Vintage homes for sale & real estate in Deschutes County, OR

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FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Deschutes County, OR:
A true Bend original that you absolutely must see in person! Built in 1946 by Olaf Skjersaa, a pioneer of Bend's ski culture, this distinctive Arts & Crafts home showcases his handcrafted front door, staircase, original woodwork and built-ins. Offering 5 beds, 3 baths, over 3,400 sq ft and two main-level primary suites, the flexible floor plan features multiple living spaces ideal for guests, work or multi-gen living. Historic charm meets modern comfort with a newer roof, replacement windows, fresh interior and exterior paint, tankless water heaters, updated HVAC and Trex deck. Hardwood floors and three fireplaces add warmth throughout. Outside, enjoy a spacious 1/3-acre lot, mature l

$799,000

5 beds3 baths3,431 sq ft

714 NE 10th St, Bend, OR 97701

Newer roof • Original woodwork • Fresh interior paint

NEW 23 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Deschutes County, OR:
Gorgeous home within easy walking distance of downtown and the dry canyon. This home includes a huge, recently painted deck, fenced yard, and fantastically maintained lawn with inground irrigation. This home features hardwood flooring, tons of cabinet space in the upgraded kitchen with quartz countertops, remodeled bathroom and 3rd bedroom, Vermont Castings gas stove for addt'l heat, recently serviced HVAC- only 8 years old, detached garage for storage, parking space with power for your RV or toys and more. This home is turnkey and priced to sell. Enjoy this beautiful home just a few blocks from historic downtown Redmond.

$459,000

3 beds1 bath1,389 sq ft

626 SW 11th St, Redmond, OR 97756

Hardwood flooring • Quartz countertops • Fenced yard

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Deschutes County, OR:
First time on the Market! Dahl Acres is a wonderful gem located in the center of Redmond offering 4 bedrooms 2 baths sitting on 2.21 irrigated Acres. This historic farm home with the kitchen at the very heart offers separated living areas for a multi-generational living opportunity. Step out back to a large covered concrete patio perfect for entertaining & unwinding. Once a dairy goat farm the property offers many outbuildings including hay storage, loafing shed with stalls, 96 s. f. grain room or storage an additional heated, insulated ''office'' and a separate 2 stall barn at the back of the property. 2 acres of flood irrigation with a pond keep the grounds and the trees green and p

$889,900

4 beds2 baths1,802 sq ft

2846 W Antler Ave, Redmond, OR 97756

Many outbuildings • Historic farm home • Hay storage

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Deschutes County, OR:
A true and rare & mdash; Midcentury Modern home could be yours, in the most coveted midtown Bend neighborhood. This expansive home, on 3.5 city lots, is ready and waiting for a revival. A unique gem with so much potential (there is nothing like it in Bend). This could be a stunning high desert modern home with its original double sided, floor to ceiling stone fireplace and dramatic high ceilings with sizable beams throughout the home. The backyard deck stretches across the width of the house, overlooking an open pasture where deer graze daily. The location is simply spectacular. Only steps away from the beautiful Pilot Butte, an Oregon State Park. If you have been dreaming of a midcentu

$1,300,000

3 beds3 baths— sq ft

1331 NE 11th St, Bend, OR 97701

Backyard deck • High ceilings • Built 1957

OPEN TODAY, 1PM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Deschutes County, OR:
OPEN HOUSE SATURDAY, OCTOBER 24 1-3pm - ADU ONLY. Main house is tenant-occupied; please do not disturb the tenant. Picture yourself on Bend's coveted westside, a short stroll to the river trail, downtown, and Newport Avenue favorites like Newport Market, Back Porch Coffee, and Spork. This rare Union Street offering pairs two charming cottages on one lot, moments from the Neighborhood Greenway for easy, car-free access by foot or bike. The 2017 back cottage is Earth Advantage Platinum and Zero Energy certified. The 1926 front bungalow keeps its original character and refinished hardwood floors, with thoughtful updates throughout: new windows and doors, a newer roof, full insulation and profe

$899,900

2 beds2 baths1,106 sq ft

1234 NW Union St Unit 1 & 2, Bend, OR 97703

Newer roof • 4,791 sq ft lot • Parking

Property at 1435 NW Baltimore Ave, Bend, OR 97703, 2 beds, 2 baths

$640,000

2 beds2 baths886 sq ft

1435 NW Baltimore Ave, Bend, OR 97703

Property at 1446 NW 5th St, Bend, OR 97703, 4 beds, 3 baths

$1,400,000

4 beds3 baths2,218 sq ft

1446 NW 5th St, Bend, OR 97703

Property at 305 W Washington Ave, Sisters, OR 97759, 2 beds, 2 baths

$799,000

2 beds2 baths1,975 sq ft

305 W Washington Ave, Sisters, OR 97759

Property at 1040 SW 15th St, Redmond, OR 97756, 4 beds, 4 baths

$529,000

4 beds4 baths2,099 sq ft

1040 SW 15th St, Redmond, OR 97756

Property at 1964 NW 1st St, Bend, OR 97703, 4 beds, 3 baths

$1,890,000

4 beds3 baths2,364 sq ft

1964 NW 1st St, Bend, OR 97703

Property at 346 SW 12th St, Redmond, OR 97756, 2 beds, 1 bath

$359,900

2 beds1 bath672 sq ft

346 SW 12th St, Redmond, OR 97756

Property at 354 NW Drake Rd, Bend, OR 97703, 3 beds, 2.5 baths

$2,595,000

3 beds2.5 baths3,359 sq ft

354 NW Drake Rd, Bend, OR 97703

Property at 639 NW 8th St, Redmond, OR 97756, 2 beds, 2 baths

$450,000

2 beds2 baths1,017 sq ft

639 NW 8th St, Redmond, OR 97756

Property at 820 NE 4th St, Bend, OR 97701, 4 beds, 2 baths

$660,000

4 beds2 baths1,738 sq ft

820 NE 4th St, Bend, OR 97701

Property at 1355 NW Jacksonville Ave, Bend, OR 97703, 3 beds, 2 baths

$734,999

3 beds2 baths876 sq ft

1355 NW Jacksonville Ave, Bend, OR 97703

Property at 61859 Dobbin Rd, Bend, OR 97702, 4 beds, 3.5 baths

$1,399,000

4 beds3.5 baths3,771 sq ft

61859 Dobbin Rd, Bend, OR 97702

Property at 942 NW Delaware Ave, Bend, OR 97703, 6 beds, 4 baths

$1,295,000

6 beds4 baths2,776 sq ft

942 NW Delaware Ave, Bend, OR 97703

Property at 63435 O. B. Riley Rd, Bend, OR 97703, 4 beds, 3 baths

$1,250,000

4 beds3 baths2,720 sq ft

63435 O. B. Riley Rd, Bend, OR 97703

Property at 305 NW Columbia St, Bend, OR 97703, 4 beds, 3.5 baths

$1,695,000

4 beds3.5 baths2,284 sq ft

305 NW Columbia St, Bend, OR 97703

Property at 20525 Reed Market Rd, Bend, OR 97702, 1 bed, 1 bath

$1,175,000

1 bed1 bath864 sq ft

20525 Reed Market Rd, Bend, OR 97702

Property at 615 NW Ogden Ave, Bend, OR 97703, 2 beds, 1 bath

$779,000

2 beds1 bath1,298 sq ft

615 NW Ogden Ave, Bend, OR 97703

Property at 240 NW Birch Ave, Redmond, OR 97756, 2 beds, 1 bath

$340,000

2 beds1 bath1,470 sq ft

240 NW Birch Ave, Redmond, OR 97756

Property at Undisclosed address, Redmond, OR 97756, 2 beds, 1 bath

$1,100,000

2 beds1 bath1,232 sq ft

Undisclosed address, Redmond, OR 97756

Property at 1730 SW Canyon Dr, Redmond, OR 97756, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths1,625 sq ft

1730 SW Canyon Dr, Redmond, OR 97756

Property at 23456 Highway 20, Bend, OR 97701, 3 beds, 2 baths

$1,599,000

3 beds2 baths1,672 sq ft

23456 Highway 20, Bend, OR 97701

Property at 429 NW State St, Bend, OR 97703, 2 beds, 1 bath

$1,070,000

2 beds1 bath1,493 sq ft

429 NW State St, Bend, OR 97703

Property at 714 SW Cascade Ave, Redmond, OR 97756, 5 beds, 2 baths

$649,000

5 beds2 baths2,231 sq ft

714 SW Cascade Ave, Redmond, OR 97756

Property at 565 SE Woodland Blvd, Bend, OR 97702, 3 beds, 1 bath

$525,000

3 beds1 bath1,110 sq ft

565 SE Woodland Blvd, Bend, OR 97702

Property at 655 SW 12th St, Redmond, OR 97756, 2 beds, 1 bath

$379,000

2 beds1 bath1,064 sq ft

655 SW 12th St, Redmond, OR 97756

Property at 475 SE Douglas St, Bend, OR 97702, 3 beds, 2 baths

$585,000

3 beds2 baths1,426 sq ft

475 SE Douglas St, Bend, OR 97702

Property at 624 NW Hill St, Bend, OR 97703, 2 beds, 1 bath

$649,000

2 beds1 bath826 sq ft

624 NW Hill St, Bend, OR 97703

Property at 637 NW Canyon Dr, Redmond, OR 97756, 3 beds, 2 baths

$847,500

3 beds2 baths2,070 sq ft

637 NW Canyon Dr, Redmond, OR 97756

Property at 946 SW 13th St, Redmond, OR 97756, 3 beds, 2 baths

$475,000

3 beds2 baths1,266 sq ft

946 SW 13th St, Redmond, OR 97756

Property at 1036 SW 13th St, Redmond, OR 97756, 3 beds, 1 bath

$399,000

3 beds1 bath1,072 sq ft

1036 SW 13th St, Redmond, OR 97756

Property at 1929 NW Hill St, Bend, OR 97703, 2 beds, 1 bath

$680,000

2 beds1 bath1,173 sq ft

1929 NW Hill St, Bend, OR 97703

Property at 15020 Remuda Rd, Sisters, OR 97759, 3 beds, 2 baths

$899,000

3 beds2 baths1,793 sq ft

15020 Remuda Rd, Sisters, OR 97759

Property at 65325 Hwy 20, Bend, OR 97703, 2 beds, 1 bath

$975,000

2 beds1 bath621 sq ft

65325 Hwy 20, Bend, OR 97703

Property at 342 W Antler Ave, Redmond, OR 97756, 2 beds, 1 bath

$384,900

2 beds1 bath775 sq ft

342 W Antler Ave, Redmond, OR 97756

Property at 654 NW 4th St, Redmond, OR 97756, 2 beds, 0.5 baths

$360,000

2 beds0.5 baths816 sq ft

654 NW 4th St, Redmond, OR 97756

Property at 21483 Bunchgrass Ct, Bend, OR 97701, 4 beds, 3 baths

$1,595,000

4 beds3 baths2,760 sq ft

21483 Bunchgrass Ct, Bend, OR 97701

Property at 4220 NE Smith Rock Way, Terrebonne, OR 97760, 2 beds, 1 bath

$749,000

2 beds1 bath964 sq ft

4220 NE Smith Rock Way, Terrebonne, OR 97760

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Vintage Homes for Sale in Deschutes County

There are currently 53 vintage homes for sale in Deschutes County at a median listing price of $680K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Deschutes County stay on the market for 93 days and receive 1 offers. This map is refreshed with the newest listings in Deschutes County every 15 minutes.

In the past month, 371 homes have been sold in Deschutes County. In addition to houses in Deschutes County, there were also 127 condos, 217 townhouses, and 35 multi-family units for sale in Deschutes County last month. Find your dream home in Deschutes County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Deschutes County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Deschutes County. If you're looking to sell your home in the Deschutes County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Deschutes County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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All information provided is deemed reliable but is not guaranteed and should be independently verified. The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS of Portland Oregon. Real estate listings held by brokerage firms other than Redfin are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2026 RMLS, Portland, Oregon. Data Last Updated Sat Oct 24 2026

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Vintage homes for sale & real estate in Deschutes County, OR

Vintage Homes for Sale in Deschutes County

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