17 Mile Drive. MPCC. The Lodge. Some of the most valuable residential real estate in North America — and owners deserve management that matches.
Pebble Beach isn't a city — it's an unincorporated community inside Monterey County with its own gated access, its own rules, and its own caliber of property. Managing here means understanding that most owners don't live here year-round, that many units are second or third homes, and that the caretaker-style relationship matters more than the leasing transaction.
Cypress & Pine's Luxury Estate package was built specifically for Pebble Beach. Mike personally walks every property quarterly, coordinates with household staff when applicable, and operates with the discretion Pebble clients expect.
Professional marketing, thorough screening, California-compliant leases. 8% monthly + 20% leasing.
See Pricing →Multi-platform listings, dynamic pricing, guest ops, and STR licensing. 22% of gross, all-in.
See Pricing →White-glove management with Sotheby's International reach. Custom retainer structure.
See Pricing →Each neighborhood has its own rhythm, tenant profile, and price point. Here's what makes each corner of Pebble Beach distinct.
Direct ocean-view estates, often featured in Sotheby's portfolios. Seasonal rental demand tied to the Pro-Am and Concours calendar.
Estates abutting the golf course. Long-term rental demand from corporate relocations and medical professionals.
Slightly more accessible price points. Good long-term leasing market; strong for families cycling in on 2–3 year stints.
Forested acreage. Caretaker-style management common — quarterly walkthroughs, vendor coordination, property retained by owners between visits.
Free, no-obligation rental analysis tailored specifically to your block. Mike personally walks every property before quoting.
Get My Pebble Beach Analysis