Where to Live in
Bend

Bend 2026: The Shortlist

The 2026 Vibe Check

Bend isn’t exploding anymore; it’s calcifying. The wild west days of 2018-2022 are over. Now, we’re seeing hard lines drawn. The Deschutes River is the primary border. West of the river is a fortress of wealth, where tear-downs on NW Wall Street fetch $1.2M before the foundation is poured. This is where the "old guard" lives—people who own companies, not just work for them.

East of the river, things are more pragmatic. This is the engine room. The Larkspur area, specifically the corridor along NE 27th Street, is the new hotspot for the "Bend-curious" tech worker who got priced out of the Westside but still wants a 10-minute commute to Downtown. Gentrification is hitting East Bend hard; the 1970s ranches off Pioneer Road are getting flipped into modern farmhouses, pushing the original blue-collar residents further out toward La Pine.

The biggest shift? The "Lifestyle" tax is now mandatory. Living here means paying a premium for trail access, not just a roof. If you're not buying into the outdoor infrastructure, you're just paying rent. The locals who remember when Bend was a sawmill town are quietly selling to the wave of remote finance workers from San Francisco who think $800k is a "steal."

The Shortlist

Old Mill District

• The Vibe: Polished Corporate
• Rent Check: High (+30%)
• The Good: This is the easiest place to live in Bend. You have the Les Schwab Amphitheater in your backyard, a dedicated Oboz shoe store, and the River Trail connects you to everything without touching a major road. The schools (High Desert Middle School) are top-tier. If you work remotely and want zero friction, this is it.
• The Bad: It feels like a movie set. You won’t find a gritty dive bar here; the closest thing is Greg’s Grill, which is hardly a dive. It lacks soul. Parking is a nightmare during summer concerts.
• Best For: The remote tech worker who wants a lock-and-leave lifestyle and spends weekends at the Arlene Schnitzer Concert Hall branch or floating the river.
• Insider Tip: Walk the River Trail at 7:00 AM on a Saturday, grab a coffee at Backporch Coffee Roasters (the one on Bond Street), and watch the rafters get lined up. That’s the Old Mill in a nutshell.

Westside / Old Bend

• The Vibe: Historic/Craftsman
• Rent Check: Highest (+45%)
• The Good: This is the gold standard. Walking distance to Downtown Bend and the Pilot Butte trailhead. The architecture has actual history (and character). You’re neighbors with the people who own the restaurants you eat at. The walkability score is 95+.
• The Bad: The price of entry is staggering. You are paying for the zip code, and the houses are old—expect drafts and settling. Street parking is non-existent. If you have more than one car, don't bother.
• Best For: Established families or high-net-worth individuals who want the "Bend Dream" and don't mind the maintenance costs.
• Insider Tip: Go to McKay Park (the "Triangle") on a Thursday evening. That’s where the power players shake hands. If you're renting here, you've made it.

Larkspur

• The Vibe: Up-and-Comer
• Rent Check: Mid (+10%)
• The Good: This is the smart money play. You get newer construction (1990s-2000s) with actual square footage and garages. It’s a 5-minute shot down NE 27th Street to Downtown, but you avoid the traffic snarl of Hawthorne. Larkspur Community Park is a beast for kids.
• The Bad: The traffic on NE 3rd Street during rush hour is a parking lot. It lacks the "charm" of the Westside; the lots are tight. You hear the highway here.
• Best For: Young families who need a 3-bedroom but can’t swing Westside prices. A great landing pad for new arrivals.
• Insider Tip: The hidden gem is Cannonball Sundries on NE 27th. It’s a bottle shop and cafe that captures the exact vibe of this neighborhood—casual but serious about quality.

East Bend / Boyd

• The Vibe: Classic Suburb
• Rent Check: Low (-5%)
• The Good: Value. This is where you get a 1960s ranch with a massive backyard for a price that doesn't require a trust fund. It’s quiet, established, and close to Pine Mountain Sports (the best bike shop in town, hands down). You get real seasons here without the pretension.
• The Bad: It’s a "drive to thrive" neighborhood. You are not walking to a coffee shop. The schools are fine, but not the top-tier draw of the west side. It feels generic if you're looking for "mountain town" aesthetics.
• Best For: First-time homebuyers, people who want space over prestige, and anyone who works at the hospital or the industrial shops on the east side.
• Insider Tip: The stretch of Pioneer Road between Brookside and 27th is seeing the most aggressive flips. Buy the 1960s box before they turn it into a $900k modern farmhouse.

Strategic Recommendations

For Families:
You want Larkspur or East Bend. Larkspur offers the newer schools and the Larkspur Park ecosystem, which is essentially a free babysitter. East Bend gives you the actual yard for a trampoline and a garage for all the gear. Avoid Old Mill; the density and tourist traffic are a nightmare for kids.

For Wall St / Tech:
Old Mill District is the winner if you value time over character. You can walk to a meeting at The Riverhouse or grab lunch at 900 Wall without moving your car. If you need to commute to Redmond for manufacturing or tech access, East Bend puts you on the highway in 5 minutes.

The Value Play (Buy Before 2027):
East Bend / Boyd. The gentrification wave is moving east. The infrastructure is there, and the prices are the last "reasonable" holdouts in the city limits. Specifically, look at the grid between Pioneer Road and Pinebrook Blvd. The ROI on a cosmetic renovation here is safer than the stock market.