535 Highland Avenue

Perched atop 3.42 private acres overlooking Monterey Bay and the lights of Santa Cruz, this extraordinary legacy estate offers a rare blend of privacy, scale, and proximity to Silicon Valley. Designed for those who value both connection and retreat, the property presents an exceptional opportunity for multigenerational living, executive respite, or a private family compound. Expansive indoor and outdoor gathering spaces create an ideal setting for entertaining on any scale, from intimate family celebrations to grand events. Sweeping views, open grounds, and thoughtfully designed living areas provide a seamless backdrop for creating lasting memories while enjoying the natural beauty of the Central Coast. The estate's generous footprint offers flexibility for extended family, guests, personal collections, creative pursuits, or executive work-from-home lifestyles. Whether envisioned as a private sanctuary, an entertainer's showcase, or a generational asset to be enjoyed for decades to come, the possibilities are as inspiring as the setting itself. Conveniently located within reach of Silicon Valley's innovation centers while offering a world apart from the demands of everyday life, this is a property that combines luxury, privacy, and lifestyle in a truly exceptional way.

Days on Market

116 days

Current Status

Contingent

Sold Price

Original Price

$5,900,000

List Price

$5,400,000

On Market Date

Mar 10, 2026

Contract Date

Jul 4, 2026

Close Date

Jul 27, 2026

Property Type

Single Family Home

Area

43 - West Santa Cruz

Zip Code

95060

MLS ID

ML82037953

APN

001-141-45-000

Year Built

1886

Stories in Building

Unavailable

Possession

Unavailable

COE

Jul 27, 2026

Data Source

MLSL

Origin MLS System

MLSListings, Inc.

Bed

8

Bath

6 (5/1)

Parking

3

Detached Garage

SQ FT

5,949

SQ FT Source

Unavailable

Lot SQ FT

148,975.2

Lot Acres

3.42 Acres

Pool Info

Yes

Cooling

None

Dining Room

Eat in Kitchen, Formal Dining Room

Disclosures

Natural Hazard Disclosure

Family Room

Separate Family Room

Flooring

Carpet, Tile, Wood

Foundation

Concrete Perimeter, Raised, Other

Fire Place

Family Room, Living Room, Primary Bedroom, Other

Heating

Radiant, Wall Furnace, Other

Views

Bay, City Lights, Ocean

Fee

Unavailable

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

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