Winchester, OR Homes

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  /44

  $599,000

  $50K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 3,580 Sq Ft

  331 Hemlock Ln, Roseburg, OR 97471

  Beautifully refinished home on 5 acres off desired Fisher Rd. area. This home has room for it all, and views all around. With 6 bedrooms, an office, living room and family room, there is no shortage of space and storage. There are 3 bedrooms upstairs, and 3 bedrooms and an office downstairs. The living room boasts 18' ceilings, a floor to ceiling fireplace, and a wet bar. The kitchen/dining room

  

  Wyndee Konopaski

  Keller Williams Southern Oregon-Umpqua Valley

  

  331 Hemlock Ln, Roseburg, OR 97471
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  /2

  Starting at $1,450 Per Month

  • 1 Bed

  331 NE Pomona St, Roseburg, OR 97470

  Oak Springs

  

  331 NE Pomona St, Roseburg, OR 97470
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  /26

  $285,000

  Sold May 29, 2026

  757 NE Clover Ave, Roseburg, OR 97470

  • 3 Beds
  • 1.5 Baths
  • 1,192 Sq Ft
  • Built 1957

  Last Sold Summary

  • 4% Above List Price
  • $239/SF
  • 5 Days On Market

  Current Estimated Value $273,455

  Last Listing Agent D'Anna Caylor RE/MAX Integrity

  

  757 NE Clover Ave, Roseburg, OR 97470
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  /18

  Not Listed For Sale

  14 NE Mary Ann Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1991

  

  14 NE Mary Ann Ln, Roseburg, OR 97470

  Last Sold Summary

  • 206 Days On Market
• 

  

  

  /48

  $639,900

  $35K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,120 Sq Ft

  786 N View Dr, Roseburg North, OR 97495

  Perfect for multi-generational living, this 3,120 sq ft Winchester home features two primary suites—one on the main level and another upstairs. With 4 bedrooms, 3.5 bathrooms, two spacious living areas, and an upstairs flex space ideal for a home office, this home provides flexibility, comfort, and room to grow. Recent updates include updated flooring, fresh interior paint, new accent lighting,

  

  Kristina Scott

  Umpqua Legacy Realty

  

  786 N View Dr, Roseburg North, OR 97495
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  /14

  Starting at $1,375 Per Month

  • 2 Beds

  101 Village Dr, Winchester, OR 97495

  This is a completely remodeled 2+ bedroom/1.5 bath condo style duplex in a quiet neighborhood with beautiful landscaping! It is approximately 1150 square feet, single level. It features granite countertops, brand new cabinets, brand new luxury plank floor, and new appliances. The unit also includes: Washer/dryer hookup in the laundry room, dishwasher, heat and air, garage with storage, and

  Saddle Butte Duplexes

  101 Village Dr, Winchester, OR 97495
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  /48

  $732,500

  Sold Aug 28, 2025

  1356 Echo Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1987

  Last Sold Summary

  • 13% Below List Price
  • $372/SF
  • 104 Days On Market

  Current Estimated Value $732,365

  Last Listing Agent Deborah Whitaker Roseburg Realty

  

  1356 Echo Dr, Roseburg, OR 97470
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  /47

  Est $247,131

  Not Listed For Sale

  1621 NE Winter St, Roseburg, OR 97470

  • 3 Beds
  • 1.5 Baths
  • 1,096 Sq Ft
  • Built 1949

  

  1621 NE Winter St, Roseburg, OR 97470

  Last Sold Summary

  • 60 Days On Market
• 

  

  /48

  $650,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  1381 Oak Hill Rd, Roseburg, OR 97471

  Tucked away on 3.28 acres of lush, park-like grounds, this one-of-a-kind Oregon retreat offers more than a home, it delivers an experience. Surrounded by mature trees and natural beauty, the property lives like a private resort, designed for both peaceful living and unforgettable gatherings. From the moment you arrive, the setting feels worlds away. Meandering paths lead to a tranquil pond with

  

  Nick Shivers

  eXp Realty, LLC

  

  1381 Oak Hill Rd, Roseburg, OR 97471
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  /20

  $900 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  123 Roseburg, Roseburg, OR 97471

  Property Id: 1440413Hi, I'm looking for a 3rd person to join 2 others in a 3bd 2ba home. Each tenant has a separate lease. The other 2 tenants are men, so ideally we're looking for another man to join.The home has a single-car garage with a side yard that can comfortably fit 2 more cars. Split level home. Washer/dryer available. Kitchen and living room are fully

  123 Roseburg, Roseburg, OR 97471
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  /8

  $255,000

  Sold May 29, 2026

  1448 NE Rocky Ridge Dr, Roseburg, OR 97470

  • Land
  • 1.63 Acres
  • $156,442 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 646 Days On Market

  Last Listing Agent Marilyn Kittelman Cutting Edge Real Estate

  

  1448 NE Rocky Ridge Dr, Roseburg, OR 97470
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  /43

  Est $735,254

  Not Listed For Sale

  257 Martha Dr, Winchester, OR 97495

  • 4 Beds
  • 4 Baths
  • 3,800 Sq Ft
  • Built 1995

  

  257 Martha Dr, Winchester, OR 97495

  Last Sold Summary

  • 61 Days On Market
• 

  

  /44

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,581 Sq Ft

  556 N View Dr, Winchester, OR 97495

  Priced to sell and offering exceptional value in Winchester's sought-after Oak Valley Loop neighborhood! This beautifully maintained 4-bedroom, 2.5-bath home offers 2,581 square feet of thoughtfully designed living space, combining timeless finishes, everyday comfort, and room to grow.Step inside to soaring vaulted ceilings, rich bamboo flooring, and a warm natural gas fireplace that creates an

  

  Kristina Scott

  Umpqua Legacy Realty

  

  556 N View Dr, Winchester, OR 97495
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  /14

  $1,800

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1897 NW Dogwood St, Roseburg, OR 97471

  DogwoodHouse for rent $1800 a monthPerfect an older couple,All one level,High on a hill , incredible views near Golf course and hospitals.Close to town. Small flat easy maintance yard, yet for the adventurous, you can grow a garden in several large garden beds . A huge covered patio area where you may sit outside anytime of the year.Romance? You can

  1897 NW Dogwood St, Roseburg, OR 97471
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  /34

  $310,000

  Sold Oct 31, 2025

  1820 NW Otie St, Roseburg, OR 97470

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft
  • Built 1973

  Last Sold Summary

  • 11% Below List Price
  • $143/SF
  • 29 Days On Market

  Current Estimated Value $384,169

  Last Listing Agent Neil Hummel The Neil Company Real Estate

  

  1820 NW Otie St, Roseburg, OR 97470
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  /48

  Est $917,145

  Not Listed For Sale

  776 Cherokee Ave, Roseburg, OR 97471

  • 3 Beds
  • 2.5 Baths
  • 2,442 Sq Ft
  • Built 2013

  

  776 Cherokee Ave, Roseburg, OR 97471

  Last Sold Summary

  • 5 Days On Market
• 

  

  /46

  $705,000

  $15K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  1062 Southridge Way, Roseburg, OR 97470

  Enter through the gates of Winchester Ridge and follow your private drive to this beautifully crafted custom home set on 2.36 serene acres. Offering 3 bedrooms plus a flexible bonus room (or 4th bedroom), 2.1 baths, and 2,104 SF, this home blends elegance, comfort, and space to unwind. Inside, soaring ceilings, expansive windows, and abundant natural light create a bright, open atmosphere. The

  

  Kathy Flowers

  All-Pro Realty Advisors, LLC

  

  1062 Southridge Way, Roseburg, OR 97470
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  /9

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 872 Sq Ft
  • NE Timberlake

  113 NE Timberlake St Unit 115-205, Roseburg, OR 97470

  Newer Built Apartment! Upper Unit available!Next to Costco!Right off HWY 99 and close to I-5Features and AmenitiesWE PAY = Water, Sewer and Garbage!Washer/Dryer: On siteParking: Dedicated SpotAir ConditioningDishwasherOutdoor Space: Patio, BalconyRefrigeratorStoveGarbage Disposal* Cable TV Hook-up Available* Internet Access Hook-up Available---E-MAIL us for link to FREE on-line Application!Credit

  113 NE Timberlake St Unit 115-205, Roseburg, OR 97470
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  /31

  $860,000

  Sold Dec 23, 2025

  650 Southridge Way, Roseburg, OR 97470

  • 4 Beds
  • 3 Baths
  • 2,758 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Below List Price
  • $312/SF
  • 5 Days On Market

  Current Estimated Value $867,151

  Last Listing Agent Christina Esterbrook J Mann Realty

  

  650 Southridge Way, Roseburg, OR 97470
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  /37

  Est $468,695

  Not Listed For Sale

  1791 NE Rocky Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft
  • Built 2012

  

  1791 NE Rocky Dr, Roseburg, OR 97470

  Last Sold Summary

  • 35 Days On Market
• 

  

  /46

  $329,900

  • 3 Beds
  • 2 Baths
  • 968 Sq Ft

  1520 NE Winter St, Roseburg, OR 97470

  Privacy and convenience offered all at once. Conveniently located just a few minutes away from the center of town while being towards the end of the road surrounded by trees and greenery for natural privacy. Decent sized lot with a fenced in garden area ready for someone to make their own. Relax on the large, shaded front porch or back deck while enjoying the view. The home has underwent multiple

  

  Ashton Faas

  Faas Realty

  

  1520 NE Winter St, Roseburg, OR 97470
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  /7

  $1,100 Per Month

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • LANJ242

  242 Currier Ave Unit SFR, Roseburg, OR 97470

  242 Currier Ave Unit SFR, Roseburg, OR 97470
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  /48

  $720,000

  Sold Jul 09, 2025

  390 Singing Waters Rd, Winchester, OR 97495

  • 2 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 2010

  Last Sold Summary

  • 1% Below List Price
  • $373/SF
  • 4 Days On Market

  Current Estimated Value $744,511

  Last Listing Agent Veronica Gillespie eXp Realty, LLC

  

  390 Singing Waters Rd, Winchester, OR 97495
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  /33

  Est $429,498

  Not Listed For Sale

  276 N View Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2003

  

  276 N View Dr, Roseburg, OR 97470

  Last Sold Summary

  • 55 Days On Market
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  /34

  $1,795,000

  • Land
  • 556.02 Acres
  • $3,228 per Acre

  2268 Sunshine Rd, Roseburg, OR 97470

  553± acres of rolling hills, timber, water, and open sky! An opportunity to own a true piece of Southern Oregon. Just minutes outside of Roseburg, this expansive EFU-zoned (Exclusive Farm Use – Grazing) property offers a rare blend of privacy, usability, and long-term potential. The land unfolds with a diverse mix of open pasture, timbered ridges, and natural creek corridors. Expansive valley and

  

  Nick Shivers

  eXp Realty, LLC

  

  2268 Sunshine Rd, Roseburg, OR 97470
• 

  

  /19

  $1,300 Per Month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • 2 bedroom 2 bathroom Roseburg Duplex

  3265 NE Johnson St, Roseburg, OR 97470

  Open concept 2 bedroom 2 bathroom duplex, with a garage, in Roseburg close to shopping, restaurants, and more. Kitchen features refrigerator, dishwasher, stove, overhead microwave, and a walk in pantry. Master bedroom has en suite bathroom and a walk-in closet. Home has central heating and cooling, sprinklers to water the front yard, and a small patio out back. No pets. Tenant responsible for all

  3265 NE Johnson St, Roseburg, OR 97470
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  /43

  $350,000

  Sold Sep 26, 2025

  2297 NE Vine St, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 54 Days On Market

  Current Estimated Value $359,155

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  2297 NE Vine St, Roseburg, OR 97470
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  /32

  Not Listed For Sale

  18 Mary Ann Ln, Roseburg, OR 97470

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1984

  

  18 Mary Ann Ln, Roseburg, OR 97470

  Last Sold Summary

  • 4 Days On Market
• 

  

  /45

  $324,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft

  1660 NE Alameda Ave, Roseburg, OR 97470

  Here's a unique opportunity for the beautiful Rocky Ridge Community! Relatively newer built home for a great price. As you enter, you will immediately notice the vaulted ceilings giving a very spacious feeling with the open floor plan. The light laminate flooring provides a lively sense to the home with nice natural lighting. The kitchen has gorgeous granite with stainless steel appliances and

  

  Ashton Faas

  Faas Realty

  

  1660 NE Alameda Ave, Roseburg, OR 97470
• 

  

  /19

  $700 Per Month

  • Studio
  • 0.5 Baths
  • 616 Sq Ft
  • Condo for Rent

  2037 NE Stephens St Unit Garage # 1, Roseburg, OR 97470

  This spacious double car garage offers an extended layout with approximately 22 feet of width and 28 feet of depth, providing ample room for parking, storage, or additional workspace. With an impressive ceiling height ranging from 12 to 15 feet, the space is ideal for larger vehicles, overhead storage, or shelving systems.The garage is equipped with an automatic door opener for

  2037 NE Stephens St Unit Garage # 1, Roseburg, OR 97470
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  /47

  $125,000

  Sold Apr 07, 2026

  593 NW Sweetbrier Ave, Roseburg, OR 97471

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1946

  Last Sold Summary

  • 14% Above List Price
  • $186/SF
  • 4 Days On Market

  Current Estimated Value $146,315

  Last Listing Agent Aaron Cherry Oregon Life Homes

  

  593 NW Sweetbrier Ave, Roseburg, OR 97471
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  /29

  Not Listed For Sale

  506 Shadow Ranch Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1978

  

  506 Shadow Ranch Ln, Roseburg, OR 97470

  Last Sold Summary

  • 76 Days On Market
• 

  

  /89

  $2,375,000

  $125K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 5,705 Sq Ft

  375 Bella Hills Ln, Roseburg, OR 97471

  Experience the pinnacle of Umpqua Valley living at 375 Bella Hills Lane--an extraordinary 80+ acre, agriculturally zoned estate with sweeping views of the Umpqua River. Peaceful, private, and rich with opportunity, this exceptional agriculturally zoned property offers limitless potential--ideal for a boutique vineyard, agricultural operations, multigenerational living, income-producing retreat,

  

  Kristina Scott

  Umpqua Legacy Realty LLC

  375 Bella Hills Ln, Roseburg, OR 97471
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  /28

  $2,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,681 Sq Ft
  • 5 acre Country property on North Bank Rd

  7654 N Bank Rd, Roseburg, OR 97470

  Well built 3 bedroom 2 bath with 2 car garage. Nice hardwood floors throughout with carpet in 2 bedrooms. Vaulted ceilings in the living room with wood stove. Kitchen has granit countertops, stainless steel appliance with convection oven. Back yard has deer fence with private back deck and paver patio area. Well water and septic tank. Tenant responsible for electric and internet. This home is

  7654 N Bank Rd, Roseburg, OR 97470
• 

  

  /25

  $202,000

  Sold Aug 05, 2025

  424 NE Kirby Ave, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $180/SF
  • 3 Days On Market

  Current Estimated Value $222,595

  Last Listing Agent Cindy Mahaffy RE/MAX Integrity

  

  424 NE Kirby Ave, Roseburg, OR 97470
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  /23

  Not Listed For Sale

  403 Shadow Ranch Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1978

  

  403 Shadow Ranch Ln, Roseburg, OR 97470

  Last Sold Summary

  • 67 Days On Market
• 

  

  /48

  $535,000

  $15K PRICE DROP Pending

  • 5 Beds
  • 2.5 Baths
  • 3,360 Sq Ft

  3257 NE Follett St, Roseburg, OR 97470

  Rare in-town acreage with space, privacy, and views. Situated on 1.52 acres, this expansive 5-bedroom, 2.5-bath home offers over 3,300 square feet of flexible living space with an open floor plan designed for both comfort and functionality. Enjoy city views while still feeling tucked away and private, with room to spread out indoors and out.The layout lends itself to multiple uses: perfect for

  

  Chelsie Siemens

  RE/MAX Integrity

  

  3257 NE Follett St, Roseburg, OR 97470
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  /15

  $2,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,385 Sq Ft
  • 3 Bedroom 2 Bath house in 55+!

  581 NE Alameda Ave, Roseburg, OR 97470

  This is a three bedroom two bath house located in a 55+ community. The kitchen provides a range, fridge, dishwasher, microwave and garbage disposal. The home also features a utility room with washer/dryer hook-ups. Call today for an appointment to view!Please go to our website at for more information or to apply!? Availability date is an estimate only and may change due to

  581 NE Alameda Ave, Roseburg, OR 97470
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  /43

  $560,000

  Sold Aug 11, 2025

  1260 NE Granite Ridge St, Roseburg, OR 97470

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $262/SF
  • 4 Days On Market

  Current Estimated Value $570,927

  Last Listing Agent Sherri Brown The Neil Company Real Estate

  

  1260 NE Granite Ridge St, Roseburg, OR 97470
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  /19

  Not Listed For Sale

  127 Northpark Ln, Roseburg, OR 97470

  • 1 Bed
  • 1 Bath
  • 504 Sq Ft
  • Built 1972

  

  127 Northpark Ln, Roseburg, OR 97470

  Last Sold Summary

  • 89 Days On Market

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