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

What is the price history for 252 SE Gregory Dr?

252 SE Gregory Dr in Winston, OR last sold for $335,000 in October 2012.

Is Winston a buyer's or seller's market?

Winston is currently a buyer's market, based on recent for-sale activity.

What do residents say about Winston?

Residents describe Winston, OR as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Winston, OR .

What are the closest schools to 252 SE Gregory Dr?

The closest schools to 252 SE Gregory Dr in Winston, OR are Brockway Elementary School (Pre-K), Douglas High School (rated 5/10), Mcgovern Elementary School (rated 7/10).

OFF MARKET

$335,000

Last sold price

Studio
2 Baths
2,184 sqft (on 0.42 acres)

252 SE Gregory Dr, Winston, OR 97496

Currently Off Market - Sold Oct 1, 2012 for $335,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1927 Green Ave, Roseburg, OR	2.63	Multi-Family Home	$280,000	11/18/25	4	2	2,092
1895 Green Ave, Roseburg, OR	2.64	Multi-Family Home	$280,000	11/18/25	4	2	2,092
1883 Green Ave, Roseburg, OR	2.65	Multi-Family Home	$280,000	11/18/25	4	2	2,092
160/162 Victoria Ct, Roseburg, OR	2.37	Multi-Family Home	$379,500	09/10/25	4	12	2,242
1911 Green Ave, Roseburg, OR	2.63	Multi-Family Home	$260,000	11/18/25	4	2	1,679
1552 SE Kane St, Roseburg, OR	6.28	Multi-Family Home	$305,000	09/08/25	4	3	2,012
2324 W Crestview Ave, Roseburg, OR	6.40	Multi-Family Home	$290,000	05/29/26	2	2	1,688
1537 SE Pine St, Roseburg, OR	6.35	Multi-Family Home	$283,000	11/26/25	5	5	2,987
2986 W Jay Ave, Roseburg, OR	6.54	Multi-Family Home	$156,000	07/20/26	4	2	1,300
512 W Center St, Roseburg, OR	6.72	Multi-Family Home	$429,000	01/29/26	3	2	1,458

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
189 SE Darrell Ave, Winston, OR 97496	0.01	$316,000	3	2	1,323	Off Market
190 SE Darrell Ave, Winston, OR 97496	0.06	$310,000	3	2	1,355	Recently Sold
200 SE Darrell Ave, Winston, OR 97496	0.06	$293,800	3	2	1,316	Off Market
180 SE Darrell Ave, Winston, OR 97496	0.06	$299,300	3	2	1,318	Off Market
261 SE Darrell Ave, Winston, OR 97496	0.08	$285,000	2	1	1,080	For Sale
170 SE Darrell Ave, Winston, OR 97496	0.07	$170,900	2	1	1,158	Off Market
221 SE Robinson St, Winston, OR 97496	0.08	$287,000	4	2	1,328	Off Market
331 SE Gregory Dr, Winston, OR 97496	0.11	$248,400	3	1	824	Off Market
160 SE Darrell Ave, Winston, OR 97496	0.09	$229,900	3	1	1,310	Off Market
110 SE Darrell Ave, Winston, OR 97496	0.09	$183,300	2	1	735	Recently Sold
120 SE Edwards Ave, Winston, OR 97496	0.12	$315,000	3	2	1,421	Recently Sold
90 SE Darrell Ave, Winston, OR 97496	0.10	$215,000	2	2	924	For Sale

Local Information

Map ViewExplore the area around 252 SE Gregory Dr.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Multi-Family

Built in 2006

0.42 acre lot

2,184 sqft

Garage

About this House

GREAT INVESTMENT. 2 NEWER DUPLEXES ON 1 LOT ALREADY RENTED AND BRING IN 750.00 EACH. THESE WELL BUILT UNITS INCLUDE AN ATTACHED GARAGE FOR EACH, WASHER-DRYER HOOKUPS, NICE MASTER SUITE AND LIVING ROOM. LOW MAINTENANCE PROPERTY.

252 SE Gregory Dr, Winston, OR 97496 is a studio, 2 bathroom, 2,184 sqft multi-family built in 2006. It last sold for $335,000 on Oct 1, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,017/month.

Home Details for 252 SE Gregory Dr

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Floors: Carpet, Concrete

Exterior Features
Exterior Home Features Roof: CompositionDeckExterior: OtherFoundation Type: Concrete Block
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2006Year Updated: 2006
Property Type / Style Property Type: Multi Family

Lot Information
Lot Area: 0.42 acres

Price and Tax history

Date	Event	Price
Oct 1, 2012 Source: RMLS (OR) #12567421	Sold	$335,000
Aug 22, 2012 Source: Agent Provided	Listed For Sale	$350,000
Jun 10, 2008 Source: N/A	Sold	$448,000

Year	Property tax	Tax assessment
2025	$6,900	$659,801

Additional Cost

Market trends in Winston

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Brockway Elementary School
PK-2
Public
224 Students
Winston-Dillard School District 116
NA
GreatSchools Rating
Parent Rating Average
Test scores at this school are above the state average.
Other Review
8y ago
1 Reviews

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
8y 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

Frequently asked questions about 252 SE Gregory Dr

What is the price history for 252 SE Gregory Dr?
252 SE Gregory Dr in Winston, OR last sold for $335,000 in October 2012.
Is Winston a buyer's or seller's market?
Winston is currently a buyer's market, based on recent for-sale activity.
What do residents say about Winston?
Residents describe Winston, OR as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Winston, OR.
What are the closest schools to 252 SE Gregory Dr?
The closest schools to 252 SE Gregory Dr in Winston, OR are Brockway Elementary School (Pre-K), Douglas High School (rated 5/10), Mcgovern Elementary School (rated 7/10).

Apartments for Rent

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$1,800/mo
3 bd
2 ba
155 Corona Loop Rd #155,
Roseburg, OR 97471
PET FRIENDLY
$1,700/mo
2 bd
1 ba
1883 & 1885 SW Green Ave,
Roseburg, OR 97471
APPLY INSTANTLY
PET FRIENDLY
$1,750/mo
3 bd
2 ba
133 Rolling Hills Rd #133,
Roseburg, OR 97471
$1,295/mo
2 bd
1 ba
1959 Green Ave #1961,
Roseburg, OR 97471
See more homes for rent in
Winston
Take a look

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Off Market Homes Near 252 SE Gregory Dr

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SOLD
SEP 4, 2026
$37,700
2 bd
2 ba
924 sqft
56 Manor Loop,
Roseburg, OR 97471
Keller Williams Southern Oregon-Umpqua Valley, Sold
SOLD
SEP 3, 2026
$115,000
3 bd
2 ba
1,188 sqft
1580 Winston Section Rd,
Winston, OR 97496
The Neil Company Real Estate, Sold
SOLD
SEP 1, 2026
$85,000
3 bd
1 ba
672 sqft
340 5th St,
Dillard, OR 97432
The Neil Company Real Estate, Sold
SOLD
AUG 31, 2026
$69,000
3 bd
2 ba
1,188 sqft
235 SE Twin Oaks Loop,
Winston, OR 97496
Stellar Realty Northwest, Sold
SOLD
AUG 27, 2026
$55,000
4 bd
2 ba
1,823 sqft
200 Emils Way #45,
Roseburg, OR 97471
Oregon Life Homes, Sold
SOLD
AUG 26, 2026
$260,000
2 bd
1 ba
1,224 sqft
66 NW Cary St,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Sold
SOLD
AUG 25, 2026
$282,500
3 bd
2 ba
1,350 sqft
1973 Castle Ave,
Roseburg, OR 97471
Oregon Life Homes, Sold
SOLD
AUG 21, 2026
$355,000
3 bd
4 ba
1,800 sqft
13471 Old Highway 99 S,
Myrtle Creek, OR 97457
Winston Realty & Insurance, Sold
SOLD
AUG 21, 2026
$270,000
3 bd
1 ba
1,080 sqft
1976 Burdette Dr,
Roseburg, OR 97471
eXp Realty, LLC, Sold
SOLD
AUG 20, 2026
$522,749
4 bd
2 ba
2,091 sqft
330 Wil Way,
Winston, OR 97496
United Real Estate Properties, Sold
See more homes for sale in
Winston
Take a look

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Homes for sale near 252 SE Gregory Dr

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$485,000
6 bd
6 ba
4,400 sqft
51 SW Brantley Dr,
Winston, OR 97496
Vera-Anne International Real Estate, Active
$300,000
4 bd
3 ba
2,032 sqft
1470 SE Jackson St,
Roseburg, OR 97470
Oregon Life Homes, Active
$575,000
8 bd
4 ba
3,020 sqft
3148 W Harvard Ave,
Roseburg, OR 97471
Berkshire Hathaway HomeServices Real Estate Professionals, Active
$325,000
3 bd
3 ba
1,846 sqft
925 SE Main St,
Roseburg, OR 97470
Oregon Life Homes, Active
0.27 ACRES
$474,900
6 bd
5 ba
2,860 sqft
522 SE Hillside Dr,
Roseburg, OR 97470
Laura J. Mauer, Active
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$335,000

252 SE Gregory Dr, Winston, OR 97496

Home Value

Comparable sales

Nearby home prices

Local Information

Home Highlights

About this House

Home Details for 252 SE Gregory Dr

Interior Features

Exterior Features

Property Information

Lot Information

Price and Tax history

Additional Cost

Market trends in Winston

Around this home

What Locals Say about Winston

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Frequently asked questions about 252 SE Gregory Dr

Apartments for Rent

Off Market Homes Near 252 SE Gregory Dr

Homes for sale near 252 SE Gregory Dr

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Oregon

97496 Neighborhoods

97496 Property Types

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