Winston, OR Homes for Sale

• 

  

  

  /48

  $270,000

  • 3 Beds
  • 1.5 Baths
  • 1,412 Sq Ft

  54 NW Rose St, Winston, OR 97496

  First time on the market in over 40 years! Whether you are a first-time home buyer, an investor or someone with a home business that wants to take advantage of the commercial zoning, this property offers a fantastic opportunity at a great price point. Built in 1947, the home carries vintage charm and the potential for updates or personalization. There are three bedrooms, a small office and a

  

  Deleta Dickson

  eXp Realty, LLC

  (458) 302-2153

  

  54 NW Rose St, Winston, OR 97496
• 

  

  

  /45

  $699,500

  • 4 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  635 Wil Way, Winston, OR 97496

  One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

  

  Ashton Faas

  Different Better Real Estate

  (458) 232-3589

  

  635 Wil Way, Winston, OR 97496
• 

  

  

  /46

  $479,900

  • 4 Beds
  • 2 Baths
  • 2,534 Sq Ft

  13224 Lookingglass Rd, Winston, OR 97496

  Experience the unique allure of this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled

  

  Deleta Dickson

  eXp Realty, LLC

  (458) 237-8628

  

  13224 Lookingglass Rd, Winston, OR 97496
• 

  

  

  /15

  $200,000

  • Land
  • 4.26 Acres
  • $46,948 per Acre

  0 Wil Way Unit 24292479, Winston, OR 97496

  Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Different Better Real Estate

  (458) 217-1693

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  

  

  /15

  $200,000

  • Land
  • 3.14 Acres
  • $63,694 per Acre

  0 Wil Way Unit 24278136, Winston, OR 97496

  Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Different Better Real Estate

  (458) 224-5797

  

  0 Wil Way Unit 24278136, Winston, OR 97496
• 

  

  /28

  $375,000

  • Land
  • 7.4 Acres
  • $50,676 per Acre

  0 Wil Way Unit 24094727, Winston, OR 97496

  Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

  

  Ashton Faas

  Different Better Real Estate

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
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  /39

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  441 NW Galaxy Dr, Winston, OR 97496

  Finished heated shop • Finished heated/cooled garage • Stunning views • Primary bedroom on main floor. Beautiful home overlooking the city w/panoramic views of surrounding mountains and valleys. Multiple decks and thoughtfully designated outdoor spaces for entertaining or relaxation. Fully finished and heated shop w/ vaulted ceilings, skylight and wood beams seamlessly attached to the fully

  

  Nichole Sharman

  Works Real Estate

  (458) 854-7182

  

  441 NW Galaxy Dr, Winston, OR 97496
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  /42

  $385,000

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

  700 SE Tokay St, Winston, OR 97496

  Welcome to this inviting 3-bedroom, 2-bathroom home offering comfort, convenience, and modern touches throughout. The bright and open kitchen features stainless steel appliances and granite countertops, making meal prep a joy. Enjoy the ease of single-level living with a functional floor plan, perfect for both everyday life and entertaining. The fenced backyard provides a safe space for pets,

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  700 SE Tokay St, Winston, OR 97496
• 

  

  /47

  $489,900

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  263 Wil Way, Winston, OR 97496

  Welcome to Your Like-New Custom Home in Winston, OR!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality and thoughtful design shine through every detail. The open concept floor plan boasts soaring vaulted ceilings, stunning floors, and an inviting layout that flows seamlessly for both everyday living and entertaining. At the heart of the home, the gourmet

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  263 Wil Way, Winston, OR 97496
• 

  

  /37

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  360 NE Rose Ridge Dr, Winston, OR 97496

  Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

  Aaron Cherry Oregon Life Homes

  

  360 NE Rose Ridge Dr, Winston, OR 97496
• 

  

  /31

  $57,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  111 Sharway Ln, Winston, OR 97496

  This charming 2-bedroom, 1-bath manufactured home is fully furnished and move-in ready, located in a well-kept 55+ community with low space rent, offering an ideal mix of comfort and convenience. The property includes a recently built carport, two storage sheds, and a beautifully landscaped yard that enhances its curb appeal. With a roof that’s just 5 years old and a brand-new HVAC system

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  111 Sharway Ln, Winston, OR 97496
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  /27

  $429,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  631 SE Rose Ridge Dr, Winston, OR 97496

  This is a gem! Single-level upgraded home built in 2020. This custom property combines quality construction with modern finishes throughout. Step inside to an open and inviting floor plan featuring vaulted living room and 9 foot ceilings, recessed lighting, ceiling fans, and a perfect blend of rich wood and stylish tile flooring in the main living areas and bathrooms. The entertainment center in

  Jacob Gilman The Neil Company Real Estate

  

  631 SE Rose Ridge Dr, Winston, OR 97496
• 

  

  /46

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  128 Watusi Ct, Winston, OR 97496

  Very desirable single level home in Lookingglass Estates. Built in 2008 with great curb appeal and no HOA. The cul-de-sac location offers a level quarter acre lot with lovely landscaping & fenced backyard. Enjoy easy care maintenance with in-ground sprinklers, "Leaf Filter" gutter system, fruit trees, garden boxes and hot tub. Inside you’ll appreciate the open concept, split floor plan with 3BR /

  Thomas Gulan RE/MAX Integrity

  

  128 Watusi Ct, Winston, OR 97496
• 

  

  /20

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 2,026 Sq Ft

  308 Helweg Rd, Winston, OR 97496

  Prime 12.91-acre agricultural property zoned (FC) Exclusive Farm Use-Cropland with 10 acres of primary pond and supplemental river irrigation rights (priority date 1983). This land is perfectly positioned for a profitable homestead, organic farm, or u-pick business. Previously used for hay production and livestock, the soil and water offer a solid foundation for success. The existing home and

  Aaron Cherry Oregon Life Homes

  

  308 Helweg Rd, Winston, OR 97496
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  /48

  $454,000

  • 2 Beds
  • 1 Bath
  • 2,056 Sq Ft

  0 Rice Creek Rd, Winston, OR 97496

  100% off-grid living on your own 20-acre slice of paradise! Located within "The Ranch" - a close-knit homesteading community of like-minded landowners who each steward their own property while embracing a shared off-grid lifestyle. Just 25 minutes southwest of Winston, Oregon, this property is accessed via a gated 4-mile gravel road through BLM and private timberlands. The resilient home features

  Aaron Cherry Oregon Life Homes

  

  0 Rice Creek Rd, Winston, OR 97496
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  /32

  $585,000

  • 4 Beds
  • 3 Baths
  • 2,660 Sq Ft

  102 Sarah Bear Ln, Winston, OR 97496

  Stately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new gas appliances,

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
• 

  

  /23

  $135,000

  • 3 Beds
  • 2 Baths
  • 1,381 Sq Ft

  260 NE Darrell Ave, Winston, OR 97496

  BRING YOUR TOOLBOX TO MAKE THIS HOME SHINE AGAIN OR REMOVE THE HOME AND START FROM SCRATCH WITH UTILITIES ALREADY IN PLACE. This 3 bedroom 2 bathroom home is going to be a project, but potential is there. High ceilings and open floor plan. Primary Bedroom offers a walk in closet with a large bathroom with shower, garden tub and double sinks. Tool Shed and Carport. Needs new roof and flooring

  Lacey Williams Trueblood Real Estate

  

  260 NE Darrell Ave, Winston, OR 97496
• 

  

  /44

  $319,900

  • 4 Beds
  • 2 Baths
  • 1,288 Sq Ft

  68 NW Rose St, Winston, OR 97496

  24x36 Shop & 7x40 inground heated lap pool!! This property offers the perfect blend of comfort, functionality, and outdoor living. The standout features are hard to miss - an impressive 24x36 shop ideal for hobbies, storage, or projects, and a 7x40 inground heated lap pool that's perfect for both exercise and relaxation. Whether you're working, unwinding, or entertaining, this backyard setup has

  Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

  

  68 NW Rose St, Winston, OR 97496
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  /10

  $249,500

  • Land
  • 0.45 Acre
  • $554,444 per Acre

  0 SW Main St, Winston, OR 97496

  Looking for a retail, office or hospitality location in Winston? This lot is strategically located near the intersection of Hwy 42 & Hwy 99 with easy access to I-5 and on the route to Oregon's coastal destinations! This lot is the best that Winston has to offer...

  Jody Tatone RE/MAX Integrity

  

  0 SW Main St, Winston, OR 97496
• 

  

  /29

  $147,000

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  140 NW Bree Dr, Winston, OR 97496

  This beautifully maintained 3-bedroom, 2-bath home offers a bright and inviting open floor plan with a split-bedroom layout for added privacy. The master suite features a generous walk-in closet and an en-suite bathroom, creating a comfortable retreat. Enjoy durable Luxury Vinyl Plank (LVP) flooring throughout, vaulted ceilings, and newer double-pane vinyl windows that fill the home with natural

  Darla Duke Lamonte Real Estate Professionals

  

  140 NW Bree Dr, Winston, OR 97496
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  /2

  $125,000

  • Land
  • 0.36 Acre
  • $347,222 per Acre

  320 5th St, Winston, OR 97496

  The perfect large, level lot to build your home or place a manufactured home on. Just outside of Winston in Dillard. This .36 lot is all flat and usable with city services already on lot. Currently there's a MFH which is of 'no value' on property. This is an Estate sale, so it is being sold "As is" Estate will do no repairs. Bring us an offer.

  Beverly Beier G. Stiles Realty

  

  320 5th St, Winston, OR 97496
• 

  

  /8

  $2,125,000

  • Land
  • 15.05 Acres
  • $141,196 per Acre

  215 Parkinson Rd, Winston, OR 97496

  Lovely acreage on South Umpqua River. Zoned agriculture. Water rights from 1953. 44x60 barn has been partially renovated. Running water at barn. Use your imagination on the uses for this wonderful acreage on the river. Buyer to do all due diligence regarding every aspect of the property. Seller makes no disclosures.

  Nick Knight Knight Realty Group LLC

  

  215 Parkinson Rd, Winston, OR 97496
• 

  

  /27

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  120 SE Edwards Ave, Winston, OR 97496

  Welcome to this 3-bedroom, 2-bath single-level custom home. Thoughtfully designed with comfort and functionality in mind, this 1,421 sq ft residence offers a spacious open-concept layout, vaulted ceilings, and abundant natural light throughout. The kitchen features wood cabinetry, stainless steel appliances, and a breakfast bar perfect for casual meals or entertaining guests. The primary suite

  Jerry Norman Oregon Life Homes

  

  120 SE Edwards Ave, Winston, OR 97496
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  /34

  $278,000

  • 3 Beds
  • 1 Bath
  • 1,085 Sq Ft

  224 5th St, Winston, OR 97496

  MOTIVATED SELLER!! Charming 3-Bedroom Home on Oversized Lot – Perfect for Entertaining! Discover comfort and charm in this updated 3-bedroom, 1-bath home situated on an expansive .36-acre lot with a spacious backyard designed for entertaining, you’ll love spending time outdoors under the beautiful custom built covered porch—perfect for enjoying your morning coffee or relaxing in the evening. Step

  Terri LeVasseur J Mann Realty

  

  224 5th St, Winston, OR 97496
• 

  

  /20

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft

  120 SW Brantley Dr, Winston, OR 97496

  Charming 3 bedroom, 2 bath home with attached 2 car garage & multiple outbuildings. Large cement patio with lots of outdoor living area. Sits on a large lot, (over 3/5ths of an acre) with lots of fruit trees & room to roam! Must see to appreciate this lovely home!

  Judith Zuver Winston Realty & Insurance

  

  120 SW Brantley Dr, Winston, OR 97496
• 

  

  /17

  $349,900

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

  185 Lebleu Ln, Winston, OR 97496

  Buyer incentive offered if under contract by 9/15. Solid 3 bed, 2 bath in Winston with a newer roof. Welcome home to this well maintained single-story home with a modern floorplan, featuring an inviting open-concept layout designed for both comfort and privacy. The spacious primary bedroom includes an attached bathroom, offering a private retreat. The living room features a gas fireplace, perfect

  Kurt Delahooke Keller Williams Realty Eugene and Springfield

  

  185 Lebleu Ln, Winston, OR 97496
• 

  

  /25

  $695,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  1090 E Willis Creek Rd, Winston, OR 97496

  Secluded private 2167 sq ft 3 br 2 bath contemporary home on 9.81 acres. Has open beam ceilings, wood stove, barn, wood shop, 2 gar garage. Garden area, city water, creek. Mostly level property. Charming kitchen with large pantry and skylight, ample dining room overlooking the garden and yard. Living room has bay window and room to entertain. Covered parking for boat or RV.

  Valynn Currie Currieco Real Estate

  

  1090 E Willis Creek Rd, Winston, OR 97496
• 

  

  /19

  $60,000

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  119 Oak Leaf Ln, Winston, OR 97496

  Small but mighty! This well-maintained 384 sq ft home, built in 2021, offers a comfortable and convenient living space in a peaceful 55+ community. Featuring laminate flooring throughout, the home includes a cozy bedroom and a bright, functional bathroom. Washer and dryer hookups are available for added convenience, and a private storage unit provides extra space for your belongings. Spacious

  Cindi Mills RE/MAX Integrity

  

  119 Oak Leaf Ln, Winston, OR 97496
• 

  

  /47

  $377,500

  • 3 Beds
  • 1 Bath
  • 1,434 Sq Ft

  10 SE Kegler Ave, Winston, OR 97496

  Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

  Anthony Beckham Different Better Real Estate

  

  10 SE Kegler Ave, Winston, OR 97496
• 

  

  /44

  $739,000

  • 4 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  1068 Rice Creek Rd, Winston, OR 97496

  This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country living space. This beautiful ranch-style home features updates, a newer roof, and recent interior and exterior paint. The gourmet kitchen includes double ovens and a walk-in pantry. The large living room features a fireplace.The huge primary bedroom includes a walk-in closet and a two-headed shower. One of the

  Joan Smith G. Stiles Realty

  

  1068 Rice Creek Rd, Winston, OR 97496
• 

  

  /28

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  140 Teresa Ln, Winston, OR 97496

  This modern, beautiful home is located in the highly sought-after Winston neighborhood. The home has been recently remodeled down to the studs and includes brand new HVAC, new appliances, and new roof. Step inside to find luxury vinyl plank flooring, recessed lighting, and soaring vaulted ceilings, and an abundance of windows that create a spacious and inviting atmosphere. The open-concept

  Jason Mann J Mann Realty

  

  140 Teresa Ln, Winston, OR 97496
• 

  

  /5

  $150,000

  • Land
  • 0.64 Acre
  • $234,375 per Acre

  873 SE Edgewood St, Winston, OR 97496

  0.64 Acre Buildable Lot zoned RR. Out of flood plain. At the end of a quiet dead St. Buyer to do all due diligence to verify buildability. Has not been septic approved.

  Nick Knight Knight Realty Group LLC

  

  873 SE Edgewood St, Winston, OR 97496
• 

  

  /47

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft

  231 NE Darrell Ave, Winston, OR 97496

  Great location with a custom built one level home located on .39 of an acre at the end of the road in Winston with City Services! Home built in 1981 with approximately 1,374 square feet, 3 bedrooms and 2 full bathrooms, primary bedroom and bathroom has a walk-in closet and slider door to deck, nice Kitchen with oodles of oak cabinets, lots of counter space, plus a pantry, Living room has

  Cynthia Johnson Johnson Group Real Estate, LLC

  

  231 NE Darrell Ave, Winston, OR 97496
• 

  

  /41

  $830,000

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

  375 Porter Creek Rd, Winston, OR 97496

  Discover the perfect blend of vineyard lifestyle and modern comfort in this beautifully 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.At the heart of the property is a spacious 3,000 sq ft home featuring four large bedrooms and

  Lorrie Normann Triple Oaks Realty LLC

  

  375 Porter Creek Rd, Winston, OR 97496
• 

  

  /39

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,835 Sq Ft

  151 Sherry St, Winston, OR 97496

  Step into this charming 1965 Ranch-style home, nestled in a peaceful neighborhood on a generous double lot in the heart of Winston, Oregon. With 3 bedrooms, 1.5 bathrooms, and a large, fully fenced corner lot, this property offers both privacy and convenience. This home boasts ample storage space throughout, with built-in shelving and closets to keep your living areas tidy. The cozy and airy

  RaNae Sams Oregon Life Homes

  

  151 Sherry St, Winston, OR 97496
• 

  

  /15

  $230,000

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

  751 SE Meadowood Dr, Winston, OR 97496

  1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot of home for the money. Central heat and air conditioning, carport and lots of room for a garden. A great home for the money. Affordable living, close to park and community center.

  Timothy A Smith RE/MAX Integrity

  

  751 SE Meadowood Dr, Winston, OR 97496
• 

  

  /32

  $469,900

  • 2 Beds
  • 2 Baths
  • 1,764 Sq Ft

  1941 Byron Creek Rd, Winston, OR 97496

  Come home to your own private escape hidden in the trees! Beautiful parklike setting with amazing views and end of the road privacy. Property features include a huge, large covered RV storage, detached guest quarters, a storeroom & workshop. The manufactured home was custom built for the current owners with many custom touches. An expansive deck is perfect for gatherings or taking in the amazing

  Andrew Stoner Roseburg Homes Realty

  

  1941 Byron Creek Rd, Winston, OR 97496
• 

  

  /14

  $199,999

  • 2 Beds
  • 1 Bath
  • 735 Sq Ft

  110 SE Darrell Ave, Winston, OR 97496

  BRAND NEW ROOF IN 2025 AT THE SAME LOW PRICE! Cute updated 2 bedroom home with small utility room. Kitchen with newer appliances. Brand New Roof and hot water heater and recently updated flooring, interior and exterior paint. Living room offers gas heater and a front bonus area. Partially fenced yard with garden shed in back. Nice corner lot with driveway. Call for your showing today!

  Lacey Williams Trueblood Real Estate

  

  110 SE Darrell Ave, Winston, OR 97496
• 

  

  /4

  $225,000

  • Land
  • 0.71 Acre
  • $316,901 per Acre

  0 SE Gregory Dr, Winston, OR 97496

  Ready to go multifamily with construction plans. See attached plans for 3 triplex buildings. Utilities are to property line. Water & sewer available. Great opportunity for a hard to find multifamily property. CLA for more information

  Larry KW Alberts Keller Williams Realty Eugene and Springfield

  

  0 SE Gregory Dr, Winston, OR 97496
• 

  

  /16

  $850,000

  • Land
  • 37.86 Acres
  • $22,451 per Acre

  0 Danielle Dr Unit 122251646, Winston, OR 97496

  Prime development opportunity in Winston, Oregon! This expansive 38-acre property has potential for 90 buildable residential lots, perfect for a new housing community. Situated in a peaceful location with easy access to local amenities, this land offers a great investment potential for developers. Ideal for those looking to create a vibrant neighborhood in a growing area. Don’t miss out on this

  Jeremy Parmenter TLC Realty

  

  0 Danielle Dr Unit 122251646, Winston, OR 97496

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