Welcome to Drew Oldfield's Real Estate Website

I was born and raised in Bend, OR. Over the years, have watched it change from a sleepy logging town to a recreation destination. I have left Central Oregon to explore the mountains of Colorado and the rivers of Idaho, but I have always been called back by what Bend has to offer. To me, Bend is not just a place to live but a life experience to be had, and it is an experience I want to share.

Prior to Real Estate, I managed a successful water sports retail shop in Bend while I attended OSU Cascades to receive a Bachelor's degree in Business Administration.

When not in the office, you can find me floating down one of the many beautiful Oregon waterways in my whitewater kayak, or raft. During summer mornings I spend my time riding around Phils’s Trail Complex with anyone willing to partake in a 5am bike rides. After work, I enjoy time walking in the National Forest with my wife and two dogs.

For me, buying a house in Central Oregon is not just buying a house, but buying an experience. The experience is the way to access all that Bend and the surrounding areas have to offer.

Bend 24-hour Hot Sheet of New Listings

You Will Love This Contemporary Beauty In Bend'...

NEW

$1,495,000 Active

• 4 Beds
• 4 Baths
• 0.43 Acres
• 3,297 ft²

Residential

2164 Nw Lolo Drive, Bend, OR

MLS® #220110956

You Will Love This Contemporary Beauty In Bend's Premier Westside Neighborhood Of Northwest Crossing. The Unobstructed Southern Exposure Is Capturedthrough Large Wood Wrapped Windows And Sky Lights. 10 Foot Ceilings And Hardwood Floors Provide A Feeling Of ...

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John L Scott Bend

Rich In Detail And Classic Finishes, This Disti...

NEW

$975,000 Active

• 4 Beds
• 3 Baths
• 0.18 Acres
• 2,436 ft²

Residential

2728 Nw Nordic Avenue, Bend, OR

MLS® #220111128

Rich In Detail And Classic Finishes, This Distinctive Valhalla Heights Home, Built By Cloninger Custom Homes, Provides Proximity To All That Bend's Westside Has To Offer. Custom Ironwork Railings, Beautiful Slate Floors & Thoughtfully Designed Cabinetry Are...

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Duke Warner Realty

Hard To Find Builder-owned Custom Home On Five ...

NEW

$879,000 Active

• 3 Beds
• 3 Baths
• 5 Acres
• 2,042 ft²

Residential

60436 Rimfire Road, Bend, OR

MLS® #220111069

Hard To Find Builder-owned Custom Home On Five Acres In A Beautiful Treed Setting. Single Story Home That Has Functional Floorplan With Vaulted Ceilings, A River Rock Fire Place, Real Hardwood Trim And Doors Throughout, A Spacious Master Suite With Walk-in ...

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Tim Davis Group Central Oregon

Beautiful Townhome Located In The Desirable Old...

NEW

$795,000 Active

• 3 Beds
• 4 Baths
• 0.04 Acres
• 2,311 ft²

Residential

890 Sw Crestline Drive, Bend, OR

MLS® #220111129

Beautiful Townhome Located In The Desirable Old Mill District Of Bend. This Is The Perfect Launching Pad For All Your Central Oregon Activities. Nearby You'll Find Shops,restaurants, Theaters, The Deschutes River, Outdoor Concert Venue, Forest Trails, White...

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Cascade Sotheby's Int'l Realty

Stunning New Construction Home On A Large 1/2 A...

NEW

$640,000 Active

• 4 Beds
• 3 Baths
• 0.48 Acres
• 2,334 ft²

Residential

17395 Kingfisher Drive, Bend, OR

MLS® #220110860

Stunning New Construction Home On A Large 1/2 Acre Corner Lot. Oregon Water Wonderland Offers Well Maintained Paved Roads, Boat Dock And 40 Acres Of Trails Along The River. Enjoy This Open & Inviting Floorplan Highlighting 9 Ft Ceilings, Natural Light, A/c ...

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Fred Real Estate Group

Amazing Opportunity To Own This One Of A Kind H...

NEW

$599,000 Active

• 2 Beds
• 3 Baths
• 0.07 Acres
• 2,688 ft²

Residential

47 Nw Hastings Place, Bend, OR

MLS® #220111042

Amazing Opportunity To Own This One Of A Kind Home In Nw Bend! Just A Few Blocks From Downtown, The Cg Zoning Allows For Short Term Rentals And/or Commercial Space. The Home Was Originally Designed To Have The Option Of The Upstairs Being Its Own Separate ...

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Assist 2 Sell Buyers & Seller

Warm And Inviting Single-level Home In Desirabl...

NEW

$557,500 Active

• 3 Beds
• 2 Baths
• 0.21 Acres
• 2,004 ft²

Residential

868 Se Shadowood Drive, Bend, OR

MLS® #220110457

Warm And Inviting Single-level Home In Desirable Tanglewood. Spacious Living Room With Dining Area Features A Cozy Gas Fireplace And Vaulted Ceilings. Arched Doorways Add Charm And Large Windows Bring In The Natural Light. Open Family Room And Kitchen Off...

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Brooks Resources Realty

Pride Of Ownership Is How To Best Describe This...

NEW

$539,900 Active

• 3 Beds
• 3 Baths
• 0.17 Acres
• 1,638 ft²

Residential

1789 Se Ironwood Court, Bend, OR

MLS® #220111048

Pride Of Ownership Is How To Best Describe This Home! Owners Have Lovingly Updated And Maintained All Aspects Of This Property. The Interior Is Nicely Updated With Slab Granite Counter Tops In The Kitchen And Baths, Hardwood, Tile And Carpet Flooring Throug...

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Coldwell Banker Bain

Gorgeous One Level Home Lives New. Light And Br...

NEW

$509,900 Active

• 3 Beds
• 2 Baths
• 0.13 Acres
• 1,912 ft²

Residential

63362 Tristar Drive, Bend, OR

MLS® #220111109

Gorgeous One Level Home Lives New. Light And Bright. Located In Upscale Ne Neighborhood Of Horizon Ridge. Energy Efficient Construction W/upgraded Finishes. Slab Granite Countertops, Hardwood Floors. Huge Master Bedroom W/luxury Master Bath Which Features...

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Cascade Sotheby's Int'l Realty

Excellent Close In Ne Location. 2 Bedrooms And ...

NEW

$475,000 Active

• 2 Beds
• 2 Baths
• 0.14 Acres
• 6,098 ft²

Multi-Family

443 Ne Clay Avenue, Bend, OR

MLS® #220111101

Excellent Close In Ne Location. 2 Bedrooms And 2 Baths, Single Level Units With Single Car Attached Garages. 950 Sq Ft Each With Newer Carpet And Storage Sheds. Long Term Tenants Who Want To Stay Pay All Utilities Except Sewer And Water.

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Coldwell Banker Bain

Immaculate Like New Home In Quiet Ne Bend Neigh...

NEW

$474,900 Active

• 3 Beds
• 2 Baths
• 0.15 Acres
• 1,668 ft²

Residential

2894 Ne Rainier Drive, Bend, OR

MLS® #220111063

Immaculate Like New Home In Quiet Ne Bend Neighborhood. You Will Love This Single Level Open Concept Home With A Spacious Kitchen And Island. The Home Features New Vinyl Plank Floors, Quartz Kitchen Counters, Stainless Steel Appliances, Gas Cook Top With ...

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Team Birtola High Desert

Beautiful Craftsman Style Home In Bend, Minutes...

NEW

$450,000 Active

• 4 Beds
• 3 Baths
• 0.12 Acres
• 1,748 ft²

Residential

61472 Brosterhous Road, Bend, OR

MLS® #220111006

Beautiful Craftsman Style Home In Bend, Minutes From The Old Mill, With 4 Bedrooms, 3 Bathrooms, Master On The Main, Updated Kitchen And Master Bathroom, Laundry Room, Gas Fireplace, Vinyl Floors Downstairs, Ac, Fenced Backyard Perfect For Entertaining Andm...

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Fred Real Estate Group