JEFF CASSERLY

YOUR CENTRAL OREGON BROKER

NAVIGATING CENTRAL OREGON REAL ESTATE

FLAG-CITY-MOONEY-Final2

After 40+ years as a broker, I know a truth that is impossible to deny: Experiences learned daily and face to face resolution of challenges (*and there are always challenges) lead to successful transactions and very happy clients. Anyone who has passed their RE license exam and paid their fees can qualify to manage a property listing or sale; and we all began our careers that way…. but is that enough for you; perhaps not?

When you list or sell a property you entrust the chosen broker with your future. When the dust settles, every penny earned through a closed transaction counts and your wellbeing may depend on the results. You know you would sleep better with a Proven local Professional on your side; a Broker who practices and has proven many times over a commitment to the rule of “Fiduciary Responsibility” to their clients. But who?

Allow me to tell you where I started and why I am worth a second look.
It all begins on the shores of Lake Michigan in the in the “Heart of the Fruit Belt” at the SW corner of that State. I was raised in a small town very similar to that of Central Oregon communities like Redmond or Prineville. I was an active and inquisitive youth with a parochial school education, plenty of sports, 11 years of Boy Scouting and an Eagle Scout rank; and my life was a continuous outside existence in summer and winter. I truly was the helpful neighborhood boy who could be relied upon.

At 18 years of age, I pulled up stakes and headed to California, joined the Marines, and spent some time in SE Asia (and other places) but always dreaming of Oregon. But first it was to Arizona, then back to California and finally in 2006 I discovered Central Oregon and my permanent spot in Crooked River Ranch. The Central Oregon community recognized something and opened its arms and said come join in.
With my previous history in business, construction, Community Service and as an active Real Estate Broker; CO turned out to be the perfect fit for my temperament, skills and knowledge; however with the welcome CO expected my integration and involvement into local community life.

Over my past 15+ year engagement in CO, and as a Redmond Rotarian, (including the Club Presidency), I’ve been involved in numerous local
support functions including Shots for Tots, our annual Daddy Daughter Dance, and the Deschutes County Fair ticket sales.
As a member Redmond VFW I have been the spearpoint of many Veterans support programs, spent 2 years as Post Commander, 3 years as House
Committee Chairman, and finally Director of an effort to bring the largest Traveling Vietnam Wall of Honor to Redmond in 2010.
Today as the Director of the Flag City USA Project I oversee and manage volunteer groups who place 1,800+/- US flags throughout the streets of Redmond at least 6 times per year with an occasional special public event or promotion project to increase awareness of our Nations Flag.

And with all these group activities, a good wife to care for, and a little ranch to maintain; I still do what I do best 5 -6 days a week: perform my duties as licensed Oregon Principal Broker which is Listing and Selling Residential, Land, and Commercial Central Oregon property.

Take a moment and Cruise through this web site, shop a little and dream a lot. All actively listed properties in our MLS area are here.
And never hesitate for request your homes current Comparative Property Market Analysis/Value Estimate.

Call or text your questions or comments and let’s discuss the market that we are in today, and where we may be headed.
So for questions about pricing or the market conditions, residential or commercial property, lease rates or land values; call, text or e-mail,
because this is what I’m continuously trained for and what I truly love to do…meet folks just like you. Central Oregon is the place to be and now it’s the only place for me.

Thanks for stopping by this site…I do look forward to meeting you. Let’s chat.

Jeff Casserly

Principal Broker, Licensed in the state of Oregon

Downtown | Redmond
622 NW Cedar Ave
Redmond, OR 97756

Featured Listings

210 matches found

$324,900
553 SW 12th Street, Redmond, OR 97756
View Photos (2)
Status: Pending
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 1
Square Footage: 1215
Year Built: 1945
Subdivision: North Mountain View
Description: Closing out a family estate in the heart of Redmond. A large corner lot, 12...
Listing Office: Desert Sky Real Estate LLC
Last Updated: June - 03 - 2026
$730,000
2428 SW Wickiup Court, Redmond, OR 97756
View Photos (9)
Status: Closed
Property Type: Residential Income
Square Footage: 3811
Year Built: 2002
Subdivision: N/A
Description: Fully rented triplex in SW Redmond. Each unit has 2 full bedrooms with addi...
Listing Office: Stellar Realty Northwest
Last Updated: May - 27 - 2026
$750,000
2416 SW Wickiup Court, Redmond, OR 97756
View Photos (17)
Status: Closed
Property Type: Residential Income
Square Footage: 3811
Year Built: 2002
Subdivision: Fieldstone
Description: Extremely clean and well maintained Triplex. . Close to shopping, parks, sc...
Listing Office: Desert Sky Real Estate LLC
Last Updated: May - 27 - 2026
$148,000
420 NE Combs Flat Road, Prineville, OR 97754
View Photos (7)
Status: Closed
Property Type: Residential Income
Square Footage: 3072
Year Built: 1938
Description: Very special property with lots of income potential and in a great area of ...
Listing Office: Simmons Realty
Last Updated: May - 27 - 2026
$285,000
Bend, OR 97702
View Photos (21)
Status: Closed
Property Type: Residential Income
Square Footage: 2461
Year Built: 2003
Subdivision: Three Sisters
Description: Clean, spacious duplex in SW Bend with a 3 bdrm, 2.5 bath unit, and a 2 bdr...
Listing Office: Desert Sky Real Estate LLC
Last Updated: May - 27 - 2026
$299,500
864 SW 3rd Street, Madras, OR 97741
View Photos (14)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 1
Square Footage: 1308
Year Built: 1949
Subdivision: Nw Townsite
Description: Possibility at the right price... Sturdy and well maintained SFR. Older but...
Listing Office: Desert Sky Real Estate LLC
Last Updated: May - 05 - 2026
$790,000
3855 NW Montgomery Avenue, Redmond, OR 97756
View Photos (41)
Status: Closed
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 1712
Year Built: 1997
Subdivision: West C Acres
Description: Looking for a hidden Country Home that's close to Redmond but just off the ...
Listing Office: Desert Sky Real Estate LLC
Last Updated: April - 22 - 2026
$499,500
2444 SW 33rd Street, Redmond, OR 97756
View Photos (32)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1409
Year Built: 2001
Subdivision: Savannah Estates
Description: ***NEW ROOF installed February 2026.*** Eliminate home repair worries. Full...
Listing Office: Desert Sky Real Estate LLC
Last Updated: April - 22 - 2026
$189,900
0 SW Copley Rd, Powell Butte, OR 97753
View Photos (9)
Status: Closed
Property Type: Land
Subdivision: N/A
Description: Fantastic opportunity to build your new home on 5.04 acres in Powell Butte!...
Listing Office: JMA Properties LLC
Last Updated: March - 18 - 2026
$392,250
3746 SW Volcano Place, Redmond, OR 97756
View Photos (20)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 1940
Year Built: 1994
Subdivision: Cascade View Estates
Description: Well maintained home in the established sought after neighborhood of Cascad...
Listing Office: Realty Net of Central Oregon
Last Updated: March - 16 - 2026
$350,000
3468 NE 29th Street, Redmond, OR 97756
View Photos (12)
Property Type: Land
Subdivision: Lake Park Estate
Description: PRIVACY WITH A VIEW.. Here's fenced acreage close to Redmond, An easy mix ...
Listing Office: Desert Sky Real Estate LLC
Last Updated: March - 04 - 2026
$360,000
7568 SW Nighthawk Lane, Terrebonne, OR 97760
View Photos (27)
Status: Closed
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 1
Square Footage: 960
Year Built: 1991
Subdivision: Crr 2
Description: Secluded home in a preferred and very private valley neighborhood. Close to...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$550,000
1144 NW Spruce Avenue, Redmond, OR 97756
View Photos (27)Virtual Tours (1)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1624
Year Built: 2005
Subdivision: Bella Sera
Description: Wonderful, single level 3 bedroom/2 Bath, 1624 SF home, located in Desirabl...
Listing Office: John L Scott Bend
Last Updated: February - 10 - 2026
$75,000
8530 NW 2nd Street, Terrebonne, OR 97760
View Photos (7)
Status: Closed
Property Type: Land
Subdivision: Hillman
Description: One of the few remaining buildable lots in Terrebonne with septic perc tes...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$40,000
8410 NW 6th Street, 1,2,3, Terrebonne, OR 97760
View Photos (7)
Status: Closed
Property Type: Land
Subdivision: Hillman
Description: Big builder corner lot. Great location across the street from elementary sc...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$417,000
494 NE Spruce Court, Redmond, OR 97756
View Photos (21)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1234
Year Built: 2010
Subdivision: Vista Dorado
Description: A corner lot on a short cul d' sac. A very comfortable well maintained home...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$659,000
West facing entry
View Photos (33)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1936
Year Built: 2006
Subdivision: Sterling Pointe
Description: Superb location overlooking Dry Canyon. Watch the sun come up in the East a...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$20,000
0 lots: 1,2,3,8,9 on 6th Street, Terrebonne, OR 97760
View Photos (3)
Status: Closed
Property Type: Land
Subdivision: Hillman
Description: Lots surrounding existing house. Tear down house and build larger home or t...
Listing Office: Red Door Realty
Last Updated: February - 10 - 2026
$85,000
546 NW 7th Street, Redmond, OR 97756
View Photos (12)
Status: Closed
Property Type: Commercial/Industrial
Subdivision: Collins
Description: Great opportunity to start a new business or move your current business to ...
Listing Office: H & H Preferred Real Estate
Last Updated: February - 10 - 2026
$600,000
424 NE Hawthorne Avenue, Bend, OR 97701
View Photos (7)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1512
Year Built: 1935
Subdivision: Center
Description: POSSIBILITIES abound in this older 3 bedroom, 2 bath home located close to ...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$550,000
8421 SW Basalt Drive, Terrebonne, OR 97760
View Photos (53)Virtual Tours (1)
Status: Closed
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 2
Square Footage: 2728
Year Built: 2003
Subdivision: Crr
Description: How about this oasis in the high desert, offering supreme privacy, seclusio...
Listing Office: Bend Premier Real Estate LLC
Last Updated: February - 10 - 2026
$74,000
6126 NW Foster Street, Prineville, OR 97754
View Photos (22)
Status: Closed
Property Type: Land
Subdivision: Golden Horseshoe
Description: Back to back lots on a subtle slope allowing for very nice views of Grizzle...
Listing Office: Coldwell Banker Sun Country
Last Updated: February - 10 - 2026
$50,000
457 SW 6th Street, Redmond, OR 97756
View Photos (5)
Status: Closed
Property Type: Business Opportunity
Description: Opportunity to purchase a well known and rapidly expanding donut and deli s...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026
$195,000
1 Parcel SW Highland Lane, Culver, OR 97734
View Photos (7)
Status: Closed
Property Type: Land
Subdivision: CLAJ
Description: 54 Acres in the country. Ready for your custom home. Cascade Mtn views, plu...
Listing Office: Keller Williams Realty Central Oregon
Last Updated: February - 10 - 2026
$165,000
242 Jefferson Avenue, Metolius, OR 97741
View Photos (1)
Status: Closed
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1212
Year Built: 2000
Subdivision: N/A
Description: SELLERS GETTING SERIOUS!!! Priced reduced for Investor/user/handyman buyer...
Listing Office: Desert Sky Real Estate LLC
Last Updated: February - 10 - 2026

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Information deemed reliable but not guaranteed.