BUY THE PERFECT HOME
About Denny Osborn
About Denny Osborn
Born and raised in Oregon, Denny Osborn brings over 30 years of hands-on experience in housing and real estate, starting his career in residential construction and rising to foreman before earning his real estate license in 2006. After moving to Bend, he quickly built a strong reputation by helping sell more than 200 homes in his first five years, combining deep market knowledge with a practical understanding of how homes are built. Today, Denny specializes in residential homes, land, farms, investment, and distressed properties across Central Oregon, offering clients clear guidance, honest advice, and a no-pressure approach. A dedicated outdoorsman and Habitat for Humanity volunteer, Denny takes pride in delivering professional, client-focused service rooted in local expertise and trust.
Recent Listings
849 SE Dacotah Ct Madras, OR 97741
$449,500
3 Beds | 2 Baths | 2,344 Sq. Ft.
Spacious single-level home offering 2,344 sq ft of comfortable living on a generous .37-acre lot in a quiet cul-de-sac. This 3 bedroom, 2 bathroom home features vaulted ceilings, an office, and a bonus room for flexible living options. The inviting family room boasts a natural gas fireplace and new laminate flooring, which also extends into the office and bonus room. Fresh exterior paint adds curb appeal. Outside, enjoy a 25x30 shop wired with 220 volt—perfect for projects, storage, or hobbies—plus plenty of room to park your RV, boat, or toys. Ideally located close to schools, parks, shopping, and the Madras Aquatic Center.
414 NW Riverside Blvd Bend, OR 97701
$900,000
3 Beds | 1 Bath | 2,274 Sq. Ft.
Enjoy all Bend has to offer in this charming home in the heart of Bend's Westside! Less than 2 blocks from the Deschutes River, Drake Park and mere minutes from Downtown Bend's vibrant restaurants, brew pubs, coffee shops, and shopping. This inviting 3 bedroom, 1 bath home sits on a spacious RM-zoned lot, offering endless opportunities for expansion, development, or personal enjoyment. Step inside to find a living room with a gas fireplace, kitchen with quartz countertops, and a full height basement with an additional bedroom. Enjoy the private fully fenced backyard great for relaxation and entertaining. The detached garage has been thoughtfully converted into a comfortable office space and additional sleeping area ideal for remote work and guests.
2116 NW Elm Ave Redmond, OR 97756
$440,000
3 Beds | 2 Baths | 1,448 Sq. Ft.
Charming single-level home in NW Redmond! This well maintained 3-bedroom, 2-bathroom home offers 1,448 sq. ft. of comfortable living space with a desirable open floor plan. Enjoy vaulted ceilings and a spacious great room that flows seamlessly into the kitchen featuring ample counter space, generous storage, and all appliances including the refrigerator. The primary suite includes a walk-in closet and nice separation from the additional bedrooms for added privacy. Modern features include central A/C, a tankless water heater, and a two-car garage. The fully fenced backyard with a patio provides the perfect setting for outdoor dining and entertaining. Conveniently located in NW Redmond, close to schools, parks, and shopping.
2727 NE Great Horned Place Bend, OR 97701
$549,500
3 Beds | 2.5 Baths | 1,731 Sq. Ft.
Beautiful craftsman style home on a corner lot in the desirable Oakview neighborhood in NE Bend! This turnkey and move in ready 3 bedroom, 2 1/2 bath, 1,731 sq ft home features an open light and bright main level living with a slate surround gas fireplace and new laminate floors. Kitchen with all new stainless steel appliances, pantry, and tile countertops with breakfast bar. Upstairs has all new carpet, primary bedroom with a walk-in closet and double vanity, two additional bedrooms, and a huge bonus room. A/C for the hot summer days and new interior paint. Enjoy the inviting covered front porch and fully fenced backyard with paver patio, great for entertaining. Conveniently located close to schools, shopping, restaurants, food carts, and the 159 acre Pine Nursery Park.
53382 Eagle Ln La Pine, OR 97739
$564,000
3 Beds | 2 Baths | 2,196 Sq. Ft.
Beautifully updated single level home on a spacious 1.27 acre lot! This 3 bedroom, 2 bathroom home offers a perfect blend of comfort, style and outdoor living. Spacious kitchen features stunning granite countertops, black stainless steel appliances, and plenty of space for culinary creations. The primary bedroom is a retreat in itself, complete with a large walk-in closet, soaking tub, and a heated tiled walk-in shower. Stay comfortable year found with a new furnace, heat pump and cozy wood stove. Step outside to enjoy the fully fenced private backyard providing the perfect space for entertaining and relaxing. The landscaped and irrigated front and back yards are ready for your enjoyment. Plenty of space for your RV, boat or other toys with additional space behind the backyard fence for more possibilities. Located near La Pine State Park and the Deschutes River, out door adventures are just minutes away.
PROPERTY GALLERY
TESTIMONIALS
We appreciated the help and advice from Denny Osborn of Bend Premier Estate, while buying our home. He was very professional, answered every call and concerns quickly. Denny was always upbeat and encouraging, even if things got a bit rough. His knowledge and experience put us at ease on purchasing our new home. Thank you very much Denny!
Lisa J
We've worked with Denny since 2007. He was so patient with usas we toured almost every house for sale in Bend over the next 3years. Finally, in 2011, we found our perfect home and he helped
us purchase it. When it was time to sell this spring, of course Denny was our firstchoice! He represented us so well, and connected us tocompetent contractors to get pre-sale work done. We unreservedly recommend Denny. He is patient,unpretentious, and will always give you his honest, highlyexperienced opinion.
Leslie and Laura C
Call +1-541-771-1578
Email: [email protected]