Los Altos & Los Altos Hills buyer intelligence

Same acreage. A very different decision.

A large lot does not automatically create a large opportunity. Simon looks at how the site, existing improvements, approval path and buyer economics work together before future potential is priced into an offer.

This is an early buyer-side assessment—not an architectural feasibility opinion. The goal is to identify what must be verified, who should verify it and whether the opportunity still makes sense after the answers are known.

Start with net land—not the headline acreage.

Gross lot size is only a starting point. In Los Altos Hills, Maximum Floor Area and Maximum Development Area depend on parcel-specific inputs including net acreage and average slope. A current survey, topography and Town worksheet can materially change the buildable picture.

Account for what is already on the site.

The main residence, garage, secondary unit, pool, patios, driveways and other hardscape can all affect how much of the property is already developed. The question is not simply “How large is the lot?” but “What existing value would a new plan preserve, repurpose or remove?”

Test placement, access and construction reality.

Setbacks, trees, drainage, grading, privacy, view corridors and the route for construction equipment may shape the plan long before finishes are discussed. Simon helps flag which conditions need a surveyor, architect, civil engineer, arborist or Town confirmation.

Verify the records and infrastructure.

Permit history, prior calculations, sewer and water conditions, utility routing and the status of existing secondary space deserve review. An attractive concept can change once the approved record and physical systems are understood.

Compare the real alternatives.

Expansion, reconfiguration and full replacement carry different costs, timelines and resale consequences. Simon puts the technical questions beside the purchase price, the home’s existing strengths and competing properties that may achieve the same goal with fewer compromises.

Get a property second opinion →Send the property after you’ve seen what deserves investigation.

A large lot doesn’t always mean a large opportunity.

Photograph: Michael Brown / Unsplash

$250M+Sales

Top 1%Performance

10+ yearsExperience

LuxuryProperty specialist

The part a checklist cannot answer

What else could change the answer?

It depends on the property.

Two Los Altos properties can look remarkably similar on paper and offer very different paths forward. Simon starts with your objective and the specific property—not a generic list of issues.

Selected buyer representation

$15M

13431 Wildcrest Drive
Los Altos Hills

7,154 sq. ft.Main residence

1.35 acresMostly level site

735 sq. ft.Second residence

3-carDetached garage

This property shows why acreage alone is not the analysis. The estate already combined a substantial three-story home, an apartment above the detached garage, pool and spa, gated drive-through parking, extensive outdoor improvements and Bay and city-light views.

For a buyer considering changes, the value question is how those existing assets, the approved record and any remaining development capacity fit together—not how much empty land appears to be available.

What Simon’s experience adds

Interpret the property before commissioning the full technical answer.

Separate valuable existing improvements from theoretical upside.
Identify the records worth obtaining: permits, surveys, site plans and parcel-specific MFA/MDA calculations.
Compare renovation, reconfiguration, addition and rebuild paths in the context of price and resale.
Bring in the appropriate architect, engineer, surveyor or Town specialist when a definitive answer is needed.

Property facts are drawn from the 2025 MLS record. This example does not state that additional development is available or that a particular project would be approved.

Property judgment, in context

Simon doesn’t replace the architect or engineer.

He helps you recognize when you need one—and which questions are worth answering before you proceed.

Notice what matters.

Surface property-specific issues that could change the buying decision.

Understand the tradeoff.

Consider technical questions alongside price, alternatives and your objectives.

Know when to go deeper.

Bring in the appropriate specialist before relying on an assumption.

Start with the property

Send it to Simon.

Share the listing and what you hope to create. Simon will identify the first two or three property-specific questions he would want answered before moving forward.

“I’ll review what you send and tell you where I would begin.”

Property address or listing link

What are you hoping to build or change?

Phone — optional

No pressure. No long questionnaire.

Send Simon a property