the elevator, the unit provides easy access while maintaining a comfortable setting. Enjoy an unbeatable location just across the street from the YMCA and a nearby park, with Woodside Road only minutes away. Shopping, dining, and major commute routes are all easily accessible. The property also features one assigned parking space, additional storage in a secure garage, a lovely pool area, and a clubhouse. Whether you're a first-time buyer, downsizing, or looking for a conveniently located home, this is an exceptional opportunity to own a condo in one of Redwood City's desirable areas

Nestled in Stanford Weekend Acres, this beautifully remodeled and expanded home offers more than 2,500 SF of sophisticated living. Light moves easily through the open floorplan, illuminating wide-plank floors, high ceilings, expansive glass, and fine craftsmanship. A fireplace anchors the living room, while the great room brings together a family room, dining area, and beautifully appointed kitchen with Thermador appliances. Folding glass doors open to the backyard, extending the living space outdoors. Four bedrooms include a main-level guest suite with its own outdoor entrance, while upstairs, the primary suite opens to a private balcony and luxurious bathroom. The secluded backyard offers a hot tub, with air conditioning and a two-car garage adding everyday convenience. Close to Stanford University, downtown Palo Alto, Stanford Shopping Center, Sand Hill Road, and the Stanford Dish Trail, with easy access to Interstate 280. Served by Las Lomitas School District (buyer to verify eligi

Beautifully updated interiors & striking architectural character define this exceptional home in the Glens newly built in 2007. Tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town shopping & acclaimed restaurants as well as the highly rated TK-8 Woodside Elementary school. Framed by custom Corten-style fencing, terraced gardens, & underground utilities rarely found in this neighborhood, the property presents an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Original architectural details are complemented by contemporary finishes, custom cabinetry, granite surfaces, & expansive windows & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. Flexible floor plan, spacious primary suite with fireplace, customized walk-in closet, & newly finished bath.

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

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

Quiet Cul-de-Sac, 3 Bedrooms plus Large Study / Potential 4th Bedroom, Two Primary Suites, Close to Nature, Minutes to Parks and Trails. Tucked away on a quiet cul-de-sac in desirable Farm Hill, this inviting home offers a peaceful setting surrounded by nature while remaining conveniently connected. Featuring 3 bedrooms plus a spacious study that can easily become a 4th bedroom, the home offers exceptional flexibility. Enjoy easy access to Peninsula outdoor destinations, including Stulsaft Park, Edgewood Park and Natural Preserve, Westwood Park, Red Morton Park and the renowned Filoli Historic House and Garden. Downtown Redwood City, Caltrain and Highway 280 are just minutes away. Inside, the thoughtfully designed floor plan features two primary suites, one on each level, providing flexibility for guests, extended family or a private retreat. Hardwood floors, abundant natural light and an inviting fireplace create a warm atmosphere. Additional features include a large walk-in pantry, d

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

A rare offering in coveted Emerald Hills, this beautifully reimagined residence blends timeless architecture with sophisticated modern living on over one-half acre of exceptionally level grounds. Framed by manicured landscaping and an expansive driveway, the home offers remarkable privacy, scale, and effortless elegance. Light-filled interiors showcase refined finishes, and a thoughtfully designed floor plan with gracious formal living and dining rooms, a private office, an inviting family room, and a beautifully appointed eat-in kitchen at the heart of the home. Four spacious bedrooms and three-and-a-half baths include a versatile main-level suite with custom built-ins, ideal for guests, a home office, or multi-generational living. Abundant storage and a three-car garage enhance everyday functionality. Designed for seamless indoor-outdoor living, multiple rooms open to expansive lawns and resort-inspired amenities, including a spa, pergola-covered lounge, and a fully equipped outdoor

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

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 throu

Welcome to 366 Alexander Avenue, a beautifully maintained 3-bedroom, 2-bathroom home offering approximately 1,550 square feet of comfortable living space in one of Redwood Citys more desirable neighborhoods. Situated on one of the area's most sought-after tree-lined streets, this move-in ready home has been lovingly cared for and features fresh interior paint, a functional floor plan, a newer roof, and charming curb appeal. The spacious backyard provides plenty of room to relax, entertain, or play, while the refreshed landscaping enhances the home's inviting presence. Just minutes from parks, shopping, restaurants, Caltrain, and major commute routes, 366 Alexander offers an exceptional opportunity for buyers looking to put down roots in one of Redwood City's most established and family-friendly neighborhoods

Ready to Move-In. Beautiful Top-Floor Condominium Welcome to this beautifully updated 3-bedroom, 2-bath condominium. Offering approximately 1,550 SqFt of living space, this desirable top-floor unit features a private balcony, abundant natural light, and a bright, airy feel throughout. Thoughtfully upgraded with engineered hardwood flooring, sound-reducing double-pane windows, updated countertops and cabinetry, a built-in microwave/convection double oven, and fresh interior paint, this home is truly move-in ready and ready to impress. The open kitchen flows into the dining area, while the inviting living room features a cozy fireplace, creating the perfect setting for relaxing evenings or effortless entertaining. The spacious primary suite offers a large walk-in closet and private bath. Additional features include an in-unit washer and dryer, two secure gated parking spaces, private garage storage, and a community swimming pool. Ideally located in the heart of the Peninsula with easy ac

Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace, attached 2-car garage, energy-efficient heat pump for heating and cooling, updated electrical service, and EV charging. Just down the street from renowned Woodside Elementary School (TK-8)

Beautifully built in 2016 and recently refreshed, Barron Park home sits on a corner lot, blending luxury and thoughtful design. Just over 1/2 mile to El Camino Real shops and restaurants, 2.5 miles to San Antonio Center, and about 10 minutes to Stanford Shopping Center and major freeways. Fletcher Middle and Gunn High are within walking distance. A limestone porch leads to a foyer with a 15-ft ceiling. The circular living room features a 12'8' ceiling, bow window and fireplace, plus frosted-glass doors to a private office with box bay window, round clerestory and closet space. 10 skylights fill the home with natural light. The chef's kitchen features quartz counters, large island and Thermador appliances. Open to the 13-ft family room, it flows to a deck with BBQ and outdoor sink, plus a patio. Five bedrooms include two en-suites. The primary suite features an 11-ft ceiling, walk-in closet and spa-like bath with heated floors, dual vanity, oversized shower and Jacuzzi tub. Lutron smart

Inviting and filled with natural light, this home offers comfortable single-level living with 3 bedrooms and 2 bathrooms in the sought after Selby Lane neighborhood. Located just moments from tremendous dining, shopping, coffee, and convenient commuting routes. Inside, the living room makes an immediate impression with vaulted ceilings and a dramatic Palladian-style window, while a separate dining area provides a welcoming space for gatherings. The generous updated kitchen opens to a family room with a cozy fireplace and direct access to the deck, creating a connected setting for everyday living and entertaining. The primary suite features a walk-in closet and private ensuite bath with dual sinks, while two additional spacious sun-filled bedrooms offer flexibility for family, guests, or work-from-home needs. Outside, a lush front lawn framed by mature trees adds wonderful curb appeal, while the private backyard features an expansive lawn and large deck perfect for dining, entertaining,

Located in one of Redwood City's most coveted neighborhoods, known by some as Little Atherton, this beautifully crafted home enjoys a mature, tree-lined setting just moments from Atherton, Menlo Park, Stanford, acclaimed public and private schools, and the best of Redwood City. Built in 2007, the home blends timeless character with thoughtful contemporary finishes and quality craftsmanship throughout. The spacious floor plan features two bedrooms on the main level, along with grand living and dining rooms with vaulted ceilings, a chef's kitchen with generous workspace, gas range, and storage, and a comfortable family room for everyday living. Upstairs are two private en-suite bedrooms, including an expansive primary suite with a walk-in closet and spa-like bath. Central air conditioning, ample storage, sun tunnels that bring in additional natural light, and numerous quality upgrades complete a rare combination of location, scale, flexibility, and enduring style. Outside enjoy the full

Located in the Selby-Atherwood neighborhood of Redwood City, this new construction Transitional style residence offers a refined blend of transitional design and modern comfort. The expansive great room is designed for both everyday living and entertaining, featuring stacking glass doors that open to the backyard for effortless indoor-outdoor connection. At the heart of the home, the chefs kitchen showcases Wolf and Sub-Zero appliances, a large center island, and a walk-in pantry. The main level also features a private ADU with its own kitchenette, bedroom, and en suite bath, ideal for guests, extended family, or flexible living needs. Upstairs, a spacious loft provides the perfect setting for a media room or additional living space, complemented by a well-equipped laundry room with sink and built-in storage. The primary suite features a spa-inspired bath featuring a freestanding soaking tub and a walk-in shower. Two secondary bedrooms complete the upper level. Enjoy close proximity to