OFF MARKET

Off Market Nov 2020 for $205K

$287,299

Est. refi paymentEst. refi $1,638/mo

•

2,288

sq ft

5408 Winding Rd, Louisville, KY 40214

About this home

Public Remarks: Welcome Home! Rare Opportunity! Home Ownership Pride since 1993. This Ranch is a 3 Bedroom 2 Bathroom Home with Gleaming Hardwood Floors on most of the 1st floor. Enter into the very large Living Room with Huge Front Window letting in Natural Light. The room Features a Gas Fireplace, Built-Ins, Neutral Paint and Beautiful Hardwood Floors. From here walk into the Dining Room that also have the Beautiful Hardwood Floors and Spacious area for the whole family! The Florida Room is to the left and. You will not find a room like this again. Brick Wall Feature with 3 sides of glass, newer flooring and custom blinds. There is also a sliding door to the Brick Patio where you will find a Great Entertaining area and a Gas hookup for a grill - NO More Propane Tanks! The Kitchen is newer with 2 year old Black Stainless Steel Appliances. There is an Eat-In area and an Enormous Pantry for tons of Storage. There is also an additional door to the backyard to help connect the entertaining area to the Patio. From the Kitchen walk down the hallway, with Gleaming Hardwood Floors, to the Primary Bedroom with Hardwood Floors, Double Closet and 3 Large Windows for Natural Light. The Primary Bedroom also features a Primary Bathroom with Walk-In Shower. SO convenient! There are 2 more bedrooms on this floor with Hardwood Floors. One Bedroom has a Washer/Dryer hookup in the closet for ease. Please know, there is a Laundry hook up in the Basement as well if you would like to move the laundry to the basement and capture the closet back for the bedroom. There is a full bathroom with a linen closet for Guests and these 2 bedrooms to share. It is Spacious with a tub/shower combo. This Home Features a New Security system installed August 2020. The basement as an additional Kitchen and Bar area, wood burning fireplace and media area. 3 Large closets for storage and a whole storage area additionally. This is where you can find the 2nd Laundry hook-up. Door to the attached Tandum 2 Car Garage with electric door opener. This home has 2 Sump Pumps, 1 in the garage and 1 in the basement. There is a drop down latter to enter the attic and there is an area of storage capability. This Home truly has it all. Schedule your Private Showing today as this one will not be around for long!

Single-familyProperty Type

1956Year Built

0.34 acresLot Size

$126Est. Price/Sq.Ft.

2 car garageParking

Listed by Karen Wallace • RE/MAX Properties East

Contact: 502407-7748

Bought with Katie Price Esterle • White Picket Real Estate

Redfin checked: 2 minutes ago

•Source:Metro Search MLS #1569420

Redfin Estimate

$287,299

$82K since sold in November 2020$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.3% higher than the average sale price ($231K) of 6 comparable homes.

SOLD JUN 12, 2026
$150,000
A
3 beds2 baths2,334 sq ft
5337 Lost Trl, Louisville, KY 40214
simpler.realestate
SOLD JUN 24, 2026
$260,000
B
3 beds2 baths2,460 sq ft
5333 New Cut Rd, Louisville, KY 40214
Epique Realty
SOLD MAY 13, 2026
$329,900
C
3 beds2.5 baths2,412 sq ft
609 Wilderness Rd, Louisville, KY 40214
Segrest Flaherty Realtors LLC
SOLD MAY 15, 2026
$185,000
D
3 beds2 baths3,168 sq ft
5331 Lost Trl, Louisville, KY 40214
Jewell REALTORS
SOLD JUN 22, 2026
$260,000
E
3 beds2 baths2,227 sq ft
122 Seneca Trl, Louisville, KY 40214
Gatewood Properties of Kentucky
SOLD JUL 20, 2026
$202,000
F
3 beds2 baths1,824 sq ft
308 W Southside Ct, Louisville, KY 40214
ZHomes Real Estate

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Earn from this home

Sell

$123,723

Est. take-home

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Refinance

Est. cash available

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Rent

$1,278/mo

Redfin rental estimate

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Market trends in 40214, KY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.3%

+0.1% MoM

Median sale price

$243K

$3K MoM

Avg. days on market

39d

1 days MoM

Recently sold homes

161

15 MoM

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See all

Provided by Redfin

Sale history for 5408 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,201 (+21.6%)

$26,500 + $227,510

$254,010

2024

$2,632 (−4.3%)

$26,500 + $227,510

$254,010

2023

$2,751 (−1.3%)

$26,500 + $178,500

$205,000

2022

$2,788 (−4.4%)

$26,500 + $178,500

$205,000

2021

$2,918 (+113.1%)

$26,500 + $178,500

$205,000

2020

$1,369 (+2.4%)

$26,500 + $178,500

$205,000

2019

$1,337 (−0.4%)

$26,000 + $112,940

$138,940

2018

$1,342 (+1.6%)

$26,000 + $112,940

$138,940

2017

$1,321 (−16.5%)

$26,000 + $112,940

$138,940

2015

$1,581 (−24.2%)

$30,000 + $127,480

$157,480

2014

$2,085

$30,000 + $127,480

$157,480

2013

$2,085

$30,000 + $127,480

$157,480

Tax history for 5408 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,201 (+21.6%)

$26,500 + $227,510

$254,010

2024

$2,632 (−4.3%)

$26,500 + $227,510

$254,010

2023

$2,751 (−1.3%)

$26,500 + $178,500

$205,000

2022

$2,788 (−4.4%)

$26,500 + $178,500

$205,000

2021

$2,918 (+113.1%)

$26,500 + $178,500

$205,000

2020

$1,369 (+2.4%)

$26,500 + $178,500

$205,000

2019

$1,337 (−0.4%)

$26,000 + $112,940

$138,940

2018

$1,342 (+1.6%)

$26,000 + $112,940

$138,940

2017

$1,321 (−16.5%)

$26,000 + $112,940

$138,940

2015

$1,581 (−24.2%)

$30,000 + $127,480

$157,480

2014

$2,085

$30,000 + $127,480

$157,480

2013

$2,085

$30,000 + $127,480

$157,480

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

Public record

Public record
Permits

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

1956

Sq. Ft.

—

Year built

1956

Style

Single Family Residential

County

Jefferson County

APN

13062J00810000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 8, 2026.

Property details

Parking

Parking Information
Garage Spaces: 2.0
Parking Features: Attached, Entry Front, See Remarks, Driveway

Interior

Virtual Tour Information

Virtual Tour Information

Bedroom Information
Bedrooms Total: 3
First Floor PBR: Yes
Primary Bedroom Level: First
# Upper Floor Bedrooms: 0.0
# 2nd Floor Bedrooms: 0.0
# 1st Floor Bedrooms: 3
# Basement Bedrooms: 0.0
Primary Bedroom: Yes

Bathroom Information
Bathrooms Full: 2
Bathrooms Half: 0
Primary Bathroom Level: First
Full Bathroom: Yes
Full Bathroom Level: First
Primary Bathroom: Yes

Kitchen & Dining Information
Dining Room: Yes
Dining Room Level: First
Kitchen: Yes
Kitchen Level: First

Interior Features
# of Rooms: 7
# of Closets: 7
# of Fireplaces: 2
Fireplaces Total: 2
Fireplaces: Basement: 1
Fireplaces: Level 1: 1
Fireplace: Yes

Living Areas
Family Room: Yes
Family Room Level: Basement
Florida Room: Yes
Florida Room Level: First
Living Room: Yes
Living Room Level: First

Other Room Information
# of Rooms: 7
Rooms Total: 11
Basement Y/N: Yes
Basement: Partially Finished
Bedroom: Yes
Bedroom Level: First
Closets: Basement: 3
Dining Room: Yes
Dining Room Level: First
Fireplaces Total: 2
Foyer: Yes
Foyer Level: First
Full Bathroom: Yes
Full Bathroom Level: First
Kitchen: Yes
Kitchen Level: First
First Floor Laundry: Yes
Primary Bathroom: Yes
Primary Bathroom Level: First
Primary Bedroom: Yes
Primary Bedroom Level: First

Room 1 Information
Room 1 Description: Tiled floor
Room 1 Length: 5.00
Room 1 Level: First
Room 1 Type: Foyer
Room 1 Width: 4.00

Room 2 Information
Room 2 Description: Hardwood, Huge Window, Gas Fireplace
Room 2 Length: 15.00
Room 2 Level: First
Room 2 Type: Living Room
Room 2 Width: 13.00

Room 3 Information
Room 3 Description: Hardwood, Spacious
Room 3 Length: 11.80
Room 3 Level: First
Room 3 Type: Dining Room
Room 3 Width: 11.60

Room 4 Information
Room 4 Description: Eat In Area, Newer Appliances
Room 4 Length: 17.00
Room 4 Level: First
Room 4 Type: Kitchen
Room 4 Width: 8.00

Room 5 Information
Room 5 Description: Glass enclosed, Vented, Newer Flooring, Brick Wall
Room 5 Length: 24.40
Room 5 Level: First
Room 5 Type: Sun Room
Room 5 Width: 11.50

Room 6 Information
Room 6 Description: Hardwood, Double Closet, Large Windows
Room 6 Length: 12.60
Room 6 Level: First
Room 6 Type: Primary Bedroom
Room 6 Width: 11.40

Room 7 Information
Room 7 Description: Walk In Shower
Room 7 Level: First
Room 7 Type: Primary Bathroom

Room 8 Information
Room 8 Description: Tile Floor, Large Closet, Large Windows
Room 8 Length: 11.50
Room 8 Level: First
Room 8 Type: Bedroom
Room 8 Width: 10.80

Room 9 Information
Room 9 Description: Hardwood, Access to Laundry, Large Windows
Room 9 Length: 12.10
Room 9 Level: First
Room 9 Type: Bedroom
Room 9 Width: 11.00

Room 10 Information
Room 10 Description: Spacious, Tub/Shower Combo
Room 10 Level: First
Room 10 Type: Full Bathroom

Room 11 Information
Room 11 Description: Extra Kitchen, Wood Fireplace and Media Area
Room 11 Level: Basement
Room 11 Type: Family Room

Exterior

Land Information
Fencing: Other, Privacy, Partial
Fencing: Other: Yes
Fencing: Partial: Yes
Fencing: Privacy: Yes

Lot Description
Lot Features: DeadEnd
Lot Size Acres: 0.34
Lot Size Area: 0.34
Lot Size Units: Acres
Dead End: Yes

Property Information
Property Sub Type: Single Family Residence
Residential
Architectural Style: Ranch

Subdivision / Condo Amenities
Subdivision Name: KENWOOD HILLS

Building Information
Building Area Source: Appraiser
Building Area Total: 1717.0
Stories: 1
Year Built: 1956
Roof: Shingle
Foundation Details: Poured Concrete
Construction Materials: Wood Frame, Brick
Above Grade Finished: 1,717
Below Grade Finished: 571
Below Grade Unfin: 875
Living Area: 2288.0

Financial

Tax Information
Tax Block: 062J
Tax Lot: 0081

Utilities

Utility Information
# of HVAC Units: 1

Heating
Heating Y/N: Yes
Heating: Forced Air, Natural Gas

Cooling
Cooling Y/N: Yes
Cooling: Central Air

Location

HOA Information
Association Fee: 0.0

Neighborhood Information
Subdivision Name: KENWOOD HILLS

School Information
High School District: Jefferson
School District: Jefferson

Location Information
Directions: From Newcut rd turn onto Southside dr then turn left onto Woodmore ave and right onto winding rd. Home is on the Left.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1956
Year Renovated: 1956
County: Jefferson County
APN: 13062J00810000

Home facts updated by county records on Sep 8, 2026

Around this home

Schools

Kenwood Elementary School

Public K-5 • Assigned • 1.0mi

3/10

Frederick Law Olmsted Academy South

Public 6-8 • Assigned • 1.5mi

3/10

Iroquois High School

Public 9-12 • Assigned • 1.7mi

1/10

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

5/10 Heat Factor

6 days above 105° expected this year, 16 days in 30 years

2/10 Wind Factor

1% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Louisville, KY • 40214

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 9.5 hours in June and 3.7 hours in December, placing it below the U.S. average for solar exposure.

9.5 hrs

3.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$273,000 – $331,000

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Home values near 5408 Winding Rd

Data from public records.

Address	Redfin Estimate
5427 Winding Road, Louisville, KY - Beds \| - Baths \| - Sq. Ft.	$523,618
5416 Winding Road, Louisville, KY 4 Beds \| 3 Baths \| 3500 Sq. Ft.	$361,113

Address	Redfin Estimate
5407 Winding Road, Louisville, KY 4 Beds \| 2 Baths \| 1836 Sq. Ft.	$265,966
5417 Winding Road, Louisville, KY 3 Beds \| 2 Baths \| 1170 Sq. Ft.	$242,475

Address	Redfin Estimate
5425 Winding Road, Louisville, KY 4 Beds \| 2 Baths \| 2924 Sq. Ft.	$330,304
5404 Winding Road, Louisville, KY 2 Beds \| 2 Baths \| 2894 Sq. Ft.	$282,498

Property information provided by Metro Search MLS when last listed in 2020. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 40214, KY

Sale history for 5408 Winding Rd

Tax history for 5408 Winding Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 40214

Home values near 5408 Winding Rd

More real estate resources