Cheap Apartments for Rent near Winchester, IL from $347 (51 Rentals)

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

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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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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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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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

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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721 South Grand Ave W
1 to 2 Bedroom Apartments

721 South Grand Ave W

721 South Grand Ave WSpringfield, IL 62704
  • Utilities Included

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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Showing Results 1-50, Page 1 of 2

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
Cobblestone ApartmentsCobblestone 1BD1BR,1BA$750
Laborer's Home Development IV, For Age 62+1 BR1BR,1BA$830
New Eastlawn ApartmentsTwo Bedroom2BR,1BA$850
Ravenwood TownhomesTownhome2BR,1BA$895
Safe Harbor Properties1 Bdr/ 1 Bath Private Balcony Capitol Views1BR,1BA$895
The Boulevard TownhomesApartment2BR,1BA$900
Smart Choice Park1 Bedroom Unit-Standard1BR,1BA$925

Best Value Apartments for Rent in Winchester, IL and Nearby

As of August 29, 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 2 Bedroom 1 Bath South Model at Orchard Park starting at $1,050 with a $1.06 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
Orchard Park2 Bedroom 1 Bath South2BR,1BA$1.06
The Boulevard TownhomesTownhouse2BR,1.5BA$1.04
Safe Harbor Properties2 Bdr 1 Bath with Balcony. Capitol View.2BR,1BA$1.08
Meadow View Landing2 Bedroom/1 Bath2BR,1BA$1.12
New Eastlawn ApartmentsTwo Bedroom2BR,1BA$1.03
Cobblestone ApartmentsCobblestone 2BD2BR,1BA$1.06
731 South Grand Ave W1/11BR,1BA$1.31
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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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.

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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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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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.