Right now in Healdsburg, roughly $2 to $3 million buys you four completely different lives. I have four homes on the market inside that band, and no two are remotely alike: a vineyard weekend retreat in Alexander Valley, a to-the-studs rebuild on one of Dry Creek's most coveted roads, a vacation-rental-eligible property with a resort backyard, and a turnkey home you can walk to the Plaza from. That spread is exactly why buying a home in Healdsburg rewards knowing the market, because the same budget produces four very different versions of wine country.
The weekend retreat with its own vineyard: 7616 Highway 128
Thirteen minutes from the Healdsburg Plaza, behind a private gate, three flat acres in Alexander Valley open to a saltwater pool and spa, a built-in outdoor kitchen, a fire pit, and a covered patio wired with heaters for year-round evenings. Roughly two and a half of those acres are professionally farmed estate vineyard, so the property pours its own bottle of Silver Oak-adjacent wine, turnkey and at no cost to you. Inside, the kitchen and bathrooms have been recently remodelled, two stone fireplaces warm the living and family rooms, and a converted barn with a bar, shuffleboard, and ping pong turns any evening into a party. This is three bedrooms, three bathrooms, about 2,287 square feet. At $2.575 million, it is the one for a buyer who wants wine country as a weekend reset, or a full-time move into the Alexander Valley Elementary district.
The premium address, minutes from town: 3229 West Dry Creek Road
West Dry Creek Road is one of the most coveted stretches in the region, and this six-acre property sits right on it, under fifteen minutes from the Plaza yet a world away in feel. The house was taken down to the studs and rebuilt, so it lives like new construction inside a genuine wine country setting. The custom kitchen is built for real cooking, with a Thermador suite, a 100-bottle wine fridge, and storage everywhere you look. The primary suite has its own spa-like bath and heated floors, three more bedrooms give family and guests room to spread out, and there is even a dedicated dog-wash room. Six private acres are rare this close to downtown. Listed at $1.995 million, this is the best-of-both-worlds home: total renovation, real acreage, and true privacy, all minutes from town.
The rare vacation-rental-eligible property: 10936 Eastside Road
This is the one investors ask me about. Ten minutes from the Plaza, at the quiet end of Eastside Road, 10936 sits on 3.25 private acres at the end of a dead-end lane, a single-level home of about 1,840 square feet with three bedrooms plus a bonus room and three bathrooms. A new pool and spa anchor the backyard, alongside a covered deck with a hanging swing and a bocce court set among mature fruit trees, with a second permitted septic already in place for a future pool house.
Here is the part that matters, and the part most people get wrong: short-term rental permits in Sonoma County do not transfer with a sale. This property is eligible for a new owner to apply for a new permit, and that eligibility is scarce. Only 28 vacation-rental-eligible homes sold in all of Healdsburg in 2025, spread fairly evenly across price points: 5 under $1 million, 9 between $1 and $2 million, 6 between $2 and $3 million, and 8 above $3 million. That range at multiple price points is unusual for a market with this much brand cachet. Healdsburg is also the county's standout for larger rentals, with the best-performing 3-bed and 4-bed properties anywhere in Sonoma County and a median annual income of $101,000 across all property types. A home like this one, with a pool, privacy acreage, and a clear path to a new permit, is genuinely hard to find. At $2.5 million it works as a second home that earns its keep, a full-time residence, or an income property you can run as a vacation rental.
The in-town home that does not feel like town: 778 South Fitch Mountain Road
The newest of the four, coming to market on South Fitch Mountain Road, solves a problem a lot of buyers assume is unsolvable: how to live within walking distance of downtown without feeling like you are in a neighbourhood. It manages both. You get real privacy on a third-of-an-acre lot with a pool, yet you can walk to the Plaza for dinner. Three bedrooms, three bathrooms, about 2,265 square feet, completely turnkey and move-in ready. At $2.7 million, it is for the buyer who wants the lock-and-leave ease of an in-town home without giving up seclusion.
Four homes, four completely different versions of Healdsburg life, all inside about a $700,000 band. You can see all four on our current listings page, and if you want to walk through any of them, or talk through which one fits how you actually want to live, email me directly at david@bruingtonhargreaves.com.
About the Author
David Hargreaves is the co-founder of BruingtonHargreaves, one of Sonoma County's top-ranked real estate teams and part of W Real Estate. Originally from the UK and an Oxford University graduate, David built and ran a digital marketing agency serving Google, Facebook, and other major brands before becoming one of Sonoma County's top agents within three years of entering real estate.
Today he and business partner Jonathan Bruington have sold more than $250 million in Sonoma County homes over the past three years, earning recognition as a RealTrends No. 2 team in the county and the No. 1 team in Healdsburg. David specialises in helping Bay Area buyers and sellers with luxury properties and vacation rentals across Healdsburg, Windsor, Santa Rosa, and the Russian River communities.
He lives in Sonoma County with his wife Nancy and is happiest cycling the back roads, exploring local wineries, or behind a camera. Have a question about buying, selling, or building in Wine Country? Book a free call.