Waterfront homes for sale & real estate in Winston, OR

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3D WALKTHROUGH

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
WOW! Panoramic valley views, over 20 acres of RM-zoned land, and a location bordering Wildlife Safari make this 4-bedroom, 3.5-bath, 3,072 SF home one of Southern Oregon’s most unique offerings. Positioned at the end of the road, it enjoys exceptional privacy while overlooking Abacela Vineyards, rolling valleys, and Wildlife Safari, with potential for 360-degree views. RM zoning adds rare flexibility for a private 20+ acre parcel, allowing a range of residential uses not commonly available at this scale. Wake up to the scent of lavender and eucalyptus on the breeze and the distant roar of lions from nearby Wildlife Safari, where giraffes, zebras, rhinos, and other remarkable animals b

$619,900

4 beds4 baths3,072 sq ft

635 Wil Way, Winston, OR 97496

Large walk in pantry • Two primary suites • Exceptional privacy

Anthony Beckham • Different Better Real Estate

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Beautiful Craftsman-style home with fantastic curb appeal and a slate-tile covered front porch. This spacious 3-bedroom plus office home offers 1,752 square feet of finished living space, along with a full 2,272-square-foot unfinished walkout basement. The main level features a large open kitchen with gas cooking, an island, granite countertops, pantry, stainless steel appliances, and a hammered copper sink. The vaulted living room includes a gas fireplace and opens to a spacious deck, creating a great flow for everyday living and entertaining. The primary suite bathroom includes a walk-in closet, slate flooring, a granite double vanity, jetted shower, and jetted soaking tub. The office fea

$499,900

3 beds2 baths4,024 sq ft

2620 NW Brockway Rd, Winston, OR 97496

Craftsman style home • Hammered copper sink • Granite countertops

Tyler Head • Turning Point Realty Group

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Escape to your own off-grid retreat on a 20-acre shared property in a gated community with coded access. This is a unique property on jointly owned lot, in an off grid community. Seller is selling 50% share in 20 acre lot. Land use agreement in place. This beautifully crafted 1,000 SF cabin showcases exceptional handcrafted woodwork and rustic charm throughout. Features include 1 bedroom plus a daybed sleeping area, solar power system with battery bank, spring-fed water system with storage tanks, solar shower, solar hot water, and wood stove hot water coil loops. Enjoy peaceful views of open fields, forested areas, and a seasonal creek. Additional improvements include an outhouse, woodshed,

$190,000

1 bed1 bath1,000 sq ft

0 Rice Creek Rd, Winston, OR 97496

Gated community • Seasonal creek • Handcrafted woodwork

Starlight Turner • Starlight Realty

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
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 bonus room and three generous bathrooms--perfectly designed for relaxed living or hosting guests. Recent upgrades include newer metal roofs, HVAC systems, a cozy woodstove, and luxury vinyl plank flooring throughout, creating a warm and inviting environment. The estate also includes 8 acres of vineyard

$775,000

4 beds4 baths3,000 sq ft

375 Porter Creek Rd, Winston, OR 97496

41 acre estate • Seasonal pond • Hvac systems

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Charming farmhouse on the South Umpqua River. Set on 6.9 acres with prime farmland and river irrigation water rights. The home features wood floors with an open living room, kitchen & dining area. A large primary bedroom with a full bathroom and walk in closet. 2nd bedroom utilized as an office. Laundry room and detached garage. Nice and private backyard with good shade. City water and new septic system installed in 2021. Zoned (F1) Exclusive Farm Use-Cropland with an established cherry orchard. Tractor and farm equipment included.

$498,000

2 beds2 baths1,440 sq ft

572 Dillard Gardens Rd, Winston, OR 97496

Covered deck • Wood floors • Ensuite bath

Mike Nichols • MORE Realty

Property at 1349 Willis Creek Rd, Winston, OR 97496, 3 beds, 3 baths

$1,099,900

3 beds3 baths2,856 sq ft

1349 Willis Creek Rd, Winston, OR 97496

Jordan Anderson • The Anderson Agency

Property at 6700 Upper Olalla Rd, Winston, OR 97496, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,720 sq ft

6700 Upper Olalla Rd, Winston, OR 97496

Daniel Gandee • Real Broker

Property at 0 Lookingglass Rd, Roseburg, OR 97471

$490,000

Land8.95 acres (lot)

0 Lookingglass Rd, Roseburg, OR 97471

D'Anna Caylor • RE/MAX Integrity

Property at 0 Willis Creek Rd, Winston, OR 97496

$99,000

Land5.78 acres (lot)

0 Willis Creek Rd, Winston, OR 97496

Thomas Gulan • RE/MAX Integrity

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ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Welcome to this immaculate and beautifully appointed 2,094 sq. ft. triple-wide manufactured home in Littlebrook, a peaceful gated 55+ community along the scenic South Umpqua River. This spacious 3-bedroom, 2-bath home offers high-end finishes, vaulted ceilings, large windows, and an inviting open floor plan. The impressive kitchen features a massive island with an eating bar and opens seamlessly to the spacious living room—perfect for entertaining and everyday living. The home also offers both living and dining areas, with French doors adding an elegant touch. Laminate flooring flows through the main living areas, while the bedrooms are comfortably carpeted. The oversized primary suit

$199,000

3 beds2 baths2,094 sq ft

136 Jacob Hale Way, Roseburg, OR 97471

Double sinks • Gated 55 community • French doors

Jennifer Kramer • RE/MAX Integrity

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Embrace the peace of country living in this stunning Camas Valley property. Nestled in a serene, valley surrounded by Oregon's natural beauty, this home offers the perfect blend of privacy and modern comforts. Sprawling acreage with room for horses, livestock or a home garden. Acreage is fenced and crossed fenced. Panoramic mountain vista views and breathtaking sunset views right from your porch. Built to last shop 36x48 perfect for projects, mechanics and secure equipment storage. Ultimate barn 42x72 features dual 24x72 lean-tos for massive covered storage, livestock shelter, or hay staging. Lean-to RV cover offers perfect blend of rugged protection with full hookups. Generator back up sys

$990,000

3 beds2 baths2,270 sq ft

1340 Upper Camas Rd, Camas Valley, OR 97416

Sprawling acreage • Built to last shop • Ultimate barn

Nancy Wood • Oregon Life Homes

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
WOW! One-of-a-kind riverfront home completed in 2024 and set on 5.16 private acres, this custom-built property offers stunning river & mountain views, river access, and exceptional flexibility. Expansive windows and vaulted ceilings fill the home with natural light while framing the surrounding landscape. A bi-parting multi-slide door opens from the living area and kitchen to a spacious deck, creating seamless indoor-outdoor living. Designed for comfort and function, the home features knotty pine accents, a custom oversized rustic-style ceiling fan, kitchen display ledges, and integrated storage maximizing every square foot. Quartz countertops, stainless steel appliances, a spacious p

$749,900

4 beds4 baths2,151 sq ft

3716 Weaver Rd, Riddle, OR 97469

Private acres • Riverfront home • River access

Anthony Beckham • Different Better Real Estate

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Nestled along the banks of Cow Creek, this private 23-acre retreat offers the perfect blend of modern comfort and natural beauty. Built in 2019, this custom single-level home features 2 bedrooms, 2 bathrooms, vaulted ceilings, luxury vinyl plank flooring, granite countertops, and a cozy wood stove. Large windows and sliding doors invite the outdoors in, showcasing peaceful views of the river, mountains, and surrounding woods. Enjoy year-round relaxation from the covered deck overlooking the property's park-like setting. The gated acreage includes a detached garage, RV parking, workshop, garden area, outbuildings, and ample space for recreation, hobbies, or a self-sufficient lifestyle. Addit

$649,000

2 beds2 baths1,344 sq ft

4696 Cow Creek Rd, Riddle, OR 97469

Covered deck • Rv parking • Garden area

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

3D WALKTHROUGH

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
Riverfront treasure with incredible views from full length newer covered deck. Serene private custom 3 br 2.5 bath home on 1.49 acres. 1932 sq ft, 1 level built in 1980. Gourmet kitchen with ample counterspace with antique working stove. The yards are manicured with easy access to the river. Master suit has river view, slider to deck, walk-in shower. Viewing patio down by the river with bench. Picturesque Gazebo in front yard for picnics. River irrigation with pump included. Finished double garage, plus RV parking carport. The basement area has shop wood storage and working area.

$675,000

3 beds3 baths1,932 sq ft

549 Bailey Dr, Roseburg, OR 97471

1.49 acre lot • 2 garage spots • Built 1980

Valynn Currie • Currieco Real Estate

VIDEO TOUR

ABOUT THIS HOME
Waterfront Home for sale in Winston, OR:
This exceptional riverfront property offers luxury, comfort, & breathtaking natural surroundings in one of Roseburg’s most desirable settings. This custom-built single-level home sits along the banks of the beautiful South Umpqua River, offering incredible views & the peaceful sound of the water. The home features a thoughtfully designed living space with an open-concept that creates a bright and spacious atmosphere. Vaulted ceilings enhance the sense of openness while large windows bring in natural light & capture the stunning river views. The living room and family room provide generous space for relaxing or entertaining, while the fireplace creates a warm

$749,900

3 beds2 baths2,484 sq ft

269 Bailey Dr, Roseburg, OR 97471

Riverfront property • Solid wood trim • Large covered deck

Jennifer Kramer • RE/MAX Integrity

Property at 8690 Lookingglass Rd, Roseburg, OR 97471, 3 beds, 2 baths

$3,500,000

3 beds2 baths1,500 sq ft

8690 Lookingglass Rd, Roseburg, OR 97471

Jennifer Kramer • RE/MAX Integrity

Property at 411 Woodland Dr, Winston, OR 97496, 4 beds, 2 baths

$680,000

4 beds2 baths2,240 sq ft

411 Woodland Dr, Winston, OR 97496

Nataly Mattox • RE/MAX Integrity

Property at 1138 Yokum Rd, Riddle, OR 97469, 3 beds, 2 baths

$675,000

3 beds2 baths2,622 sq ft

1138 Yokum Rd, Riddle, OR 97469

Cindy Mahaffy • RE/MAX Integrity

Property at 464 Homestead Dr, Myrtle Creek, OR 97457, 3 beds, 2 baths

$324,900

3 beds2 baths3,027 sq ft

464 Homestead Dr, Myrtle Creek, OR 97457

Craig Warmouth • Berkshire Hathaway HomeServices Real Estate Professionals

Property at 180 Ruckles Dr, Myrtle Creek, OR 97457, 4 beds, 3 baths

$499,000

4 beds3 baths2,398 sq ft

180 Ruckles Dr, Myrtle Creek, OR 97457

Jason Mann • J Mann Realty

Property at 4359 Canyonville Riddle Rd, Riddle, OR 97469, 2 beds, 1 bath

$394,900

2 beds1 bath1,032 sq ft

4359 Canyonville Riddle Rd, Riddle, OR 97469

Scott Barraza • Village Realty

Property at 1263 Yokum Rd, Riddle, OR 97469

$285,000

Land165.00 acres (lot)

1263 Yokum Rd, Riddle, OR 97469

Tim Bare • Umpqua Legacy Realty

Property at 505 Sibold Canyon Rd, Tenmile, OR 97481

$249,000

Land16.59 acres (lot)

505 Sibold Canyon Rd, Tenmile, OR 97481

Aaron Cherry • Oregon Life Homes

Property at Hard Cash Ln, Camas Valley, OR 97416

$115,000

Land2.40 acres (lot)

Hard Cash Ln, Camas Valley, OR 97416

Ashton Faas • Different Better Real Estate

Property at 751 E Happy Valley Rd, Roseburg, OR 97471

$50,000

Land0.44 acre (lot)

751 E Happy Valley Rd, Roseburg, OR 97471

Valynn Currie • Currieco Real Estate

Waterfront Homes for Sale in Winston

There are currently 9 waterfront homes for sale in Winston at a median listing price of $409K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winston stay on the market for 55 days. This map is refreshed with the newest listings in Winston every 15 minutes.

In the past month, 5 homes have been sold in Winston. In addition to houses in Winston, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Winston last month. Find your dream home in Winston 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 Winston are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winston. Our Winston real estate stats and trends will give you more information about home buying and selling trends in Winston. If you're looking to sell your home in the Winston area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winston 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 Fri Aug 28 2026

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Waterfront homes for sale & real estate in Winston, OR

Waterfront Homes for Sale in Winston

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