When it comes to buying a home in Bend, Oregon, style matters just as much as location. Two of the most beloved architectural styles in Central Oregon are Craftsman and Mid-Century, each offering its own sense of charm, livability, and design appeal. Whether you're drawn to the warm woodwork and hand-built details of a Craftsman or the clean lines and open layouts of a Mid-Century home, these styles continue to capture the attention of buyers who value both character and comfort.
Craftsman homes, originally popularized in the early 1900s, are known for their covered porches, exposed rafters, tapered columns, and rich architectural detail. They're often nestled in walkable, historic neighborhoods with mature trees and close proximity to local shops, parks, and the Deschutes River. In Bend, these homes speak to those who want authenticity, timeless design, and a strong connection to the city’s original neighborhoods.
Mid-Century homes, on the other hand, emerged in the postwar era of the 1950s and ‘60s, favoring simplicity, functionality, and indoor-outdoor living. Defined by flat or low-pitched roofs, wide horizontal layouts, and large windows, these homes offer bright interiors, open floor plans, and a seamless relationship with the surrounding landscape. Bend’s Mid-Century properties often sit on larger lots and feel tucked away in peaceful, established areas with a quiet, nostalgic charm.
Both styles have enduring appeal in Bend’s market, whether for full-time living, second homes, or investment properties. And because they're harder to replicate in today’s new builds, well-maintained examples of each continue to be in high demand.
Where to Find Craftsman Homes in Bend
Bend’s Craftsman homes are most commonly found in the city’s oldest and most walkable neighborhoods like Old Bend, River West, and pockets of Downtown Bend. These areas were among the first to be developed in the early 1900s, and many of the homes here still reflect the hallmarks of classic Craftsman design: wide front porches, gabled roofs, exposed rafters, and beautiful built-in woodwork that speak to a time when craftsmanship was the defining standard of homebuilding.
These neighborhoods aren’t just rich in architectural detail but they also offer lifestyle benefits that make them especially attractive to today’s buyers. You’re within walking or biking distance of Drake Park, Mirror Pond, the Galveston Corridor, and many of Bend’s best restaurants, breweries, and events. Whether you’re floating the Deschutes River in the summer or grabbing coffee in the off-season, living in these districts feels like stepping into the heartbeat of Bend’s vibrant culture.
Several standout listings showcase what makes Craftsman homes in these areas so special:
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104 NW Congress Street – A 1920s home reimagined with designer finishes and a rare short-term rental permit, all just blocks from downtown.
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402 NW 12th Street – A fully remodeled 1919 Westside bungalow with an ADU, EV-ready garage, and walkability score of 91.
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232 NW Congress Street – A vintage craftsman with mountain views, original details, and zoning that opens the door to flexible use.
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139 NW Broadway Street – A 1916 cottage mill house located steps from the Old Mill District, rich with historic context and rental potential.
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7536 SW Powell Butte Highway – Though outside city limits, this 1915 farmhouse blends Craftsman-era charm with sweeping Cascade views on 76 acres.
Craftsman homes offer more than architectural interest; they anchor you to the history and community of Bend, making them an ideal choice for buyers who want connection, character, and centrality.
Where to Find Mid-Century Homes in Bend
Mid-Century homes in Bend reflect the postwar optimism and architectural shift of the 1950s and 60s, prioritizing space, simplicity, and connection to the outdoors. These homes are most often found in established areas like Midtown, the Orchard District, sections of the Westside, and even parts of Redmond, where Bend’s growth first pushed outward from its historic core.
What sets these homes apart is their emphasis on clean design and livability. Expect open floor plans, large windows that flood interiors with natural light, low-slung rooflines, and subtle exterior detailing. Many sit on larger lots, offering privacy and a more expansive feel, ideal for homeowners who want both style and room to grow. Original finishes, retro details, and smart updates make them especially appealing to buyers who appreciate design-forward living with a touch of nostalgia.
Bend and surrounding areas feature several examples of standout Mid-Century homes that blend architectural integrity with modern comfort:
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17606 Fairway Lane, Sunriver – A landmark 1969 estate by John Gray, combining true mid-century craftsmanship with resort-like amenities, including a pool and guest structure.
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1349 NW Quincy Avenue – Built in 1956 and located in a peaceful Westside enclave, this home offers timeless character, expansive outdoor living, and floor-to-ceiling windows.
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1528 NE 8th Street – A 1954 Midtown property featuring hickory floors, modern upgrades, and rental potential in one of Bend’s most accessible neighborhoods.
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2076 SW 58th Street, Redmond – A beautifully reimagined 1969 home on over 4 acres with Cascade views, multi-generational potential, and luxury rural amenities.
For those drawn to a more minimalist, nature-connected way of living, Bend’s Mid-Century properties offer a rare combination of architectural identity and practical comfort, all within easy reach of town centers, parks, and outdoor recreation.
Style Comparison: Which One’s Right for You?
Choosing between a Craftsman and a Mid-Century home often comes down to the kind of lifestyle and aesthetic you value most. While both styles offer timeless appeal, they cater to different sensibilities in design, layout, and everyday living.
Craftsman homes are ideal for those who appreciate traditional character, handcrafted details, and a strong connection to neighborhood history. These homes tend to have cozy, segmented layouts with rich woodwork, built-ins, and architectural accents that feel warm and personal. You’ll often find them in walkable areas close to Bend’s downtown core, where community events, parks, and local shops are just steps away. If you’re drawn to classic architecture, early 20th-century charm, and the feeling of a rooted, established neighborhood, a Craftsman may be the perfect fit.
Mid-Century homes, by contrast, appeal to those who favor clean lines, open spaces, and a more modern relationship between indoor and outdoor living. These homes often have larger lots, bigger windows, and layouts designed for flow and functionality. They suit buyers who appreciate simplicity, mid-century design cues, and the potential for contemporary updates. If you value light-filled rooms, open floor plans, and understated elegance, a Mid-Century home delivers a more streamlined and minimalist experience.
In short, Craftsman homes speak to buyers who want character and tradition; Mid-Century homes speak to those who want space and simplicity. Both offer enduring value in Bend’s market, but the right fit depends on your personal design language and how you want to live day to day.
Work With Team Fitch Real Estate
Craftsman and Mid-Century homes each offer something uniquely special in Bend’s housing landscape. Whether you’re searching for early 20th-century charm with custom woodwork and porch-front character, or mid-century simplicity with open layouts and light-filled interiors, the key is knowing where to look and what to prioritize.
Start by focusing your search by era—Craftsman homes are typically built between 1905 and 1930, while Mid-Century homes range from the late 1940s to the 1960s. Use style-specific keywords like “Craftsman,” “bungalow,” “mid-century,” or “ranch” when browsing listings, and pay close attention to the neighborhoods where these homes are most common—Old Bend and River West for Craftsman, Midtown and the Orchard District for Mid-Century.
If you’re unsure where to begin or want to tour these styles in person, Team Fitch Real Estate Team is here to help. Our local expertise and deep knowledge of Bend’s architectural landscape can guide you toward the perfect home that matches your vision and lifestyle. Contact us today to schedule a private showing or start a style-specific search tailored to your needs.
