SOLD NOV 21, 2025

Off Market Nov 2025 for $462K

$453,713

Est. refi paymentEst. refi $3,017/mo

•

2,727

sq ft

865 Pretty Run Rd, Winchester, KY 40391

About this home

Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard. Through the breezeway, a large rec room offers plenty of space for entertaining, hobbies, or a play area with additional storage options up the stairs in the rec room. It also connects to the 1.5 car garage. Two additional bedrooms are ideal for family, guests, or office use. Outside, enjoy an inviting covered front porch with farm views, as well as peaceful farm views from the back. There is a Trex deck for relaxing or outdoor dining out back, plus a separate deck surrounding the above ground pool. A 10x28 storage shed adds convenience and additional storage. The sprawling 1.5 acres are flat, usable, and serene. Newer HVAC (2022). Experience country living just minutes from town, and make this charmer yours!

Single-familyProperty Type

1989Year Built

1.56 acresLot Size

$166Est. Price/Sq.Ft.

1 car garageParking

Listed by Shane Underwood • Keller Williams Commonwealth

Listed by Terra Long • Keller Williams Commonwealth

Bought with Robert Bratton • Bluegrass Sotheby's International Realty

Redfin checked: a few seconds ago

•Source:ImagineMLS #25015822

Redfin Estimate

$453,713

$8,287 since sold in November 2025$4,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 21.1% higher than the average sale price ($375K) of 6 comparable homes.

SOLD JUL 22, 2026
$359,000
A
3 beds2 baths2,000 sq ft
133 Shala-mar Rue, Winchester, KY 40391
SOLD AUG 7, 2026
$315,000
B
3 beds2 baths1,932 sq ft
13 Lakeview Dr, Winchester, KY 40391
SOLD MAY 26, 2026
$450,000
C
3 beds2.5 baths3,444 sq ft
222 Ashton Oak Way, Winchester, KY 40391
SOLD JUL 13, 2026
$168,000
D
3 beds2 baths1,289 sq ft
128 Bay Hill Dr, Winchester, KY 40391
SOLD MAY 29, 2026
$600,000
E
3 beds3.5 baths3,391 sq ft
905 Pretty Run Rd, Winchester, KY 40391
SOLD JUL 10, 2026
$356,000
F
4 beds2 baths2,208 sq ft
274 Greenway Dr, Winchester, KY 40391

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Earn from this home

Sell

$60,585

Est. take-home

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Refinance

Est. cash available

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Rent

$2,637/mo

Redfin rental estimate

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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

NEW 7 HRS AGO
$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
$489,000
4 beds3.5 baths3,584 sq ft
1137 Lafayette Blvd, Winchester, KY 40391
$279,500
3 beds2.5 baths1,963 sq ft
304 Newcastle Ln, Winchester, KY 40391
$175,000
3 beds1 bath1,173 sq ft
24 Spring St, Winchester, KY 40391
See all

Provided by Redfin

Sale history for 865 Pretty Run Rd

Tax history for 865 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

350 ft.

Lot depth

182 ft.

Lot size

1.56 Acres

Year renovated

—

Sq. Ft.

—

Year built

1989

Style

Other

County

Clark County

APN

061-0000-012-00

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 8, 2026.

Property details

Parking

Parking Information
Parking Features: Detached Garage, Driveway, Off Street, Garage Faces Side

Garage Information
Has Garage

Interior

Bathroom Information
Bathrooms (Full): 2

Heating & Cooling
Has Heating
Heating: Electric, Heat Pump
Cooling: Electric, Heat Pump

Interior Features
Interior Features: Breakfast Bar, Entrance Foyer, Eat-in Kitchen, In-Law Floorplan, Primary First Floor, Walk-In Closet(s), Ceiling Fan(s)
Appliances: Dishwasher, Refrigerator, Range
Flooring: Hardwood, Laminate, Tile, Vinyl
Window Features: Insulated Windows, Blinds, Screens
Laundry Features: Electric Dryer Hookup, Main Level, Washer Hookup

Room Information
Rooms (Total): 6
Basement: Crawl Space
Fireplace: Yes

Exterior

Exterior Features
Other Structures: Guest House, Shed(s)
Foundation Details: Block
Roof: Shingle
Construction Materials: Stone, Vinyl Siding
Pool Features: Above Ground

Lot Information
Lot Size Square Feet: 67,954
Lot Size Acres: 1.56
Lot Size Source: Public Records
Water Source: Public
On Waterfront: No
Has View: Yes
View: Rural, Trees/Woods, Farm

Property Information
Structure Type: House
Levels: One

Building Information
Building Area Total: 2,727

Financial

Tax Information
Parcel Number: 061-0000-012-00

Utilities

Utility Information
Sewer: Septic Tank

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: From I-64, take exit 96. Take Paris Rd. towards the Industrial Park. After about 4 miles, turn right onto Pretty Run Rd. Follow approximately 0.8 of a mile, and the property will be on your right, look for yard sign.
Subdivision Name: Rural

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.56 acres
Style: Other
Year Built: 1989
Year Renovated: —
County: Clark County
APN: 061-0000-012-00

Home facts updated by county records on Jul 8, 2026

Around this home

Schools

Conkwright Elementary School

Public K-4 • Assigned • 4.6mi

4/10

Robert D Campbell Junior High School

Public 7-8 • Assigned • 6.6mi

5/10

George Rogers Clark High School

Public 9-12 • Assigned • 8.2mi

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

7% chance of strong winds in next 30 years

2/10 Air Factor

1 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

$432,000 – $522,000

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Nearby similar homes

$1,599,000

3 beds2.5 baths4,518 sq ft

3166 Colby Rd, Winchester, KY 40391

$329,900

5 beds4 baths4,456 sq ft

410 W Lexington Ave, 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

FOR SALE BY OWNER

$320,000

3 beds3 baths1,632 sq ft

118 Sturbridge Ln, Winchester, KY 40391

$274,500

3 beds2 baths1,420 sq ft

137 Eastridge Dr, Winchester, KY 40391

New listings for sale in 40391

NEW 7 HRS AGO

$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

$489,000

4 beds3.5 baths3,584 sq ft

1137 Lafayette Blvd, Winchester, KY 40391

$279,500

3 beds2.5 baths1,963 sq ft

304 Newcastle Ln, Winchester, KY 40391

Home values near 865 Pretty Run Rd

Data from public records.

Address	Redfin Estimate
489 Pretty Run Road, Winchester, KY 3 Beds \| 2.5 Baths \| 2294 Sq. Ft.	$620,812
1459 Pretty Run Road, Winchester, KY 3 Beds \| 2.5 Baths \| 2000 Sq. Ft.	$379,982

Address	Redfin Estimate
1415 Pretty Run Road, Winchester, KY 3 Beds \| 2 Baths \| 1733 Sq. Ft.	$365,420
905 Pretty Run Road, Winchester, KY 3 Beds \| 3.5 Baths \| 3391 Sq. Ft.	$591,686

Address	Redfin Estimate
1387 Pretty Run Road, Winchester, KY 3 Beds \| 2 Baths \| 1567 Sq. Ft.	$334,663
1335 Pretty Run Road, Winchester, KY 3 Beds \| 3 Baths \| 3569 Sq. Ft.	$497,428

Property information provided by ImagineMLS when last listed in 2025. This data may not match . Learn more.

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