558 Winston Rd, Oakland, KY 42159
OFF MARKET

558 Winston Rd
Oakland, KY 42159

  • Studio

$296,900

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $1,766/mo*
Refinance Your Home

$296,900

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $1,766/mo*
Refinance Your Home
Studio
(on 1 acre)

Local Information

  • Map ViewExplore the area around 558 Winston Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Lot Size
1 acre

About this House

This single-family home is located at 558 Winston Rd, Oakland, KY. 558 Winston Rd is in Oakland, KY and in ZIP code 42159. This property has a lot size of 1 acre.
558 Winston Rd, Oakland, KY 42159 is a studio single-family home. It is currently off market. The Trulia Estimate is $296,900, with a rent estimate of $1,581/month.

Home Details for 558 Winston Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 1 acre

Market trends in Oakland

Last updated June 2026
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Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Property Tax and Assessment

Year2024
Tax$1,581
Assessment$180,000
Home facts updated by county records

Comparable Sales for 558 Winston Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
891 Three Forks Flatrock Rd, Oakland, KY
0.42
Single-Family Home
$117,250
05/06/26
3
2
1,478
525 Three Forks Flatrock Rd, Oakland, KY
0.52
Single-Family Home
$288,000
02/24/26
3
2
1,411
11480 Porter Pike, Oakland, KY
0.34
Single-Family Home
$230,000
05/15/26
3
2
1,800
10321 Smiths Grove Scottsville Rd, Oakland, KY
0.63
Single-Family Home
$320,000
08/21/25
3
2
1,500
264 Martinsville Rd, Oakland, KY
0.94
Single-Family Home
$265,000
04/27/26
3
2
1,475
1936 Upper Iron Bridge Rd, Oakland, KY
0.93
Single-Family Home
$250,000
06/26/26
3
2
1,248
913 Upper Iron Bridge Rd, Oakland, KY
1.14
Single-Family Home
$364,900
09/24/25
3
3
1,830
4470 Oakland Flatrock Rd, Oakland, KY
2.25
Single-Family Home
$259,900
07/01/26
3
2
1,485
2398 Three Forks Rd, Smiths Grove, KY
2.77
Single-Family Home
$262,000
01/07/26
3
2
1,880
992 Mount Union Church Rd, Smiths Grove, KY
2.87
Single-Family Home
$289,999
08/21/25
3
2
1,550

Nearby homes

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Assigned Schools

These are the assigned schools for 558 Winston Rd.
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 Oakland

At least 2 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 100 % Say kids play outside

  • 75 % Say there are sidewalks

  • 75 % Say there's holiday spirit

  • 67 % Say people would walk alone at night

  • 67 % Say there's wildlife

  • 67 % Say neighbors are friendly

  • 50 % Say it's dog friendly

  • 50 % Say they plan to stay for at least 5 years

  • 50 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Bradyounglmark
    "We have lived here over a year and the neighbors are great. The neighborhood is well cared for and the neighbors care for each other. It’s quite and safe. "
    1
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Apartments for Rent

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Homes for sale near 558 Winston Rd

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Off Market Homes Near 558 Winston Rd

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