Retiring in Winston County, Mississippi
By Kaspar Caldwell, REALTOR® · Reviewed
Thinking of retiring in Winston County, Mississippi? Local perks, home prices, what to look for in a retirement home and real homes under $250k for sale now.
Short answer
Winston County offers louisville is the county seat, with Lake Tiak-O'Khata nearby, plus affordable homes (22 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
- Louisville is the county seat, with Lake Tiak-O'Khata nearby.
- Nanih Waiya, a sacred mound of the Choctaw people, is in the county.
- Part of the Tombigbee National Forest lies nearby.
- Look for single-level homes with low-maintenance lots.
Local perks in Winston County
- Louisville is the county seat, with Lake Tiak-O'Khata nearby.
- Nanih Waiya, a sacred mound of the Choctaw people, is in the county.
- Part of the Tombigbee National Forest lies nearby.
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 Winston County and sell their current home, with honest guidance on price, condition and timing.
Example homes for sale in Winston County
$17,500
20899 MS 14
Louisville · 2 bd · 1 ba · 1,148 sqft
$27,200
16789 MS 490
Louisville · 3 bd · 2 ba · 1,152 sqft
$40,000
343 N Hight Ave
Louisville · 3 bd · 2 ba · 1,675 sqft
$85,000
14865 MS 397
Louisville · 3 bd · 1.5 ba · 1,600 sqft
$88,000
6095 Young Crossing Rd
Louisville · 3 bd · 1 ba · 936 sqft
$89,000
6535 MS 14
Louisville · 3 bd · 2 ba · 1,680 sqft
Listed by various brokerages. Verified for sale October 7, 2026; availability changes daily.
Frequently asked questions
Are homes in Winston County affordable for retirees?
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Yes, 22 homes with 3 or fewer bedrooms were listed under $250,000 in USDA-eligible areas as of October 8, 2026.
Can retirees use USDA?
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Yes, with qualifying income such as Social Security or pensions, in an eligible area.