Woodside Homes under $2 million

Woodside Homes under $2 million

Welcome to Woodside, California—a hidden gem nestled in the heart of San Mateo County. Known for its lush landscapes and serene atmosphere, Woodside offers a unique blend of rural charm and upscale living. With its sprawling estates, majestic redwoods, and picturesque trails, this enchanting town is the perfect escape from the hustle and bustle of city life, while still being conveniently located just a short drive from the vibrant communities of Silicon Valley.

Woodside is renowned for its commitment to preserving its natural beauty, with numerous parks and open spaces that invite outdoor enthusiasts to explore. Whether you enjoy hiking, horseback riding, or simply basking in the tranquility of the great outdoors, Woodside has something for everyone. The town is also home to a close-knit community that values privacy and a slower pace of life, making it an ideal place for families and individuals seeking a peaceful retreat.

For those looking to invest in this idyllic locale, there are homes available under $2 million, offering a fantastic opportunity to own a piece of Woodside's charm without breaking the bank. These properties often feature spacious lots, stunning views, and a variety of architectural styles that reflect the town's unique character. Whether you’re searching for a cozy cottage or a modern family home, Woodside’s real estate market provides options that cater to diverse tastes and budgets.

Discover the allure of Woodside, where nature meets luxury, and find your dream home in this enchanting Californian town today!

Newest Woodside Homes under $2 million

13660 Skyline Boulevard, Woodside
$1,890,000
3 Beds ⋅ 2 Baths ⋅ ML82065423 MLS ⋅ Active Status
ONE LEVEL LIVING- The Comfort of a Classic Discover life among the redwoods in this inviting single-level California ranch home, situated on approximately half an acre of level, fenced grounds along Woodside's Scenic Skyline Boulevard. Surrounded by towering redwoods and beautiful natural scenery, this private woodland retreat combines the warmth of solid redwood construction with natural stone accents, vaulted ceilings, skylights, and generous windows that bring the outdoors in. The dramatic living room features exposed beams, wood floors, and a handsome stone fireplace, with views of the woods/garden and flagstone patio. A remodeled kitchen with stainless steel appliances opens to a spacious dining area overlooking the surrounding forest. The thoughtfully designed floor plan includes three bedrooms with generous closets, two full bathrooms, a separate laundry room, ample storage, and an attached two-car garage. Just around the corner from the iconic Mountain House restaurant and nearby hiking trails, the property offers convenient access to the Peninsula, Silicon Valley, and the coast. Possible ADU and expansion potential.

13660 Skyline Boulevard, Woodside
252 Blakewood Way, Woodside
$1,725,000
3 Beds ⋅ 2 Baths ⋅ ML82064962 MLS ⋅ Active Status
One-of-a-kind mountain oasis on a spacious, sunny lot! This charming 1930s log cabin cottage getaway features an impeccable newer construction primary suite addition, set on a fenced ~1/3 acre of natural, drought-resistant landscaping surrounded by majestic redwoods. The open kitchen boasts granite counters and a six-burner gas range, flowing seamlessly into light-filled living spaces with high ceilings and radiant heated hardwood and tile floors throughout. Relax or entertain on the expansive south-facing deck with morning and afternoon sun and stunning views. Includes a large detached single-car garage with an EV charger, extra storage, and attic, plus parking for multiple vehicles. Enjoy an ideal location within walking distance to Alices Restaurant, Skywood Trading Post, and endless hiking and biking trails. Excellent proximity for commuting: top-rated Portola Valley Elementary and Middle School, Woodside High School, just 15 minutes to HWY 280 at Sand Hill Rd, and 20 minutes to Stanford University. Easy access to HWY 35 (Skyline Blvd) and HWY 84 (Woodside Rd) connecting to Silicon Valley or the coast. Old-world character meets modern amenities in a welcoming, close-knit community!

252 Blakewood Way, Woodside
164 Filbert Road, Woodside
$1,599,000
3 Beds ⋅ 2 Baths ⋅ ML82063250 MLS ⋅ Active Status
This enchanting Woodside retreat offers an exceptional blend of privacy, natural beauty, and effortless indoor-outdoor living. Take in the magical, natural setting capturing serene views of the redwood trees, valley, and spectacular sunsets. The thoughtful floor plan and wood throughout, combine timeless character with inviting warmth. On the main level, a formal living room with fireplace flows to the dining area, full bath, with claw foot tub, whiskey bar, and welcoming kitchen and family room, with wood-burning stove. Upstairs, three bedrooms and a bathroom, provide comfort and privacy. Most notable, a light-filled primary suite is a true sanctuary, featuring built-in cabinetry, two walk-in closets, and double doors opening to breathtaking valley and sunset views. Wrap around Ipe decks extend the living space outdoors, offering ideal venues for morning coffee, sunset gatherings, entertaining, or quiet moments beneath the redwoods. Extra storage for firewood, next to detached two-car garage. Near coveted Kings Mountain Elem. School. Rarely does a home offer the combination of seclusion, scenery, lifestyle appeal, with easy access to 92, 280, and 101. Additional two lots, next to the house, included in the sale. This Woodside property is an opportunity not to be missed.

164 Filbert Road, Woodside
115 Forest View Road, Woodside
$1,950,000
3 Beds ⋅ 3 Baths ⋅ ML82059245 MLS ⋅ Active Status
Skyline corridor on nearly one-half acre with spectacular unobstructed ocean views and easy access to both the Peninsula and the coast. The two-story floor plan features vaulted beamed ceilings, angled transom windows, and abundant natural light. The main level has a spacious living room with fireplace, dining area opening to the view deck, an updated eat-in kitchen, plus the primary suite, two additional bedrooms, and a bath. The lower level includes a large family room with fireplace and wet bar, full bath, laundry room, and access to the 2-car garage. Detached bonus studio with wet bar and bath provides flexible space for guests, office, or hobbies. Expansive wraparound deck with ocean views plus covered and open patios extend the living space outdoors. Just one-half mile from a trailhead to Purisima Creek Redwoods Preserve with miles of hiking and equestrian trails, 5 miles to Highways 92 and 8 miles to Highway 84 for access throughout the Peninsula and to the coast. Excellent Kings Mountain Elementary School.

115 Forest View Road, Woodside
155 Native Sons Road, Woodside
$895,000
1 Beds ⋅ 1 Baths ⋅ ML82038622 MLS ⋅ Active Status
Hidden at the end of a quiet country lane beneath a magnificent canopy of redwoods lies one of Kings Mountain's rarest opportunities, 3.63 private acres where nature, privacy, and possibility come together. Tucked away on picturesque Native Sons Road, this extraordinary property offers a peaceful woodland setting with an existing cottage and valuable infrastructure already in place, including a newer foundation, updated well, septic system, and pump. The home is served by electrical utility service, private well, septic, and delivered propane. Surrounded by towering redwoods and just moments from El Corte de Madera Open Space Preserve, this special property offers a rare opportunity to restore, thoughtfully expand, or create a personal retreat over time. The unfinished lower level presents exciting potential for additional living or bonus space, subject to buyer verification and applicable approvals. Whether envisioned as a weekend escape, artist's studio, writer's retreat, or future custom residence, this is a place where the pace slows, nature takes center stage, and imagination can flourish. A truly uncommon opportunity to own a private slice of Kings Mountain just minutes from the Peninsula's vibrant communities.

155 Native Sons Road, Woodside
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Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.

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