top of page

Glen Ellen Enterprise Road

Glen Ellen, CA

CHECK AVAILABILITY

All Inclusive Price

Month
SUN
MON
TUE
WED
THU
FRI
SAT

Opening Snapshot

Tucked into the foothills just outside of Glen Ellen, this home doesn’t reveal itself easily. The drive in winds along a bumpy gravel road that makes you wonder if you’ve taken a wrong turn and then suddenly, you arrive. Wild turkeys crossing your path, deer in the distance, towering trees all around. You’re not just near nature here. You’re in it. The home sits perched on a knoll, surrounded by forest and layered landscaping that feels intentional and serene. From a distance, the classic clay tile roof and warm architectural lines immediately evoke a hacienda hideaway vibe. As you step closer, courtyards begin to reveal themselves, pathways unfold, and expansive ceramic tile floors anchor the interiors with an earthy authenticity. It feels less like a typical Wine Country retreat and more like a coastal villa in Puerto Vallarta - sun-soaked, soulful, and effortlessly inviting - the kind of place where doors stay open, indoor and outdoor spaces blur together, and life slows a bit.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

Virtual Tour

Screenshot 2025-12-12 at 2.29.52 PM.png

What we love

The exterior transformation is extraordinary. Over $1 million has been invested into the landscaping, hardscape, pool, and outdoor living areas and it shows. Every pathway, patio, and planted corner feels deliberate and thoughtfully designed. The backyard is where this home truly shines. A large outdoor kitchen equipped with nearly every appliance you could want anchors the entertaining space. There’s a bocce ball court, a fire pit area, patios for dining and lounging, and a striking infinity-edge pool. And notably the pool is not the standard rectangle. In a world of ubiquitous straight lines, this modern, non-rectangular pool feels refreshing and custom. It’s the kind of pool that practically calls for salt on the rim, a pitcher of margaritas, and a long, unhurried afternoon leaning fully into the villa vibe. There’s even a putting green below, reinforcing that this property is designed for play as much as relaxation. Inside, the home is comfortable and light-filled. The kitchen is spacious and welcoming, an easy gathering hub. Upstairs, four bedrooms offer peaceful views, especially from the primary suite. A guest cottage near the pool provides bonus flexibility for a nanny or visiting friends.

Keep in mind

The drive in requires patience. The winding gravel road is part of the privacy package, but it’s not for those who prefer a quick, paved approach. While the interior has been updated and is very livable, it does show its age in places. Bathrooms are in good condition but lean more functional than spa-like. Flooring transitions from wood to tile to different wood tones throughout, which creates a slightly less cohesive feel inside. The guest cottage is practical and welcome but not opulent, think comfortable and useful rather than luxurious. Ultimately, the interior is solid and comfortable. The true luxury here lives outside, in the landscape, views, and amenities designed to pull you into the fresh air.

The brag

Work Mode:
Joe B. lens:
That outdoor kitchen and infinity pool combination is where I’m hosting every night. Add bocce, fire pits, and a putting green, this is how you do extended wine country living. The exterior investment completely elevates the property.
Joe R. lens:
I love the wildlife and forest vibe. Hearing turkeys on arrival sets the tone. It feels like a private camp for adults - active, social, outdoorsy - with just enough comfort inside to recharge. And if you squint at the meadow long enough, those turkeys almost look like little brontosaurus grazing in the distance.
Together we agree:
This is a property for guests who prioritize privacy, nature, and outdoor entertaining above all else.

Getting around

You’re just outside Glen Ellen, with easy access to Sonoma Valley wineries, hiking trails, and restaurants but you’ll feel worlds away once home. The location offers seclusion without being completely disconnected from the heart of wine country.

Joe-Tested,
Joe-Approved

If your ideal stay revolves around infinity pools, outdoor kitchens, bocce at sunset, and living among the trees, this Glen Ellen estate delivers. Comfortable inside, exceptional outside and unmistakably wine country.

060_Joes_LT_Rental_06272025_paigegreen_U6A5827.jpg

Additional Property Details

City & State:

Maximum Capacity:

Property Type:

Year Built: 

Renovation:

Property Size:

Bedroom Configuration:

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

From the Owner:

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

656_Joes_LT_Rental_06272025_paigegreen_U6A8895.jpg

Amenities

House Rules

I'm a paragraph. Click here to add your own text and edit me. It's easy.

More Information

I'm a paragraph. Click here to add your own text and edit me. It's easy.

  • Instagram
  • Facebook
  • X
  • LinkedIn
bottom of page