Median Price
$670,000
Walk Score
32
Schools
A
Where it sits
Sherwood is situated about 17 miles southwest of downtown Portland, bordered by SW Elwert Road to the east, SW Oregon Street to the north, SW Murdock Road to the west, and SW Roy Rogers Road to the south. Officially incorporated as its own city, Sherwood blends quiet suburban living with the character of a historic small town—best known for its charming "Old Town" district, walkable streets, and proximity to wine country.
The Neighborhood
Sherwood’s housing leans suburban—expect well-kept single-family homes from the 1980s to today, a mix of classic Oregon Craftsman, ranch styles, and newer two-story builds. Around Old Town, you’ll spot some early 20th-century cottages and bungalows, while new developments on the outskirts offer contemporary layouts with plenty of yard space.
Life here moves at a comfortable pace. Old Town Sherwood is the heart of local shops and weekend markets, and the Cannery Square plaza creates a lively yet relaxed gathering space. While the core is walkable with coffee shops and family restaurants, most daily errands require a short drive. Scenic parks, green spaces, and small-town festivals define the neighborhood's friendly, outdoorsy spirit.
“Charming "Old Town" district, walkable streets”
Parks, Trails & Green Space
Top 5 places to get outside
Stella Olsen Memorial Park — A favorite for families, this park features open lawns, a playground, sports courts, and a stage that hosts outdoor concerts in summer. Walking trails wind through wooded areas and connect to the nearby YMCA.
Sherwood Old Town Plaza (Cannery Square) — This small urban plaza serves as the neighborhood’s social heart, hosting the summer farmers market, concerts, and community events amid shaded seating and public art.
Edgy Ridge Park — Located in the Edy Ridge neighborhood, this local park offers a playground, picnic shelter, basketball courts, and trails through green spaces—popular for casual walks and neighborhood gatherings.
Snyder Park — A large community park boasting sports fields, tennis courts, a playground, a skate park, and walking paths. Dogs enjoy its off-leash dog park nestled among mature trees.
Woodhaven Park — Set along trails and greenways, this spacious park is known for its playground, open fields, and sport courts. It's a regular destination for neighborhood picnics and birthday celebrations.
Coffee Shops
Top 5 places for a coffee
Symposium Coffee — A welcoming local café in Old Town Sherwood, Symposium provides a cozy atmosphere ideal for relaxed meetups or remote work. Known for specialty coffee drinks and pastries. *(Verified open June 2026. Search: Symposium Coffee Sherwood)*
Black Rock Coffee Bar — Pacific Northwest-based chain with a comfortable Sherwood location; offers espresso drinks, cold brews, and grab-and-go snacks. Known for friendly service and a lively atmosphere. *(Verified open June 2026. Search: Black Rock Coffee Bar Sherwood)*
Insomnia Coffee Company — A regional favorite, Insomnia’s Sherwood shop serves craft-roasted coffee, teas, and house-baked treats in a bright setting. It’s a popular spot to meet up or read in the afternoon. *(Verified open June 2026. Search: Insomnia Coffee Sherwood)*
Sherwood Center for the Arts Café — A quiet gem inside Sherwood's arts center; offers coffee, light pastries, and occasional art shows—perfect for a peaceful break near Old Town. *(Verified open June 2026. Search: Sherwood Center for the Arts Café)*
Restaurants & Food Carts
Top 5 places for a bite to eat
Fat Milo’s Family Kitchen — This family-run diner is a Sherwood staple, known for hearty breakfasts, homestyle comfort food, and warm service in a retro-inspired setting. *(Verified open June 2026. Search: Fat Milo’s Sherwood)*
Crazy Sushi — A locally owned spot for fresh sushi, sashimi, and imaginative Japanese bites. Popular for its creative rolls and friendly staff. *(Verified open June 2026. Search: Crazy Sushi Sherwood)*
Clancy’s Pub & Restaurant — Located in Old Town, Clancy’s offers Irish pub fare, classic burgers, and weekend live music in a cheerful, historic tavern setting. *(Verified open June 2026. Search: Clancy’s Pub Sherwood)*
Symposium Coffee (serves breakfast & lunch) — Besides coffee, Symposium also serves breakfast sandwiches, salads, and baked goods, making it a daytime go-to for a quick, quality meal. *(Verified open June 2026. Search: Symposium Coffee Sherwood food)*
The Hungry Hero Dessert Co. — A locally owned bakery specializing in pies, cupcakes, cookies, and decadent treats, with charming decor and friendly faces. *(Verified open June 2026. Search: The Hungry Hero Dessert Sherwood)*
Bars
Top 5 places for a drink
Clancy’s Pub & Restaurant — A fixture in Sherwood for more than a century, Clancy’s serves local craft beer, cocktails, and pub classics. Frequented for trivia nights, live music, and a lively local crowd. *(Verified open June 2026. Search: Clancy’s Pub Sherwood)*
2nd Street Pub — Neighborhood watering hole known for its relaxed vibe, signature cocktails, rotating taps, and dartboards. Regulars love its weekly karaoke and community events. *(Verified open June 2026. Search: 2nd Street Pub Sherwood)*
Langer’s Entertainment Center Bar — Inside Sherwood’s popular bowling and entertainment complex, Langer’s offers a full bar with beer, wine, cocktails, and bar snacks for guests enjoying arcade games and bowling. *(Verified open June 2026. Search: Langer’s Entertainment Sherwood bar)*
Fat Milo’s Family Kitchen — In addition to breakfast and comfort food, Fat Milo’s offers a selection of local beer and wine for a casual drink with your meal. *(Verified open June 2026. Search: Fat Milo’s Sherwood bar)*
Things To Do
Top 5 things worth your time
Sherwood Center for the Arts — A modern arts hub in the heart of Sherwood, hosting rotating art exhibits, classes, theater performances, and concerts for every age. *(Verified open June 2026. Search: Sherwood Center for the Arts)*
Langer’s Entertainment Center — Family-friendly destination offering bowling, arcade games, laser tag, indoor climbing, and a lively events calendar—great for groups and rainy days alike. *(Verified open June 2026. Search: Langer’s Entertainment Sherwood)*
Old Town Sherwood Farmers Market — Held downtown during the growing season, this weekly market supports local farmers, bakers, and artisans—known for farm-fresh produce and live tunes. *(Verified open June 2026. Search: Old Town Sherwood Farmers Market)*
Sherwood Historical Society & Heritage Center — Explore Sherwood’s roots through local exhibits, artifacts, and the historic Morback House, open for community tours and seasonal events. *(Verified open June 2026. Search: Sherwood Historical Society)*
Sherwood Robin Hood Festival — A long-standing summer tradition, this lively festival features parades, music, food, crafts, and costumed "Merry Men" celebrating the city’s namesake. *(Verified open June 2026. Search: Sherwood Robin Hood Festival)*
Community Resources
Local services & organizations
Sherwood Public Library — Full-service community library with events, storytimes, and meeting spaces.
Sherwood Center for the Arts — Event venue and hub for classes, workshops, and local performances.
City of Sherwood — City Hall offering permits, resources, and information for residents.
Sherwood YMCA — Fitness center, after-school programs, and community swim classes.
Sherwood Old Town Association — Organization supporting local businesses and events in the historic district.
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Is It Right For You?
How Sherwood balances out.
Every neighborhood trades one thing for another. Each scale is drawn from real data — price, walkability, era, and architectural character.
Everyday comfortA trade-off to weigh
Who it suits
You’ll likely love it if…
- Families seeking quality schools and community events
- Those who appreciate small-town festivals and local businesses
- Homebuyers wanting newer single-family homes with space to grow
It might not fit if…
- Limited walkability—most errands require driving (Walk Score: 32)
- Longer commute to Portland (30–40 minutes, traffic variable)
- Fewer nightlife options compared to city neighborhoods
Sherwood FAQ
The questions we hear most about Sherwood — and honest answers from people who know it.
Ask us anything →Sherwood features a blend of Oregon Craftsman and contemporary suburban homes, with ranch-style layouts and early 20th-century cottages especially present around Old Town. Newer developments showcase modern two-story floorplans with larger lots.
With a Walk Score of 32, Sherwood is best described as car-dependent outside its Old Town core. Some cafes, parks, and schools are walkable, but most daily errands require driving.
Sherwood is widely recognized for its tight-knit community spirit, highlighted by events like the Robin Hood Festival, its expanding wine country access, and a downtown that balances Old West heritage with new, family-friendly amenities and parks.
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