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

248 SE Gregory Dr
Winston, OR 97496

3 Beds
2 Baths
1,302 sqft

$345,300

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,956/mo*

Refinance Your Home

$345,300

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,956/mo*

Refinance Your Home

3 Beds

2 Baths

1,302 sqft

Local Information

Map ViewExplore the area around 248 SE Gregory Dr.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 248 SE Gregory Dr, Winston, OR. 248 SE Gregory Dr is in Winston, OR and in ZIP code 97496. This property has 3 bedrooms, 2 bathrooms and approximately 1,302 sqft of floor space. This property has a lot size of 8712 sqft and was built in 2021.

248 SE Gregory Dr, Winston, OR 97496 is a 3 bedroom, 2 bathroom, 1,302 sqft single-family home built in 2021. It last sold for $289,900 on Oct 20, 2021. It is currently off market. The Trulia Estimate is $345,300, with a rent estimate of $1,964/month.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 248 SE Gregory Dr

Interior Features
Heating & Cooling Heating: Heat PumpHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Floors: Concrete, Hardwood

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: OtherFoundation Type: Concrete

Property Information
Year Built Year Built: 2021
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 8712 sqft

Price History for 248 SE Gregory Dr

Date	Price	Event	Source
10/20/2021	$289,900	Sold	RMLS (OR) #21566042
Recording Date 10/20/2021 County Transfer Tax N/A Total Transfer Tax N/A
09/13/2021	$289,900	Pending	RMLS (OR) #21566042

08/25/2021	$289,900	Listed For Sale	RMLS (OR) #21566042

Market trends in Winston

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

—

Available listings

8MoM

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Property Tax and Assessment

Year	2024
Tax	$4,691
Assessment	$340,982

Home facts updated by county records

Comparable Sales for 248 SE Gregory Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
200 SE Darrell Ave, Winston, OR	0.08	Single-Family Home	$299,000	08/27/25	3	2	1,316
180 SE Darrell Ave, Winston, OR	0.07	Single-Family Home	$305,000	08/21/25	3	2	1,318
190 SE Darrell Ave, Winston, OR	0.08	Single-Family Home	$310,000	11/20/25	3	3	1,355
120 SE Edwards Ave, Winston, OR	0.11	Single-Family Home	$315,000	02/27/26	3	2	1,421
350 SE Tokay St, Winston, OR	0.23	Single-Family Home	$225,000	05/18/26	3	2	1,431
68 NW Rose St, Winston, OR	0.28	Single-Family Home	$300,000	01/09/26	4	2	1,288
54 NW Rose St, Winston, OR	0.27	Single-Family Home	$200,000	10/10/25	3	3	1,412
430 SE Carrol St, Winston, OR	0.33	Single-Family Home	$270,000	04/20/26	3	2	1,249
430 SE Carroll St, Winston, OR	0.33	Single-Family Home	$270,000	04/20/26	3	2	1,249
600 SE Carrol St, Winston, OR	0.35	Single-Family Home	$321,000	03/31/26	3	2	1,692

Nearby homes

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

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OFF MARKET
Est. $319,600
3 bd
2 ba
1,323 sqft
189 SE Darrell Ave,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Sold
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
Est. $296,200
3 bd
2 ba
1,316 sqft
200 SE Darrell Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
OFF MARKET
Est. $302,100
3 bd
2 ba
1,318 sqft
180 SE Darrell Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
OFF MARKET
Est. $192,100
2 bd
1 ba
1,158 sqft
170 SE Darrell Ave,
Winston, OR 97496
The Neil Company Real Estate, Sold
OFF MARKET
Est. $290,100
4 bd
2 ba
1,328 sqft
221 SE Robinson St,
Winston, OR 97496
Oregon Life Homes, Sold
OFF MARKET
Est. $251,900
3 bd
1 ba
824 sqft
331 SE Gregory Dr,
Winston, OR 97496
Oregon Life Homes, Sold
OFF MARKET
Est. $243,900
3 bd
1 ba
1,310 sqft
160 SE Darrell Ave,
Winston, OR 97496
Oregon Life Homes, Sold
SOLD
APR 8, 2026
$183,300
2 bd
1 ba
735 sqft
110 SE Darrell Ave,
Winston, OR 97496
Trueblood Real Estate, Sold
SOLD
FEB 27, 2026
$315,000
3 bd
2 ba
1,421 sqft
120 SE Edwards Ave,
Winston, OR 97496
Oregon Life Homes, Sold
FOR SALE
$215,000
2 bd
2 ba
924 sqft
90 SE Darrell Ave,
Winston, OR 97496
eXp Realty, LLC, Active
OFF MARKET
Est. $90,800
241 SE Gregory Dr,
Winston, OR 97496
Karen Volk Realty, Sold

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Additional Cost

Assigned Schools

These are the assigned schools for 248 SE Gregory Dr.

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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$995/mo
2 bd
1 ba
aupark | SE Park St,
Winston, OR 97496
$1,200/mo
3 bd
1 ba
577 NW T St #577,
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
NEW - 1 DAY AGO
$695/mo
1 bd
1 ba
1 NE Main St #101-206-88,
Winston, OR 97496
See more homes for rent in
Winston
Take a look

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Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Winston, OR

APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2 ba
1,370 sqft
36 NW Brantley Dr,
Winston, OR 97496
$2,600/mo
3 bd
2 ba
1,734 sqft
109 Citation Ct,
Winston, OR 97496
$2,600/mo
3 bd
2 ba
1,586 sqft
105 Citation Ct,
Winston, OR 97496
PET FRIENDLY
$1,650/mo
3 bd
1 ba
988 sqft
310 SE Gregory Dr,
Winston, OR 97496
$1,150/mo
2 bd
1 ba
1,000 sqft
491 NW Barbur Blvd,
Winston, OR 97496
PET FRIENDLY
$2,495/mo
5 bd
2 ba
2,560 sqft
120 Winston Section Rd,
Winston, OR 97496

Homes for sale near 248 SE Gregory Dr

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NEW CONSTRUCTION
$409,900
3 bd
2 ba
1,555 sqft
265 SE Logan St,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Active
$318,000
3 bd
1 ba
1,000 sqft
340 SE Darrell Ave,
Winston, OR 97496
Keller Williams Realty Eugene and Springfield, Active
AUCTION
0.45 ACRES
Est. $286,700
3 bd
2 ba
1,284 sqft
41 NE Ronald St,
Winston, OR 97496
$389,000
3 bd
1 ba
1,440 sqft
10 SW Peach Ln,
Winston, OR 97496
Stellar Realty Northwest, Active
NEW CONSTRUCTION
$439,900
3 bd
2 ba
1,629 sqft
260 SE Logan St,
Winston, OR 97496
Keller Williams Southern Oregon-Umpqua Valley, Active
$315,000
3 bd
1 ba
1,348 sqft
101 SW Peach Ln,
Winston, OR 97496
Berkshire Hathaway HomeServices Real Estate Professionals, Active
0.25 ACRES
$249,000
2 bd
1 ba
939 sqft
71 SE Ronald St,
Winston, OR 97496
ICON Real Estate Group, Active
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
0.34 ACRES
$524,900
3 bd
2 ba
2,431 sqft
605 SE Deerwood Ct,
Winston, OR 97496
RE/MAX Integrity, Active
See more homes for sale in
Winston
Take a look

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Off Market Homes Near 248 SE Gregory Dr

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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
SOLD
JUN 24, 2026
$338,000
3 bd
2 ba
1,848 sqft
210 NW Timothy Ave,
Winston, OR 97496
RE/MAX Integrity, Sold
SOLD
JUN 24, 2026
$320,000
3 bd
2 ba
1,295 sqft
356 Dark Horse St,
Roseburg, OR 97471
Keller Williams Southern Oregon-Umpqua Valley, Sold
SOLD
JUN 24, 2026
$275,000
3 bd
1 ba
1,434 sqft
10 SE Kegler Ave,
Winston, OR 97496
Different Better Real Estate, Sold
SOLD
JUN 24, 2026
$299,000
3 bd
2 ba
1,296 sqft
621 Highland Vista Ln,
Roseburg, OR 97471
Different Better Real Estate, Sold
SOLD
JUN 23, 2026
$240,000
2 bd
1 ba
748 sqft
387 4th St,
Dillard, OR 97432
Oregon Life Homes, Sold
See more homes for sale in
Winston
Take a look

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248 SE Gregory Dr
Winston, OR 97496

$345,300

$345,300

Local Information