535 HIGHLAND AVENUE, SANTA CRUZ
Retreat-Like Legacy Estate with Panoramic Monterey Bay Views
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.
Highlights:
• 3.42-acre private hilltop setting
• Panoramic views of Monterey Bay and Santa Cruz
• Ideal for multigenerational living or family compound use
• Executive retreat with convenient Silicon Valley access
• Expansive indoor and outdoor entertaining spaces
• Exceptional privacy and natural surroundings
• Flexible spaces for collectors, creatives, and remote professionals
• Close proximity to vibrant downtown Santa Cruz, beaches, municipal wharf and the Santa Cruz Boardwalk
• Rare opportunity to own a true legacy estate
A place to gather, retreat, and create a lasting family legacy.
Presented by Tim Allen, Coldwell Banker Global Luxury. 2.5% Buyers Brokerage Compensation. Brokerage Compensation not binding unless confirmed by separate agreement among applicable parties.
PROPERTY INFORMATION
TOTAL SQUARE FOOTAGE: 5,949 SqFt LOT SIZE: 3.42 Acres
NUMBER OF BEDROOMS: 8
NUMBER OF BATHS: 5 Full, 1 Half
INTERIOR: Drywall, Wood
EXTERIOR: Wood
HEAT: Boiler and Radiator System, Wall Furnaces
FIREPLACE: 4
ROOF: Composition
FLOORS: Douglas Fir, Carpet, Tile
GARAGE: 3-Car
YEAR BUILT: 1886
LIVING ROOM
DINING ROOM
