Horse racing runs on a schedule nobody else lives by. Jockeys, trainers, assistant trainers, exercise riders, grooms, farm managers and owners follow the meets from track to track, and the money comes in waves: a big purse one month, a quiet stretch the next. That makes real estate both more important and a little more complicated for racing people. This guide is for anyone who makes their living around Churchill Downs, Keeneland and the Kentucky circuit and wants their money to keep working when they're on the road or when the riding days are over.

Start your private plan or text Rob at (502) 305-8915.

Why racing professionals need a different plan

• Your income is uneven. Jockeys typically earn a fee for every mount plus a share of the purse when they finish near the top. Trainers earn day rates plus a share of winnings. Great months and slow months can sit right next to each other.
• You move with the meets. A lot of people in racing split the year between Kentucky and tracks in Florida, New York or elsewhere. You need a home base that works when you're here and pays you when you're gone.
• Careers can end fast. Riding is one of the most dangerous jobs in sports. Planning for life after the saddle isn't negative thinking, it's smart.
• Lenders don't always understand racing income. Purse shares, mount fees and contract work don't look like a normal paycheck on paper.

The Kentucky circuit, in plain terms

Kentucky is the center of the racing world, and the tracks spread across the state. Churchill Downs in Louisville hosts the Kentucky Derby on the first Saturday in May. Keeneland in Lexington runs spring and fall meets and holds some of the biggest horse sales in the world. There are also tracks in Northern Kentucky, Henderson and Franklin, plus training centers and farms all over the Bluegrass. Where you buy should match where you actually spend your weeks, and how far you're willing to drive before sunrise.

Three ways racing people use real estate

1. A home base near the track that pays you while you're away

A lot of racing people buy close to the track they work most, then rent it out when the meet moves on. A duplex works especially well: you live in one side and the other side brings in rent all year. When you leave to follow the meets, a property manager can lease your side too, or you can rent it furnished for a few months at a time. Read our house hacking guide to see how the numbers work.

2. Derby week and race-weekend income

Derby week is one of the busiest weeks of the year for Louisville rentals, and Keeneland meets and big race weekends bring their own crowds. Some owners rent out their place for those weeks only. Short-term rentals in Louisville have real rules, including registration and spacing limits, so read our Louisville short-term rental guide before you count on that money.

3. Land and a farm for the long run

Many trainers and owners eventually want acreage: a barn, pasture, a few stalls, maybe a training track. The counties around Louisville, like Oldham, Shelby, Spencer and Bullitt, have farms and land with room to grow. Farm property is its own animal. Zoning, barns, fencing, water, well and septic, and how a lender values land all matter. We help you look at the property the way a horse person would, not just the way a homebuyer would.

Getting a loan with racing income

• Keep clean records: purse statements, mount fee records, training contracts and every 1099 form you receive.
• File your taxes on time. Most lenders want two years of tax returns for self-employed income.
• If your income history is short or uneven, a bigger down payment or a lender that uses bank statements instead of pay stubs can help.
• Read how to get pre-approved for a mortgage in Kentucky, and we'll connect you with a lender who has worked with self-employed and seasonal income.

Plan for taxes before you plan the house

Most racing income is self-employment income, which means federal income tax, self-employment tax and Kentucky's flat 3.5% state income tax in 2026. If you race in other states, those states may want their share too. Sit down with a CPA (certified public accountant) first. The planner below gives you a rough idea of what to set aside.

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How long will your money last?

This calculator shows how many years your savings would last at your current spending, and how much longer they could last with rental income coming in.

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Why racing people work with Winner Realty

Rob Bergeron has been in Louisville real estate for 13 years and has been part of more than 2,000 residential and commercial transactions since 2013. He served three elected terms on the board of Louisville's local real estate investors association. We already work with investors who live in other states and other countries and never set foot in the property until closing, so a client who's at Saratoga or Gulfstream for the season is no problem. We do video showings, coordinate inspections and contractors, and keep you updated by text and email.

Winner Realty is licensed in Kentucky and Indiana. Two units or more counts as commercial property, and our Winner Commercial team handles duplexes, small apartment buildings and land.

See everything we do for athletes and entertainers at Winner Sports & Entertainment.

Frequently asked questions

Can a jockey or trainer get a mortgage?

Yes. Lenders treat most racing income as self-employment income, so they usually want two years of tax returns. If your history is short, a bigger down payment or a bank-statement loan can help.

Should I buy near Churchill Downs or Keeneland?

Buy near where you actually work most weeks, and choose something that would rent well when you're gone. We'll look at your schedule with you before we look at houses.

Can I rent my place out during Derby week?

Often, yes, but Louisville has short-term rental rules, including registration and limits on how close rentals can be to each other. Check the rules for the specific property before you buy.

Can you help me buy a horse farm?

Yes. We look at zoning, barns, fencing, water, well and septic, and access, and we connect you with lenders who understand land and farm loans.

I'm on the road half the year. How do I buy?

We do video walk-throughs, handle inspections and contractors, and you sign electronically or with a mobile notary wherever you are.

Start privately

Tell us where you race, where you want to land, and what you're hoping to build. Nothing is shared. Start your private plan, text (502) 305-8915, or email rob@thewinnerrealty.com.

Winner Realty provides real estate services only. Nothing on this page is tax, legal or investment advice. Talk to your CPA, attorney and financial advisor before making decisions. Equal Housing Opportunity.