Retiring in Chickasaw County, Mississippi

By Kaspar Caldwell, REALTOR® · Reviewed October 7, 2026

Thinking of retiring in Chickasaw County, Mississippi? Local perks, home prices, what to look for in a retirement home and real homes under $250k for sale now.

Short answer

Chickasaw County offers the Natchez Trace Parkway passes through the county, plus affordable homes (14 homes with 3 or fewer bedrooms under $250,000 were listed in USDA-eligible areas as of October 8, 2026). Mississippi also exempts qualified retirement income from state income tax.

Key takeaways

The Natchez Trace Parkway passes through the county.
Davis Lake in the Tombigbee National Forest offers camping, fishing and trails.
Houston and Okolona are short drives to Tupelo.
Look for single-level homes with low-maintenance lots.

Chickasaw County, Mississippi (county seat: Houston).

Local perks in Chickasaw County

The Natchez Trace Parkway passes through the county.
Davis Lake in the Tombigbee National Forest offers camping, fishing and trails.
Houston and Okolona are short drives to Tupelo.

Retirement home checklist

Single-level layout
Bedroom and full bath on the main floor
Small, easy yard
Newer roof and HVAC
Short drive to medical care

How Kaspar helps

Kaspar Caldwell, REALTOR®, helps retirees and downsizers buy in Chickasaw County and sell their current home, with honest guidance on price, condition and timing.