Bend Homes with Two Stories

Welcome to Bend, Oregon – a picturesque gem nestled in the heart of Deschutes County. Renowned for its stunning natural beauty, Bend is a paradise for outdoor enthusiasts and those seeking a vibrant community. With the majestic Cascade Mountains as a backdrop, residents enjoy year-round recreational activities, from skiing and snowboarding in the winter to hiking, biking, and river sports in the warmer months. The city boasts a thriving arts scene, delicious local cuisine, and a friendly atmosphere that makes it easy to feel at home.

One of the most sought-after housing options in Bend is the charming two-story home. These residences not only provide ample space for families and individuals alike but also offer a unique blend of style and functionality. With spacious layouts, two-story homes often feature open-concept living areas that seamlessly connect the kitchen, dining, and living spaces, creating an inviting environment for gathering with loved ones.

Imagine waking up in a sunlit master suite, with the stunning views of the surrounding mountains just outside your window. The second floor often provides additional bedrooms or office space, perfect for remote work or accommodating guests. Many two-story homes in Bend also come equipped with outdoor patios or decks, ideal for enjoying the breathtaking sunsets that grace the region.

Whether you’re looking to settle down or invest in a vacation home, Bend’s two-story properties offer the perfect blend of comfort, style, and access to the great outdoors. Discover your dream home in this enchanting city and experience all that Bend has to offer!

Newest Bend Homes with Two Stories

$1,479,000

5 Beds ⋅ 4 Baths ⋅ 220226195 MLS

Discover your home away from home, your primary residence, or vacation rental property in the heart of Bend's outdoor recreational paradise. Located minutes to Mount Bachelor, the Cascade Lakes or town, with neighborhood access to the Deschutes River Trail system, and bordering Widgi Creek golf course, you'll find this turnkey single family home in the desirable neighborhood Milepost 1. Featuring a rare 5 bedrooms and 4 full bathrooms, an open floorplan that is tastefully finished in designer elements, an attached 2 car garage with plenty of room for vehicles and recreational toys, a .26 acre lot, a spacious primary on the main, and so much more! When you're not out enjoying Bend, relax on your private patio, take a dip in the hot tub, and soak in the incredible setting that is nestled in the pines with expansive views. HOA's allow for true lock and go living. Why look any further? This is the perfect Bend escape!

60484 Kangaroo Loop, Bend

Listing courtesy of Cascade Hasson SIR.

$849,000

3 Beds ⋅ 4 Baths ⋅ 220226192 MLS

Embrace the luxury lifestyle in Broken Top, one of Bend's premier gated golf communities. Perfectly positioned along the 18th fairway, this versatile 2,193 sq. ft. townhome blends timeless design with effortless living. The dramatic great room welcomes you with soaring vaulted ceilings, abundant natural light, and a warm gas fireplace. Three bedrooms all with en-suites - the main-level primary suite offering a soaking tub and dual vanities, while upstairs, two private en-suite bedrooms provide exceptional comfort for family and guests, including one with golf course views. Unwind on the covered stamped concrete patio, surrounded by mature trees for privacy, or soak in the hot tub while enjoying peaceful fairway views. Optional club memberships offer access to championship golf, tennis, pickleball, a fitness center, pool, and an exceptional country club lifestyle. Just minutes from all NW Bend's celebrated dining and recreation.

335 Mount Washington Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$1,325,000

4 Beds ⋅ 3 Baths ⋅ 220226176 MLS

This is the home you have been looking for in desirable Awbrey Glen. Meticulous attention to detail in every room. Gourmet chef's kitchen features Wolf induction range, two ovens with both standard and convection features and warming drawer; Mesquite butcher block island, slab granite counters, beautiful cherry cabinetry, built in china hutch and new wine refrigerator create a perfect space for cooking and entertaining. Hardwood floors throughout have been recently refinished. Primary on the main level with gas fireplace and wonderful natural light. En-suite offers built in custom cherry dresser and radiant floor heat. Additional bedroom/office on main level with attached full bath. Two cozy bedrooms with full bath occupy the upper level. Three car garage. Solar system provides very low electric bills. Central vacuum system. Tons of storage throughout the house. Recent upgrades include new gutters, refrigerator, dishwasher, water heater, furnace and roof.

3511 NW Braid Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC.

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 220226171 MLS

Welcome to this exceptional custom home nestled on nearly one-third of an acre in one of Bend's most desirable neighborhoods. Perfectly positioned to back onto a peaceful common area and walking trails, this private retreat offers an incredible connection to nature with stunning views of a beautiful lava rock waterfall framed by floor to ceiling windows. The home features sand-in-place hardwood floors, leather-finished granite countertops, and an impressive kitchen completely updated in 2023 with premium Café appliances. A cozy gas fireplace, wrought iron accents add warmth. A barnwood wine room showcases your collection. Main-level living w/ primary suite overlooking the water feature. Step outside to your own multi-level backyard oasis. Mature landscaping, raised garden beds, horseshoe pits, an olive tree, three flowering crabapple trees, vibrant irises, on a huge lot. Add'l features include new dual-zone air conditioning for year-round comfort and exterior paint completed in 2019.

60875 Goldenwood Loop, Bend

Listing courtesy of RE/MAX Key Properties.

$613,000

3 Beds ⋅ 3 Baths ⋅ 220226168 MLS

Move-in ready with recent upgrades and a versatile small flex space, this beautiful Bend home offers nearly 2,000 square feet of comfortable living. The open great room floor plan features gorgeous new flooring, a gas fireplace, oversized kitchen island, granite countertops, and stainless steel appliances. Upstairs, the bonus space is ideal for a home office, yoga room, playroom, media room, or reading nook. Recent updates include new LVP flooring, new carpet, a remodeled upstairs bathroom, and updated kitchen fixtures. Enjoy a fully fenced backyard with low-maintenance turf, patio, and large gated side yard. Additional features include central A/C, Ring doorbell, keypad entry, smart home technology, ADT security system hook ups, and an attached two-car garage. Conveniently located near Silver Rail Elementary, Alpenglow Park, the canal trail, and just two blocks from the community pool and park!

20526 SE Cameron Avenue, Bend

Listing courtesy of RE/MAX Key Properties.

$815,000

3 Beds ⋅ 3 Baths ⋅ 220226123 MLS

Beautiful like-new construction by COBA Award-winning Structure Development NW, ideally located in SE Bend near Caldera High School, Bend Golf Club, new library, Alpenglow Park, and Central Oregon recreation. Thoughtfully designed open-concept floor plan with a main-level primary suite, this home blends craftsmanship with modern functionality. The great room features a gas fireplace flowing into the chef's kitchen with professional-grade appliances, large island, walk-in pantry, custom cabinetry, and quartz countertops. The primary suite offers a spa-inspired bath with dual vanities, tile shower, and walk-in closet. Upstairs find two additional bedrooms, a full bath, and bonus room. Step outside to a landscaped, fenced backyard with low-maintenance turf. An oversized two-car garage completes this exceptional home - comfort, style, and convenience in one of Bend's most desirable neighborhoods.

20501 Aberdeen Drive, Bend

Listing courtesy of The Agency Bend.

$1,649,500

5 Beds ⋅ 5 Baths ⋅ 220226132 MLS

One-of-a-kind fully renovated custom home on a peaceful lavender farm in the Sisters School District. Features a vaulted great room, chef's kitchen with quartzite countertops, white oak cabinetry, Thermador appliances, and a luxurious main-level primary suite. Two permitted barn guest suites with ensuite baths plus a bonus room offer flexible guest or rental space. Private access to adjacent BLM land creates the feel of your own dog park with endless trails and Cascade views. Expansive grounds offer limitless potential to build pool, additional shop/barn, sport courts, another garden area, or simply enjoy the privacy and room to roam.

18025 Cascade Estates Drive, Bend

Listing courtesy of The Agency Bend.

$2,150,000

4 Beds ⋅ 4 Baths ⋅ 220226146 MLS

What defines luxury living? It is the perfect blend of elevated design, effortless comfort, & peace of mind, which are exactly what this beautifully updated Awbrey Butte home offers. Step inside the interiors showcasing a vaulted great room with beamed ceilings, custom casework, & an impressive built-in wine bar. Significant capital updates like a new roof, recent exterior paint, new HVAC, & custom deck railings ensure your everyday is made more enjoyable. Dedicated spaces easily cater to work-from-home needs, game room fun, & flawless entertaining with a home office, bonus room, dual living spaces with fireplaces, plus a versatile lower-level flex room with exterior access. Unwind daily in the private sanctuary of the main-level primary suite that leads to the outdoor hot tub & a spa-like bath complete with heated floors. Epic adventures await from this location just minutes to Downtown Bend, NorthWest Crossing, scenic trails, & golf. Embrace the remarkable lifestyle you deserve!

1804 NW Remarkable Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$1,050,000

3 Beds ⋅ 4 Baths ⋅ 220226162 MLS

Located in Skyliner Summit in Northwest Bend, this custom home borders one of the neighborhood's expansive HOA greenspaces, creating a park-like setting with nearby trails, parks and easy access to Phil's Trail, Shevlin Park and Northwest Crossing. Designed for entertaining, the chef's kitchen features granite countertops, double ovens, double dishwashers and generous prep space flowing to multiple decks overlooking mature trees and a tranquil water feature. The main-level office sits beside a full bath, offering an ideal fourth bedroom or guest suite. Upstairs, all three bedrooms feature ensuite baths, while the expansive bonus room has been transformed into a stadium-style home theater with projector and built-in surround sound. Two wet bars, abundant storage--including a large under-house storage area--and thoughtfully designed gathering spaces complete this exceptional Northwest Bend home.

121 NW Outlook Vista Drive, Bend

Listing courtesy of eXp Realty, LLC.

$725,000

4 Beds ⋅ 3 Baths ⋅ 220226145 MLS

Looking for a big lot with enough square footage in a prime west side Bend location offering that rare combination of convenience, value, and living flexibility? Found! Welcome to a beautiful Northwest Craftsman home offering 4 bedrooms, 2.5 baths, and a main-level office with a closet that could easily serve as a 5th bedroom. Enjoy a covered front porch, formal living and dining rooms, a gas fireplace, wood interior doors, and central A/C. The kitchen features maple cabinetry, tile countertops and backsplash, SS appliances, and hickory hardwood flooring on the main. Upstairs a spacious primary suite awaits, featuring 2 closets, a ceiling fan, soaker tub, dual vanity, and tiled shower. Three additional bedrooms complete the second level. Unwind in the huge fully fenced backyard with a patio, fire pit, large storage shed, and alley access to your detached two car garage with additional parking for all your toys. Close to the Deschutes River, schools, parks, Costco, and downtown Bend!

63319 O. B. Riley Road, Bend

Listing courtesy of RE/MAX Key Properties.

$444,500

2 Beds ⋅ 2 Baths ⋅ 220226142 MLS

Recently remodeled, this 2-bedroom, 2-bath condo in desirable Mt. Bachelor Village Resort is the perfect choice for a full-time residence, vacation getaway, or income-producing short-term rental. Offering approximately 900 sq. ft., the condo features an updated interior and access to resort-style amenities including a seasonal pool, hot tubs, and a fireside room. Enjoy direct access to the Deschutes River Trail and a prime location just minutes from the Old Mill District, historic downtown Bend, dining, shopping, and entertainment. Ideally situated on the road to Mt. Bachelor, you'll have quick access to world-class skiing, snowboarding, hiking, and year-round recreation. Experience the best of the Central Oregon lifestyle.

19717 SW Mount Bachelor UNIT 260 Unit UNIT 260, Bend

Listing courtesy of RE/MAX Key Properties.

$599,000

3 Beds ⋅ 3 Baths ⋅ 220226129 MLS

Midtown Gem with Rare Short-Term Rental Eligibility! This exceptional end-unit townhome offers a rare opportunity for a future owner to pursue a STR, an increasingly valuable feature in Bend. Enjoy low-maintenance living with no HOA in desirable Midtown, with easy access to parks, restaurants, shopping, and downtown. The inviting great room features abundant natural light and a cozy gas fireplace. The thoughtfully designed kitchen features a large island, quartz countertops, a full tile backsplash, pantry, and modern finishes. Upstairs, you'll find 3 spacious bedrooms and two full baths, highlighted by a light-filled primary suite with an ensuite bathroom and generous walk-in closet. Recent upgrades include central A/C, a patio, and a radiant roof de-icing system. A rare opportunity to enjoy flexibility, convenience, and investment potential in one of Bend's most desirable neighborhoods.

750 NE Isabella Lane, Bend

Listing courtesy of Harcourts The Garner Group Real Estate.

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