Is parking easy in Oakland, KY?

As of early 2026, 100% of users say parking is easy

Is a car needed in Oakland, KY?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Oakland, KY?

As of early 2026, 100% of users say yards are well-kept

Do kids play outside in Oakland, KY?

As of early 2026, 100% of users say kids play outside

Does Oakland, KY have sidewalks?

As of early 2026, 75% of users say there are sidewalks

Does Oakland, KY show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Would people walk alone at night in Oakland, KY?

As of early 2026, 67% of users say people would walk alone at night

Is there wildlife in Oakland, KY?

As of early 2026, 67% of users say there's wildlife

Are neighbors friendly in Oakland, KY?

As of early 2026, 67% of users say neighbors are friendly

Is Oakland, KY dog-friendly?

As of early 2026, 50% of users say it's dog friendly

Do residents of Oakland, KY plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are the streets well-lit in Oakland, KY?

As of early 2026, 50% of users say streets are well-lit

What is 505 Winston Rd estimated to be worth?

Trulia's estimated value for 505 Winston Rd in Oakland, KY is $207,800 .

What is the price history for 505 Winston Rd?

505 Winston Rd in Oakland, KY last sold for $14,000 in January 1999.

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

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

What are the closest schools to 505 Winston Rd?

The closest schools to 505 Winston Rd in Oakland, KY are North Warren Elementary School (Pre-K, rated 6/10), Warren East High School (rated 5/10), Warren East Middle School (rated 5/10).

Does 505 Winston Rd have air conditioning?

Yes, 505 Winston Rd in Oakland, KY has air conditioning.

How big is the lot at 505 Winston Rd?

The lot at 505 Winston Rd in Oakland, KY is about 2 acres .

OFF MARKET

$207,800

Trulia Estimate

3 Beds
2 Baths
1,526 sqft (on 1.96 acres)

505 Winston Rd, Oakland, KY 42159

Refinance Your Home

Currently Off Market - Sold Jan 16, 1999 for $14,000

Home Value

Trulia Estimate

$208K

Since last month

$20K (+10.4%)

Since last year

$35K (+20.4%)

Since last sale

$195K (+1,390%)

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

Trulia Estimate

The of this home's value increased by +131% in the last 10 years

Month	Estimated value
2026
August 2026	$209K
August 2026	$208K
July 2026	$189K
June 2026	$189K
May 2026	$189K
April 2026	$193K
March 2026	$189K
February 2026	$184K
January 2026	$181K
2025
December 2025	$185K
November 2025	$185K
October 2025	$178K
September 2025	$179K
August 2025	$173K
July 2025	$178K
June 2025	$182K
May 2025	$192K
April 2025	$186K
March 2025	$185K
February 2025	$182K
January 2025	$179K
2024
December 2024	$183K
November 2024	$183K
October 2024	$174K
September 2024	$173K
August 2024	$175K
July 2024	$176K
June 2024	$179K
May 2024	$178K
April 2024	$176K
March 2024	$173K
February 2024	$168K
January 2024	$163K
2023
December 2023	$165K
November 2023	$166K
October 2023	$167K
September 2023	$167K
August 2023	$165K
July 2023	$170K
June 2023	$168K
May 2023	$162K
April 2023	$157K
March 2023	$154K
February 2023	$149K
January 2023	$148K
2022
December 2022	$151K
November 2022	$151K
October 2022	$152K
September 2022	$153K
August 2022	$152K
July 2022	$150K
June 2022	$147K
May 2022	$145K
April 2022	$141K
March 2022	$136K
February 2022	$131K
January 2022	$131K
2021
December 2021	$131K
November 2021	$132K
October 2021	$132K
September 2021	$133K
August 2021	$132K
July 2021	$130K
June 2021	$121K
May 2021	$108K
April 2021	$108K
March 2021	$102K
February 2021	$101K
January 2021	$100K
2020
December 2020	$99K
November 2020	$95K
October 2020	$95K
September 2020	$95K
August 2020	$103K
July 2020	$130K
June 2020	$128K
May 2020	$127K
April 2020	$127K
March 2020	$128K
February 2020	$125K
January 2020	$124K
2019
December 2019	$134K
November 2019	$143K
October 2019	$139K
September 2019	$144K
August 2019	$148K
July 2019	$141K
June 2019	$128K
May 2019	$140K
April 2019	$143K
March 2019	$136K
February 2019	$137K
January 2019	$129K
2018
December 2018	$131K
November 2018	$123K
October 2018	$114K
September 2018	$115K
August 2018	$122K
July 2018	$126K
June 2018	$117K
May 2018	$106K
April 2018	$107K
March 2018	$110K
February 2018	$111K
January 2018	$106K
2017
December 2017	$97K
November 2017	$94K
October 2017	$98K
September 2017	$105K
August 2017	$101K
July 2017	$105K
June 2017	$113K
May 2017	$111K
April 2017	$109K
March 2017	$105K
February 2017	$106K
January 2017	$103K
2016
December 2016	$98K
November 2016	$91K
October 2016	$92K
September 2016	$90K

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
891 Three Forks Flatrock Rd, Oakland, KY	0.45	Single-Family Home	$117,250	05/06/26	3	2	1,478
11480 Porter Pike, Oakland, KY	0.51	Single-Family Home	$230,000	05/15/26	3	2	1,800
525 Three Forks Flatrock Rd, Oakland, KY	0.70	Single-Family Home	$288,000	02/24/26	3	2	1,411
1936 Upper Iron Bridge Rd, Oakland, KY	0.73	Single-Family Home	$250,000	06/26/26	3	2	1,248
913 Upper Iron Bridge Rd, Oakland, KY	0.97	Single-Family Home	$364,900	09/24/25	3	3	1,830
264 Martinsville Rd, Oakland, KY	1.11	Single-Family Home	$265,000	04/27/26	3	2	1,475
4470 Oakland Flatrock Rd, Oakland, KY	2.06	Single-Family Home	$259,900	07/01/26	3	2	1,485
280 Louie Meeks Rd, Oakland, KY	1.32	Single-Family Home	$812,500	08/07/26	3	3	6,140
3701 Oakland Flatrock Rd, Oakland, KY	2.67	Single-Family Home	$315,000	02/17/26	3	2	1,340
2398 Three Forks Rd, Smiths Grove, KY	2.97	Single-Family Home	$262,000	01/07/26	3	2	1,880

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
891 Three Forks Flatrock Rd, Oakland, KY 42159	0.45	$161,500	3	2	1,478	For Sale
11480 Porter Pike, Oakland, KY 42159	0.51	$230,000	3	2	1,800	Recently Sold
11509 Porter Pike, Oakland, KY 42159	0.57	$194,900	3	1	765	For Sale
1936 Upper Iron Bridge Rd, Oakland, KY 42159	0.73	$250,000	3	2	1,248	Recently Sold
525 Three Forks Flatrock Rd, Oakland, KY 42159	0.70	$288,000	3	2	1,411	Recently Sold
1930 Upper Iron Bridge Rd, Oakland, KY 42159	0.75	$240,000	3	2	1,293	For Sale
10541 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.83	$259,900	-	-	-	For Sale
10321 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.83	$328,300	3	2	1,500	Off Market
10592 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.91	$290,900	3	2	1,485	Off Market
913 Upper Iron Bridge Rd, Oakland, KY 42159	0.97	$372,500	3	2	1,830	Off Market
264 Martinsville Rd, Oakland, KY 42159	1.11	$265,000	3	2	1,475	Recently Sold

Local Information

Map ViewExplore the area around 505 Winston Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1999

1.96 acre lot

1,526 sqft

$136/sqft

Garage

About this House

This single-family home is located at 505 Winston Rd, Oakland, KY. 505 Winston Rd is in Oakland, KY and in ZIP code 42159. This property has 3 bedrooms, 2 bathrooms and approximately 1,526 sqft of floor space. This property has a lot size of 1.96 acres and was built in 1999.

505 Winston Rd, Oakland, KY 42159 is a 3 bedroom, 2 bathroom, 1,526 sqft single-family home built in 1999. It last sold for $14,000 on Jan 16, 1999. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $207,800, with a rent estimate of $1,703/month.

Home Details for 505 Winston Rd

Interior Features
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1
Interior Details Types of Rooms: Family Room

Exterior Features
Exterior Home Features Roof: MetalExterior: OtherFoundation Type: Concrete BlockPatio
Parking & Garage GarageParking: Garage Attached, Garage Detached, Off Street

Property Information
Year Built Year Built: 1999
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 1.96 acres

Price and Tax history

Date	Event	Price
Jan 16, 1999 Source: N/A	Sold	$14,000

Year	Property tax	Tax assessment
2025	$899	$100,800

Additional Cost

Market trends in Oakland

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Around this home

North Warren Elementary School
PK-6
Public
439 Students
Warren County School District
6/10
GreatSchools Rating
Parent Rating Average
I am a parent of an Autistic Child who also has ADHD. My child was bullied by other students. As a result, my child was made to look like the bad guy by the students and faculty. We moved after the incident to a better school, one that understands our son and his needs. Do I recommend this school to any parent with a child with Autism and ADHD? My answer is, NO!
Parent Review
8mo ago
3 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 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
Resident
8y ago
"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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Frequently asked questions about 505 Winston Rd

What is 505 Winston Rd estimated to be worth?
Trulia's estimated value for 505 Winston Rd in Oakland, KY is $207,800.
What is the price history for 505 Winston Rd?
505 Winston Rd in Oakland, KY last sold for $14,000 in January 1999.
Is Oakland a buyer's or seller's market?
Oakland is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 505 Winston Rd?
The closest schools to 505 Winston Rd in Oakland, KY are North Warren Elementary School (Pre-K, rated 6/10), Warren East High School (rated 5/10), Warren East Middle School (rated 5/10).
Does 505 Winston Rd have air conditioning?
Yes, 505 Winston Rd in Oakland, KY has air conditioning.
How big is the lot at 505 Winston Rd?
The lot at 505 Winston Rd in Oakland, KY is about 2 acres.