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BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

  • Bedrooms
    3
  • Bathrooms
    2
  • Year Built
    1929
  • Stories
    1.0
  • Foundation
    Slab
  • Garage Spaces
    2.0
  • Parking Features
    Attached, Garage, Off Street
  • Living Area
    1500.0
  • Interior Features
    Breakfast Bar
  • Appliances
    Dishwasher
  • Flooring
    Hardwood, Tile
  • Cooling
    Central Air
  • Heating
    Forced Air

  • Acres
    0.4697
  • Water
    Public


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Frequently Asked Questions

How do I schedule a tour of 235 Hillside Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 235 Hillside Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 235 Hillside Dr?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 2 bath, listed for $2,150,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Woodside, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 235 Hillside Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 235 Hillside Dr at around $12,235. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 235 Hillside Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in San Mateo County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 235 Hillside Dr?

In most cases, yes. Whether 235 Hillside Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Woodside's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 235 Hillside Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Woodside and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $2,150,000 with 1,500 sqft of space—that comes out to approximately $1,433 per square foot.

How long has this property been on the market?

235 Hillside Dr was listed on April 03, 2026, which means it's been on the market for 221 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1929, making it approximately 97 years old.

What is the lot size of this property?

235 Hillside Dr sits on a 0.47-acre lot, which is 20,473 square feet.

Is 235 Hillside Dr still available for sale?

This home is pending sale, which means the seller has accepted an offer. You can favorite it to track status or ask our expert to help you find similar homes in this area. We'll also let you know if this property comes back on the market.

Source: ez Home Search, MLS Data

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Bay East ©2026. CCAR ©2026. bridgeMLS ©2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated at November 10, 2026 at 06:07PM.

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