Your REALTOR® for Winston County, MS
By Kaspar Caldwell, REALTOR® · Reviewed
Looking for a real estate agent in Winston County? Kaspar Caldwell is a REALTOR® with Keller Williams (2185 Hutchinson St, Tupelo, MS 38801), license # S-62291, with 45+ completed affordable housing transactions, including manufactured homes. 32 homes in USDA-eligible areas in Winston County were verified for sale on October 8, 2026, with a median list price of $159,450.
How Kaspar helps you in Winston County
- Local knowledge of Winston County and nearby towns, including which areas are USDA-eligible
- Buyers: $0 down USDA, FHA, first-time buyer and land purchases
- Sellers: pricing, listing, or comparing an as-is cash offer with the open market
- Investors: fixer uppers and rentals, with honest numbers
- Answers by call or text at 662.321.1585
Homes for sale in Winston County
- Homes listed
- 32
- Median list price
- $159,450
- Median $/sq ft
- $93
- Median days listed
- 114.5
Source: listings verified for sale on October 8, 2026.
$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
$59,000
210 N Columbus Ave
Louisville · 4 bd · 3 ba · 3,683 sqft
$75,000
202 N Spring Ave
Louisville · 4 bd · 2 ba · 1,934 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
$95,000
411 N Water Ave
Louisville · 3 bd · 1 ba · 1,178 sqft
$110,000
794 S Columbus Ave
Louisville · 3 bd · 2 ba · 1,610 sqft
Common questions
What should I look for in a Winston County real estate agent?
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A licensed agent who knows the local towns, answers quickly, explains your loan options plainly and puts your agreement in writing. Ask how many deals like yours they have closed.
How is a buyer's agent paid?
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Under current rules, you and your agent agree in writing on compensation before touring. Sellers sometimes offer to cover part or all of it, which can be negotiated in your offer.
Does Kaspar work with first-time buyers?
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Yes. Much of his work is helping first-time and affordable housing buyers, including $0 down USDA purchases.