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Built by the OBrien Group, 23666 Black Oak Way blends timeless character with thoughtful updates. Offering approximately 3,786 square feet of living space, this beautifully maintained two-story home features five bedrooms and four-and-one-half bathrooms on an expansive 12,206-square-foot lot. It enjoys a premier cul-de-sac setting and backs to the Rancho San Antonio Open Space Preserve. Subtle Craftsman influences complement a well-designed floor plan with formal living and dining rooms, a spacious kitchen and family room combination, and a recreation/media room ideal for enjoyment. Fresh interior paint, updated lighting, and refreshed finishes create a bright and welcoming atmosphere. Outside, renewed landscaping provides a peaceful retreat featuring a stone pathway, lush new lawn, an updated pond and waterfall, and fresh front-yard plantings. Served by highly regarded Cupertino schools and moments from Rancho San Antonio County Park with miles of scenic hiking trails, this beautiful estate offers serenity, space, and an exceptional connection to nature. Dont miss the opportunity to make it yours!

Highlights

  • Residential
  • Single Family Residence
  • Built in 2000
  • 2 Car Garage
  • 92 days on Market

  • Bedrooms
    5
  • Bathrooms
    4
  • Year Built
    2000
  • Stories
    2.0
  • Garage Spaces
    2.0
  • Parking Features
    Attached, Garage
  • Living Area
    3786.0
  • Pool Features
    None
  • Cooling
    Central Air
  • Heating
    Forced Air
  • Basement
    Crawl Space

  • County
    Santa Clara
  • City
    Cupertino
  • Zip Code
    95014

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Frequently Asked Questions

How do I schedule a tour of 23666 Black Oak Way?

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 23666 Black Oak Way.

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 23666 Black Oak Way?

Click Ask a Question to talk with our team. You already know it is a 5 bed, 4 bath, listed for $5,400,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Cupertino, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 23666 Black Oak Way?

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 23666 Black Oak Way at around $30,730. 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 23666 Black Oak Way?

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 Santa Clara 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 23666 Black Oak Way?

In most cases, yes. Whether 23666 Black Oak Way is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Cupertino'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 23666 Black Oak Way?

We can handle that for you. Our preferred local agent specializes in residentials in Cupertino 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 $5,400,000 with 3,786 sqft of space—that comes out to approximately $1,426 per square foot.

How long has this property been on the market?

23666 Black Oak Way was listed on August 13, 2026, which means it's been on the market for 92 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 2000, making it approximately 26 years old.

Is 23666 Black Oak Way still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

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 13, 2026 at 06:06PM.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.