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

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ABOUT THIS HOME
Vintage Home for sale in Douglas County, OR:
Wow! Enjoy exceptional privacy, breathtaking sunsets, and the peaceful feel of country living, just minutes from the city’s hustle and bustle. Tucked away at the end of a quiet hilltop nook off Lookingglass Rd. , this unique property offers space, views, and versatility on . 84 acres, set privately behind a house of worship. This 3-bedroom, 2-bath, 2,428 sq ft home features original hardwood floors, updated vinyl windows, and a comfortable, functional layout. A covered breezeway connects the home to an impressive 40’ x 24’ detached garage/shop, complete with a built-in cold storage room, ideal for hobbies, projects, or extra storage. Outdoor living shines with a covered co

$499,900

3 beds2 baths2,428 sq ft

1183 Lookingglass Rd, Roseburg, OR 97471

Rv parking • Detached garage shop • Built-in fire pit

Anthony Beckham • Different Better Real Estate

ABOUT THIS HOME
Vintage Home for sale in Douglas County, OR:
Don’t miss your chance to own this charming home featuring a spacious, fully fenced backyard with a covered deck—perfect for outdoor relaxation or entertaining! Inside, you'll find upgraded appliances, fresh interior paint, and a range of other thoughtful updates. Ready to take a tour? Call today to schedule your viewing!

$279,900

3 beds1 bath896 sq ft

1551 NE Morris St, Roseburg, OR 97470

Covered deck • Upgraded appliances • Fresh interior paint

Emily McCurry • Safari Village Real Estate

ABOUT THIS HOME
Vintage Home for sale in Douglas County, OR:
Tucked into a quiet, peaceful neighborhood, this charming 2-bedroom, 1-bath home invites you to slow down, breathe deeply, and settle into a simpler rhythm of life. With 900 square feet of thoughtfully arranged space, the home feels warm and intimate—just the right size to feel connected, yet roomy enough to live comfortably.

$269,000

2 beds1 bath900 sq ft

420 W D Ave, Drain, OR 97435

1.44 acre lot • Built 1900 • Listed 4 days

Erin Sparhawk • Oregon Life Homes

ABOUT THIS HOME
Vintage Home for sale in Douglas County, OR:
Updated and versatile Roseburg property offering a beautifully maintained main residence plus a fully separate ADU—ideal for multi-generational living or rental income. The 1,229 sq ft main home features 2 bedrooms and 1 bathroom with original hardwood floors flowing through the living room, dining area, and kitchen. The kitchen and bathroom have been updated, plus a large pantry. Complemented by a gas furnace and on-demand hot water. The 640 sq ft ADU offers a comfortable 1-bedroom, 1-bath layout with vaulted ceilings, laminate flooring, recessed lighting, ceiling fan, and a modern kitchen. A custom barn door made from reclaimed materials adds unique character. Both homes have been i

$319,000

2 beds1 bath1,229 sq ft

1321 SE Mill St, Roseburg, OR 97470

Gas furnace • Fully separate adu • Updated kitchen

Theresa Montoya • Vantage Point Brokers, LLC

ABOUT THIS HOME
Vintage Home for sale in Douglas County, OR:
Nestled in the quiet, peaceful setting of Tiller, Oregon, this charming rural property offers the perfect blend of comfort, functionality and country living. The 3-bedroom, 1-bathroom home features an open and inviting living room that opens to the deck—ideal for relaxing, entertaining or simply enjoying the surrounding natural beauty. A dedicated laundry room adds everyday convenience, while the covered front porch provides a welcoming place to enjoy your morning coffee or unwind in the evenings. This property is well-equipped for those seeking a self-sufficient lifestyle. A huge shop with 220 power offers ample space for tools, hobbies or small business use. In addition, there is a

$310,000

2 beds1 bath1,350 sq ft

22240 Tiller Trail Hwy, Days Creek, OR 97429

Covered front porch • Fully fenced land • Raised garden beds

Rebekah Sexauer • eXp Realty, LLC

Property at 1638 SE Mill St, Roseburg, OR 97470, 3 beds, 1 bath

$169,000

3 beds1 bath1,307 sq ft

1638 SE Mill St, Roseburg, OR 97470

Nile Stark • RE/MAX Integrity

Property at 523 W Broccoli St, Roseburg, OR 97471, 4 beds, 2 baths

$405,000

4 beds2 baths1,408 sq ft

523 W Broccoli St, Roseburg, OR 97471

Nataly Mattox • RE/MAX Integrity

Property at 412 Gardner Ave, Drain, OR 97435, 4 beds, 2 baths

$279,000

4 beds2 baths2,374 sq ft

412 Gardner Ave, Drain, OR 97435

Linnea Kittrell • TLC Realty

Property at 1770 N Myrtle Rd, Myrtle Creek, OR 97457, 4 beds, 4 baths

$679,900

4 beds4 baths2,518 sq ft

1770 N Myrtle Rd, Myrtle Creek, OR 97457

Anthony Beckham • Different Better Real Estate

Property at 255 Shady Dr, Roseburg, OR 97471, 3 beds, 1 bath

$489,000

3 beds1 bath2,247 sq ft

255 Shady Dr, Roseburg, OR 97471

Jerry Chartier • Berkshire Hathaway HomeServices Real Estate Professionals

Property at 811 Laurel Ave, Reedsport, OR 97467, 2 beds, 1 bath

$195,000

2 beds1 bath832 sq ft

811 Laurel Ave, Reedsport, OR 97467

Ron Jackimowicz • eXp Realty, LLC

Property at 1224 NE Freemont Ave, Roseburg, OR 97470, 4 beds, 2 baths

$219,000

4 beds2 baths1,344 sq ft

1224 NE Freemont Ave, Roseburg, OR 97470

Tammi Ellison • eXp Realty, LLC

Property at 142 S Comstock Ave, Sutherlin, OR 97479, 1 bed, 1 bath

$149,500

1 bed1 bath768 sq ft

142 S Comstock Ave, Sutherlin, OR 97479

Gregory Johnson • G. Stiles Realty

Property at 331 NE Laurel Ave, Myrtle Creek, OR 97457, 3 beds, 1 bath

$265,000

3 beds1 bath1,137 sq ft

331 NE Laurel Ave, Myrtle Creek, OR 97457

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

Property at 3721 Joe Ave, Roseburg, OR 97471, 3 beds, 2 baths

$389,900

3 beds2 baths1,409 sq ft

3721 Joe Ave, Roseburg, OR 97471

Jordan Anderson • The Anderson Agency

Property at 940 W Luellen Dr, Roseburg, OR 97471, 3 beds, 2 baths

$425,000

3 beds2 baths1,518 sq ft

940 W Luellen Dr, Roseburg, OR 97471

Nataly Mattox • RE/MAX Integrity

Property at 450 E 3rd Ave, Riddle, OR 97469, 3 beds, 2 baths

$275,000

3 beds2 baths1,800 sq ft

450 E 3rd Ave, Riddle, OR 97469

Shane Mast • Oregon Life Homes

Property at 151 NW Sherry St, Winston, OR 97496, 3 beds, 2 baths

$272,000

3 beds2 baths1,835 sq ft

151 NW Sherry St, Winston, OR 97496

Robert Zuver • Winston Realty & Insurance

Property at 339 Justa Ln, Sutherlin, OR 97479, 3 beds, 1 bath

$299,900

3 beds1 bath744 sq ft

339 Justa Ln, Sutherlin, OR 97479

Deleta Dickson • eXp Realty, LLC

Property at 512 W Center St, Roseburg, OR 97471, 3 beds, 2 baths

$429,000

3 beds2 baths— sq ft

512 W Center St, Roseburg, OR 97471

Cindy Beach • The Neil Company Real Estate

Property at 635 NW 4th Ave, Myrtle Creek, OR 97457, 2 beds, 1 bath

$245,000

2 beds1 bath736 sq ft

635 NW 4th Ave, Myrtle Creek, OR 97457

Rebekah Sexauer • eXp Realty, LLC

Property at 606 NW Nichol Ave, Myrtle Creek, OR 97457, 5 beds, 3 baths

$225,000

5 beds3 baths1,926 sq ft

606 NW Nichol Ave, Myrtle Creek, OR 97457

Rebekah Sexauer • eXp Realty, LLC

Property at 1530 SE Hamilton St, Roseburg, OR 97470, 3 beds, 2 baths

$284,900

3 beds2 baths1,104 sq ft

1530 SE Hamilton St, Roseburg, OR 97470

Anthony Beckham • Different Better Real Estate

Property at 260 SW Ford Ave, Winston, OR 97496, 3 beds, 1 bath

$289,900

3 beds1 bath1,180 sq ft

260 SW Ford Ave, Winston, OR 97496

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

Property at 532 2nd St, Elkton, OR 97436, 2 beds, 1 bath

$265,000

2 beds1 bath696 sq ft

532 2nd St, Elkton, OR 97436

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

Property at 342 W Chapman Ave, Roseburg, OR 97470, 4 beds, 2 baths

$463,000

4 beds2 baths2,281 sq ft

342 W Chapman Ave, Roseburg, OR 97470

Kurt Clements • ListWithFreedom.com

Property at 168 Breezy Ln, Roseburg, OR 97470, 2 beds, 1 bath

$299,000

2 beds1 bath912 sq ft

168 Breezy Ln, Roseburg, OR 97470

Veronica Gillespie • eXp Realty, LLC

Property at 1871 Mccullough Creek Rd, Glendale, OR 97442, 3 beds, 2 baths

$499,999

3 beds2 baths2,066 sq ft

1871 Mccullough Creek Rd, Glendale, OR 97442

Property at 422 Elder St, Drain, OR 97435, 3 beds, 1 bath

$294,000

3 beds1 bath1,008 sq ft

422 Elder St, Drain, OR 97435

Julie Wisely • Hybrid Real Estate

Property at 324 W Berdine St, Roseburg, OR 97471, 3 beds, 1 bath

$245,000

3 beds1 bath1,018 sq ft

324 W Berdine St, Roseburg, OR 97471

John Owen • RE/MAX Integrity

Property at 1880 Linnell Ave, Roseburg, OR 97471, 3 beds, 2 baths

$335,000

3 beds2 baths1,610 sq ft

1880 Linnell Ave, Roseburg, OR 97471

Catherine Shipley • RE/MAX Integrity

Property at 1010 W Luellen Dr, Roseburg, OR 97471, 3 beds, 2 baths

$410,000

3 beds2 baths1,508 sq ft

1010 W Luellen Dr, Roseburg, OR 97471

Wyndee Konopaski • Keller Williams Southern Oregon-Umpqua Valley

Property at 663 NE Knoll Ave, Roseburg, OR 97470, 3 beds, 3 baths

$380,000

3 beds3 baths1,836 sq ft

663 NE Knoll Ave, Roseburg, OR 97470

Elena Mackey • eXp Realty, LLC

Property at 202 NE Fulton St, Roseburg, OR 97470, 5 beds, 2 baths

$215,000

5 beds2 baths2,095 sq ft

202 NE Fulton St, Roseburg, OR 97470

Kayla Wehe • Lamonte Real Estate Professionals

Property at 165 Robinson St, Sutherlin, OR 97479, 3 beds, 1 bath

$208,700

3 beds1 bath1,075 sq ft

165 Robinson St, Sutherlin, OR 97479

Mark Townsend • Keller Williams Southern Oregon-Umpqua Valley

Property at 12829 Wildwood Dr, North Bend, OR 97459, 3 beds, 1 bath

$139,000

3 beds1 bath1,324 sq ft

12829 Wildwood Dr, North Bend, OR 97459

Kathy Clemens • Coastal Properties

Property at 939 Buckhorn Rd, Roseburg, OR 97470, 3 beds, 2 baths

$465,000

3 beds2 baths1,594 sq ft

939 Buckhorn Rd, Roseburg, OR 97470

Jacob Gilman • The Neil Company Real Estate

Property at 188 Robin St, Roseburg, OR 97470, 2 beds, 1 bath

$186,560

2 beds1 bath859 sq ft

188 Robin St, Roseburg, OR 97470

Troy Schuyler • Keller Williams Southern Oregon-Umpqua Valley

Property at 27403 State Highway 38, Elkton, OR 97436, 3 beds, 3 baths

$750,000

3 beds3 baths1,344 sq ft

27403 State Highway 38, Elkton, OR 97436

Pamela Dietz • Keller Williams Realty Eugene and Springfield

Property at 1118 SE Washington Ave, Roseburg, OR 97470, 3 beds, 2 baths

$300,000

3 beds2 baths1,970 sq ft

1118 SE Washington Ave, Roseburg, OR 97470

Neil Hummel • The Neil Company Real Estate

Property at 1289 Ivy Ave, Reedsport, OR 97467, 3 beds, 2 baths

$289,900

3 beds2 baths1,230 sq ft

1289 Ivy Ave, Reedsport, OR 97467

Rachele Widdifield • Central Coast Realty

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Vintage Homes for Sale in Douglas County

There are currently 149 vintage homes for sale in Douglas County at a median listing price of $415K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Douglas County stay on the market for 102 days and receive 3 offers. This map is refreshed with the newest listings in Douglas County every 15 minutes.

In the past month, 94 homes have been sold in Douglas County. In addition to houses in Douglas County, there were also 8 condos, 7 townhouses, and 13 multi-family units for sale in Douglas County last month. Find your dream home in Douglas 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 Douglas County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Douglas County. If you're looking to sell your home in the Douglas County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Douglas 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 © 2025 RMLS, Portland, Oregon. Data Last Updated Sun Dec 21 2025

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