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
Experience An Extraordinary Life. Oregon Green ...
$14,500,000 Active
- 4 Beds
- 6 Baths
- 123.74 Acres
- 8,358 ft²
Residential
65245 Cline Falls Road, Bend, OR
MLS® #220106751
Experience An Extraordinary Life. Oregon Green Splendor Blends With Equestrian Excitement On This 123 Acre Private Ranch In The Heart Of Central Oregon Minutes From Bend. Surrounded By The Cascade Range, The Mountain Views Are Breath Taking & With Central O...
Century Drive Development Site At Century Drive...
$7,450,000 Active
- 4.87 Acres
- 212,137 ft²
Land
1081 Mount Bachelor Drive, Bend, OR
MLS® #220104338
Century Drive Development Site At Century Drive And Mt. Washington Drive With Cascade Mountain Views. Zoned Cl - Commercial Limited Which Permits Multi-family, Residential, Office, Retail, Restaurant, Hotel, Medical, Entertainment And Mixed Use Projects. Th...
A Unique Opportunity For A Luxury Estate Home O...
$4,500,000 Active
- 4 Beds
- 6 Baths
- 1.48 Acres
- 5,516 ft²
Residential
65823 Bearing Drive, Bend, OR
MLS® #220105134
A Unique Opportunity For A Luxury Estate Home On The 2nd Hole Of The Jack Nicklaus Course At The Exclusive Pronghorn Golf Club. This 5516 Sq Ft Custom Home Is Timeless, Great Room With Stone Fireplace, Gourmet Kitchen, Formal Dining Room, Custom Bar, Master...
The Lifestyle Of Bend Oregon Is All Wrapped Up ...
$3,300,000 Active
- 3 Beds
- 4 Baths
- 40 Acres
- 4,001 ft²
Residential
18776 Hakamore Drive, Bend, OR
MLS® #220106814
The Lifestyle Of Bend Oregon Is All Wrapped Up In This Incredible Home Beautifully Situated On 40 Acres. Only 15 Minutes To Downtown And All The Incredible Activities Central Oregon Is Famous For. Take A Dip In The Infinity Pool, Ride Your Mountain Bike, Hi...
Beautiful And Meticulously Cared For Peaceful R...
$2,200,000 Active
- 5 Beds
- 3 Baths
- 12.85 Acres
- 2,935 ft²
Residential
63440 Hamehook Road, Bend, OR
MLS® #220106590
Beautiful And Meticulously Cared For Peaceful Retreat Just Minutes From Town. 12.85 Acres Of Very Private Park-like Grounds With 5 Acres Of Irrigation Make For An Oasis Like No Other. Wonderful Wrap Around Decks To Find The Perfect Spot Of Sun Or Shade Th...
High Desert Landscape, Cascade Mountain Views A...
$1,689,750 Active
- 3 Beds
- 4 Baths
- 0.56 Acres
- 3,466 ft²
Residential
19202 Cartwright Court Lot 255, Bend, OR
MLS® #220105829
High Desert Landscape, Cascade Mountain Views And The Big Bend Sky Are Just A Few Natural Elements To Be Enjoyed From Back Of This New Nw Modern Home In Tartan Druim. Situated On Just Over A Half Acre, This 3,466 Sf Home Features A Main Level Master Suite, ...
If There Is A Better Down Town Bend Parcel To D...
$1,600,000 Active
- 0.37 Acres
- 16,117 ft²
Land
1563 Nw 1st Street, Bend, OR
MLS® #220106146
If There Is A Better Down Town Bend Parcel To Develop We Don't Know Of It. Located In The Heart Of Historic Down Town Bend With Easy Access To Parks, Shopping, Markets, Restaurants And More. These Two Rm Tax Lots Contain An Old Church Building And The Re...
Peace-privacy-beauty-quality, Inside And Out. A...
$1,599,999 Active
- 3 Beds
- 4 Baths
- 9.48 Acres
- 3,468 ft²
Residential
65800 Mariposa Lane, Bend, OR
MLS® #220106977
Peace-privacy-beauty-quality, Inside And Out. A Star Gazers Paradise With Stunning Mountain Views, Ideally Situated 20 Minutes To Bend, Redmond And Sisters. Custom Details Begin At The Leaded Glass Entry Door, Leading To A Barrel Vaulted Gallery With Heated...
One-of-a-kind Texas Style Farmhouse Resting On ...
$1,595,000 Active
- 3 Beds
- 4 Baths
- 5.17 Acres
- 4,321 ft²
Residential
60540 Billadeau Road, Bend, OR
MLS® #220106916
One-of-a-kind Texas Style Farmhouse Resting On Over 5 Acres. Just Minutes From Bend, You'll Appreciate The Convenience Yet Feel Distanced Enough To Enjoy The Serenity Of Private Small Acreage Living. Down A Long Paved Driveway, Surrounded By Mature Pine Tre...
Rare Opportunity To Purchase A Home In The Hear...
$1,590,000 Active
- 4 Beds
- 2 Baths
- 0.24 Acres
- 2,949 ft²
Residential
525 Nw Broadway Street, Bend, OR
MLS® #220106651
Rare Opportunity To Purchase A Home In The Heart Of The Historic District! This Venerable Residence, Built In 1936, Is Located Just Twoblocks From Drake Park And Two Blocks From Downtown -- Within Easy Walking Distance Of Bend's Central Shopping District An...
Privacy, Tranquility, Space And Stunning Views ...
$1,549,000 Active
- 3 Beds
- 4 Baths
- 0.54 Acres
- 3,591 ft²
Residential
65885 Pronghorn Estates Drive, Bend, OR
MLS® #220106869
Privacy, Tranquility, Space And Stunning Views Within 25 Minutes From Downtown Bend. Graciously Situated On .54/acre With Breathtaking Fairway, Lake And Cascade Mountain Views, This Timeless Pronghorn Home Offers Unsurpassed Craftsmanship And Design. Dramat...
Beautiful And Timeless, This Custom Built Craft...
$1,388,000 Active
- 5 Beds
- 4 Baths
- 0.45 Acres
- 4,733 ft²
Residential
19445 Tam Lake Court, Bend, OR
MLS® #220106902
Beautiful And Timeless, This Custom Built Craftsman Is Situated On A Private .45 Acre Lot In Broken Top - One Of Bend's Premiere Golf Communities. Fine Craftsmanship, Elegant Hardwoods And Quality Finishes Are Found Throughout This Impressive Home. Large ...
© 2020 Oregon Datashare (KCAR | MLSCO | SOMLS). All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Oregon Datashare. Real estate listings held by IDX Brokerage firms other than Bend Premier Real Estate are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. The consumer will not copy, retransmit nor redistribute any of the content from this website. Information provided is deemed reliable, but not guaranteed. Listing courtesy of Bend Premier Real Estate. Data last updated: August 14th, 2020 at 11:45pm PDT.