
Cheap Homes for Rent near Winchester, MO from $700 (9 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.


111 Creek Dr

39 Pansy Dr

307 Alsobrook St
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

1725 W Golden Cir

1231 Creve Coeur Crossing Ln

437 S Clay Ave

12800 Portulaca Dr
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

14512 Cazado Dr
Winchester, MO Local Guide

How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $1,791 | $1,395 | $2,850 |
| Winchester 3 Bedroom Homes for Rent | $2,566 | $1,150 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $3,192 | $1,550 | $4,500 |
| Winchester 5 Bedroom Homes for Rent | $3,500 | $3,500 | $3,500 |
Browse Top Homes for Rent in Winchester
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Winchester, MO Local Guide
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Cheapest Available Winchester Apartments for Rent and Nearby
 The cheapest available apartment rental in Winchester, MO is a 1 Bed unit found at Waterford West in the Valley Park neighborhood priced from $1,020. 15Seventy Chesterfield in the Chesterfield neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,122. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Waterford West | Brandon Park | 1BR,1BA | $1,020 |
| 15Seventy Chesterfield | The Abbey | 1BR,1BA | $1,122 |
| Park Meadows Apartments | Magnolia | 2BR,1BA | $1,133 |
Best Value Apartments for Rent in Winchester, MO and Nearby
As of July 12, 2026 the best value apartment in the Winchester area is the $1.22 price per square foot 3 Bedroom 1 Full & 2 Half Bathrooms Model at Cherry Creek Apartments in the in the Ballwin neighborhood starting from $1,833. The second greatest value Winchester apartment is the 2 Bedroom, 3 Bathroom with Den Model at Highgrove at Big Bend starting at $1,648 with a $1.23 price per square foot in the Ballwin neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Cherry Creek Apartments | 3 Bedroom 1 Full & 2 Half Bathrooms | 3BR,2BA | $1.22 |
| Highgrove at Big Bend | 2 Bedroom, 3 Bathroom with Den | 2BR,3BA | $1.23 |
| Carriage Place at Lake Chesterfield | 2 Bed 2 Bath - Washer/Dryer | 2BR,2BA | $1.35 |
| Peachtree | 2 Bed 2 Bath A | 2BR,2BA | $1.48 |
| Vance Station | 2 Bedroom | 2BR,2BA | $1.37 |
| Schoettler Village | Bradford | 2BR,2BA | $1.40 |
| Madison Rockwood | The LaFayette | 2BR,2BA | $1.44 |
| Forest Lake Apartments | 2 Bedroom Garden A | 2BR,1BA | $1.34 |
| Park Meadows Apartments | Magnolia | 2BR,1BA | $1.24 |
| Retreat at Seven Trails | The Breckenridge | 2BR,1BA | $1.42 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
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See the most popular apartments and homes in Winchester, MO
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 51 Apartments for Rent in Winchester, MO with pricing that ranges from $810 to $5,744. There are also 42 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $725 to $5,500.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $725 to $5,500 with an average monthly rent of $2,492.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.