Google street view image for 14272 Lookingglass Rd, Winston, OR 97496

Off market

$442,639

•

4 ba

•

3,598

sq ft

14272 Lookingglass Rd, Winston, OR 97496

About this home

14272 Lookingglass Rd is a 3,598 square foot house on a 0.37 acre lot with 5 bedrooms and 4 bathrooms. Based on Redfin's Winston data, we estimate the home's value is $442,639.

Single-familyProperty Type

1979Year Built

0.37 acresLot Size

$123Est. Price/Sq.Ft.

2 car garageParking

Source:Public Records

Redfin Estimate

$442,639

$17K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 40% higher than the average sale price ($316K) of 6 comparable homes.

SOLD MAY 15, 2026
$255,000
A
3 beds2 baths1,835 sq ft
151 NW Sherry St, Winston, OR 97496
SOLD MAY 26, 2026
$314,549
B
4 beds3 baths1,782 sq ft
591 SE Carrol St, Winston, OR 97496
SOLD JUN 24, 2026
$338,000
C
3 beds2 baths1,848 sq ft
210 NW Timothy Ave, Winston, OR 97496
SOLD JUL 17, 2026
$290,000
D
4 beds2 baths1,782 sq ft
70 SE Darrell Ave, Winston, OR 97496
SOLD OCT 8, 2026
$420,000
E
3 beds2 baths1,442 sq ft
535 SE Parkway Dr, Winston, OR 97496
SOLD AUG 11, 2026
$280,000
F
4 beds3 baths2,270 sq ft
150 SW Brantley Dr, Winston, OR 97496

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Earn from this home

Rent

$2,696/mo

Redfin rental estimate

List your home for rent

Market trends in 97496, OR

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

98.8%

+2.0% MoM

Median sale price

$369K

$10K MoM

Avg. days on market

43d

17 days MoM

Recently sold homes

1 MoM

New listings for sale

$250,000
3 beds1 bath1,700 sq ft
621 SE Thompson Ave, Winston, OR 97496
Jackie Twyman • eXp Realty, LLC
$340,000
3 beds2 baths1,809 sq ft
124 NW Woodland Dr, Winston, OR 97496
Makayla Lippis • The Neil Company Real Estate
$250,000
4 beds2 baths— sq ft
251 SE Grape Ave, Winston, OR 97496
Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley
$409,900
3 beds2 baths1,580 sq ft
630 SE Rose Ridge Dr, Winston, OR 97496
Jodi Brecht • Stellar Realty Northwest
$375,000
3 beds3 baths2,610 sq ft
11 NE Brosi Orchard Rd, Winston, OR 97496
Anthony Beckham • Different Better Real Estate
See all

Provided by Redfin

Sale history for 14272 Lookingglass Rd

As the MLS and public records start to fill up, we'll list the details here.

Tax history for 14272 Lookingglass Rd

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Heating & Cooling
Heating Type: Heat Pump

Fireplace Information
Fireplace Type: Wood Stove
Has Fireplace

Exterior

Exterior Information
Physical Condition: Fair
Floor Construction Type: Asphalt
Foundation Type: Concrete
Roof Shape Type: Gable
Building Improvement Type: Residential

Property Information
Subdivision Name: GLEN D HART TR
Living Sq. Ft: 3,598
Ground Floor Sq. Ft: 2,998
Building Sq. Ft: 3,598
Legal Description: GLEN D HART TRACTS, LOT PT 1, ACRES 0.37

Parking & Garage Information
Parking Type: Unfinished Detached Garage
Garage/Parking Sq. Ft: 792
Garage / Carport Type: Unfinished Detached

Lot Information
# of Buildings: 1
Land Sq. Ft: 16,117
Legal Lot Number: 1
Acres: 0.37
State Use Description: RESIDENTIAL-IMPROVED

Financial

Assessor Information
Assessment Year: 2025
Tax Area: 116.04

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,598
Stories: —
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1979
Year Renovated: 1979
County: Douglas County
APN: R51713

Home facts updated by county records on Oct 19, 2026

Around this home

Schools

K - 12
Preschool & daycare

Mcgovern Elementary School

Public 3-5 • Assigned • 0.5mi

7/10

Winston Middle School

Public 6-8 • Assigned • 1.0mi

4/10

Douglas High School

Public 9-12 • Assigned • 1.3mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

4/10 Fire Factor

1% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 95° expected this year, 16 days in 30 years

1/10 Wind Factor

Minimal risk of severe winds over next 30 years

9/10 Air Factor

10 unhealthy days expected this year, 11 days in 30 years

Provided by First Street

Historical weather

Winston, OR • 97496

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 11 hours in June and 2.4 hours in December, which is comparable to the U.S. average for solar exposure.

11 hrs

2.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$421,000 – $510,000

Sell confidently with a local market expert in Winston. 3 minutes to get started.

Nearby similar homes

$1,990,000

2 beds1 bath1,312 sq ft

5961 Lookingglass Rd, Roseburg, OR 97471

Multiple residences • Income potential • Multiple ponds

Brett Veatch • Berkshire Hathaway HomeServices NW Real Estate

$385,000

3 beds2 baths1,498 sq ft

675 SE Brush Ct, Winston, OR 97496

Cul-de-sac • Open-concept layout • Spacious island

Christina Esterbrook • J Mann Realty

$340,000

3 beds2 baths1,559 sq ft

411 Sunnyside Dr, Winston, OR 97496

Covered porch • Large connected deck • Tool shed

Dannielle Glines • Neath The Wind Realty, Inc.

OPEN NOV 28, 11AM TO 1PMVIDEO TOUR

$344,000

3 beds2 baths1,579 sq ft

3085 W Shasta Ave, Roseburg, OR 97471

Granite countertops • Tile flooring • Separate family room

Julie Bancroft • The Neil Company Real Estate

OPEN TODAY, 10AM TO 12PM3D WALKTHROUGH

$327,000

3 beds2 baths1,221 sq ft

125 Aloha Ct, Roseburg, OR 97471

Move in ready • Covered back deck • Fully fenced yard

Lacey Williams • Trueblood Real Estate

$409,900

3 beds2 baths1,580 sq ft

630 SE Rose Ridge Dr, Winston, OR 97496

Quartz counter tops • Recessed lighting • Vaulted ceilings

Jodi Brecht • Stellar Realty Northwest

New listings for sale in 97496

$250,000

3 beds1 bath1,700 sq ft

621 SE Thompson Ave, Winston, OR 97496

Stick-built addition • Accessibility ramp • 0.44 acre lot

Jackie Twyman • eXp Realty, LLC

$340,000

3 beds2 baths1,809 sq ft

124 NW Woodland Dr, Winston, OR 97496

New flooring • 8,712 sq ft lot • 2 garage spots

Makayla Lippis • The Neil Company Real Estate

$250,000

4 beds2 baths— sq ft

251 SE Grape Ave, Winston, OR 97496

Bright open living • Raised deck • Mature trees

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

$409,900

3 beds2 baths1,580 sq ft

630 SE Rose Ridge Dr, Winston, OR 97496

Quartz counter tops • Recessed lighting • Vaulted ceilings

Jodi Brecht • Stellar Realty Northwest

$375,000

3 beds3 baths2,610 sq ft

11 NE Brosi Orchard Rd, Winston, OR 97496

Daylight basement • Oversized garage • Loft with storage

Anthony Beckham • Different Better Real Estate

Home values near 14272 Lookingglass Rd

Data from public records.

Address	Redfin Estimate
14195 Lookingglass Rd, Winston, OR 3 Beds \| 3 Baths \| 1818 Sq. Ft.	$369,663
14236 Lookingglass Rd, Winston, OR 3 Beds \| 1 Baths \| 896 Sq. Ft.	$126,429
14208 Lookingglass Rd, Winston, OR 1 Beds \| 1 Baths \| 540 Sq. Ft.	$235,399
290 Northwest Glenhart Ave, Winston, OR 8 Beds \| 3 Baths \| 2680 Sq. Ft.	$378,663
335 Northwest Glen Ct, Winston, OR 3 Beds \| 2 Baths \| 1480 Sq. Ft.	$315,805
359 Northwest Morgan Ave, Winston, OR 3 Beds \| 2 Baths \| 1142 Sq. Ft.	$315,278
310 Northwest Lost Ln, Winston, OR 4 Beds \| 2 Baths \| 1769 Sq. Ft.	$358,856

Address	Redfin Estimate
14173 Lookingglass Rd, Winston, OR 3 Beds \| 1 Baths \| 1484 Sq. Ft.	$261,835
14236 Lookingglass Rd, Winston, OR 2 Beds \| 1 Baths \| 1211 Sq. Ft.	$218,061
320 Northwest Lost Ln, Winston, OR 3 Beds \| 1 Baths \| 1056 Sq. Ft.	$252,919
343 Northwest Glenhart Ave, Winston, OR 3 Beds \| 1 Baths \| 1620 Sq. Ft.	$301,709
361 Northwest Civil Bend Ave, Winston, OR 2 Beds \| 1 Baths \| 1119 Sq. Ft.	$251,315
331 Northwest Glen Ct, Winston, OR 3 Beds \| 2 Baths \| 2008 Sq. Ft.	$346,809
380 Northwest Civil Bend Ave, Winston, OR 2 Beds \| 1 Baths \| 768 Sq. Ft.	$252,766

Address	Redfin Estimate
14235 Lookingglass Rd, Winston, OR 3 Beds \| 2 Baths \| 1469 Sq. Ft.	$407,254
14192 Lookingglass Rd, Winston, OR 2 Beds \| 1 Baths \| 940 Sq. Ft.	$280,414
360 Northwest Morgan Ave, Winston, OR 3 Beds \| 1 Baths \| 1392 Sq. Ft.	$279,487
341 Northwest Glen Ct, Winston, OR 3 Beds \| 2 Baths \| 1481 Sq. Ft.	$322,858
340 Northwest Lost Ln, Winston, OR 3 Beds \| 1 Baths \| 1092 Sq. Ft.	$261,276
337 Northwest Glen Ct, Winston, OR 3 Beds \| 2 Baths \| 1280 Sq. Ft.	$295,318
380 Northwest Morgan Ave, Winston, OR 2 Beds \| 1 Baths \| 1356 Sq. Ft.	$178,678

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