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Rural ResidenceResidential
$248,520$211 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 82How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Aug 30, 2026
Last sold for $96,800 on Apr 7, 2017

3950 PRETTY RUN RD

WINCHESTER, KY 40391
0
Baths
1,176 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
10.63 ac
Lot SizeThe size of the land the home sits on, from county records.
1
StoriesHow many floors the home has above ground.

Valuation

$249K
$203K low$294K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$96,800 · Apr 7, 2017

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,387 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$394,750 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$5,550
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$389,200
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$394,750
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$394,750

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Rural Residence
CountyBourbon
Lot (acres)The size of the land the home sits on, from county records.10.63
HeatingThe type of heating system in the home.Yes
CoolingThe type of cooling or air conditioning in the home.Yes

Transaction History(1)

Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
North Middletown Elementary SchoolB
Elementary · Grades KG–5 · 3.3 mi
H
Bourbon County High SchoolC
High · Grades 9–12 · 9.6 mi
M
Bourbon County Middle SchoolB-
Middle · Grades 6–8 · 9.7 mi

District: Bourbon County School District

Neighborhood · ZIP 40391These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.99
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.172
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.60

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.92%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.13%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.15%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.4%
PopulationHow many people live in this area.37,318
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.155 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$66,193
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$89,528
Average tempThe average temperature here across a full year.55°F
Annual precipHow much rain and melted snow falls here in a typical year.46 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.55%

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Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.

How this home compares

3950 Pretty Run Rd measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.

  • Costs more per square foot than 88% of homes in Winchester 40391
  • Smaller than 73% of homes in Winchester 40391
  • Among the largest lots in Winchester 40391

What homes are worth in Winchester 40391

Each bar is how many homes fall in that price range. The marker is this home.

This home
$75K$608K

This home is worth more than 54% of homes in Winchester 40391.

How it measures up in Winchester 40391

The dot is this home. The mark in the middle is the typical home in Winchester 40391.

Estimated value$248,520
CheaperTypical $238,714Pricier

Pricier than 54% of homes nearby

Price per ft²$211
CheaperTypical $166Pricier

Pricier than 88% of homes nearby

Living area1,176 ft²
SmallerTypical 1,489 ft²Bigger

Bigger than 27% of homes nearby

Lot size10.63 ac
SmallerTypical 0.24 acBigger

Bigger than almost all homes nearby

How 3950 Pretty Run Rd ranks against every home in each area.
MeasureThis homeWinchester 40391Bourbon County
Estimated valuepricier than$248,52054% of homes57% of homes
Price per ft²pricier than$21188% of homes83% of homes
Living areabigger than1,176 ft²27% of homes27% of homes
Lot sizebigger than10.63 acalmost all homes60% of homes

About 3950 Pretty Run Rd

How much is 3950 Pretty Run Rd, Winchester, KY worth?

The TopHap Estimate for 3950 Pretty Run Rd, Winchester, KY is $248,520 as of Aug 30, 2026. The likely range is $202,735 to $294,305. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 3950 Pretty Run Rd, Winchester, KY last sell?

3950 Pretty Run Rd, Winchester, KY last sold on Apr 7, 2017 for $96,800, according to the county's recorded deed.

How big is 3950 Pretty Run Rd, Winchester, KY?

3950 Pretty Run Rd, Winchester, KY has 1,176 square feet of living space and a 10.63-acre lot.

What schools serve 3950 Pretty Run Rd, Winchester, KY?

3950 Pretty Run Rd, Winchester, KY is assigned to North Middletown Elementary School (elementary), rated B; Bourbon County High School (high), rated C; Bourbon County Middle School (middle), rated B-. All sit in Bourbon County School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 3950 Pretty Run Rd, Winchester, KY compare to other homes in Winchester 40391?

Among the 13,392 homes in Winchester 40391, it is worth more than 54% of them ($248,520 against a typical $238,714), its price per square foot is higher than 88% of them ($211 against a typical $166), it is bigger than 27% of them (1,176 ft² against a typical 1,489 ft²) and its lot is bigger than almost all of them (10.63 ac against a typical 0.24 ac). These shares are recounted nightly from the full county assessor record for each area, not from active listings.

What are the property taxes on 3950 Pretty Run Rd, Winchester, KY?

The 2025 property tax bill for 3950 Pretty Run Rd, Winchester, KY was $3,387. The county assessed it at $394,750.

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Assigned schools

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