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 434 Winston Rd estimated to be worth?

Trulia's estimated value for 434 Winston Rd in Oakland, KY is $142,600 .

What is the price history for 434 Winston Rd?

434 Winston Rd in Oakland, KY last sold for $30,000 in September 2011.

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 434 Winston Rd?

The closest schools to 434 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).

How big is the lot at 434 Winston Rd?

The lot at 434 Winston Rd in Oakland, KY is about 1 acre .

Does 434 Winston Rd have parking?

Yes, 434 Winston Rd in Oakland, KY has on-site parking.

OFF MARKET

$142,600

Trulia Estimate

3 Beds
2 Baths
1,152 sqft (on 1 acre)

434 Winston Rd, Oakland, KY 42159

Refinance Your Home

Currently Off Market - Sold Sep 9, 2011 for $30,000

Home Value

Trulia Estimate

$143K

Since last month

$8K (-5%)

Since last year

$22K (-13.3%)

Since last sale

$114K (+380%)

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 +121% in the last 10 years

Month	Estimated value
2026
August 2026	$144K
August 2026	$143K
July 2026	$152K
June 2026	$155K
May 2026	$156K
April 2026	$156K
March 2026	$157K
February 2026	$144K
January 2026	$146K
2025
December 2025	$155K
November 2025	$149K
October 2025	$144K
September 2025	$147K
August 2025	$166K
July 2025	$168K
June 2025	$168K
May 2025	$169K
April 2025	$167K
March 2025	$165K
February 2025	$161K
January 2025	$158K
2024
December 2024	$147K
November 2024	$144K
October 2024	$140K
September 2024	$137K
August 2024	$141K
July 2024	$150K
June 2024	$152K
May 2024	$150K
April 2024	$147K
March 2024	$143K
February 2024	$134K
January 2024	$131K
2023
December 2023	$130K
November 2023	$135K
October 2023	$129K
September 2023	$133K
August 2023	$131K
July 2023	$140K
June 2023	$138K
May 2023	$138K
April 2023	$133K
March 2023	$129K
February 2023	$121K
January 2023	$121K
2022
December 2022	$124K
November 2022	$127K
October 2022	$128K
September 2022	$128K
August 2022	$126K
July 2022	$127K
June 2022	$127K
May 2022	$127K
April 2022	$125K
March 2022	$125K
February 2022	$127K
January 2022	$124K
2021
December 2021	$123K
November 2021	$122K
October 2021	$122K
September 2021	$119K
August 2021	$119K
July 2021	$114K
June 2021	$97K
May 2021	$66K
April 2021	$65K
March 2021	$60K
February 2021	$60K
January 2021	$59K
2020
December 2020	$59K
November 2020	$55K
October 2020	$55K
September 2020	$57K
August 2020	$71K
July 2020	$127K
June 2020	$125K
May 2020	$127K
April 2020	$126K
March 2020	$122K
February 2020	$108K
January 2020	$98K
2019
December 2019	$102K
November 2019	$95K
October 2019	$96K
September 2019	$93K
August 2019	$94K
July 2019	$96K
June 2019	$89K
May 2019	$92K
April 2019	$91K
March 2019	$85K
February 2019	$87K
January 2019	$89K
2018
December 2018	$82K
November 2018	$71K
October 2018	$78K
September 2018	$67K
August 2018	$68K
July 2018	$67K
June 2018	$71K
May 2018	$67K
April 2018	$73K
March 2018	$73K
February 2018	$64K
January 2018	$65K
2017
December 2017	$72K
November 2017	$70K
October 2017	$70K
September 2017	$70K
August 2017	$72K
July 2017	$66K
June 2017	$70K
May 2017	$76K
April 2017	$62K
March 2017	$63K
February 2017	$66K
January 2017	$63K
2016
December 2016	$70K
November 2016	$66K
October 2016	$66K
September 2016	$65K

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	0.53	Single-Family Home	$117,250	05/06/26	3	2	1,478
11480 Porter Pike, Oakland, KY	0.43	Single-Family Home	$230,000	05/15/26	3	2	1,800
525 Three Forks Flatrock Rd, Oakland, KY	0.71	Single-Family Home	$288,000	02/24/26	3	2	1,411
1936 Upper Iron Bridge Rd, Oakland, KY	0.76	Single-Family Home	$250,000	06/26/26	3	2	1,248
264 Martinsville Rd, Oakland, KY	1.02	Single-Family Home	$265,000	04/27/26	3	2	1,475
913 Upper Iron Bridge Rd, Oakland, KY	0.95	Single-Family Home	$364,900	09/24/25	3	3	1,830
4470 Oakland Flatrock Rd, Oakland, KY	2.15	Single-Family Home	$259,900	07/01/26	3	2	1,485
280 Louie Meeks Rd, Oakland, KY	1.27	Single-Family Home	$812,500	08/07/26	3	3	6,140
2398 Three Forks Rd, Smiths Grove, KY	2.95	Single-Family Home	$262,000	01/07/26	3	2	1,880
5807 Carl Jordan Rd, Oakland, KY	3.09	Single-Family Home	$259,900	10/24/25	3	2	1,598

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
11480 Porter Pike, Oakland, KY 42159	0.43	$230,000	3	2	1,800	Recently Sold
11509 Porter Pike, Oakland, KY 42159	0.49	$194,900	3	1	765	For Sale
891 Three Forks Flatrock Rd, Oakland, KY 42159	0.53	$161,500	3	2	1,478	For Sale
525 Three Forks Flatrock Rd, Oakland, KY 42159	0.71	$288,000	3	2	1,411	Recently Sold
1936 Upper Iron Bridge Rd, Oakland, KY 42159	0.76	$250,000	3	2	1,248	Recently Sold
1930 Upper Iron Bridge Rd, Oakland, KY 42159	0.77	$240,000	3	2	1,293	For Sale
10541 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.78	$259,900	-	-	-	For Sale
10321 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.78	$328,300	3	2	1,500	Off Market
10592 Smiths Grove Scottsville Rd, Oakland, KY 42159	0.84	$290,900	3	2	1,485	Off Market
913 Upper Iron Bridge Rd, Oakland, KY 42159	0.95	$372,500	3	2	1,830	Off Market
264 Martinsville Rd, Oakland, KY 42159	1.02	$265,000	3	2	1,475	Recently Sold

Local Information

Map ViewExplore the area around 434 Winston Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1970

1 acre lot

1,152 sqft

$124/sqft

About this House

Peaceful, country setting lot. Great for a family or single renter.

Year to year lease. $300.00 Damage Deposit at time of signing. Owner is responsible for all utility bills & the up keep of lawn care.

434 Winston Rd, Oakland, KY 42159 is a 3 bedroom, 2 bathroom, 1,152 sqft single-family home built in 1970. It last sold for $30,000 on Sep 9, 2011. More recently, it was listed as a rental in January 2020 with an asking price of $650 per month. That rental listing was removed on March 24, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $142,600, with a rent estimate of $1,306/month.

Home Details for 434 Winston Rd

Interior Features
Heating & Cooling Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1
Interior Details Types of Rooms: Family Room
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: CompositionExterior: OtherFoundation Type: Concrete BlockPatio
Parking & Garage Parking: Off Street

Property Information
Year Built Year Built: 1970
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 1 acre

Price and Tax history

Date	Event	Price
Mar 24, 2021 Source: N/A	ListingRemoved
Feb 7, 2020 Source: N/A	ListingRemoved	$650
Jan 29, 2020 Source: N/A	Listed For Rent	$650
Oct 27, 2011 Source: Agent Provided	ListingRemoved	$33,500
Oct 13, 2011 Source: Agent Provided	Listed For Sale	$33,500
Sep 9, 2011 Source: RASK #119463	Sold	$30,000
Mar 2, 2011 Source: Agent Provided	ListingRemoved	$64,900
Dec 28, 2010 Source: Agent Provided	Listed For Sale	$64,900

Year	Property tax	Tax assessment
2025	$550	$59,300

Additional Cost

Market trends in Oakland

Last updated July 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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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 434 Winston Rd

What is 434 Winston Rd estimated to be worth?
Trulia's estimated value for 434 Winston Rd in Oakland, KY is $142,600.
What is the price history for 434 Winston Rd?
434 Winston Rd in Oakland, KY last sold for $30,000 in September 2011.
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 434 Winston Rd?
The closest schools to 434 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).
How big is the lot at 434 Winston Rd?
The lot at 434 Winston Rd in Oakland, KY is about 1 acre.
Does 434 Winston Rd have parking?
Yes, 434 Winston Rd in Oakland, KY has on-site parking.