Welcome to Island Farm, San Gregorio

Island Farm presents a unique and unparalleled opportunity, offering the canvas for a family enclave, refined ranch, rustic retreat, or versatile event venue – all conveniently accessible from Silicon Valley. This extraordinary estate has been under the stewardship of a single family for over a century and has graciously welcomed numerous dignitaries and notable figures throughout its rich history.

The crown jewel of this remarkable property stands the Main Residence, boasting two bedrooms and two bathrooms, adorned with a picturesque wrap-around deck that overlooks a serene pond. The estate’s landscape showcases diverse features, encompassing 80 acres of majestic redwood groves, meandering Corte Madera and Bogess creeks, idyllic cattle pastures, and the lofty pinnacle of High Hill, soaring 1,000 feet above sea level, affording breathtaking vistas of the Pacific Ocean.

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Embark on a journey of exploration across the 564 acres, traversable on foot, horseback, or dirt bike, transforming Island Farm into your very own private playground. Within the property’s expanse, four residences beckon, plus two more which need restoration, and are complemented by three barns and three additional outbuildings, each offering a multitude of possibilities for the estate’s next captivating chapter.

Island Farm is set amid San Gregorio’s mild year-round climate and natural splendor with its rugged cliffs, enchanting sandy beaches, and captivating wildlife, all just moments away from this exceptional property.


Property Details

Home Totals

  • 4 Homes
  • 13 Beds
  • 11.5 Baths
  • ±7,240 Combined Square Feet

Additional Structures

  • 3 Outbuildings
  • 3 Barns
  • ±9,470 Combined Square Feet


  • 564 Acres
  • 5 Parcels

Offered At


As Featured In
Robb Report

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Family Compound

Experience the unparalleled charm of Island Farm alongside your cherished friends and family. This remarkable estate comprises four distinct residences, making it an ideal setting for multi-generational and multi-family living. The Main Residence, Cook’s Cabin, and Rose Cottage are strategically positioned near the entrance of the property. Each of these homes offers the privacy and comfort characteristic of a traditional single-family dwelling while being conveniently close to the other two residences.

The Foreman’s Residence serves as a versatile space, suitable for either a property caretaker’s abode or as a welcoming haven for visiting guests. Adding to the estate’s potential, two more dwellings –Bee Bee’s Cabin and the Green Farmhouse – although currently not habitable, possess the foundational infrastructure necessary for restoration.



Embark on a personalized adventure at Island Farm, where the untouched natural expanse becomes yours for exploration. Discover tranquility through serene hikes, indulge in yoga sessions amidst the majestic redwood trees, and immerse yourself in the captivating world of birdwatching. Seek exhilaration as you gallop on horseback, zip around on a dirt bike, or navigate rugged terrain via mountain bike. Or cultivate outdoor expertise through activities like skeet shooting, archery, canoeing, and fishing. Island Farm operates on your timetable, inviting you to shape your experience into an idyllic playground of your own making.


Dive into the realm of farming possibilities offered by this property, where the potential is endless. Cultivate fields of red oat hay and barley, oversee a thriving cattle farming venture, actualize your vision of equestrian excellence by constructing top-notch facilities for riding and boarding, or explore embarking on an organic agricultural venture that harmonizes with the land’s essence. This is your chance to forge a profound connection with the land and all the prospects it holds.

The property boasts an array of infrastructure, including three spacious barns and three supplementary outbuildings. The water system includes six large water tanks already in place, with the potential to re-integrate an additional pair. With these existing amenities, Island Farm stands fully prepared to support your agricultural ambitions.


Events & Opportunities

Island Farm presents well-established avenues for generating income. Cherished for its enchanting ambiance, the venue has been the site of numerous exquisite wedding ceremonies and receptions throughout its history. The distinct allure and magnificence of the location have been showcased in advertising campaigns through both print and video, with notable brands such as Neiman Marcus and SoFi. Beyond this, the property holds further potential for diverse utilization, including transforming parts of it into a corporate retreat center, a summer camp, or a wellness center.


Building 1

  • 2 Beds
  • 2 Baths
  • 2,240 Square Feet

Building 3

  • 3 Beds
  • 3 Baths
  • 1,255 Square Feet

Building 4

  • 5 Beds
  • 4 Baths
  • 1,595 Square Feet

Building 5

  • 2,120 Square Feet

Building 6

  • 1,055 Square Feet

Building 9

  • 1,505 Square Feet

Building 10

  • 3 Beds
  • 2.5 Baths
  • 2,150 Square Feet

Building 12

  • 2,045 Square Feet


High Hill

The Location: San Gregorio

Located in San Mateo County, San Gregorio is an unincorporated community with a population of just 214. Its history unfolds as a favored getaway for the magnates of San Francisco’s industrial era. Most notably, the General Store, an establishment steeped in heritage since 1889, stands as a testament to this past. The region’s allure is equally drawn from its awe-inspiring natural vistas, sun-kissed beaches, enchanting tidal pools, rugged cliffs, and thriving tapestry of wildlife. This locale exudes an air of sublime tranquility, conveniently located 16 miles south of Downtown Half Moon Bay, and accessible within an hour from both Silicon Valley and San Francisco, making it an idyllic haven within easy reach of urban centers.

Regional Attractions

San Gregorio Village

2.1 mi

3 min

Pescadero Village

9.8 mi

15 min

Ritz-Carlton Half Moon Bay

11.2 mi

16 min

Downtown Half Moon Bay

15.6 mi

24 min

Palo Alto

23.5 mi

45 min


30.5 mi

54 min

San Francisco International Airport

32.3 mi

43 min

Apple Park

34.3 mi

50 min

Meta Headquarters

37.9 mi

54 min

Santa Cruz

40.5 mi

53 min

San Francisco

40.6 mi

1 hr 6 min

San Jose International Airport

41.1 mi

56 min


86.4 mi

1 hr 52 min