Cheap Apartments for Rent in Winchester, IL from $300 (10 Rentals)

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

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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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 $462. The Hickox Collection in the Downtown Springfield neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $628. 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$462
The Hickox CollectionThe HickoxStudio,1BA$628
Denison PlaceOne Bedroom1BR,1BA$675

Best Value Apartments for Rent in Winchester, IL and Nearby

As of August 29, 2025 the best value apartment in the Winchester area is the $0.88 price per square foot Townhome Model at Ravenwood Townhomes in the starting from $875. The second greatest value Winchester apartment is the 3x2 Model at 1500 N Carolina St starting at $1,000 with a $1.00 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$0.88
1500 N Carolina St3x23BR,2BA$1.00
Meadow View Landing2 Bedroom/1 Bath2BR,1BA$1.04
Safe Harbor PropertiesDowntown1BR,1BA$1.03
3TENB12BR,1BA$1.01
New Eastlawn ApartmentsTwo Bedroom2BR,1BA$0.97
Denison PlaceOne Bedroom1BR,1BA$0.84
Cobblestone ApartmentsCobblestone 2BD2BR,1BA$1.06
Lincoln Tower Apartments1 Bed 1 Bath1BR,1BA$1.07
Jacksonville Affordable Housing1 Bedroom 60%1BR,1BA$0.84

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

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Getting Around Winchester, IL

Walk Score®

31 / 100

Car-Dependent

Most errands require a car

Bike Score®

38 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Winchester Apartments

What is the Cheapest Studio apartment in Winchester?

Currently the most affordable Cheap Studio Apartment in Winchester is at The Hickox Collection listed at $628.

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

The lowest price for a Cheap One Bedroom Winchester Apartment is $462 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 $515 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 1500 N Carolina St and starts from $775.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.