Rolling Bay Neighborhood

Rolling Bay is a charming, rural-chic enclave on the eastern side of Bainbridge Island, where farm heritage meets coastal serenity. With gently rolling hills, tree-lined roads, and a tight-knit community, it feels like stepping into a slower-paced, storybook village.

Some properties offer sweeping water views toward Puget Sound and ferries crossing the Sound, while others sit inland on large, pastoral lots — where you’ll even find sheep, alpacas, or goats. Rolling Bay’s central hub — a small cluster of shops around the intersection of Sunrise Drive NE and Valley Road — includes longtime island staples like Bay Hay & Feed, an Italian market/café (Via Rosa 11), and a cozy café (Rolling Bay Café).

The community spirit is strong: residents ride bikes along quiet roads, walk to nearby trails, pick blueberries in season, and shop locally. Rolling Bay is also recognized as one of Bainbridge Island’s Neighborhood Service Centers, meaning it supports local commerce in a way that preserves its rural charm.

With its pastoral roots, elevated views, and relaxed pace, Rolling Bay offers a peaceful yet connected lifestyle. It’s just a short drive (or bike ride) to Winslow — under 10 minutes — giving residents easy access to island amenities without giving up their countryside sanctuary.

📍 Points of Interest in Rolling Bay

• 🛍️ Bay Hay & Feed — An iconic general store and community anchor offering garden supplies, gifts, and more.

• 🍝 Via Rosa 11 — A beloved Italian Market & Kitchen serving handmade pasta, brick-oven pizzas, and local flavors.

• ☕ Rolling Bay Café — A cozy café where locals gather, tucked into the garden of Bay Hay & Feed.

• 🍷 Rolling Bay Winery — A boutique, artisan winery with a charming tasting room in a garden-like setting.

• 🌲 Ted Olson Nature Preserve — A peaceful 15-acre forested preserve with trails, wetlands, and conserved open space.

• 🌳 8-Acre Woods Park — A newly gifted wooded parcel with informal trails, benches, and restored habitat.

• 🚜 Rolling Bay Walk & Rural Roads — Scenic, walkable roads through farms, forest, and hidden nooks where locals bike and stroll.

🎓 Schools Serving Rolling Bay

Rolling Bay is part of the Bainbridge Island School District (BISD, District 303). Based on location, children in Rolling Bay are likely zoned for:

• Elementary (PK–4):

  • x̌alilc (Halilts) Elementary School

  • Captain John Wilkes Elementary School (zoning may vary)

• Intermediate (Grades 5–6):

  • Sonoji Sakai Intermediate School

• Middle (Grades 7–8):

  • Woodward Middle School

• High School (Grades 9–12):

  • Bainbridge High School – the main public high school in BISD. Wikipedia

  • Eagle Harbor High School – part of the district’s alternative / independent study program (Commodore Options).

Rolling Bay is a pastoral haven with authentic island charm — a place where history, nature, and community converge. Between its rolling hills, rustic farmhouses, neighborhood shops, and nearby forest preserves, Rolling Bay feels like a retreat — yet it remains just minutes from Winslow and the rest of Bainbridge Island. Whether you’re sipping wine at the local winery, strolling through the Ted Olson Preserve, or grabbing coffee at the café, life here moves at a gentle, grounded rhythm. For those who value connection — to nature, to their neighbors, and to a simpler way of life — Rolling Bay is a deeply inviting place to call home.