8.9 out of 10

Woodside Glen

Ranked 1st best neighborhood in Woodside
37.4374442444396 -122.255412738169
Great for
  • Clean & Green
  • Parks & Recreation
  • Neighborly Spirit
  • Safe & Sound
  • Peace & Quiet
Not great for
  • Public Transport
  • Cost of Living
  • Pest Free
  • Childcare
  • Internet Access
Who lives here?
  • Families with kids
  • Retirees
  • Country Lovers
  • Professionals
  • Trendy & Stylish

Reviews

C-S C-S
5/5 rating details
  • Neighborly Spirit 5/5
  • Safe & Sound 5/5
  • Clean & Green 5/5
  • Pest Free 3/5
  • Peace & Quiet 5/5
  • Eating Out 4/5
  • Nightlife 2/5
  • Parks & Recreation 5/5
  • Shopping Options 3/5
  • Gym & Fitness 4/5
  • Internet Access 3/5
  • Lack of Traffic 5/5
  • Parking 5/5
  • Cost of Living 2/5
  • Resale or Rental Value 5/5
  • Public Transport 2/5
  • Medical Facilities 4/5
  • Schools 5/5
  • Childcare 4/5
2yrs+

"Wonderful, welcoming neighborhood. Rural atmosphere, yet close (as in a bike ride away) to the epicenter of silicon valley."

If your checklist for a neighborhood includes a woodsy and rural ambiance, a safe neighborhood where you know all of your neighbors, and a short commute to work, then the "Glens" ticks all of those boxes. Situated off of Canada Road between the Farm Hills and Woodside Ave exits off of Highway 280, the neighborhood began as a collective of vacation cabins for well-to-do San Franciscans in the 20's and 30's. While several homes have been modernized, there remain a few original homes with family-owners dating back to that era. Situated within the city limits of the Town of Woodside, the Glens is has become an attractive location for families with younger children who would attend Woodside Elementary School, with its Great Schools 10/10 rating.

The Glens has been undergoing a renaissance in recent years coincident with the rise in local real estate prices prices. Home sales in recent years (2012-2014) have ranged from <$1m for an original structure to >$4m for a newly built home. Several homeowners in the neighborhood have taken advantage of growing equity and are updating, modernizing and expanding.

The Glens is renown among local Trick-or-Treaters; this is because a loop of neighborhood in the Glens traditionally closes off to car traffic on Halloween night so children and families can safely experience a wonderful and memorable Halloween experience, representing the exemplary community and family spirit of the neighborhood. The holiday season brings local carolers to the doorstep, and most homes are decorated with holiday lights.

Pros also include several nearby walkable trails, minimal traffic (the speed limit is 20 mph and much of the neighborhood is single-lane or one-way), and nearby hills which promote a wonderful view and provide nearly perfect weather. Both Stanford and Sequoia Hospitals are within a 10 min drive away.

Cons would primarily affect younger, profession couples without children who would be concerned with the limited choices of nearby (walkable) restaurants and bars, and of course the cost of real estate. However, the Glens represents one of the few pockets of real estate in San Mateo county with "affordable" homes outside of the tracts of Redwood City and San Carlos.
Pros
  • Beautiful Homes
  • Close to Town and Highway
  • Great Schools
Cons
  • A Little Dull Side
Recommended for
  • Professionals
  • Families with kids
  • Retirees
  • Gay & Lesbian
  • Hipsters
  • Country Lovers
  • Beach Lovers
5/5 rating details
  • Neighborly Spirit 5/5
  • Safe & Sound 5/5
  • Clean & Green 5/5
  • Pest Free 2/5
  • Peace & Quiet 4/5
  • Eating Out 3/5
  • Nightlife 2/5
  • Parks & Recreation 4/5
  • Shopping Options 2/5
  • Gym & Fitness 2/5
  • Internet Access 3/5
  • Lack of Traffic 4/5
  • Parking 4/5
  • Cost of Living 1/5
  • Resale or Rental Value 5/5
  • Public Transport 1/5
  • Medical Facilities 2/5
  • Schools 5/5
  • Childcare 2/5
2yrs+

"Attractive and Well Located"

Leaning up against the western side of Highway 280, Woodside Glens is one of those neighborhoods where narrow roads creep off into dead ends. The main artery through this neighborhood is Canada Road, which is long and straight and has several surface streets that slide off it to the homes in Woodside Glens.

Homes here run from just over $1 million to $4.25 million, with the median being around $3 million. The desirability of this location is reflected in the meticulous upkeep of the homes here. You can find everything from a classic Mediterranean style home here to an East Coast style manner. Most homes here take full advantage of the location to high light cottage like elements of their architectural styles. That means lots of exposed timbering, wood porches, and stonework.

You are not quite as isolated here in Woodside Glens as you are in other parts of Woodside. With the freeway on one side and the “downtown” Woodside area on the other, Woodside Glens just generally feels more populated and more active than other locations in Woodside. The “downtown” area has a supermarket and few restaurants and all the basics that you need to live. So if you live here it is possible, in theory, to go weeks without leaving Woodside.

There isn’t much more to it than this however, and if given the affluence of Woodside residents, I doubt many of them go long without heading out for some entertainment.

It is a very nice spot, though prices definitely make it out of the reach of most of us.
Pros
  • Beautiful Homes
  • Close to Town and Highway
  • Great Schools
Cons
  • Very, Very Expensive
  • A Little Dull Side
  • Country-Side Concerns (pest, etc.)
Recommended for
  • Professionals
  • Families with kids
  • Retirees
  • Gay & Lesbian
  • Country Lovers
  • Trendy & Stylish
4/5 rating details
  • Neighborly Spirit 4/5
  • Safe & Sound 3/5
  • Clean & Green 4/5
  • Peace & Quiet 4/5
  • Nightlife 2/5
  • Parks & Recreation 2/5
  • Shopping Options 2/5
  • Cost of Living 4/5
2yrs+

"Not just a Highway 280 passover community"

Woodside Glen is a democratically leaning, upper middle-class community situated within the shallower woodlands of the Santa Cruz Mountains. Aesthetically speaking, you’re living in the land of luxury. The neighborhood is saturated with some long and narrow country roads, ranch-like homes and elegantly gated properties. And although exclusively residential, Woodside Glen isn’t that far from some commercial real-estate, like many other Woodside communities. As such, the neighborhood offers a perfect balance of independence and connection with its city and its neighboring Menlo Park community (not to mention Stanford University).

For the perspective resident, the community offers a wide range of housing options. Some homes are nestled along the hillside, while others are hidden beneath the brushy residential terrain. For the most part, homes are beautifully large (some gorgeous California Ranch homes). They are commonly single storied with charming house fronts and a peaceful escape from the rigors of downtown. These homes usually lay ground to some very enormous and well-groomed properties with driveways curling up/down into the street. With all these luxuries, you should probably have some deep pockets in order to live here. In fact, the city’s average annual income is above $215,000, with homes estimated somewhere around $1.5 million.

For young families, Woodside is very much in-tune with its public school system and the kind of reputation one might evoke. Almost all students within the area attend Woodside High School, which just so happens to be up the road. The school provides a great academic student life garnering a 4-out-of-5 on greatschools.org. Elsewhere, Canada College (two-year program) skirts the northern edge of the community and helps its students advance into four-year universities (like Stanford University that’s just across the way). And for commuters, Highway 280 is quick option to connect residents up and down the San Francisco peninsula.
Recommended for
  • Professionals
  • Families with kids
  • Retirees
  • Students
  • Country Lovers
  • Trendy & Stylish

Unranked Streets in Woodside Glen

Canada Rd

3.5/5
"Beautiful Place"
37.4389727374249 -122.263438363017

Hacienda Dr

3.5/5
"Lifestyles of the Rich and Famous..."
37.4309456306085 -122.249567967367

Woodside Rd

3.5/5
"Stock Up Here Before Hiking"
37.4311333005558 -122.246969006909

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