Bend, Oregon isn’t just a place, it’s a lifestyle. Framed by the Cascade Mountains and threaded with rivers, trails, and alpine wilderness, Bend is a year-round playground for outdoor enthusiasts. Whether you're hiking through pine-scented forests, biking world-class singletrack, or skiing down fresh powder at Mt. Bachelor, every season brings a new adventure. For those who want to live where they play, finding the right neighborhood means more than just location, it means immediate access to the trails, terrain, and experiences that define life here.
This guide is designed to help you discover homes that are not only close to Bend’s best outdoor offerings, but that also embody the lifestyle itself. Each property featured here sits within minutes of trailheads, lifts, or bike routes; ideal for buyers who want outdoor access right outside their door. Let’s explore where you can live in Bend if your free time is spent hiking, biking, or skiing, and the exact properties that make it possible.
Why Outdoor Enthusiasts Love Bend
Bend offers one of the most diverse outdoor landscapes in the Pacific Northwest: rugged mountains, high desert trails, alpine lakes, and over 300 days of sunshine each year. From morning trail runs to après-ski evenings, the city is built for people who enjoy and live in the outdoors.
What sets Bend apart is the seamless integration of recreation into daily life. Trails like the Deschutes River Trail run right through town. World-class mountain biking begins just minutes from downtown. Mt. Bachelor is a short drive away for skiers and snowboarders. And whether it’s a weekend paddle, an early-morning hike, or a sunset ride, there’s a neighborhood and a home that puts you right at the edge of it all.
Where to Live if You Love Hiking
Bend is a hiker’s paradise, with trailheads that start practically in your backyard and wind through pine forests, canyons, riverbanks, and alpine wilderness. From the rugged beauty of Shevlin Park and the Deschutes River Trail to the dramatic cascades of Tumalo Falls, the region offers year-round hiking opportunities that begin just minutes from home. But if you're serious about your trail time, you need a home that matches your lifestyle, not just in proximity, but in design, setting, and comfort.
One such property is 65160 Highland Road, located just outside Tumalo and only six miles from Bend. Set on over five acres of pristine land with sweeping views of the Cascade Mountains, this $2.05M equestrian estate offers direct access to open terrain and peaceful landscapes. Aside from being a residential property, it’s also a retreat, complete with a wraparound porch, expansive deck, and rustic stone fireplaces that invite you to unwind after a long day on the trails. Whether you’re heading out for a morning trek or a weekend ride, the surroundings and layout support a deeply immersive outdoor lifestyle.
For those who want to live closer to Shevlin Park, 19160 NW Mt Shasta Court offers modern sustainability without sacrificing style. Priced at $1.499M, this midcentury-inspired home integrates floor-to-ceiling windows, radiant flooring, and spa-quality finishes, all within walking distance of one of Bend’s most beloved trail networks. A tandem three-car garage with built-in bike and dog wash stations shows just how well this home was built with outdoor adventurers in mind.
You can also consider 2264 NW Lemhi Pass Drive in Northwest Crossing. Just minutes from trails, parks, and the Deschutes River, this $1.749M home pairs high-end finishes with everyday functionality. The 4-season covered deck, white oak flooring, Earth Advantage Silver rating, and spa-like primary suite make it the ideal home base for those who want nature and city access in one seamless package.
For buyers looking to pair luxury with trailhead access, the North Rim community is unmatched. Properties like 2060 NW Perspective Drive ($3.495M) and 3487 NW Greenleaf Way ($3.275M) offer panoramic mountain views, massive indoor-outdoor entertaining spaces, and quick access to the river canyon and Shevlin Park. These homes are ideal for serious hikers who value solitude, elegance, and quick immersion into nature.
Lastly, for buyers seeking truly elevated living, 664 NW Powell Butte Loop on Awbrey Butte delivers a modern masterpiece set against the hillside, with sleek interiors and unobstructed views. At $4.9M, this property offers quick access to summit trails and a short drive into town, all from a serene, elevated vantage point.
Where to Live if You Love Biking
Bend’s biking culture is nationally recognized, offering some of the best singletrack in the West and a tight-knit community of riders. Whether you’re heading for the iconic Phil’s Trail system, looping through the Wanoga Complex, or cruising along the Deschutes River Trail in the Old Mill District, this city is built for cyclists of all levels. But for those who ride often, convenience matters: neighborhoods that back up to trailheads, with easy garage storage, and even space for tuning and rinsing gear, are top priority.
In Discovery West, 3122 NW Crossing Drive delivers exactly that. Designed by BendTrend Homes, this $2.4M single-level home blends high-end mid-century style with direct access to the Discovery Park trail system. Just minutes from Phil’s Trailhead, the home’s layout is made for a cyclist’s lifestyle. Think oversized garage with RV bay for gear storage, radiant heat for post-ride recovery, and glass sliders that open right onto trails. Walnut cabinetry and white oak floors complement the natural surroundings, while modern features like AC and a private hot tub patio ensure you recover in comfort.
Next door, 3110 NW Crossing Drive offers a $2.1M modern craftsman option with the same trail-side advantage. This home is ideal for riders who need room to store gear, work from home, and entertain. The spacious three-car garage accommodates bikes, tools, and a van with ease, while the vaulted great room and slab quartz kitchen provide a polished space to unwind after rides.
If urban cycling access and riverfront trails are more your style, the Old Mill District is unmatched and 210 SW Log Court puts you at the heart of it all. These luxury townhomes, priced at $1.799M, offer designer interiors, a lock-off ADU/flex space for gear or guests, and rare zoning that allows for short-term rentals. These amenities make this property a prime choice for investment-minded bikers. With the Box Factory, Crosscut, Crux, and the Deschutes River Trail just outside your door, every ride can end with a craft beer or riverside hangout.
Meanwhile, 363 SW Bluff Drive, UNIT 208 provides a different take—luxury condo living in The Plaza, right above the Old Mill. At $899K, this two-bedroom unit offers vaulted ceilings, mountain views, and a private balcony perfect for watching live events or simply taking in the Cascade backdrop. It’s ideal for buyers who want lock-and-leave convenience with biking trails right below and secure garage parking for gear storage.
Just across the Deschutes River, 857 SW Crestline Drive in Deschutes Landing delivers a tranquil, upscale retreat with riverfront views and immediate access to kayaking and trail loops. Priced at $1.55M, this townhome offers the best of both worlds: close proximity to the biking action with a private setting to return to.
If you’re looking for views as epic as the rides, 961 SW Vantage Point Way brings panoramic vistas of the Cascade Mountains, Deschutes River, and Old Mill life in a fully furnished $1.287M townhome. With two en-suite primaries, flex space, and decks on both levels, this home caters to full-time cyclists or short-term stays alike.
Finally, 109 SW Taft Avenue delivers everyday functionality in a custom-built home just steps from the river and trail network. At $899K, this three-bedroom residence is updated throughout and provides easy access to the Old Mill, trails, and Mt. Bachelor highway. This is ideal for those who want to ride local during the week and hit the mountains on weekends.
Where to Live if You Love Skiing
For skiers in Bend, proximity to Mt. Bachelor is more like a lifestyle than a convenience. With the resort less than 30 minutes from many westside neighborhoods, the best homes combine direct mountain access with luxury amenities, year-round functionality, and plenty of room for gear, guests, and après-ski relaxation. Whether you're seeking a full-time mountain residence or a vacation retreat, these properties offer elite comfort within minutes of the slopes.
In The Highlands at Broken Top, 18883 Sutherland Court sets the standard for high-alpine luxury. Listed at $8.9M, this nearly 10,000 sq ft estate sits on over 10 acres behind a private gate, ideal for buyers seeking total privacy without sacrificing access to Mt. Bachelor. With a main home, guest house, wine cellar, swimming pool, hot tub, and garages for up to nine vehicles, this residence functions as a mountain compound. After a powder day, retreat to the warmth of the great room’s stone fireplace or soak in the spa-level primary suite.
For something closer to the resort and golf course lifestyle, 19300 SW Seaton Loop in Tetherow offers a $4.35M retreat that blends rustic warmth with mountain elegance. Overlooking the fairways and framed by snow-capped peaks, this home is perfect for winter and summer enthusiasts alike. Vaulted timber ceilings, stone accents, and an open-concept design make it ideal for gathering post-ski. With a primary suite on the main level and guest accommodations above, it transitions easily between vacation use and full-time living.
Also in Tetherow, 61655 Hosmer Lake Drive emphasizes year-round flexibility. This $4.099M home features a sauna, hot tub, and gym, all with unobstructed views of Mt. Bachelor. The floorplan includes multiple en-suites, an office, bonus spaces, and a solar-powered system that ensures sustainability through all seasons. With oversized garage storage, it easily accommodates skis, boards, and snow gear.
For those looking for architectural boldness, 61913 Hosmer Lake Drive redefines what a ski-adjacent home can be. At $3.695M, this one-level modern home was designed by award-winning architects and sits on a private ridge blending conifer forest and desert. Interior courtyards and aluminum paneling create dynamic light play throughout the space. Fully furnished in key areas, it’s ready for immediate occupancy and tailored for buyers who value aesthetics as much as access.
Lastly, 19345 Roswell Drive completes the picture with timeless Northwest lodge charm. Priced at $3.665M, this Tetherow home opens to the 16th hole of the golf course with mountain views in nearly every room. With a grand great room, two main-level suites, wine cellar, and oversized garage, it's built for entertaining after ski days and unwinding in style. The chef’s kitchen and expansive outdoor area make it just as enjoyable in warmer months, too.
Outdoor Lifestyle Amenities to Look For
Living in Bend is about choosing a home that enhances your active lifestyle year-round. For buyers who hike, bike, or ski, the right amenities can make all the difference in comfort, convenience, and daily function.
Gear Storage & Oversized Garages: Whether it's mountain bikes, skis, paddleboards, or snowmobiles, gear storage is essential. Many featured homes offer three-car or tandem garages with custom cabinetry, gear walls, or even RV/sprinter bays. Properties like 3122 NW Crossing Drive and 61655 Hosmer Lake Drive provide the space and layout to store, maintain, and access your equipment with ease.
Trail & Lift Access: True outdoor living means hitting the trails or slopes straight from your door. Look for homes near the Discovery Park trail system, Shevlin Park, or directly off Mt. Bachelor’s access road. Homes in Northwest Crossing, Tetherow, and The Highlands offer unparalleled access without sacrificing privacy or luxury.
Outdoor Recovery Spaces: Features like hot tubs, saunas, and covered patios elevate post-activity recovery. Whether it's the spa-quality bath at 19160 NW Mt Shasta Court or the hot tub with mountain views at 61655 Hosmer Lake Drive, these details matter when you live actively.
Seasonal Functionality: Homes in Bend need to perform across all seasons. Earth Advantage certifications, radiant heating, efficient insulation, and solar power (as seen in homes like 2264 NW Lemhi Pass Drive) ensure year-round comfort and lower energy costs.
Community Perks: Gated communities like North Rim and The Highlands at Broken Top offer HOA amenities such as private lodges, tennis courts, and parklands. It’s ideal for socializing, staying active, and enjoying your surroundings without leaving the neighborhood.
Your Next Steps
Bend offers not just stunning scenery but it also delivers a lifestyle deeply rooted in outdoor adventure. Whether you're a hiker seeking access to Shevlin Park, a cyclist drawn to the trails of Discovery West and the Old Mill, or a skier looking to live within striking distance of Mt. Bachelor, there’s a home here that aligns perfectly with your passions.
Each neighborhood, from Tumalo to Tetherow, brings you closer to the activities you love, while the properties themselves provide the gear space, recovery amenities, and thoughtful design to support your lifestyle year-round.
Ready to find your basecamp for adventure? Contact Team Fitch today to explore homes near Bend’s best hiking, biking, and skiing destinations. Let us help you live where you play.
