The 25 Best Small Towns to Retire in Kentucky
Ranked on The Town Files lifestyle rankings among 94 towns of 500–10,000 people in Kentucky. #1 is Prospect, KY.
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25Cynthiana, Kentucky
Better for retirees than 69% of Kentucky towns
Cynthiana is a city of 6,333 people in Harrison County, Kentucky. The median home is worth $172,500 (typical Kentucky town: $161,450).
6,333 people · Harrison County · median home $172,500 · income $54,647 · Jan low 23°F · 16 in snow
Full Cynthiana, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
24Russell Springs, Kentucky
Better for retirees than 72% of Kentucky towns
Russell Springs is a city of 2,715 people in Russell County, Kentucky. It also ranks better for first-time buyers than 95% of Kentucky towns and more of a college town than 94% of Kentucky towns.
2,715 people · Russell County · median home $170,300 · income $38,697 · Jan low 25°F · 5 in snow
Full Russell Springs, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
23Highland Heights, Kentucky
Better for retirees than 73% of Kentucky towns
Highland Heights is a city of 6,662 people in Campbell County, Kentucky. It also ranks better for first-time buyers than 98% of Kentucky towns and better for young professionals than 91% of Kentucky towns.
6,662 people · Campbell County · median home $169,700 · income $53,275 · Jan low 24°F · 17 in snow
Full Highland Heights, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
22Edgewood, Kentucky
Better for retirees than 73% of Kentucky towns
Edgewood is a city of 8,435 people in Kenton County, Kentucky. It also ranks better for families than 95% of Kentucky towns and more of a college town than 95% of Kentucky towns.
8,435 people · Kenton County · median home $312,200 · income $119,028 · Jan low 23°F · 23 in snow
Full Edgewood, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
21Rineyville, Kentucky
Better for retirees than 75% of Kentucky towns
Rineyville is a community of 3,039 people in Hardin County, Kentucky. It also ranks better for cycling than 99% of Kentucky towns and better transit than 81% of Kentucky towns.
3,039 people · Hardin County · median home $257,100 · income $84,511 · Jan low 24°F · 5 in snow
Full Rineyville, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
20Crescent Springs, Kentucky
Better for retirees than 75% of Kentucky towns
Crescent Springs is a city of 4,319 people in Kenton County, Kentucky. It also ranks better for young professionals than 89% of Kentucky towns and more upscale than 89% of Kentucky towns.
4,319 people · Kenton County · median home $302,100 · income $83,066 · Jan low 23°F · 23 in snow
Full Crescent Springs, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
19Hurstbourne, Kentucky
Better for retirees than 76% of Kentucky towns
Hurstbourne is a city of 4,683 people in Jefferson County, Kentucky. It also ranks better for young professionals than 99% of Kentucky towns and more vibrant than 98% of Kentucky towns.
4,683 people · Jefferson County · median home $542,600 · income $116,094 · Jan low 27°F · 13 in snow
Full Hurstbourne, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
18Cold Spring, Kentucky
Better for retirees than 76% of Kentucky towns
Cold Spring is a city of 6,216 people in Campbell County, Kentucky. It also ranks better for first-time buyers than 91% of Kentucky towns and better transit than 90% of Kentucky towns.
6,216 people · Campbell County · median home $253,600 · income $75,000 · Jan low 24°F · 18 in snow
Full Cold Spring, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
17Villa Hills, Kentucky
Better for retirees than 78% of Kentucky towns
Villa Hills is a city of 7,310 people in Kenton County, Kentucky. It also ranks more upscale than 91% of Kentucky towns and better for young professionals than 85% of Kentucky towns.
7,310 people · Kenton County · median home $362,500 · income $107,859 · Jan low 23°F · 23 in snow
Full Villa Hills, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
16Wilmore, Kentucky
Better for retirees than 80% of Kentucky towns

Photo: Nyttend (public domain, Wikimedia Commons) Wilmore is a city of 5,999 people in Jessamine County, Kentucky. It also ranks better for young professionals than 93% of Kentucky towns and more of a college town than 87% of Kentucky towns.
5,999 people · Jessamine County · median home $248,900 · income $77,665 · Jan low 27°F · 10 in snow
Full Wilmore, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
15Russell, Kentucky
Better for retirees than 81% of Kentucky towns
Russell is a city of 3,744 people in Greenup County, Kentucky. It also ranks better for families than 91% of Kentucky towns and more walkable than 81% of Kentucky towns.
3,744 people · Greenup County · median home $211,900 · income $76,182 · Jan low 23°F · 6 in snow
Full Russell, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
14Flemingsburg, Kentucky
Better for retirees than 83% of Kentucky towns
Flemingsburg is a city of 2,953 people in Fleming County, Kentucky. It also ranks better for cycling than 88% of Kentucky towns and easier by car than 82% of Kentucky towns.
2,953 people · Fleming County · median home $132,800 · income $35,493 · Jan low 23°F · 9 in snow
Full Flemingsburg, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
13Douglass Hills, Kentucky
Better for retirees than 83% of Kentucky towns
Douglass Hills is a city of 5,456 people in Jefferson County, Kentucky. It also ranks more upscale than 93% of Kentucky towns and more walkable than 88% of Kentucky towns.
5,456 people · Jefferson County · median home $346,300 · income $78,482 · Jan low 27°F · 10 in snow
Full Douglass Hills, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
12Benton, Kentucky
Better for retirees than 84% of Kentucky towns

Photo: Tennessee Valley Authority (public domain, Wikimedia Commons) Benton is a city of 4,756 people in Marshall County, Kentucky. It also ranks quieter than 93% of Kentucky towns.
4,756 people · Marshall County · median home $157,000 · income $66,827 · Jan low 27°F · 4 in snow
Full Benton, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
11Indian Hills, Kentucky
Better for retirees than 85% of Kentucky towns
Indian Hills is a city of 2,860 people in Jefferson County, Kentucky. It also ranks more upscale than 100% of Kentucky towns and more walkable than 86% of Kentucky towns.
2,860 people · Jefferson County · median home $699,200 · income $192,000 · Jan low 27°F · 4 in snow
Full Indian Hills, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
10Barbourville, Kentucky
Better for retirees than 85% of Kentucky towns
Barbourville is a city of 3,222 people in Knox County, Kentucky. It also ranks more of a college town than 100% of Kentucky towns and hipper than 99% of Kentucky towns.
3,222 people · Knox County · median home $182,400 · income $22,046 · Jan low 25°F · 9 in snow
Full Barbourville, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
9Crestview Hills, Kentucky
Better for retirees than 86% of Kentucky towns
Crestview Hills is a city of 3,246 people in Kenton County, Kentucky. It also ranks better for young professionals than 97% of Kentucky towns and more of a college town than 94% of Kentucky towns.
3,246 people · Kenton County · median home $279,800 · income $95,441 · Jan low 23°F · 23 in snow
Full Crestview Hills, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
8Greenville, Kentucky
Better for retirees than 86% of Kentucky towns
Greenville is a city of 4,492 people in Muhlenberg County, Kentucky. It also ranks easier by car than 94% of Kentucky towns and more of a college town than 79% of Kentucky towns.
4,492 people · Muhlenberg County · median home $116,400 · income $46,054 · Jan low 24°F · 6 in snow
Full Greenville, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
7Park Hills, Kentucky
Better for retirees than 89% of Kentucky towns
Park Hills is a city of 3,162 people in Kenton County, Kentucky. It also ranks better for young professionals than 100% of Kentucky towns and more walkable than 98% of Kentucky towns.
3,162 people · Kenton County · median home $282,100 · income $99,861 · Jan low 24°F · 23 in snow
Full Park Hills, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
6Fort Wright, Kentucky
Better for retirees than 91% of Kentucky towns
Fort Wright is a city of 5,851 people in Kenton County, Kentucky. It also ranks better for young professionals than 95% of Kentucky towns and more walkable than 93% of Kentucky towns.
5,851 people · Kenton County · median home $328,900 · income $105,024 · Jan low 23°F · 23 in snow
Full Fort Wright, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
5Springfield, Kentucky
Better for retirees than 94% of Kentucky towns
Springfield is a city of 2,846 people in Washington County, Kentucky. It also ranks easier by car than 81% of Kentucky towns and quieter than 73% of Kentucky towns.
2,846 people · Washington County · median home $168,600 · income $48,750 · Jan low 26°F · 3 in snow
Full Springfield, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
4Providence, Kentucky
Better for retirees than 94% of Kentucky towns
Providence is a city of 2,892 people in Webster County, Kentucky. It also ranks quieter than 94% of Kentucky towns and better for first-time buyers than 86% of Kentucky towns.
2,892 people · Webster County · median home $60,300 · income $55,121 · Jan low 25°F · 9 in snow
Full Providence, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
3Reidland, Kentucky
Better for retirees than 94% of Kentucky towns
Reidland is a community of 4,526 people in McCracken County, Kentucky. It also ranks easier by car than 93% of Kentucky towns and better for families than 84% of Kentucky towns.
4,526 people · McCracken County · median home $228,000 · income $99,423 · Jan low 25°F · 4 in snow
Full Reidland, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
2Columbia, Kentucky
Better for retirees than 95% of Kentucky towns
Columbia is a city of 4,845 people in Adair County, Kentucky. It also ranks more of a college town than 97% of Kentucky towns and better for young professionals than 83% of Kentucky towns.
4,845 people · Adair County · median home $143,600 · income $47,299 · Jan low 26°F · 8 in snow
Full Columbia, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns. -
1Prospect, Kentucky
Better for retirees than 97% of Kentucky towns

Photo: Nyttend (public domain, Wikimedia Commons) Prospect is a city of 4,592 people in Jefferson County, Kentucky. It also ranks more upscale than 99% of Kentucky towns and better for families than 87% of Kentucky towns.
4,592 people · Jefferson County · median home $538,400 · income $163,462 · Jan low 27°F · 9 in snow
Full Prospect, Kentucky profile: weather, storms, schools, jobs →
The Town Files lifestyle rankings, percentile vs Kentucky towns.
Price vs ranking
More Kentucky rankings
- The 17 Quietest Small Towns in Kentucky
- The 25 Most Affordable Small Towns in Kentucky
- The 21 Best Small Towns for Families in Kentucky
- 22 Small Towns in Kentucky With the Cheapest Homes
- 22 Small Towns in Kentucky With the Mildest Winters
- The 25 Most Walkable Small Towns in Kentucky
- 25 Small Towns in Kentucky With the Fewest Tornadoes Since 1950
- The 25 Best Small Towns for First-Time Home Buyers in Kentucky
- The 13 Best Affordable Small Towns for Remote Workers in Kentucky
Same ranking, other places
- The 50 Best Small Towns to Retire in America
- The 25 Best Small Towns to Retire in Pennsylvania
- The 25 Best Small Towns to Retire in New York
- The 25 Best Small Towns to Retire in Michigan
- The 25 Best Small Towns to Retire in Texas
- The 25 Best Small Towns to Retire in California
- The 25 Best Small Towns to Retire in New Jersey
- The 25 Best Small Towns to Retire in Florida
- The 25 Best Small Towns to Retire in Wisconsin
- The 25 Best Small Towns to Retire in Ohio
- U.S. Census Bureau, American Community Survey 5-year estimates (2020–2024)
- U.S. Census Bureau, 2020 Census and 2025 Gazetteer (2020 / 2025)
- NOAA NCEI U.S. Climate Normals (1991–2020)
- NOAA NCEI Storm Events Database (1950–2026)
- FEMA OpenFEMA Disaster Declarations (this product uses the FEMA OpenFEMA API but is not endorsed by FEMA) (1953–2026)
- NCES Common Core of Data (2023–24)
- BLS Quarterly Census of Employment and Wages; USDA ERS county unemployment (BLS LAUS) (2000–2024)
- The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025)