Nestled in amazing locations, five extraordinary estates await, each a masterful blend of modern luxury and rustic charm. Priced between $2,250,000 and $8,495,000, these Healdsburg properties—spanning Chiquita Road to Dry Creek Road—offer serene privacy, vineyard views, and European-inspired designs. From sprawling gated retreats to award-winning homes recognized by the Wall Street Journal, they embody a lifestyle of exclusivity and sustainability, with features like wine cellars, spa-like baths, and flexible living spaces. Discover how these residences harmonize natural beauty with unparalleled sophistication in a coveted corner of California.
339 El Verano Avenue | $3,300,000 (Sold)


Listing agents: Nancy Soliz

Listing agents: Nancy Soliz
Location, location, location! Come by and see the possibilities of this vintage fixer in the heart of Midtown Palo Alto! Top-rated, excellent schools nearby (El Carmelo & JLS), between Hoover & Mitchell Parks, close to shopping, and easy access to freeways 101 & 280 for a smooth commute. This is a 3-bedroom, 2-bathroom contractor’s dream on a corner lot (El Verano & South Court) with ample opportunities for beautiful landscaping, vegetable garden, fruit trees, and more. Let your imagination run wild and join this ideal neighborhood.
Price: $3,300,000 (Sold)
- Size:
- 1,445 sq ft
- Contact:
- Nancy Soliz, Coldwell Banker Realty, 650.630.0419
1421 Chiquita Road | $8,495,000


Listing agents: Samantha Marquis & Linda Farwell

Listing agents: Samantha Marquis & Linda Farwell
Rising above Healdsburg’s picturesque rolling hills, this gated estate captures the timeless allure of the Italian countryside while embracing modern sophistication. Just minutes from the vibrant Plaza, the property offers an unparalleled blend of seclusion and accessibility. The main residence impresses with soaring ceilings, a private elevator, a butler’s kitchen, and an exquisite wine cellar. French doors open to expansive patios, revealing a serene pool, spa, and charming bathhouse. Beyond the main home, a cozy one-bedroom guest cottage provides a private haven for visitors. Spanning 23.5 acres, the estate is a true wine country retreat, adorned with lush gardens, fruitful orchards, chicken coops, and a thriving vineyard. Here, every detail invites a life of tranquility and connection to nature, with the cultural heartbeat of Healdsburg just a short drive away.
- Price:
- $8,495,000
- Size:
- 6,167 sq ft
- Contact:
- Samantha Marquis & Linda Farwell, Compass, 707.955.5442 , 707.695.0123
28462848 Monticello Road | $7,460,900


Listing agents: Cody Avetoom & Jeffrey Earl Warren

Listing agents: Cody Avetoom & Jeffrey Earl Warren
Situated in an enviable location, this remarkable residence has earned acclaim as the Wall Street Journal’s House of the Week and House of the Month. Thoughtfully designed, the home seamlessly blends timeless elegance with modern functionality, offering a sanctuary for both relaxation and entertainment. Spacious living areas flow effortlessly, with expansive windows framing captivating views and flooding the interiors with natural light. The gourmet kitchen, equipped with high-end appliances, serves as the heart of the home, ideal for crafting culinary masterpieces or hosting intimate gatherings. Outside, meticulously landscaped gardens provide a serene escape, perfect for unwinding after a busy day. With its prime setting and unparalleled attention to detail, this property embodies a lifestyle of sophistication and comfort, inviting residents to savor every moment in a space that truly feels like home.
- Price:
- $7,460,900
- Size:
- 4,382 sq ft
- Contact:
- Cody Avetoom & Jeffrey Earl Warren, Sotheby’s International Realty, 707.815.0814 , 707.486.1025
332 East Street | $3,695,000


Listing agents: Samantha Marquis & Linda Farwell

Listing agents: Samantha Marquis & Linda Farwell
Positioned just a block from the vibrant Healdsburg Plaza, this 4-bedroom, 4-bath estate embodies modern farmhouse elegance. Its soaring ceilings and thoughtful design create a seamless flow between indoor and outdoor spaces, inviting a lifestyle of ease and connection. The European-inspired backyard offers a tranquil retreat, while the serene primary suite, complete with a spa-like bath and private veranda, promises relaxation. Versatile areas, including a loft with a separate entrance, provide flexibility for creative or professional pursuits. A spacious basement and elevator-ready infrastructure add convenience and future-proofing to the home. With a one-car garage, additional parking, and proximity to the heart of Wine Country, this property effortlessly blends rural charm with urban accessibility. It’s an ideal setting for those seeking a refined yet grounded way of life in a coveted location.
- Price:
- $3,695,000
- Size:
- 3,770 sq ft
- Contact:
- Samantha Marquis & Linda Farwell, Compass, 707.955.5442 , 707.695.0123
838 Dry Creek Road | $2,250,000


Valerie Ruma

Valerie Ruma
Nestled in the heart of Dry Creek Valley, 838 Dry Creek Road in Healdsburg presents a rare chance to embrace the tranquility of Sonoma’s renowned wine country. Spanning ±9.63 acres, this exceptional estate parcel is just a seven-minute drive from Healdsburg’s vibrant central plaza, offering a seamless balance of rural serenity and urban accessibility. Panoramic vineyard views stretch across the horizon, while creekfront access and valuable Riparian rights enhance the property’s allure. The gently rolling terrain, enveloped by untouched natural beauty, serves as an ideal canvas for crafting a bespoke retreat or a modern vineyard estate. Whether envisioning a private sanctuary or a legacy investment, this land invites endless possibilities. Here, the art of living well unfolds amidst the quiet charm of one of California’s most cherished regions, where seclusion and connection harmoniously coexist.
Size: 10.00 acres
- Price:
- $2,250,000
- Contact:
- Valerie Ruma, Compass, 510.579.3614
























