Windsor Town Green district
Walk-to-the-green living — townhomes and detached homes built around the square itself.
Communities / Windsor & Healdsburg
Windsor & Healdsburg
Two wine-country markets fifteen minutes apart—Windsor's Town Green neighborhoods and Healdsburg's plaza, river, and vineyard properties.
County
Sonoma
Anchors
Windsor Town Green · Healdsburg Plaza
Rail
SMART — Windsor station
Feels like
Town Green neighborhoods meet plaza-centered wine country
Living Here
Life in Windsor & Healdsburg
North of Santa Rosa, Windsor is organized around its Town Green, summer concerts, a farmers market, restaurants, and civic events. Much of its housing stock is relatively recent, with contemporary floor plans, garages, sidewalks, and planned-neighborhood parks.
Healdsburg, fifteen minutes up US-101, centers on a 19th-century plaza with tasting rooms, galleries, and restaurants at the junction of the Dry Creek, Alexander, and Russian River valleys. Its market includes in-town cottages and remodels, river properties, second homes, and vineyard acreage.
Areas to know
Windsor east side
The classic master-planned neighborhoods: newer schools, parks, and cul-de-sacs.
Foothill / Shiloh edges
Larger lots against the regional parks, some with vineyard views.
Healdsburg in-town
Blocks off the Plaza — cottages, Victorians, and remodels that trade at a premium for walkability.
Fitch Mountain & Memorial Beach
River-bend living east of town, from cabins to contemporary view homes.
Dry Creek & Westside Road
Vineyard estates and country properties in the appellations themselves.
Out your front door
- Windsor Town Green — Summer concert series, farmers market, restaurants, and a year-round civic event calendar.
- Foothill Regional Park — Oak-hill trails and three small lakes on Windsor's northwest shoulder.
- Healdsburg Plaza — The square that made the town famous — tasting rooms, galleries, restaurants.
- Russian River beaches — Memorial Beach and river access for summer swimming and paddling.
- Three appellations — Dry Creek, Alexander, and Russian River valleys all begin at Healdsburg's edge.
Schools & essentials
- Windsor Unified — K–12 in town, including Windsor High and its well-known athletics.
- Healdsburg Unified — Small-district schools a short walk from the Plaza.
- Healdsburg Hospital — District hospital serving northern Sonoma County.
- US-101 & SMART — Windsor is the current northern SMART terminus; Healdsburg is a 15-minute drive up-valley.
Local Market Structure
How the local market differs
Windsor and Healdsburg should be compared as related but distinct markets. Windsor offers more planned-neighborhood and relatively recent housing; Healdsburg adds in-town walkability, river properties, second homes, and vineyard acreage. Current comparable sales should be evaluated separately for each town and property type.
The combined guide is a starting point. For a specific property, both agents prepare the comparison around the correct town, setting, and recent local evidence.
For current comparable sales on a specific street or property, call either agent and we will prepare a focused local review.
Considering Windsor & Healdsburg?
Buying, selling, or comparing options in Windsor & Healdsburg? Send the street, property, budget, or question. Your message reaches both agents, and one of us will respond the same day.
Photography: Windsor downtown — Sarah Stierch, CC0 · Dry Creek Valley — Fuzchia, CC BY-SA 4.0 — via Wikimedia Commons.