OFF MARKET

Off Market Feb 2017 for $250K

$367,518

Est. refi paymentEst. refi $1,339/mo

•

1,414

sq ft

4108 Winchester Rd, Saint Matthews, KY 40207

About this home

Public Remarks: ST. MATTHEWS GEM! This darling home in St. Matthews has many desirable features including convenience, move-in ready condition, and location, location, location! An inviting front porch beckons you to the cheerful front door and into the spacious living room with a cozy fireplace for cold winter evenings. The front storm door allows you to leave the door open and enjoy the additional natural light in warm weather. You will find beautiful, freshly refinished wood flooring throughout the first floor living room, dining room, and two bedrooms. The front bay window, fireplace and arched doorways in the living room are wonderful features and add great charm! In the first floor bathroom where the bathtub has been recently refinished there is tile flooring. The kitchen has granite counter tops and backsplash, tile flooring, a ceiling fan, garbage disposer, refrigerator, built-in microwave and dishwasher. The dining room flows through French doors onto a screened-in porch where you can enjoy your coffee or tea on those warm summer mornings. In addition to the two first floor bedrooms, the second floor of this charming Cape Cod has a large private master suite with wood and tile flooring, a full bath including tub with shower and generous walk-in closet space. All three bedrooms boast ceiling fans and overhead lighting. This home has an unfinished basement providing great space for storage or finishing for a family room, play room, exercise room, craft room, study...the possibilities abound! The fenced-in yard is good sized and gives you garden, play, and entertaining space. In the detached, one car garage your vehicle and lawn care equipment can find protection from the elements. Enjoy easy access to I-64, I-71, the Watterson Expressway, Mall St. Matthews, Oxmoor, Shelbyville Road, and Crescent Hill!

Single-familyProperty Type

1940Year Built

6,050 sq ftLot Size

$260Est. Price/Sq.Ft.

1 car garageParking

Listed by Excellent Communication Every Step of the Way Wieting • Semonin Realtors

Bought with Gant Hill • Gant Hill & Associates, LLC

Bought with Lori Willinghurst • Gant Hill & Associates, LLC

Redfin checked: 2 minutes ago

•Source:Metro Search MLS #1463932

Redfin Estimate

$367,518

$118K since sold in February 2017$7,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.5% lower than the average sale price ($370K) of 6 comparable homes.

SOLD SEP 4, 2026
$413,000
A
4 beds2 baths1,462 sq ft
4015 Springhill Rd, Saint Matthews, KY 40207
simpler.realestate
SOLD JUN 8, 2026
$390,000
B
3 beds2 baths1,700 sq ft
231 S Hubbards Ln, Saint Matthews, KY 40207
simpler.realestate
SOLD SEP 10, 2026
$421,000
C
3 beds2 baths1,544 sq ft
207 S Sherrin Ave, Saint Matthews, KY 40207
Schuler Bauer Real Estate Services ERA Powered
SOLD APR 16, 2026
$398,000
D
3 beds2 baths1,399 sq ft
3919 Hycliffe Ave, Saint Matthews, KY 40207
Lenihan Sotheby's Int'l Realty
SOLD DEC 24, 2025
$335,000
E
3 beds2 baths1,306 sq ft
4217 Briarwood Rd, Saint Matthews, KY 40207
Lenihan Sotheby's Int'l Realty
SOLD JUL 17, 2026
$260,000
F
3 beds2 baths1,261 sq ft
122 Bonner Ave, Saint Matthews, KY 40207
Family Realty LLC

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Earn from this home

Sell

$185,338

Est. take-home

List your home with Redfin and save $3,675

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$1,567/mo

Redfin rental estimate

List your home for rent

Market trends in 40207, KY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.1%

0.0% MoM

Median sale price

$425K

$18K MoM

Avg. days on market

30d

2 days MoM

Recently sold homes

170

0 MoM

New listings for sale

NEW 2 HRS AGO
$850,000
3 beds3 baths3,458 sq ft
4101 Brownsboro Rd, Louisville, KY 40207
Arnold Realty, LLC
NEW 24 HRS AGO
$430,000
3 beds2 baths2,669 sq ft
213 Heady Ave, Richlawn, KY 40207
Hasty REALTORS
$499,900
3 beds3 baths2,148 sq ft
3915 Alton Rd, Saint Matthews, KY 40207
RE/MAX Premier Properties
$329,900
3 beds1 bath1,354 sq ft
313 Iola Rd, Saint Matthews, KY 40207
White Picket Real Estate
$295,000
3 beds1 bath1,560 sq ft
3535 Warner Ave, Saint Matthews, KY 40207
Schuler Bauer Real Estate Services ERA Powered
OPEN SUN, 2PM TO 4PM
$579,900
4 beds2.5 baths3,203 sq ft
115 Don Allen Rd, Richlawn, KY 40207
White Picket Real Estate
$425,000
4 beds2 baths2,300 sq ft
4428 Blenheim Rd, Louisville, KY 40207
Semonin Realtors
$389,000
3 beds2.5 baths1,800 sq ft
609 Wallace Ave, Saint Matthews, KY 40207
Julie Pogue Properties
$674,840
4 beds3 baths4,810 sq ft
5407 Navajo Rd, Indian Hills, KY 40207
Edelen & Edelen REALTORS
OPEN SUN, 2PM TO 4PM
$359,900
2 beds2 baths1,638 sq ft
210 Cornell Pl, Saint Matthews, KY 40207
simpler.realestate
See all

Provided by Redfin

Sale history for 4108 Winchester Rd

Date

Event

Price

TENANTTURNER2 #2

Jan 27, 2026

Rental Removed

$1,825

$1/sq ft

Jan 23, 2026

Listed for Rent

$1,825

$1/sq ft

RENT. #1

Nov 27, 2022

Rental Removed

—

Metro Search MLS #1463932

Feb 22, 2017

Sold

$250,000

$177/sq ft

Feb 20, 2017

Pending

—

Jan 24, 2017

Contingent

—

Dec 9, 2016

Listed

$269,000

$190/sq ft

Metro Search MLS #1209193

Jul 31, 2008

Sold

$209,000

$148/sq ft

Jun 25, 2008

Listed

$209,000

$148/sq ft

Public Remarks

Adorable Doll House! Wonderful updated home perfectly decorated and ready to move in! Kitchen with granite counters and ceramic tiled floor. Beautiful hardwood floors throughout first and second floor. Living Room with wood burning fireplace has fantastic floor to ceiling bay window. Updated bathrooms. French Doors to porch off Kitchen/Dining is fully screened and overlooks back yard. This house has all the charm and up-to-date amenities you want! Master Suite upstairs is huge and has full bath, private dressing room with window and lots of closet space. Unfinished basement can be finished for a great media room, family room, etc. Everything is in wonderful condition and so charming! See Pictures. St. Matthews location >> close to everything. This one won't last long.

Metro Search MLS #1090732

Jul 1, 2005

Sold

$191,000

$135/sq ft

May 26, 2005

Listed

$194,978

$138/sq ft

Public Remarks

This truly exceptional St. Matthews home is a dream come true. The moment you step into this wonderful house you are greeted by bright open spaces with a fantastic flow. The hardwood floors throughout look fantastic and add to that St. Matthews charm. The family room boasts arched doorways, a wood burning fireplace with tile surround and a classic mantle. The recently updated kitchen is bright and airy and opens directly to the dining room. Other recent updates include dimensional shingles on the roof, paint inside and outside, concrete driveway, and a complete ADT security system that is also has smoke/heat detectors. You can enjoy the beautiful backyard from the privacy of your screened in porch or you can sit out front and watch the neighborhood from the spacious front porch. The full basement is very clean and has lots of room for a workshop or additional storage. The upstairs Master Suite runs the length of the house and boasts all wood floors, a full bath and an extra large walk-in closet. Your not going to be disappointed showing this home as its in great condition and the inside is immaculate. The house is also located just a short walk from St Matthews Elementary, Waggner HS, & a TARC bus stop. All appliances remain and the home comes with a 1 year home warranty. Click on the photo for additional pictures and the virtual tour.

Metro Search MLS #1013006

Oct 31, 2002

Sold

$170,000

$120/sq ft

Oct 14, 2002

Listed

$169,740

$120/sq ft

Metro Search MLS #910620

Jul 2, 1999

Sold

$132,000

$93/sq ft

Jun 16, 1999

Listed

$132,000

$93/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$2,974 (+1.0%)

$75,000 + $189,080

$264,080

2024

$2,945 (+11.1%)

$75,000 + $189,080

$264,080

2023

$2,651 (−0.3%)

$75,000 + $189,080

$264,080

2022

$2,660 (−7.8%)

$60,000 + $170,930

$230,930

2021

$2,885 (−0.3%)

$60,000 + $170,930

$230,930

2020

$2,893 (+2.0%)

$60,000 + $170,930

$230,930

2019

$2,835 (+1.2%)

$45,000 + $205,000

$250,000

2018

$2,801 (+19.1%)

$45,000 + $205,000

$250,000

2017

$2,352 (+4.3%)

$45,000 + $168,930

$213,930

2016

$2,255 (+2.1%)

$45,000 + $168,930

$213,930

2015

$2,209

$45,000 + $168,930

$213,930

2014

$2,210

$37,000 + $172,000

$209,000

Tax history for 4108 Winchester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$2,974 (+1.0%)

$75,000 + $189,080

$264,080

2024

$2,945 (+11.1%)

$75,000 + $189,080

$264,080

2023

$2,651 (−0.3%)

$75,000 + $189,080

$264,080

2022

$2,660 (−7.8%)

$60,000 + $170,930

$230,930

2021

$2,885 (−0.3%)

$60,000 + $170,930

$230,930

2020

$2,893 (+2.0%)

$60,000 + $170,930

$230,930

2019

$2,835 (+1.2%)

$45,000 + $205,000

$250,000

2018

$2,801 (+19.1%)

$45,000 + $205,000

$250,000

2017

$2,352 (+4.3%)

$45,000 + $168,930

$213,930

2016

$2,255 (+2.1%)

$45,000 + $168,930

$213,930

2015

$2,209

$45,000 + $168,930

$213,930

2014

$2,210

$37,000 + $172,000

$209,000

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

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

6,050 Sq. Ft.

Year renovated

1940

Sq. Ft.

—

Year built

1940

Style

Single Family Residential

County

Jefferson County

APN

22052100330000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 8, 2026.

Property details

Parking

Parking Information
Garage Spaces: 1.0
Parking Features: Detached, Entry Front

Interior

Virtual Tour Information

Virtual Tour Information

Bedroom Information
Bedrooms Total: 3
First Floor PBR: Yes
# Upper Floor Bedrooms: 0.0
# 2nd Floor Bedrooms: 1.0
# 1st Floor Bedrooms: 2
# Basement Bedrooms: 0.0

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

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

Interior Features
# of Rooms: 6
# of Closets: 6
# of Fireplaces: 1
Fireplaces Total: 1
Fireplaces: Level 1: 1
Fireplace: Yes

Living Areas
Living Room: Yes
Living Room Level: First

Other Room Information
# of Rooms: 6
Rooms Total: 9
Basement Y/N: Yes
Basement: Unfinished
Bedroom: Yes
Bedroom Level: First
Closets: Basement: 1
Dining Room: Yes
Dining Room Level: First
Fireplaces Total: 1
Full Bathroom: Yes
Full Bathroom Level: First
Kitchen: Yes
Kitchen Level: First
Other: Yes
Other Level: First

Room 1 Information
Room 1 Length: 18.00
Room 1 Level: First
Room 1 Type: Living Room
Room 1 Width: 14.00

Room 2 Information
Room 2 Description: Formal
Room 2 Length: 9.00
Room 2 Level: First
Room 2 Type: Dining Room
Room 2 Width: 12.00

Room 3 Information
Room 3 Length: 10.00
Room 3 Level: First
Room 3 Type: Kitchen
Room 3 Width: 9.00

Room 4 Information
Room 4 Length: 11.00
Room 4 Level: First
Room 4 Type: Bedroom
Room 4 Width: 11.00

Room 5 Information
Room 5 Length: 14.00
Room 5 Level: First
Room 5 Type: Bedroom
Room 5 Width: 11.00

Room 6 Information
Room 6 Length: 6.00
Room 6 Level: First
Room 6 Type: Full Bathroom
Room 6 Width: 7.00

Room 7 Information
Room 7 Description: Master Bedroom & Bath (9x6)combination
Room 7 Length: 16.00
Room 7 Level: Second
Room 7 Type: Bedroom
Room 7 Width: 12.00

Room 8 Information
Room 8 Level: Second
Room 8 Type: Full Bathroom

Room 9 Information
Room 9 Description: Screened Porch
Room 9 Length: 9.00
Room 9 Level: First
Room 9 Type: Other
Room 9 Width: 9.30

Exterior

Land Information
Fencing: Full, Wood, Chain Link
Fencing: Chain Link: Yes
Fencing: Full: Yes
Fencing: Wood: Yes

Lot Description
Lot Features: Sidewalk, Level
Lot Size Area: 0.0
Lot Size Units: Acres
Lot Size Dimensions: 55 x 110
Level: Yes
Sidewalk: Yes

Property Information
Property Sub Type: Single Family Residence
Residential
Architectural Style: Cape Cod

Subdivision / Condo Amenities
Subdivision Name: WINCHESTER PLACE

Building Information
Building Area Source: Appraiser
Building Area Total: 1414.0
Stories: 2
Year Built: 1940
Roof: Shingle
Foundation Details: Poured Concrete
Construction Materials: Aluminum Siding, Stone
Above Grade Finished: 1,414
Below Grade Unfin: 947.9
Living Area: 1414.0

Financial

Tax Information
Tax Block: 0521
Tax Lot: 0033

Utilities

Utility Information
Utilities: Electricity Connected, Fuel:Natural

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

Cooling
Cooling Y/N: Yes
Cooling: Central Air

Location

Neighborhood Information
Subdivision Name: WINCHESTER PLACE

School Information
High School District: Jefferson
School District: Jefferson

Location Information
Directions: Shelbyville Road, left on to S. Hubbards Lane, right onto Winchester Road.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 6,050 square feet
Style: Single Family Residential
Year Built: 1940
Year Renovated: 1940
County: Jefferson County
APN: 22052100330000

Home facts updated by county records on Sep 8, 2026

Around this home

Schools

St Matthews Elementary School

Public K-5 • Assigned • 0.2mi

7/10

Westport Middle School

Public 6-8 • Assigned • 3.1mi

4/10

Waggener High School

Public 9-12 • Assigned • 0.3mi

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 105° expected this year, 20 days in 30 years

2/10 Wind Factor

3% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Saint Matthews, KY • 40207

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 9.3 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

9.3 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$350,000 – $423,000

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Nearby similar homes

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Edelen & Edelen REALTORS

Home values near 4108 Winchester Rd

Data from public records.

Address	Redfin Estimate
4109 Winchester Road, Saint Matthews, KY 3 Beds \| 2 Baths \| 1456 Sq. Ft.	$375,270
4104 Winchester Road, Saint Matthews, KY 3 Beds \| 2 Baths \| 2107 Sq. Ft.	$398,963

Address	Redfin Estimate
4102 Winchester Road, Saint Matthews, KY 3 Beds \| 1 Baths \| 1355 Sq. Ft.	$335,842
4103 Winchester Road, Saint Matthews, KY 3 Beds \| 2 Baths \| 2100 Sq. Ft.	$440,250

Address	Redfin Estimate
4105 Winchester Road, Saint Matthews, KY 3 Beds \| 2 Baths \| 2158 Sq. Ft.	$428,708
4101 Winchester Road, Saint Matthews, KY 3 Beds \| 2.5 Baths \| 2241 Sq. Ft.	$568,252

Property information provided by undefined .

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About this home

Redfin Estimate

Earn from this home

Market trends in 40207, KY

Sale history for 4108 Winchester Rd

Tax history for 4108 Winchester Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 40207

Home values near 4108 Winchester Rd

More real estate resources