Homes for Sale near Douglas High School

• 

  

  

  /23

  $60,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  124 Country Side Ln, Winston, OR 97496

  Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

  Jason Mann J Mann Realty

  

  124 Country Side Ln, Winston, OR 97496
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• 

  

  

  /48

  $487,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  104 Kenya Ct, Winston, OR 97496

  This remarkable home showcases incredible attention to detail throughout, offering a spacious and unique floor plan designed for both comfort and functionality. The large kitchen features an eating bar, granite countertops, new appliances, abundant cabinet storage, overhead and can lighting, and walk-in pantry. The dining room offers beautiful built-in storage, adding both character and

  Shae Ellison Platinum Realty

  

  104 Kenya Ct, Winston, OR 97496
• 

  

  

  /48

  $379,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  754 SE Hall St, Winston, OR 97496

  Move right into this beautifully built 3-bedroom, 2-bathroom home offering 1,245 square feet of thoughtfully designed living space. Set on a spacious, fully fenced lot with mountain views, this like-new construction blends modern comfort with low-maintenance living.Step inside to an open-concept living area featuring rich luxury vinyl plank flooring and a ductless mini-split system for efficient

  Jase Nielsen J Mann Realty

  

  754 SE Hall St, Winston, OR 97496
• 

  

  

  /43

  $99,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  180 Twin Oaks Loop, Winston, OR 97496

  WOW! Enjoy affordable living in the sought-after 55+ Twin Oaks community! This spacious 3-bedroom, 2-bath double-wide offers 1404 square feet of comfortable living space with a thoughtful split-bedroom floor plan and vaulted ceilings. The oversized living room flows into the dining area, where a built-in hutch adds both charm and extra storage. The kitchen features granite tile countertops,

  Anthony Beckham Different Better Real Estate

  

  180 Twin Oaks Loop, Winston, OR 97496
• 

  

  

  /48

  $595,000

  • 5 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  307 Towhee Ln, Tenmile, OR 97481

  Welcome to your own slice of country paradise in Tenmile, Oregon! Set on 6 acres, this spacious property offers the perfect combination of comfortable living, room for animals and endless possibilities for enjoying the outdoors.The large 5-bedroom, 2.5-bath home features an inviting open living concept providing plenty of space for gatherings, entertaining and everyday living. Upstairs, you’ll

  Rebekah Sexauer eXp Realty, LLC

  

  307 Towhee Ln, Tenmile, OR 97481
• 

  

  /21

  $329,900

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft

  185 SE Lebleu Ln, Winston, OR 97496

  Picture enjoying your morning coffee on the back deck looking out over a peach orchard! This very tidy and well-maintained 3 bedroom, 2 bath house is situated in a quiet neighborhood and borders Brosi Orchards. Step inside to the living room with vaulted ceilings and gas fireplace, perfect for relaxing after a long day. Smartly designed layout with private master suite on one end of the home.

  Sandra Hart The Neil Company Real Estate

  

  185 SE Lebleu Ln, Winston, OR 97496
• 

  

  /23

  $364,900

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  10 SW Peach Ln, Winston, OR 97496

  Welcome to 10 SW Peach Ln, where every day feels like a peaceful retreat and every corner invites you to slow down and savor the moment. This special property blends warmth, character, and an unforgettable backyard oasis designed to elevate your everyday living.Step outside and imagine hosting summer gatherings on the resort-style brick patio, unwinding beside the soothing sounds of your private

  Kimberly Krebs Stellar Realty Northwest

  

  10 SW Peach Ln, Winston, OR 97496
• 

  

  /48

  $1,050,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  6700 Upper Olalla Rd, Winston, OR 97496

  One of a kind custom cedar home on 5 level, usable acres—an incredible country property with space, privacy, and outstanding amenities! This Lindal style home includes a massive 2,400 sq ft shop with a full bathroom, dual garage doors, and room for a 40-foot motorhome. Three RV hookups provide power, water, and dump access—an exceptional setup for guests, RV parking, recreational vehicles, and

  Dan Gandee Real Broker

  

  6700 Upper Olalla Rd, Winston, OR 97496
• 

  

  /30

  $250,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft

  3707 Willis Creek Rd, Winston, OR 97496

  Rare rural opportunity priced at land and utility value — for the investor, builder, or country-living dreamer ready to create something truly their own in the hills of Douglas County, Oregon. Utilities are already in place — a significant head start on any rural build. The property is served by Pacific Power electric and Winston City Water (public water), with an on-site septic system. Septic

  Michelle Kohlhoff Sundance Realty LLC

  

  3707 Willis Creek Rd, Winston, OR 97496
• 

  

  /48

  $399,000

  • Land
  • 159.97 Acres
  • $2,494 per Acre

  0 Strickland Canyon Rd Unit TL100, Tenmile, OR 97481

  Discover 159.97 acres of diverse timberland, recreation ground, dramatic rock formations and panoramic views just outside Roseburg in Douglas County. A rocked driveway approach from county-maintained Strickland Canyon Road transitions to dirt, with approximately 1 mile of internal roads providing access through the property. About 65 acres were harvested in 2022-2023 and remain unplanted, while

  Lauren Read Made Out West Land Company, LLC

  

  0 Strickland Canyon Rd Unit TL100, Tenmile, OR 97481
• 

  

  /26

  $270,000

  Open Mon 4PM - 6:30PM $48K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  340 SE Darrell Ave, Winston, OR 97496

  Bring an offer, VERY motivated seller. Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fenced yard with covered patio, and front porch.The home features a ductless heat pump for efficient heating and cooling, along with comfortable interior living spaces. Roof replaced within the last few years. Primary bedroom includes a walk-in closet and crown molding.

  Aaron Stansbury Keller Williams Realty Eugene and Springfield

  

  340 SE Darrell Ave, Winston, OR 97496
• 

  

  /4

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  0 Berry Creek Rd, Winston, OR 97496

  This private, level 4-acre parcel offers convenient access to Ben Irving Reservoir and is the perfect setting for recreation, relaxation, or a future getaway retreat. The property features a large natural meadow surrounded by 20-year-old Douglas fir reprod, creating a peaceful and secluded atmosphere. Adjacent to BLM land, it provides direct access to endless outdoor opportunities. Improvements

  Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Berry Creek Rd, Winston, OR 97496
• 

  

  /19

  $18,499

  $11K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,022 Sq Ft

  228 Estate Loop, Winston, OR 97496

  2 bed, 1 bath home in a desirable 55+ park featuring spacious living areas and a well-appointed kitchen with breakfast bar. Attached dining area includes built-ins for added storage and charm. Separate laundry room, plus a bathroom with walk-in shower for convenience. Outside features include covered porch, carport with attached storage area. Located close to shopping, dining, and other amenities.

  Jason Mann J Mann Realty

  

  228 Estate Loop, Winston, OR 97496
• 

  

  /4

  $2,000,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  80 NW Lost Ln, Winston, OR 97496

  Great Property for future Developing. 2007 Manufactured Home on .68 of a Ac. City Water and Sewer.

  Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

  

  80 NW Lost Ln, Winston, OR 97496
• 

  

  /9

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,242 Sq Ft

  70 NE Brosi Orchard Rd, Winston, OR 97496

  This home sits on an oversized lot with room for RV parking, extra vehicles, and all your toys. It includes a two-bay garage plus a separate one-car garage—ideal for storage, hobbies, or a workshop. Hardwood floors run throughout the home, giving the 2-bedroom, 1-bath layout timeless appeal and tons of potential. Outside, enjoy a spacious cement patio in the back and a fully fenced yard in front,

  Janet Stringfellow Oregon Life Homes

  

  70 NE Brosi Orchard Rd, Winston, OR 97496
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  /48

  $329,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  900 Mulberry Ln, Roseburg, OR 97471

  Discover the potential at 900 Mulberry Lane! This approximately 20-acre parcel offers a mix of pasture and hillside terrain, with spectacular views of the surrounding hills and valley from the homesite. Utilities are already in place, providing a great foundation for your future plans. Conveniently located just 2 miles from the Lookingglass Store and school. The existing single-wide manufactured

  Boyd Bartke All-Pro Realty Advisors, LLC

  

  900 Mulberry Ln, Roseburg, OR 97471
• 

  

  /48

  $1,099,900

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,856 Sq Ft

  1349 Willis Creek Rd, Winston, OR 97496

  Quiet country living on private acreage! Offered for the first time ever, this exceptional estate presents a rare opportunity to own a truly special piece of the Pacific Northwest. Featuring two separate residences, this property is perfectly suited for multi-generational living, guest accommodations, or potential rental income. The primary home offers over 2,800 square feet of inviting living

  Jordan Anderson The Anderson Agency

  

  1349 Willis Creek Rd, Winston, OR 97496
• 

  

  /29

  $469,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  161 Collins Rd, Winston, OR 97496

  Brand-new construction in the desirable Lookingglass Creek Estates subdivision! This functionally designed home features an open floor plan with high-end finishes throughout. Offering 3 bedrooms, 2 bathrooms, & 1770 sqft. The kitchen offers beautiful custom soft-close cabinets, quartz countertops, pantry, and waterproof luxury vinyl plank flooring. The spacious primary suite offers a walk-in

  Jacob Gilman The Neil Company Real Estate

  

  161 Collins Rd, Winston, OR 97496
• 

  

  /30

  $399,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft

  675 SE Brush Ct, Winston, OR 97496

  This beautifully maintained home is tucked away in a cul-de-sac in the heart of Winston, offering both privacy and convenience. With three comfortable bedrooms and two well-appointed bathrooms, the open-concept layout creates a welcoming atmosphere that’s ideal for hosting gatherings. The kitchen features a spacious island, perfect for preparing meals and entertaining guests. Vaulted ceilings in

  Christina Esterbrook J Mann Realty

  

  675 SE Brush Ct, Winston, OR 97496
• 

  

  /17

  $979,500

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  591 NW Douglas Blvd, Winston, OR 97496

  Recently remodel 3 bedroom/2bath, with bonus areas, front and back patios, 1 bed/1 bath apartment, (or mother-in-law or office space) storage shed, 3 bay shop with car lift and compressor to convey. Great commercial property (wheel/ tire shop or any retail business) work and live on site. There is too much to detail come and see the possibilities. With highway exposure businesses coming to this

  Beverly Walters Gold Standard Realty

  

  591 NW Douglas Blvd, Winston, OR 97496
• 

  

  /45

  $575,000

  $24K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,405 Sq Ft

  1177 Dairy Loop Rd, Roseburg, OR 97471

  Country living in the desirable Lookingglass area! This farmhouse sits on 10.6 level acres featuring a seasonal pond, pasture area, fruit trees, gardening space with raised beds, chicken coop, and multiple outbuildings including a barn, storage areas, and covered parking. Whether you have animals, hobbies, equipment, or simply want room to spread out, this property offers the space and setting to

  Najla Slater Stellar Realty Northwest

  

  1177 Dairy Loop Rd, Roseburg, OR 97471
• 

  

  /11

  $350,000

  • Land
  • 50 Acres
  • $7,000 per Acre

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496

  Custom home site on 50 acres. Adjacent to Abacela vineyard with incredible views of the countryside. Set in the Umpqua Valley AVA. Zoned Residential Medium Density. Do not access this property without authorization.

  Mike Nichols MORE Realty

  

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496
• 

  

  /39

  $649,900

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,038 Sq Ft

  460 Little Branch Ln, Roseburg, OR 97471

  Welcome to your own private retreat on approximately 7 beautiful acres just outside of Roseburg, Oregon. Offering the perfect blend of country living and modern comfort, this spacious 2,038-square-foot single-level home is designed for those who appreciate room to spread out both inside and out.Step inside to an inviting open floor plan that creates a seamless flow between the living room and

  Rebekah Sexauer eXp Realty, LLC

  

  460 Little Branch Ln, Roseburg, OR 97471
• 

  

  /45

  $775,000

  • 4 Beds
  • 5 Baths
  • 3,000 Sq Ft

  375 Porter Creek Rd, Winston, OR 97496

  Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently updated 41-acre estate, nestled in the heart of Oregon's Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential. A spacious 3,000 sq ft home featuring four large bedrooms, large

  Lorrie Normann Triple Oaks Realty LLC

  375 Porter Creek Rd, Winston, OR 97496
• 

  /2

  $209,900

  $10K PRICE DROP

  • Land
  • 40 Acres
  • $5,248 per Acre

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496

  Exceptional Farm Forest–zoned timber property offers both natural beauty and strong investment potential. A recent professional timber cruise, inventory, and valuation completed by Resource Management Services highlights the value of this well-managed stand. Timber prices fluctuate but as of March, the net timber value is estimated at $174,749, consisting primarily of healthy, marketable Doug

  Craig Warmouth Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496
• 

  

  /28

  $309,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  351 SE Darrell Ave, Winston, OR 97496

  JUST REDUCED!! This 3 Bedroom/1 Bath, family home on over 1/3-acre has been completely updated for your enjoyment. There are many new items, including roof, mini split system, LVP flooring throughout, interior and exterior paint, plumbing and outside waterline. The bathroom/laundry room has been completely renovated. The yards are fully fenced, and there is a nice large deck on the back

  Debra Moore Currieco Real Estate

  

  351 SE Darrell Ave, Winston, OR 97496
• 

  

  /8

  $590,000

  • Land
  • 4.77 Acres
  • $123,690 per Acre

  350 View Point Terrace, Winston, OR 97496

  Excellent investment opportunity! 31 platted lots prime for development in the growth seeking city of Winston! This early 1980's subdivision is prominently located next to a newer construction community to strengthen the potential development value. Pacific Power just confirmed power is available! Call Winston city manager with all your building/development questions as he will accommodate all

  Michael Fischer Oregon Life Homes

  

  350 View Point Terrace, Winston, OR 97496
• 

  

  /39

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  895 Mulberry Ln, Roseburg, OR 97471

  Welcome to your slice of Southern Oregon paradise! Enjoy sweeping views from the deck overlooking the serene countryside. Whether you're exploring the acreage amongst the trees or taking in the beauty of the private pond, you'll love life on Mulberry Lane just 10 minutes to the amenities and conveniences of town.

  Leah Hyland Haven Lane Realty

  

  895 Mulberry Ln, Roseburg, OR 97471
• 

  

  /10

  $439,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  158 Collins Ct, Winston, OR 97496

  Nestled in the highly desired Lookingglass Creek Estates Subdivision in Winston. This brand-new home provides exceptional design and craftsmanship, with a popular floor plan that ensures comfort and style. The heart of this home, the kitchen, is adorned with quartz countertops & custom cabinets that extend to the bathrooms, adding elegance and durability. The property comes with the added

  Jacob Gilman The Neil Company Real Estate

  

  158 Collins Ct, Winston, OR 97496
• 

  

  /16

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  261 SE Darrell Ave, Winston, OR 97496

  Wonderful little cottage for the first time home buyer or the investor needing one more rental in there portfolio. This home is located on a double lot. Per city of Winston, lot is dividable. Build an additional house on its own lot, or leave it as-is and build an ADU or shop in your backyard. Come check this out and make your appointment today.

  Angel Smith Trueblood Real Estate

  

  261 SE Darrell Ave, Winston, OR 97496
• 

  

  /13

  $99,000

  $10K PRICE INCREASE

  • Land
  • 5.78 Acres
  • $17,128 per Acre

  0 Willis Creek Rd Unit 23389927, Winston, OR 97496

  One of the last vacant lots on Willis Creek Rd. .76 acres between roadway and the creek. 5.02 wooded acres up the hill that levels off to a rather flat area for building site. With a bit of road grading and building pad clearing. This location offers seclusion in the trees with views of the surrounding hills and valley.

  Thomas Gulan RE/MAX Integrity

  

  0 Willis Creek Rd Unit 23389927, Winston, OR 97496

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