Oak & Sky Ranch

This home is proudly managed by LegacyRnR, your local Wine Country hospitality experts. We're here to make your stay effortless and unforgettable, from arrival to check out.

Need transportation for wine tasting or group outings?
We offer two private, comfortable options:

11 Passenger Wine Tour Van: perfect for group tastings, birthday trips, or bachelorette weekends.
6 Passenger Cadillac Escalade: ride in style for intimate wine tours, airport pickups, or dinner reservations.

When you book with LegacyRnR, you're not just booking a home, you're booking your entire Wine Country experience, curated by locals who care.

Welcome to Oak & Sky Ranch, a 44 acre private hilltop estate above the Alexander Valley, Sonoma County's most celebrated wine appellation and about 25 minutes from Healdsburg Plaza. A half mile private road winds past oak groves, rock outcroppings and a romantic old barn before the farmhouse appears, with no neighbors in sight. Four king suites, a chef's kitchen with a marble island, an eco pool with a hilltop deck, a hot tub for stargazing, a private pickleball court, a Play Barn with billiards, foosball, darts and bocce, and an Art Barn for yoga or workshops. Most groups never want to leave.

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.

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.

Property License: LIC24-0204