Are yards well-kept in Winston, OR?

As of early 2026, 98% of users say yards are well-kept

Is Winston, OR dog-friendly?

As of early 2026, 98% of users say it's dog friendly

Is parking easy in Winston, OR?

As of early 2026, 89% of users say parking is easy

Is a car needed in Winston, OR?

As of early 2026, 87% of users say car is needed

Does Winston, OR show holiday spirit?

As of early 2026, 76% of users say there's holiday spirit

Do kids play outside in Winston, OR?

As of early 2026, 73% of users say kids play outside

Is there wildlife in Winston, OR?

As of early 2026, 68% of users say there's wildlife

Is Winston, OR quiet?

As of early 2026, 67% of users say it's quiet

Does Winston, OR have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are neighbors friendly in Winston, OR?

As of early 2026, 60% of users say neighbors are friendly

Do residents of Winston, OR plan to stay at least 5 years?

As of early 2026, 57% of users say they plan to stay for at least 5 years

Is Winston, OR walkable to grocery stores?

As of early 2026, 56% of users say it's walkable to grocery stores

Is Winston, OR walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Would people walk alone at night in Winston, OR?

As of early 2026, 53% of users say people would walk alone at night

Are the streets well-lit in Winston, OR?

As of early 2026, 51% of users say streets are well-lit

Are there community events in Winston, OR?

As of early 2026, 23% of users say there are community events

OFF MARKET

281 SE Darrell Ave
Winston, OR 97496

3 Beds
2 Baths
1,292 sqft

$308,500

Trulia Estimate

as of Jul 21, 2026

Est. Refi. Payment $1,787/mo*

Refinance Your Home

$308,500

Trulia Estimate

as of Jul 21, 2026

Est. Refi. Payment $1,787/mo*

Refinance Your Home

3 Beds

2 Baths

1,292 sqft

Local Information

Map ViewExplore the area around 281 SE Darrell Ave.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Nice three bedroom, 2 bath w/large back yard. Quiet neighborhood, close to park and extra RV parking. Tile floor kichen, newer oak cabinets, extra lrg. dining area.

281 SE Darrell Ave, Winston, OR 97496 is a 3 bedroom, 2 bathroom, 1,292 sqft single-family home built in 1977. It last sold for $136,250 on Sep 3, 2013. It is currently off market. The Trulia Estimate is $308,500, with a rent estimate of $1,845/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 281 SE Darrell Ave

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningCooling System: OtherHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1Floors: Other, Carpet, Concrete
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DishwasherRefrigerator
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherExterior: WoodFoundation Type: Concrete
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1977Year Updated: 1985
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Price History for 281 SE Darrell Ave

Date	Price	Event	Source
09/03/2013	$136,250	Sold	RMLS (OR) #13085617
Recording Date 09/03/2013 County Transfer Tax N/A Total Transfer Tax N/A
08/13/2013	$139,777	Listed For Sale	Agent Provided

06/26/2013	$139,777	ListingRemoved	Agent Provided

03/22/2013	$139,777	Listed For Sale	Agent Provided

08/01/1990	$53,000	Sold	N/A
Recording Date 08/01/1990 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Winston

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2025
Tax	$2,910
Assessment	$291,783

Home facts updated by county records

Comparable Sales for 281 SE Darrell Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
350 SE Tokay St, Winston, OR	0.16	Single-Family Home	$225,000	05/18/26	3	2	1,431
481 SE Gregory Dr, Winston, OR	0.18	Single-Family Home	$90,000	09/25/25	3	2	1,008
200 SE Darrell Ave, Winston, OR	0.09	Single-Family Home	$299,000	08/27/25	3	2	1,316
180 SE Darrell Ave, Winston, OR	0.10	Single-Family Home	$305,000	08/21/25	3	2	1,318
190 SE Darrell Ave, Winston, OR	0.10	Single-Family Home	$310,000	11/20/25	3	3	1,355
54 NW Rose St, Winston, OR	0.38	Single-Family Home	$200,000	10/10/25	3	3	1,412
600 SE Carrol St, Winston, OR	0.26	Single-Family Home	$321,000	03/31/26	3	2	1,692
600 SE Carroll St, Winston, OR	0.27	Single-Family Home	$321,000	03/31/26	3	2	1,692
120 SE Edwards Ave, Winston, OR	0.12	Single-Family Home	$315,000	02/27/26	3	2	1,421
50 NE Ronald St, Winston, OR	0.35	Single-Family Home	$185,000	10/06/25	3	1	1,104

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $295,100
3 bd
2 ba
1,316 sqft
200 SE Darrell Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
SOLD
MAR 27, 2026
$250,000
3 bd
2 ba
1,080 sqft
265 SE Grape Ave,
Winston, OR 97496
Stellar Realty Northwest, Sold
FOR SALE
$270,000
3 bd
1 ba
1,000 sqft
340 SE Darrell Ave,
Winston, OR 97496
Keller Williams Realty Eugene and Springfield, Active
SOLD
NOV 20, 2025
$310,000
3 bd
2 ba
1,355 sqft
190 SE Darrell Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
OFF MARKET
3 bd
2 ba
1,318 sqft
180 SE Darrell Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
OFF MARKET
Est. $318,200
3 bd
2 ba
1,323 sqft
189 SE Darrell Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Sold
OFF MARKET
Est. $260,900
3 bd
1 ba
960 sqft
351 SE Darrell Ave,
Winston, OR 97496
Currieco Real Estate, Sold
OFF MARKET
Est. $235,700
2 bd
1 ba
802 sqft
261 SE Grape Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Sold
OFF MARKET
Est. $189,300
2 bd
1 ba
1,158 sqft
170 SE Darrell Ave,
Winston, OR 97496
The Neil Company Real Estate, Sold
FOR SALE
0.74 ACRES
$459,000
3 bd
1 ba
1,250 sqft
311 SE Grape Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Active
OFF MARKET
Est. $250,200
2 bd
1 ba
762 sqft
390 SE Gregory Dr,
Winston, OR 97496
Rogue Real Estate, LLC, Sold
OFF MARKET
Est. $238,200
3 bd
1 ba
1,310 sqft
160 SE Darrell Ave,
Winston, OR 97496
Oregon Life Homes, Sold

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Additional Cost

Assigned Schools

These are the assigned schools for 281 SE Darrell Ave.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winston

At least 37 Trulia users voted on each feature.

98 % Say yards are well-kept
98 % Say it's dog friendly
89 % Say parking is easy
87 % Say car is needed
76 % Say there's holiday spirit
73 % Say kids play outside
68 % Say there's wildlife
67 % Say it's quiet
62 % Say there are sidewalks
60 % Say neighbors are friendly
57 % Say they plan to stay for at least 5 years
56 % Say it's walkable to grocery stores
55 % Say it's walkable to restaurants
53 % Say people would walk alone at night
51 % Say streets are well-lit
23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Amy
Resident
7y ago
"I just moved here in December of 2018. So far, the neighbors are friendly, and the police frequently roam around town to show their presence. "
1
Flag
Trulia User
Resident
7y ago
"An alleged shooting happened recently on Jorgens street next door to a house pending sale. Otherwise for the most part not a bad neighborhood just a few bad houses. Drugs...."
10
Flag
Sissyboy2011
Resident
7y ago
"That there are thieves and tweekers everywhere. Watch out at the parks for needles and the streets. Lock up everything you keep outside including your vehicles. Kids bikes get stolen daily. most of the time WPD is running a skeleton crew. "
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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NEW - 10 HRS AGO
$1,350/mo
4 bd
1 ba
181-187 NE Baker St,
Winston, OR 97496
$1,200/mo
3 bd
1 ba
577 NW T St #577,
Winston, OR 97496
$995/mo
2 bd
1 ba
410 SE Park St #8,
Winston, OR 97496
Contact for price
1-2 bd
1-2 ba
189 NW Glenhart Ave #776f18ccb,
Winston, OR 97496
Contact for price
1-2 bd
1-2 ba
209 NW Glenhart Ave #776f18ccb,
Winston, OR 97496
APPLY INSTANTLY
PET FRIENDLY
$1,800/mo
3 bd
2 ba
Address Not Disclosed,
Roseburg, OR 97471
See more homes for rent in
Winston
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Homes for sale near 281 SE Darrell Ave

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AUCTION
0.45 ACRES
Est. $283,600
3 bd
2 ba
1,284 sqft
41 NE Ronald St,
Winston, OR 97496
0.74 ACRES
$459,000
3 bd
1 ba
1,250 sqft
311 SE Grape Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Active
0.61 ACRES
$205,000
2 bd
1 ba
1,323 sqft
381 SE Gregory Dr,
Winston, OR 97496
Platinum Realty, Active
$270,000
3 bd
1 ba
1,000 sqft
340 SE Darrell Ave,
Winston, OR 97496
Keller Williams Realty Eugene and Springfield, Active
0.25 ACRES
$249,000
2 bd
1 ba
939 sqft
71 SE Ronald St,
Winston, OR 97496
ICON Real Estate Group, Active
$365,000
3 bd
1 ba
1,440 sqft
10 SW Peach Ln,
Winston, OR 97496
Stellar Realty Northwest, Active
$315,000
3 bd
1 ba
1,348 sqft
101 SW Peach Ln,
Winston, OR 97496
Berkshire Hathaway HomeServices Real Estate Professionals, Active
$355,000
4 bd
2 ba
1,710 sqft
380 NW Cary St,
Winston, OR 97496
Oregon Life Homes, Active
$315,000
3 bd
2 ba
1,594 sqft
340 NW Elizabeth Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Active
See more homes for sale in
Winston
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Off Market Homes Near 281 SE Darrell Ave

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SOLD
JUL 17, 2026
$280,000
2 bd
1 ba
832 sqft
807 Callahan Dr,
Roseburg, OR 97471
Trueblood Real Estate, Sold
SOLD
JUL 13, 2026
$450,000
3 bd
2 ba
891 sqft
13474 Old Highway 99 S,
Myrtle Creek, OR 97457
eXp Realty, LLC, Sold
SOLD
JUL 13, 2026
$310,000
3 bd
2 ba
1,343 sqft
202 NE Plum Ridge Dr,
Winston, OR 97496
RE/MAX Integrity, Sold
SOLD
JUL 10, 2026
$205,000
3 bd
2 ba
1,280 sqft
345 Littlebrook Ln,
Roseburg, OR 97471
eXp Realty, LLC, Sold
SOLD
JUL 10, 2026
$332,000
3 bd
2 ba
1,406 sqft
153 Quincy Ave,
Roseburg, OR 97471
Oregon Life Homes, Sold
SOLD
JUL 7, 2026
$349,000
3 bd
2 ba
1,212 sqft
4216 Stella St,
Roseburg, OR 97471
eXp Realty, LLC, Sold
SOLD
JUL 6, 2026
$325,000
3 bd
2 ba
1,156 sqft
301 NW Midway St,
Winston, OR 97496
Faas Realty, Sold
SOLD
JUL 1, 2026
$380,000
3 bd
1 ba
1,352 sqft
421 NW Cary St,
Winston, OR 97496
eXp Realty, LLC, Sold
SOLD
JUN 26, 2026
$330,000
3 bd
1 ba
1,000 sqft
10 Carmel Ct,
Roseburg, OR 97471
Brighthome Real Estate Group
SOLD
JUN 26, 2026
$310,100
3 bd
1 ba
1,056 sqft
113 Shaffer Ct,
Roseburg, OR 97471
The Neil Company Real Estate, Sold
See more homes for sale in
Winston
Take a look

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281 SE Darrell Ave
Winston, OR 97496

$308,500

$308,500

Local Information