OFF MARKET

Off Market Aug 2025 for $525K

$502,097

Est. refi paymentEst. refi $2,736/mo

•

1,724

sq ft

2689 Pretty Run Rd, Winchester, KY 40391

About this home

This beautiful and peaceful piece of Kentucky country living is ready and waiting for you to call it home. The home sits on the back of a well maintained, 11-acre lot that qualifies as a mini-farm. The ranch style home has been lovingly maintained and updated with modern colors in the fresh paint. The open concept floor plan includes a lovely family room, dining area, and kitchen with a large island, granite countertops, and stainless appliances. The primary bedroom has a beautiful trey style ceiling and attached bathroom with a tile shower and double vanity. Out the back french doors is a lovely deck and plenty of yard space for outdoor activities. Schedule your private showing today!

Single-familyProperty Type

2016Year Built

11.89 acresLot Size

$291Est. Price/Sq.Ft.

2 car garageParking

Listed by Joshua Wood • Freedom Realty & Property Management

Bought with Joshua Wood • Freedom Realty & Property Management

Redfin checked: a minute ago

•Source:ImagineMLS #25019229

Redfin Estimate

$502,097

$23K since sold in August 2025$2,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 33.1% higher than the average sale price ($377K) of 6 comparable homes.

SOLD JUN 24, 2026
$444,000
A
3 beds2 baths2,442 sq ft
1478 Donaldson Rd, Winchester, KY 40391
SOLD JUN 22, 2026
$407,900
B
3 beds2 baths2,391 sq ft
5665 Paris Rd, Mt Sterling, KY 40353
SOLD SEP 17, 2025
$519,000
C
3 beds2 baths1,692 sq ft
693 White Turley Pike, Mt Sterling, KY 40353
SOLD JUL 28, 2026
$249,900
D
3 beds2 baths1,284 sq ft
312 Buffalo Trce, Winchester, KY 40391
SOLD JUL 13, 2026
$168,000
E
3 beds2 baths1,289 sq ft
128 Bay Hill Dr, Winchester, KY 40391
SOLD NOV 21, 2025
$475,000
F
3 beds2 baths1,524 sq ft
526 Steele Rd, Paris, KY 40361

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Earn from this home

Sell

$59,192

Est. take-home

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Refinance

Est. cash available

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Market trends in 40391, KY

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.0%

+0.6% MoM

Median sale price

$259K

$4K MoM

Avg. days on market

48d

6 days MoM

Recently sold homes

106

3 MoM

New listings for sale

SHORT SALE
$244,000
3 beds2 baths1,692 sq ft
54 Locust Dr, Winchester, KY 40391
$639,000
5 beds3.5 baths5,011 sq ft
104 Teal Ln, Winchester, KY 40391
$135,000
2 beds1 bath807 sq ft
3208 Ford Hampton Rd, Winchester, KY 40391
$275,000
2 beds1 bath1,231 sq ft
682 Athens Boonesboro Rd, Winchester, KY 40391
$289,900
4 beds2 baths1,752 sq ft
198 Hilltop Dr, Winchester, KY 40391
$235,500
3 beds1 bath1,100 sq ft
125 Kittison Dr, Winchester, KY 40391
$359,900
3 beds2 baths2,269 sq ft
15 Moundale Ave, Winchester, KY 40391
$460,000
3 beds2 baths2,062 sq ft
2195 Pretty Run Rd, Winchester, KY 40391
$174,900
2 beds1.5 baths1,100 sq ft
148 Hidden Grove Ln, Winchester, KY 40391
$225,000
3 beds2 baths1,319 sq ft
3 Nunnelly Ct, Winchester, KY 40391
See all

Provided by Redfin

Sale history for 2689 Pretty Run Rd

Date

Event

Price

ImagineMLS #25019229

Aug 28, 2025

Pending

—

Aug 28, 2025

Sold

$525,000

$305/sq ft

Aug 27, 2025

Listed

$525,000

$305/sq ft

Public Records

Jul 16, 2025

Sold

$525,000

$305/sq ft

ImagineMLS #1605070

Jun 29, 2016

Sold

$49,500

$29/sq ft

May 23, 2016

Pending

—

Mar 18, 2016

Listed

$50,300

$29/sq ft

5+ Acres! Live near the farmland that legendary race horse American Pharaoh grew up!! Just down the road from the Pretty Run Farm (where American Pharaoh resided), these acres are as pretty as their name. Gently rolling land (parcel 7) runs onto flat areas perfect for a residence or small farm. Also available: Parcel 8 (5.66ac), Parcel 9 (7.ac), and the entire farm (96.23 acres): all listings on LBAR under same address: Seller says this farm has approx. 90% tillable land that currently is used for farming. Farm includes an eleven bent barn and one barn used as corn crib/shed. See attached MAP for approx. property; parcels 3&4 are not included and a survey will need to be completed prior to the sale. Rural location but with easy, direct access to Interstate.

ImagineMLS #1524230

Jul 22, 2016

Sold

$294,000

$171/sq ft

Jun 8, 2016

Pending

—

May 25, 2016

Price Changed

$471,527

$274/sq ft

Apr 27, 2016

Price Changed

$585,060

$339/sq ft

Feb 18, 2016

Price Changed

$680,580

$395/sq ft

Nov 11, 2015

Listed

$776,100

$450/sq ft

+24

Live near the farmland that legendary race horse American Pharaoh grew up!! Just down the road from the Pretty Run Farm (where American Pharaoh resided), are these 96.23 Acres. True as the Pretty Run name, this gently rolling land runs onto flat areas perfect for a residence or farming. Seller says this farm has approx. 90% tillable land that currently is used for farming. Farm includes an eleven bent barn and one barn used as corn crib/shed. (Acreage includes Parcel 5 (5.ac) + parent track to equal 96.23 total acres). See attached MAP for approx. property; parcels 3&4 are not included and a survey will need to be completed prior to the sale. Road frontage lots available: Parcel 7 (5.03ac), Parcel 8 (5.66ac) and Parcel 9 (7.ac). at $10,000/acre. Rural location but with easy, direct access to Interstate.

ImagineMLS #1605062

May 20, 2016

Listing Removed

—

May 9, 2016

Sold

$49,500

$29/sq ft

Mar 25, 2016

Pending

—

Mar 18, 2016

Listed

$50,000

$29/sq ft

ImagineMLS #1602853

Feb 26, 2016

Listing Removed

—

Feb 18, 2016

Listed

$50,000

$29/sq ft

Tax history for 2689 Pretty Run Rd

*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

11.89 Acres

Year renovated

—

Sq. Ft.

—

Year built

1930

Style

Ranch

County

Clark County

APN

073-0000-001-02

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 8, 2026.

Property details

Parking

Parking Information
Parking Features: Attached Garage, Driveway, Off Street

Garage Information
Has Garage

Interior

Virtual Tour URL
Virtual Tour (External Link)

Bathroom Information
Bathrooms (Full): 2

Heating & Cooling
Has Heating
Heating: Heat Pump
Cooling: Heat Pump

Interior Features
Interior Features: Ceiling Fan(s)
Appliances: Dishwasher, Refrigerator, Range
Flooring: Carpet, Laminate
Laundry Features: Electric Dryer Hookup, Washer Hookup

Exterior

Exterior Features
Other Structures: Shed(s)
Foundation Details: Block
Roof: Composition, Shingle
Construction Materials: Vinyl Siding
Patio And Porch Features: Deck, Porch

Lot Information
Lot Size Square Feet: 517,928
Lot Size Acres: 11.89
Lot Size Source: Public Records
Water Source: Public
On Waterfront: No
Has View: Yes
View: Rural, Farm

Property Information
Structure Type: House
Levels: One

Building Information
Building Area Total: 1,724

Financial

Tax Information
Parcel Number: 073-0000-001-02

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Electricity Available

Location

School Information
Elementary School: Conkwright
Middle Or Junior School: Robert Campbell
High School: GRC
High School District: Clark County - 7

Location Information
County Or Parish: Clark
Directions: Paris Road to Pretty Run Rd. House on right
Subdivision Name: Rural

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 11.89 acres
Style: Ranch
Year Built: 1930
Year Renovated: —
County: Clark County
APN: 073-0000-001-02

Home facts updated by county records on Jul 8, 2026

Around this home

Schools

Conkwright Elementary School

Public K-4 • Assigned • 5.7mi

4/10

Robert D Campbell Junior High School

Public 7-8 • Assigned • 7.9mi

5/10

George Rogers Clark High School

Public 9-12 • Assigned • 9.6mi

5/10

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

4/10 Heat Factor

7 days above 102° expected this year, 19 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Winchester, KY • 40391

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 8.3 hours in June and 3.2 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

3.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$477,000 – $578,000

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Nearby similar homes

$1,599,000

3 beds2.5 baths4,518 sq ft

3166 Colby Rd, Winchester, KY 40391

$279,500

3 beds2.5 baths1,963 sq ft

304 Newcastle Ln, Winchester, KY 40391

$120,000

2 beds1 bath912 sq ft

3050 Cane Ridge Rd, Paris, KY 40361

$460,000

3 beds2 baths2,062 sq ft

2195 Pretty Run Rd, Winchester, KY 40391

$219,500

3 beds2 baths1,200 sq ft

491 Hidden Hills Way, Winchester, KY 40391

$724,889

4 beds4.5 baths4,255 sq ft

132 Lana Ln, Winchester, KY 40391

New listings for sale in 40391

SHORT SALE

$244,000

3 beds2 baths1,692 sq ft

54 Locust Dr, Winchester, KY 40391

$639,000

5 beds3.5 baths5,011 sq ft

104 Teal Ln, Winchester, KY 40391

$135,000

2 beds1 bath807 sq ft

3208 Ford Hampton Rd, Winchester, KY 40391

$275,000

2 beds1 bath1,231 sq ft

682 Athens Boonesboro Rd, Winchester, KY 40391

$289,900

4 beds2 baths1,752 sq ft

198 Hilltop Dr, Winchester, KY 40391

$235,500

3 beds1 bath1,100 sq ft

125 Kittison Dr, Winchester, KY 40391

$359,900

3 beds2 baths2,269 sq ft

15 Moundale Ave, Winchester, KY 40391

$460,000

3 beds2 baths2,062 sq ft

2195 Pretty Run Rd, Winchester, KY 40391

$174,900

2 beds1.5 baths1,100 sq ft

148 Hidden Grove Ln, Winchester, KY 40391

Home values near 2689 Pretty Run Rd

Data from public records.

Address	Redfin Estimate
2345 Pretty Run Rd, Winchester, KY 3 Beds \| 2 Baths \| 1944 Sq. Ft.	$299,957
2950 Pretty Run Rd, Winchester, KY 4 Beds \| 3 Baths \| 2912 Sq. Ft.	$683,443

Address	Redfin Estimate
2721 Pretty Run Rd, Winchester, KY 3 Beds \| 2 Baths \| 1456 Sq. Ft.	$254,279
2890 Pretty Run Rd, Winchester, KY 5 Beds \| 3.5 Baths \| 3024 Sq. Ft.	$656,733

Address	Redfin Estimate
2565 Pretty Run Rd, Winchester, KY 4 Beds \| 3.5 Baths \| 3200 Sq. Ft.	$692,094

Property information provided by ImagineMLS when last listed in 2025. 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 40391, KY

Sale history for 2689 Pretty Run Rd

Tax history for 2689 Pretty Run Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 40391

Home values near 2689 Pretty Run Rd

More real estate resources