Cheap Apartments for Rent near Winchester, IL from $300 (55 Rentals)

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Search the lowest-cost Apartments available for rent right now in Winchester.

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.

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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.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Butler Place
2 Bedroom Apartments

Butler Place

3100 Butler StSpringfield, IL 62703
  • Utilities Included
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Pine Woods Apartments
1 to 3 Bedroom Apartments

Pine Woods Apartments

1665 Seven Pines RdSpringfield, IL 62704
  • Utilities Included

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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721 South Grand Ave W
1 to 2 Bedroom Apartments

721 South Grand Ave W

721 South Grand Ave WSpringfield, IL 62704
  • Utilities Included

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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Winchester, IL Local Guide

Cheapest Available Winchester Apartments for Rent and Nearby

 

The cheapest available apartment rental in Winchester, IL is a 1 Bed unit found at Jacksonville Affordable Housing priced from $485. Lotts Landing Senior Apartments in the Macoupin County neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $560. Here is today’s list of the most affordable Winchester apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Jacksonville Affordable Housing1 Bedroom 50%1BR,1BA$485
Lotts Landing Senior Apartments1 Bedroom 1 Bathroom1BR,1BA$560
Whispering Pines Apartments1 Bed, 1 Bath - Essential1BR,1BA$600
The Hickox CollectionThe HickoxStudio,1BA$657
Beardstown Apartments2 Bedroom2BR,1BA$703
Cobblestone ApartmentsCobblestone 1BD1BR,1BA$750
Laborer's Home Development IV, For Age 62+1 BR1BR,1BA$830
New Eastlawn ApartmentsTwo Bedroom2BR,1BA$850
Pine Ridge ApartmentsOne Bedroom1BR,1BA$875
Ravenwood TownhomesTownhome2BR,1BA$895

Best Value Apartments for Rent in Winchester, IL and Nearby

As of July 15, 2026 the best value apartment in the Winchester area is the $0.90 price per square foot Townhome Model at Ravenwood Townhomes in the starting from $895. The second greatest value Winchester apartment is the Townhouse Model at The Boulevard Townhomes starting at $975 with a $1.04 price per square foot . Here is today’s list of the best values for Winchester apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Ravenwood TownhomesTownhome2BR,1.5BA$0.90
The Boulevard TownhomesTownhouse2BR,1.5BA$1.04
Safe Harbor Properties2 Bdr 1 Bath with Balcony. Capitol View.2BR,1BA$1.08
3TEN Apartments2 Bed 1 Bath2BR,1BA$1.05
New Eastlawn ApartmentsTwo Bedroom2BR,1BA$1.03
Cobblestone ApartmentsCobblestone 2BD2BR,1BA$1.06
Pine Ridge ApartmentsOne Bedroom1BR,1BA$1.17
Beardstown Apartments2 Bedroom2BR,1BA$0.99
Lotts Landing Senior Apartments1 Bedroom 1 Bathroom1BR,1BA$0.87
Jacksonville Affordable Housing1 Bedroom 60%1BR,1BA$0.88

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.

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Real 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.

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Quick 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.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winchester, IL Rentals by Map

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See the most popular apartments and homes in Winchester, IL

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Frequently Asked Questions about Cheap Winchester Apartments

How much is rent for a Cheap One Bedroom Winchester Apartment?

The lowest price for a Cheap One Bedroom Winchester Apartment is $485 at Jacksonville Affordable Housing.

What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $540 at Jacksonville Affordable Housing.

What is the most affordable Winchester Three Bedroom Apartment?

The best deal on a cheap Winchester Three Bedroom Apartment rental is at Huntington Ridge Apartments and starts from $1,387.

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

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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.

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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.

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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.

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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.