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
Bendtrend's Mountain Modern Luxury Coupled With...
$2,500,000 Active
- 5 Beds
- 5½ Baths
- 0.55 Acres
- 4,756 ft²
Residential
61846 Sw Hosmer Lake Drive, Bend, OR
MLS® #201910799
Bendtrend's Mountain Modern Luxury Coupled With An Unsurpassed Design Makes This Home One Of Tetherow's Finest Properties. 5 Spacious Bedrooms Including 4 En-suites, 5 Full Baths And A Powder Bath. Spacious Den, Bonus Room And Additional Separate Flex Room ...

Chic New Modern Home In Tartan Druim. Currently...
$1,819,750 Active
- 4 Beds
- 4½ Baths
- 0.62 Acres
- 3,994 ft²
Residential
19226 Cartwright Court, Bend, OR
MLS® #201910822
Chic New Modern Home In Tartan Druim. Currently Under Construction, This Open 4 Bedroom, 4.5 Bath Home Features Two Main Level Suites, Study And Two Additional Second Level En-suites And Media/bonus Room. Luxuriously Finished W/solid Surfaces, Woods, Custom...

Ne Bend 2-homes, 13+ Acres, 4000sf Shop! Proper...
$1,097,000 Active
- 4 Beds
- 3½ Baths
- 13.25 Acres
- 3,140 ft²
Residential
23367 Alfalfa Market Road, Bend, OR
MLS® #201910815
Ne Bend 2-homes, 13+ Acres, 4000sf Shop! Property Consists Of A Remodeled 3140sf 3bd/3.5ba Home W/2 Suites, Great Room W/gas Fp, Sep Family Room W/wood Stove, 2+car Heated-garage W/office + 1100sf 2bd/1ba Log Cabin Guest-house And A 4000sf Heated-shop W/2 1...

Whether Your Travels Lead You Around The Resort...
$829,000 Active
- 5 Beds
- 5½ Baths
- 0.21 Acres
- 2,592 ft²
Residential
19216 Lot 19 Gateway Loop, Bend, OR
MLS® #201910838
Whether Your Travels Lead You Around The Resort Or Across The Region, The Trailhead Vacation Homes At Tetherow Serve As Your Basecamp. Conveniently Begin Your Adventure Of Biking Phil's Trail, Skiing Mt. Bachelor Or Climbing Smith Rock Right From Tetherow. ...

Charming Northwest Crossing Prairie Styled Home...
$799,000 Active
- 3 Beds
- 2½ Baths
- 0.14 Acres
- 2,127 ft²
Residential
2299 Nw High Lakes Loop, Bend, OR
MLS® #201910823
Charming Northwest Crossing Prairie Styled Home Has Been Lovingly Updated With Newer Interior Finishes. Solid Pentel Quartz Counter, Subway Tile, Maple Hardwood Floors, Floor To Ceiling Stone Fireplace, Barn Doors. Master Bedroom On Main With Two Larger Be...

Development Potential, Currently Zoned Rs. This...
$780,000 Active
- 5 Beds
- 3 Baths
- 1.11 Acres
- 1,800 ft²
Residential
61621 Se 27th Street, Bend, OR
MLS® #201910820
Development Potential, Currently Zoned Rs. This Property Can Be Sold With 61626 Daly Estate Dr To Create A Contiguous 2.2 Acre Replat Of Land Partition With Multiple Opportunities. Home Has Attached Mother-in-law Suite. Shared Utility Room. Great Mult-gener...

Whether Your Travels Lead You Around The Resort...
$774,000 Active
- 5 Beds
- 5½ Baths
- 0.19 Acres
- 2,289 ft²
Residential
19126 Lot 3 Gateway Loop, Bend, OR
MLS® #201910837
Whether Your Travels Lead You Around The Resort Or Across The Region, The Trailhead Vacation Homes Serve As Your Base Camp. Conveniently Begin Your Adventure Of Biking Phil's Trail, Skiing Mt Bachelor Or Climbing Smith Rock Right From Tetherow. This Turn-ke...

Situated On A Spacious .18 Acre Corner Lot 1 Bl...
$759,900 Active
- 4 Beds
- 3 Baths
- 0.18 Acres
- 1,902 ft²
Residential
2427 Nw High Lakes Loop, Bend, OR
MLS® #201910758
Situated On A Spacious .18 Acre Corner Lot 1 Block From Compass Park And Across From High Lakes Elementary, This Solaire Built Single Level Home Provides Plenty Of Elbow Room In Desirable Northwest Crossing. This Home Benefits From A Few Unique Energy-effic...

1920's Mountain Cottage In Historic Distr...
$649,000 Active
- 2 Beds
- 1 Baths
- 0.13 Acres
- 960 ft²
Residential
201 Nw Harriman Street, Bend, OR
MLS® #201910808
1920's Mountain Cottage In Historic District On Rm Lot. Value Is In The Extensive Remodel And Rm Zoning With Great Potential For Additional Dwellings. 2 Bedroom, 1 Bath, 960 Sq Ft And Useful Basement. Superb Location By Market Of Cho...

Incredibly Charming Craftsman Style Home Offers...
$530,000 Active
- 3 Beds
- 2½ Baths
- 0.13 Acres
- 2,452 ft²
Residential
19757 Baneberry Avenue, Bend, OR
MLS® #201910811
Incredibly Charming Craftsman Style Home Offers Quick Access To The River Trail And Old Mill. This Home Sits In One Of Bend's Most Popular Sw Neighborhoods And Welcomes You Into A Spacious Great Room With Vaulted Ceilings And Fireplace. The Light And Bright...

Peaceful Single Level, Ranch-style Home Nestled...
$468,000 Active
- 4 Beds
- 2 Baths
- 0.93 Acres
- 2,404 ft²
Residential
60282 Cree Circle, Bend, OR
MLS® #201910841
Peaceful Single Level, Ranch-style Home Nestled In The Pines Of Sw Bend. Perfect For A Growing Family With Room For Lots Of Toys And Space For All-terrain Vehicles. On Nearly 1 Acre With Bamboo And Wood Floors Throughout, This 4 Bedroom, 2 Bath Home Draws Y...

Development Potential, Currently Zoned Rs. This...
$405,800 Active
- 0.95 Acres
- 41,382 ft²
Land
61620 Se Daly Estates Dr Drive, Bend, OR
MLS® #201910826
Development Potential, Currently Zoned Rs. This Property Can Be Sold With 61621 Se 27th Street To Create A Contiguous 2.2 Acre Replat Of Land Partition With Multiple Opportunities.

The content relating to real estate for sale on this website comes in part from the MLS of Central Oregon. Real Estate listings held by Brokerages other than Bend Premier Real Estate are marked with the Reciprocity/IDX logo, and detailed information about these properties includes the name of the listing Brokerage. © MLS of Central Oregon (MLSCO).
This content last updated on December 13th, 2019 at 1:59pm PST. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.
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