Property Category: Healdsburg

Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life. As you enter the estate you'll be enchanted by the tastefully designed interior, adorned with high-end…...

Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country. As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional…...

Welcome to Healdsburg Homestead! In the heart of Sonoma County’s Dry Creek Valley, tucked along a quiet country road, Healdsburg Homestead is your peaceful escape surrounded by vineyards, gardens, and the soft murmur of a seasonal creek. Though it feels worlds away, you're just minutes from downtown Healdsburg and some of the region’s best wine, food, and outdoor adventures. Wake up to birdsong and garden views, spend the day exploring…...

This charming 2-bedroom cottage, dating back to the 1880s, offers an ideal wine country escape for a party of four. Situated just two blocks from the historic Downtown Plaza, you'll enjoy close access to restaurants, boutique shops, and delightful wine-tasting experiences. Nearby, savor culinary excellence at Michelin-starred restaurants and explore renowned, award-winning wineries. The recently refurbished interior showcases a contemporary and well-appointed design, perfectly suited to meet your vacation needs.…...

Retreat to the exquisite Heron House, a riverside haven where the grandeur of the Redwoods meets the flowing beauty of the Russian River. This special riverfront dwelling offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain's wooded knoll, the home provides a secluded feel above the river. The Heron House is a 3-bedroom, 2-bathroom home designed to accommodate…...

Our luxurious retreat is undergoing a major remodel this Spring! New pictures to come when completed. ETA May 2025 Indulge in your private Wine Country retreat, mere minutes from the enchanting Dry Creek and Alexander Valley wineries, and just a short 10-minute drive to Healdsburg Plaza. This home boasts an open concept floor plan on the main level, leading to an expansive entertainment deck that overlooks the property. The well-equipped…...

This luxurious 2BR/2BA home offers the ultimate wine country escape. Spanning 1,439 square feet, it features a gourmet kitchen and stunning floor-to-ceiling folding glass doors that open completely, transforming the wall into a seamless gateway to vineyard vistas and California sunshine. From the back deck or patio, take in the views of your private Sauvignon Blanc vineyard, complete with a fire pit, outdoor seating areas and BBQ. There's also a…...

Nestled between redwoods and vineyards, Puccioni Paradise is a peaceful escape just 10 minutes from Healdsburg Plaza. Ideal for two guests (plus a third for an additional fee), this stylish, light-filled home offers the perfect blend of comfort, nature, and wine country charm. Whether you're sipping coffee on the patio, working remotely from the dedicated workspace, or exploring nearby tasting rooms, this is your place to relax, reconnect, and recharge.…...

Escape to peace and privacy at Redwood River House, a beautifully updated 2-bedroom, 1-bath cottage nestled along the Russian River—just 1.5 miles from downtown Healdsburg. Perfect for couples, small families, or friends, this upscale getaway offers a seamless blend of comfort, nature, and Wine Country charm. Highlights: Prime riverfront location with private river access Expansive deck with hot tub, BBQ, and outdoor dining Kayaks included for river adventures Bright, open…...

Relax and recharge in this warm and inviting Russian River bungalow, nestled in a peaceful neighborhood just 5 minutes from Healdsburg. Whether you're sipping coffee on the front deck, soaking in the private hot tub under the stars, or walking across the street to the river, this home is the perfect blend of rustic charm and modern comfort. With space for families, couples, or a group of friends, it's an…...

Tucked along the Russian River just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful escape designed for romantic retreats, family vacations, and even remote work with a view. With stunning river frontage, your own private dock, two kayaks, a hot tub, and a deck that stretches above the water, this home offers a truly unforgettable Wine Country experience. Whether you're sipping coffee at sunrise, unwinding in…...

Slow down, unplug, and breathe in the beauty of riverfront living. Tucked along a peaceful stretch of river and just minutes from downtown Healdsburg and nearby wedding venues, Rivers Breeze is a charming cabin retreat that invites you to reconnect—with nature, with loved ones, and with yourself. From morning coffee on the deck to stargazing by the water, every corner of this cabin is designed to help you unwind and…...

An Extraordinary Oasis for your Group, 3 units, pool/hot tub and bird sanctuary! This exclusive 11.67 acre estate venue is located in Alexander Valley, the heart of wine country, just 7min from the Healdsburg Plaza. Convenient location is ideal, yet the space holds an intimate sense of privacy essential for your friends/family retreat or corporate event. A hidden gem with a beautiful pond and open views of Alexander valley and…...

This exclusive Farmhouse estate is located in the picturesque Dry Creek Valley, which is known for its vineyards and wine production. It's conveniently situated just west of the new 5-Star Montage resort and only 8 miles away from the charming Healdsburg Plaza. The location of the house is particularly appealing for cycling enthusiasts, as it is situated on the main cyclery route of Dry Creek Valley's largest races. Additionally, Lake…...

Nestled amidst the picturesque landscapes of wine country, this charming 3-bedroom country home offers a captivating escape just minutes away from the vibrant Healdsburg Plaza. Known for its renowned tasting rooms and top-rated restaurants, the plaza is easily accessible, ensuring an array of experiences at your fingertips. Additionally, the Merriam and Limerick Lane wineries, conveniently within walking distance, add further allure to your wine country stay. Upon entering, guests are…...

New York City and Ireland fuse with California wine country in this modern farmhouse! The home is tastefully decorated with artwork that reflects the owners origins and their travels and pastimes. Completely remodeled with stunning views of Dry Creek Valley. This Immaculate home is just blocks away from shops, restaurants and tasting rooms of downtown Healdsburg. Just 10 minutes walk to Healdsburg historica Plaza, this house features an . open…...

Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just 5 minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award Winning Restaurants and Boutique Shops . Xanadu Healdsburg is a Blu Home with Green Solar Technology offering a large great room, gourmet…...

Experience the perfect launchpad for your wine country adventures, just minutes from the countryside. This recently remodeled gem is ideally located, a mere 2 blocks from the historic Downtown Healdsburg Plaza, where you'll find award-winning restaurants, charming boutiques, and wine tasting experiences. Designer touches and high-end finishes welcome you to the sleek, bright, and open space of this reimagined historic home. The sophisticated setting exudes a sense of tranquility, making…...

Nestled just 2 short blocks away from the historic Downtown Healdsburg Plaza, our Heavenly Hideaway offers a prime location that seamlessly connects residents to the vibrant heart of the area. This carefully curated space ensures easy access to an array of experiences, including the lively atmosphere of local restaurants, the quaint charm of boutique shopping, and the delightful indulgence of wine tasting venues. All of these elements are harmoniously set…...

Experience the best of Healdsburg living in this charming 2-bedroom Tuscan-style cottage, just steps from the Plaza. Imagine waking up to the California sunshine streaming through the windows and stepping out onto your private patio, surrounded by lush greenery, for a peaceful start to your day. This inviting retreat offers a perfect blend of comfort and convenience. Inside, you'll find a bright and airy living space, ideal for relaxing after…...

This Elegant Villa offers World Class Views, High End Appointments, a Chef Inspired Kitchen, Indoor and Outdoor Dining and Entertainment Areas, including a Firepit to enjoy the evening with family and friends. The property is private yet only 10 minutes to town, with spectacular views of the entire valley and beyond. The Estate offers 4 Bedrooms and 3.5 baths, including Master Suite with jacuzzi tub and open floor plan that…...