535 Highland Avenue, Santa Cruz, CA 95060
Retreat-Like Legacy Estate with Panoramic Monterey Bay Views
$5,400,000

SOLD. 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.

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8
beds

6
baths

5,949 Sq.Ft. LIVING AREA

3.42 Acres lot

Features & Amenities

Interior

  • total bedrooms8
  • Total bathrooms6
  • full bathrooms5
  • half bathroom1
  • Flooring Douglas fir floors, carpet, tile

Area & Lot

  • Status Sold
  • Date Sold July 28, 2026
  • Living Area5,949 Sq.Ft.
  • Lot Area3.42 Acres
  • TypeResidential
  • YEAR BUILT1886
  • NeighborhoodSanta Cruz
  • Architecture StylesVictorian
  • View DescriptionOcean
  • School DistrictSanta Cruz

Exterior

  • Garage Space3
  • roofComposition
  • HEAT TYPEBoiler and radiator system, wall furnaces
  • other exterior FeaturesPool, park-like grounds, gated entry, deck, balcony, ocean-view patio

Financial

  • Sales Price$5,400,000
  • Buyer Agency Compensation 2.5%

Santa Cruz

Santa Cruz has a myriad of activities to entice visitors, from the historic Santa Cruz Beach Boardwalk, redwood forests, sandy beaches and sea lions.

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Tim Allen

Tim Allen

Local Knowledge & Global Connections

With many decades of combined knowledge, the Tim Allen Properties team looks forward to providing you with a real estate experience that is second to none. Please feel free to explore our website, and contact Tim or any one of the team members with any questions you may have.