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

Welcome To Villa Tranquille! This Custom Chatea...

NEW

$1,125,000 Active

• 4 Beds
• 3½ Baths
• 0.29 Acres
• 2,543 ft²

Residential

61249 Gorge View Street, Bend, OR

MLS® #201908287

Welcome To Villa Tranquille! This Custom Chateau-style Retreat Offers A Chef's Kitchen, High Ceilings, Built-in Hot Tub And Must-see Outdoor Kitchen. From The Main House, Just Across The Courtyard Is The 1 Bd, 1 Ba Cottage With Kitchenette And Beautiful Sto...

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eXp Realty, LLC

Located On The High Plateau At Tetherow Featuri...

NEW

$1,100,000 Active

• 4 Beds
• 3 Baths
• 0.2 Acres
• 2,736 ft²

Residential

19325 Lot 9 Outrider Loop, Bend, OR

MLS® #201908305

Located On The High Plateau At Tetherow Featuring Amazing Solar Exposure & Long-range Views Of The Paulina Mountains, Find This Impressive Nw Contemporary Home. Slated For A Fall 2019 Completion By Award-winning Simplicity Homes, Find Mostly Main Level Livi...

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Cascade Sotheby's International Realty

The Northwest Crossing Lifestyle Is Epitomized ...

NEW

$799,000 Active

• 4 Beds
• 2½ Baths
• 0.14 Acres
• 2,378 ft²

Residential

2336 Nw Dorion Way, Bend, OR

MLS® #201908291

The Northwest Crossing Lifestyle Is Epitomized At The Inviting Front Patio And Into The Open Great Room Where Friends & Family Love To Gather. The Main Floor Master Has Privacy From The Upstairs Bedrooms; The Main Floor Office Enjoys Sunshine And A Quiet Pl...

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Cascade Sotheby's International Realty

Endless Charm In This 1,218 Sq Ft, 3 Bed, 1 Bat...

NEW

$699,500 Active

• 4 Beds
• 2 Baths
• 0.13 Acres
• 1,768 ft²

Residential

1446 Nw 5th Street, Bend, OR

MLS® #201908318

Endless Charm In This 1,218 Sq Ft, 3 Bed, 1 Bath Home With Ample Parking And A Permitted 550 Sq Ft 1 Bed, 1 Bath Adu With Alley Access/parking In Back! This Tudor Cottage Was Lovingly Built By Kirby Nagelhout For His Personal Residence To Raise His Family....

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Stellar Realty Northwest

This Beautiful Nw Craftsman Home Provides The P...

NEW

$559,000 Active

• 3 Beds
• 3 Baths
• 0.09 Acres
• 1,905 ft²

Residential

19372 Brookside Way, Bend, OR

MLS® #201907688

This Beautiful Nw Craftsman Home Provides The Perfect Base Camp For All The Best Of Central Oregon. The Community Of Braeburn Is Tucked Just Off Of Century Drive, On The Westside Of Bend. Biking, Hiking & The Deschutes River Trail Are Just Minutes Away & On...

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Duke Warner Realty

If You're Looking For A Sophisticated, Contempo...

NEW

$539,990 Active

• 4 Beds
• 2 Baths
• 0.31 Acres
• 1,996 ft²

Residential

60995 Se Sweet Pea Drive, Bend, OR

MLS® #201908290

If You're Looking For A Sophisticated, Contemporary Home That Doesn't Sacrifice Warmth, This Home May Have Your Name On It. Built By Simplicity Homes In 2019, This Beautiful Home In Cascade Heights Offers Single-level Living, Quartz Countertops Throughout, ...

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Cascade Sotheby's International Realty

Stunning Single Level Home In Bend Or From Qual...

NEW

$537,900 Active

• 3 Beds
• 2½ Baths
• 0.13 Acres
• 2,105 ft²

Residential

20878 Lot 327 Se Sunniberg Lane, Bend, OR

MLS® #201908316

Stunning Single Level Home In Bend Or From Quality Builder - Pahlisch Homes! Open Great Room With Chef's Kitchen, Walk In Pantry, Built In Kitchenaid Appliances, Quartz Counters, Hardwood Flooring. Master Features A Tile Shower, Soaker Tub & Large Walk-in...

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Pahlisch Real Estate, Inc.

Luxurious Upgrades Galore In This Mid-century M...

NEW

$529,000 Active

• 3 Beds
• 2 Baths
• 0.15 Acres
• 1,600 ft²

Residential

63360 O B Riley Road, Bend, OR

MLS® #201908215

Luxurious Upgrades Galore In This Mid-century Modern/usonian-style Home. Inspired By Frank Lloyd Wright, This Home Focuses On Creating A Connection Between Indoor & Outdoor Living Areas With Large Windows, Outdoor Spaces & Lots Of Natural Light. Thoughtfull...

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RE/MAX Key Properties

Woodhill Homes Built 3 Bedroom, 2.5 Bathroom, P...

NEW

$480,000 Active

• 3 Beds
• 2½ Baths
• 0.14 Acres
• 2,325 ft²

Residential

2972 Ne Conners Avenue, Bend, OR

MLS® #201908149

Woodhill Homes Built 3 Bedroom, 2.5 Bathroom, Plus An Office, Plus A Bonus Room. This Home Is Light And Bright, Quality Heavy Construction With A Superb Flow Layout. Tons Of Windows Bring In Beautiful Light And Landscaping Views, Awesome Cook's Kitchen, Org...

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Bend Premier Real Estate LLC

Beautiful Single Level Home On A Quiet Cul-de-s...

NEW

$479,900 Active

• 3 Beds
• 2 Baths
• 0.14 Acres
• 1,893 ft²

Residential

63140 Peale Street, Bend, OR

MLS® #201908200

Beautiful Single Level Home On A Quiet Cul-de-sac In The Highly Desirable Community Of Yardley Estates! This Like-new Home Built By Bearup Construction Features A Great Room Floor Plan, Chef's Kitchen, Soaring Vaulted Ceilings With Skylights, Spacious Mast...

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Duke Warner Realty

Fantastic Single Level Home On A .25 Of An Acre...

NEW

$425,000 Active

• 4 Beds
• 2 Baths
• 0.25 Acres
• 1,900 ft²

Residential

20859 Dione Way, Bend, OR

MLS® #201908298

Fantastic Single Level Home On A .25 Of An Acre Lot In The Tranquil Starwood Community In Nw Bend. Cascade Mountains And Wide-open Field Views From The Expansive Deck. Vaulted Ceilings Allow This Four Bedroom Home To Live Large And Bright. One Bedroom Is Pe...

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Keller Williams Realty Central Oregon

A Wonderful Open Concept Floor-plan In Emerging...

NEW

$409,900 Active

• 4 Beds
• 2½ Baths
• 0.1 Acres
• 2,192 ft²

Residential

61134 Brown Trout Place, Bend, OR

MLS® #201908280

A Wonderful Open Concept Floor-plan In Emerging Se Bend. This House Lives Large With 4 Bedrooms And 2.5 Bathrooms Plus A Flex/office Space. Upgrades Include Ac, Slab Granite Counter-tops, Stainless Steel Appliances, A Subway Tile Back-splash In The Kitchen ...

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Coldwell Banker Morris Real Estate