Healdsburg's downtown area is blessed with great restaurants, wonderful wine tasting rooms, and an activity-filled plaza surrounded by great retail outlets. Just blocks away from this social and commercial activity are streets lined with beautiful examples of architecture from the last 150 years. Proximity to the Healdsburg Plaza is one of the key factors in determining value here, and reasaonable walking distance is often hotly debated. What's clear is that among all the streets, both Tucker and Matheson streets offer some great examples of authentic architecture close to the Plaza. There are other deserving historic areas in Healdsburg, but I'm going to focus on these two streets.
Matheson is the main drag running from downtown to Fitch Mountain. Many successful growers who had country properties built a "town house" so their kids could get to school more easily in the winter. Other homes in the area were built by merchants. This example of a beautiful Queen Anne was built around 1895. The lots here tended to the large size and many had additional structures added since then. The Healdsburg historic downtown listing featured in the top photo has two duplexes and a small cottage in the "back yard". The units are grandfathered into the zoning, but would never be allowed for someone who wanted to build something similar today. This Victorian is ready for a buyer who wants to put their imprint on the property. It's a reasonably sound structure, but needs to be updated.
Tucker and Haydon are architecturally similar to Matheson, but are much quieter streets since they aren't a through route to anywhere. They are an extra block or two from the plaza because of that, but the tradeoff for less traffic is clearly worth it for many buyers. This charming 1881 farmhouse at 527 Tucker St is a well preserved example of the California farm house tradition. It is currently set up as a multi-unit building, but could easily be turned back into a single family home. My colleague, Gail Ryan, has this listed for $895,000.
A few blocks closer to the Plaza, another one of my colleagues, Felicia Carlson, has a listing for a beautifully updated Edwardian with a complete guest cottage, pool, and full garage with alley access. This lovely home with nearly 3,000 square feet is completely move-in ready for the person who wants all the charm of Healdsburg without the trouble of fixing up an old place on their own.

This downtown gem represents the top of the heap as far as architecture, historic interest, modern conveniences, and access to all the amenities of the downtown area.
Healdsburg's historic downtown will retain the area's strongest residential values for reasons of location, charm, and historic authenticity. New subdivisions may have bigger, more modern homes, but it's impossible to recreate a 100 year old neighborhood close to downtown. The several hundred homes that are lucky enough to be within a few blocks of the Healdsburg Plaza are always going to be sought after.
Look for the Healdsburg Plaza. That is the cornerstone that everything in Healdsburg is measured from. "How many blocks to the plaza?" and "How long to get to the plaza?" are two of the most common questions we answer about real estate in Healdsburg. This map should help understand the main streets that I discussed in this post. For more information on all residential listings in Healdsburg, you can visit my site and do your own searching for historic homes in downtown Healdsburg. Happy hunting.
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Hi Dave - Lovely presentation on Healdsburg CA Historic Homes - the downtown area looks so inviting - if I were looking for a home for sale there, I would be calling you right now!