Skyline Area Real Estate

Situated in the picturesque city of Woodside, California, the Skyline Area is a charming neighborhood nestled within San Mateo County. With its idyllic location, this region offers a perfect blend of natural beauty and suburban convenience.

One of the most notable features of the Skyline Area is its stunning views. As the name suggests, this neighborhood is perched on the hills, providing residents with breathtaking vistas of the surrounding landscape. From the rolling hills to the lush greenery, every direction offers a picturesque sight.

In addition to its natural beauty, the Skyline Area boasts a tranquil and peaceful atmosphere. The neighborhood is known for its spacious properties and large lots, providing residents with privacy and a sense of serenity. With its low population density, residents can enjoy a quiet and secluded lifestyle away from the hustle and bustle of the city.

For outdoor enthusiasts, the Skyline Area offers a wealth of recreational activities. The nearby Skyline Ridge Open Space Preserve provides ample opportunities for hiking, biking, and exploring nature trails. Residents can also enjoy horseback riding and picnicking in the beautiful surroundings.

Despite its serene surroundings, the Skyline Area is conveniently located near major amenities. The nearby Woodside Plaza offers a variety of shops, restaurants, and services, ensuring residents have easy access to everyday conveniences.

With its stunning views, peaceful ambiance, and proximity to amenities, the Skyline Area in Woodside, California, is a highly sought-after neighborhood for those seeking a serene and nature-filled lifestyle.

Newest Listings in Skyline Area

$1,950,000

3 Beds ⋅ 3 Baths ⋅ ML82059245 MLS

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 RD, Woodside

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

$2,299,000

4 Beds ⋅ 3 Baths ⋅ ML82058136 MLS

Panoramic Views, Absolute Privacy Perched high above the valley on over six acres, this rare 4-bedroom, 3-bath mountain sanctuary pairs total seclusion with sweeping, unobstructed views stretching clear across the Bayfrom vibrant sunrises over the water to shimmering city lights at night. Inside, three thoughtfully designed levels of living space are anchored by soaring ceilings, expansive glass, and two cozy wood-burning fireplaces. The main floor centers around a functional kitchen with a central island and walk-in pantry, opening directly to a multi-level wraparound deck designed for effortless indoor-outdoor living and scenic dining. The layout includes a primary suite positioned to capture morning light, complete with an oversized bath and walk-in closet. Three additional bedrooms feature a built-in loft, a walk-in closet, and a ground-floor room with private outdoor entry ideal for a peaceful home office. Sprawling level lawn areas, mature trees, and a hot tub set for stargazing complete the grounds. Extras include an attached 2-car garage, large utility room, ample parking, Jackery backup battery, and a Tesla EV charger. Located minutes from trailheads, preserves, central Woodside, and I-280-a high-elevation retreat moments from Silicon Valley.

255 Allen RD, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

$1,888,000

4 Beds ⋅ 4 Baths ⋅ ML82056831 MLS

An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's renowned rural charm, it offers a peaceful retreat just minutes from downtown Woodside, Stanford University, Sand Hill Road, and major employment centers. Residents enjoy a rare balance of tranquility, open space, and access to world-class dining, shopping, and recreation. Whether creating a private estate, preserving a long-term investment, or capitalizing on one of the Bay Area's most desirable locations, 26 Big Tree Rd presents a rare opportunity in a market where exceptional properties are seldom available. Woodside remains one of Northern California's premier residential destinations, known for expansive estates, an equestrian lifestyle, enduring property values, and unmatched privacy, prestige, and long-term appreciation.

26 Big Tree RD, Woodside

Listed by Matthew Dapolito, 408-202-9202 from Intero Real Estate Services
(If provided) CoList: Scott Bishop from Intero Commercial

$1,829,950

3 Beds ⋅ 2 Baths ⋅ ML82053343 MLS

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!

252 Blakewood WAY, Redwood City

Listed by Allen Nazari, 650-313-7619 from Park Lane Capital Inc
(If provided) CoList: from

$3,195,000

3 Beds ⋅ 3 Baths ⋅ ML82045702 MLS

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

1100 Old La Honda RD, Woodside

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

$2,195,000

3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(If provided) CoList: from

$500,000

ML82033277 MLS

Lovely flat development spot near a seasonal creek. Excellent opportunity to build on this oak-studded parcel. 4000 ft2 home deemed possible by Lea and Braze engineers; price includes feasibility study, survey, and septic perc test results. This land could be a great location for your estate home or quiet get-away. One mile from Thomas Fogarty Winery. Plenty of room for horses, animals and/or hobby farm, you'll find that you are well-situated to access the hiking and riding trails that abound in the open space near this property. Seller has 2 lots for sale (0-220 and 0-250 Heacox) and the actual address is not yet determined. Electric pole on site. You add septic and well for water, which is plentiful here.

0-250 Heacox, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$550,000

ML82033274 MLS

Tranquil land. Excellent opportunity to build or ? on this sun-drenched parcel that has gentle grade for development. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animals and/or hobby farm, you'll find that you are conveniently located to access the hiking and riding trails that abound in the area's open space. Seller has 2 lots for sale (0-220 and 0-250 Heacox); the actual address is not yet determined. Electric pole on site. Old well on-site (plentiful water here), you add septic system. Invest in your future!

0-220 Heacox RD, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$3,088,000

4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS

SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost RD, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than JABEZ REALTY are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.