Chianti: Secluded Luxury Estate with Pool, Pickleball, Game Barn & Views

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays.

Escape to Chianti, your elegant and exclusive farmhouse ranch nestled atop a hill in scenic Sonoma County, CA. A hidden gem, this retreat offers breathtaking nature views and unparalleled privacy, accessible via a private road winding through picturesque landscapes.

As you approach Chianti you'll be transported to a world of serenity and grandeur. Surrounded by rolling hills and ancient oak trees, you'll feel a world away from the hustle and bustle of everyday life while being only 5 minutes away from town. Immerse yourself in the seclusion and stunning surroundings, and enjoy the true wine country ranch experience.

Step into the heart of Chianti, where modern luxury meets farmhouse charm. Soaring ceilings greet you in the gourmet chef’s kitchen. The large marble island elevates the farmhouse-style blue cabinetry and rustic wood accents. Plenty of barstool seats allow you to conversate with your group while cooking. The stunning space is complemented by an array of high-end stainless steel appliances including a 64” inch double refrigerator, two built-in ovens, two dishwashers, two sinks, and a wine fridge. Enjoy a delicious home-cooked meal in the adjacent dining room, or opt for alfresco dining at the screened-in porch.

Two living areas each boast an elevated yet cozy ambiance, perfect for a movie night. The sunroom serves as additional living space, with plenty of seating and floor-to-ceiling windows that flood the space with natural light and sweeping views. Tranquility flows throughout the enclosed wrap-around porch. Retreat to one of the egg chairs to unwind in solitude, or grab your friends and play a game at the shuffleboard table.

Chianti is well-equipped for remote work, providing digital nomads with ease of mind. Every bedroom features its own workstation, with an additional desk on the enclosed porch offering a productive space for everyone. Starlink Internet and an EERO mesh wifi network that covers every part of the house ensure fast, reliable connectivity from this private and secluded location. Whether you're looking to stay connected for an extended stay or disconnect and relax during your getaway, Chianti has you covered.

The outdoor spaces are thoughtfully designed for fun and quality time with your group. Gather around the outdoor fire pit to roast marshmallows and share stories, and end the evening with a dip in the hot tub. From sweeping views to starry skies, the outdoor area sets the scene for relaxation all day long. Bring your camera and capture stunning photographs of the local birdlife, a delightful experience for hobbyists and professional photographers alike.

Our modern, water-saving container pool has less than 5000 gallons of water and is entirely above ground, giving you a unique, eco-friendly way to stay cool under the Sonoma sunshine.

Chianti’s Playbarn offers the perfect space to socialize with your guests. The exterior features a covered bocce ball court, lined with wine barrels and bar stools. Fire up the grill for the ultimate evening BBQ accompanied by lots of laughter and friendly competition. Inside the barn sits a pool billiard table, a foosball table, darts, and a 74” TV with a sound system. Entertainment is effortless at the Playbarn, ensuring hassle-free hosting during your stay!

Unwind from the day in one of four bedrooms, each with a king bed. The primary bedroom, located on the first floor, and the loft suite (bedroom 4), located above the garage, each feature an ensuite bathroom for added privacy and convenience. On the second floor, Bedrooms 2 and 3 boast stunning views and a spacious shared bathroom with a soaking tub.

Lovers of pickleball rejoice — Chianti has a top-of-the-line court and all of the gear you’ll need to get moving. This high-performance court from FlexCourt uses elite tiles specifically designed for pickleball. Basketball enthusiasts can also enjoy the space, as it doubles as a basketball court. With a synthetic, cushioned surface, you won’t have to worry about playing on concrete, giving you enhanced traction and texture for better playability, safety, cushion to extend court time, and horizontal/lateral forgiveness. Play easy with reduced joint stress, superior ball bounce and rebound, and a quick-draining design which won’t puddle after the rain or morning mist.

Bonus: you don’t even need to bring your own equipment. We have the latest paddle technology available for our guests. It’s the Owl Paddle: a high-performance pickleball paddle which is not only the quietest and best playing paddle in the industry, but the very first certified quiet paddle. It’s easier on arms and elbows, and provides incredible balance and maneuverability. We have four available for use so our guests can try the latest in paddle technology from a leader in the market, officially certified by the USA Pickleball Association for its new quiet category.

Chianti lies within the Alexander Valley AVA, known for its vineyards and Cabernet Sauvignon wine. In only 20 minutes, you can be dining at the Michelin-starred restaurants in the Healdsburg Plaza, or taste testing at the Anderson Valley Brewing Co. brewery in Boonville. Anderson Valley, famous for Pinot Noir, is a stone’s throw away. This incredible location provides the perfect home base for exploring Northern California’s famous wine country.

With its unparalleled privacy, stunning views, and ample amenities, Chianti is more than just a vacation rental—it's an unforgettable escape promising relaxation, rejuvenation, and cherished memories for your next friends and family getaway.

Enhance your stay with tailored concierge services by Booker & Butler in Sonoma & Napa.

Experience Sonoma, AvantStay style.

AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team and a tech-enabled concierge to book services, such as fridge stocking, mid-stay cleanings, and private chefs. For anything you need (or never knew you needed), we’re at your service!

Known for its vineyards, local cuisine, and nature parks, Sonoma County (45 minutes from San Francisco) offers a wide array of activities for those looking to retreat from city life. Touring local wineries, dining at farm-to-table restaurants, and visiting world-class spas are just a few ways to experience this pristine destination. While unwinding is certainly the attitude in Sonoma, activities such as horseback riding and hot-air balloon rides attract those looking for an adventure.

Local Attractions: Healdsburg, Russian River, Lake Sonoma, Boonville, Geyserville, Francis Ford Coppola Winery, BBQ Diner, Cyrus Michelin-Starred Restaurant, Anderson Valley Brewing Co, Bear Republic Brewing Co, Hopland, Papa's Pizza Cafe, River Rock Casino

Home Truths:
- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.
- Yoga mats are provided in the dining room closet
- A pasture on the property may have two horses, which are owned and cared for by a neighbor. These horses are old and very gentle. Guests are not allowed to feed or pet them.
- Home is well-equipped for remote work, with Starlink satellite internet and a fast EERO mesh wifi that covers every part of the house, including the playbarn.
- Rest assured that PG&E outages will not affect your stay: Heat in the winter, Air conditioning in the summer, Wifi, and all other amenities are backed up with double whole-house backup systems.
- The owner is occupying another house (not visible from the main house) on the property
- EV charger is free for guest use.

Parking Details:
- 4-5 cars can park onsite.
- There is space for RVs/trailers, as well as water, electricity, and black-water hookups.

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Room configuration:
Primary Bedroom / King
Bedroom 2 / King
Bedroom 3 / King
Loft suite / King
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Accidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.

This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff.

We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 28 days require a security deposit.

We report and prosecute all Credit Card Fraud.

Permit: Sonoma County 4393 / 4393N