Oak & Sky Ranch

Summary:
Fall brings golden hillsides and crisp starlit nights to Alexander Valley, and this 44 acre hilltop estate is built for savoring both with family or friends. Four king suites, a chef's kitchen, a stargazing hot tub, and a private pool and pickleball court keep everyone close and comfortable, just 25 minutes from Healdsburg Plaza. Request your dates and start planning your Wine Country gathering.

The Space:
Oak & Sky Ranch is a refreshed and reimagined wine country farmhouse with more than 4,000 square feet of living space on 44 private acres. The house is invisible from the street, reached by a half mile private road from the gate.

The Kitchen
The heart of the house. Cathedral ceilings with exposed wood beams and skylights frame a huge marble island with a gas cooktop built for communal cooking, a second sink, a second dishwasher and a wine refrigerator. Around the perimeter you'll find a 64 inch double refrigerator, two built in ovens, a farmhouse sink and a dishwasher. The butler's pantry adds a third sink, a second refrigerator, extra counter space and the washer and dryer.

Living and Dining
The kitchen opens to a large dining room under a chandelier, with a sliding door to a covered, screened deck for alfresco dinners or morning coffee. Two separate living and entertainment areas let different groups watch their own movies, sports or kids' shows. The sunroom has panoramic views over the Alexander Valley and is perfect for yoga.

Bedrooms (4 king beds, 3.5 baths)
Primary suite: main level, modern king bed, very large walk in shower, quick access to the wrap around porch and sunroom.
Upstairs bedrooms (2): each with a king bed and epic views over the Alexander Valley and the oak studded hills, sharing a large bathroom between them with a modern soaking tub, a large shower and two sinks.
Loft suite: a separate, very private suite above the garage with a king bed and its own bathroom.
Every bedroom has a workstation for remote work. The first floor has central heating and air, and each upstairs bedroom has its own mini split.

Outdoors
Eco pool (unheated) with a large surrounding deck, misters, umbrellas and a pool cover. Hot tub placed for stargazing. Propane fire pit circled by Adirondack chairs, with a BBQ grill alongside. Screened wrap around porch with egg chairs, shuffleboard and ceiling fans. Private Flexcourt pickleball court and basketball hoop.

The Barns
The Play Barn is a converted barn and stable with a 74 inch smart TV and soundbar, pool table, foosball, darts, wine barrel bar tables, a second BBQ grill and a covered bocce court. The Art Barn has gallery walls, exposed beams and flexible lounge seating for yoga, private tastings or workshops.

Tech
Starlink internet with a mesh network throughout the house and Play Barn, an AT&T cell signal booster, and five smart TVs.

Parking
A large driveway with plenty of open parking plus two carports that each cover two cars. RV parking with water, electric and sewer hookups is available on request. A Level 2 EV charger outside the garage is available for guest use.

Wine Country without the driving: book our 11 passenger wine tour van or 6 passenger Cadillac Escalade for tastings, dinners or airport pickups.

Guest Access:
Guests have exclusive, private use of the entire 44 acre estate during their stay: the main farmhouse, the loft suite above the garage, the Play Barn, the Art Barn, the eco pool and deck, the hot tub, the fire pit and BBQ area, the pickleball and basketball court, the bocce court, the walking trails and the seasonal pond. The garage, pump house, supply closet and upper barn are locked and reserved for staff. Self check in is through the gate code and a keypad smart lock at the formal front entrance; codes are sent before arrival.

The Neighborhood:
Oak & Sky Ranch sits in the hills above the Alexander Valley AVA, surrounded by oak covered hills, vineyards and pasture, with Healdsburg about 25 minutes away. Spend the day on Healdsburg Plaza among its tasting rooms, boutiques and restaurants, then come home to 44 private acres with no neighbors in sight. Downtown Cloverdale is about 8 minutes away for a morning latte and fresh pastry, and Highway 101 takes you straight to Geyserville, Healdsburg, Hopland and the Anderson Valley.

Drive times from the ranch:
Downtown Cloverdale: about 8 minutes
J. Rickards Winery: about 18 minutes
Cyrus (Michelin starred), Geyserville: about 20 minutes
Francis Ford Coppola Winery: about 20 minutes
Lake Sonoma, for hiking and boating: about 20 minutes
Healdsburg Plaza and SingleThread: about 25 minutes
Jordan Winery: about 25 minutes
Sonoma County Airport (STS): about 35 minutes
Anderson Valley wineries in Boonville: about 50 minutes

Planning a full day of tastings? Let our chauffeur drive your group in the LegacyRnR van or Escalade, so everyone can enjoy the day and nobody has to drive Pine Mountain Road home after the last pour.

Getting Around:
A car is essential. The estate is reached by Pine Mountain Road, a small, winding country road that was once a stagecoach line, followed by a half mile private road from the gate. San Francisco is about 1 hour 45 minutes away (1.5 hours from the Golden Gate Bridge), the Sonoma County Airport (STS) is about 35 minutes away, and a private airstrip is about 15 minutes away. For wine tasting days and airport transfers, LegacyRnR offers private chauffeured transportation in our 11 passenger van or 6 passenger Escalade.

Other Things to Note:
Oak & Sky Ranch sleeps 8 overnight guests in 4 king beds. Children under 3 do not count toward the guest total. Up to 14 guests are welcome during the daytime, and events are welcome within Sonoma County regulations with prior written approval. Up to four pets are welcome, with a pet fee of $400 per pet. Pets may never be left unattended in the home, including while crated. Please disclose all pets when booking. Smoking is not permitted anywhere on the property.

This is a rural estate at the wildlife interface. Deer visit often, and there are reports of mountain lions, coyotes and, in spring, snakes. Never leave small children out of sight or pets unsupervised. Two gentle older horses, owned by a neighbor, graze the pastures; you are welcome to pet them but please do not feed or ride them. The seasonal pond is not for swimming, and the steep ravine to the west is off limits.

Internet is via Starlink satellite, which is fast but may have brief outages.

Check in is 4:00 PM and check out is 10:00 AM. Quiet hours are 9:00 PM to 7:00 AM. The minimum booking age is 25. Exterior cameras, used mainly for wildfire monitoring, are located at the gate, on the driveway facing north, on the roof facing west, and at the upper barn facing east.

Early check ins and late check outs are subject to availability, must be approved in writing in advance, and are charged at 50% of the nightly rate.

Property licenses: TVR22-0093, LIC24-0204, PMR26-0051. County tax number 4393N.

Interaction with Guests:
Your privacy is complete, but our LegacyRnR team is always a message away. Reach out through your booking platform for anything at all, from questions about the home to winery reservations, private chefs, wine tours, nanny services, baby gear rental or transportation. We monitor messages closely and respond promptly.