119 N 1st St
ClarksvilleMO63336
Cheap Homes for Rent near Winchester, IL from $800 (17 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
430 W Edwards St
SpringfieldIL62704
2525 W Monroe St
SpringfieldIL62704
229 W Allen St
SpringfieldIL62704
1509 W Monroe St
SpringfieldIL62704
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.
14420 Highway UU Hwy
Bowling GreenMO63334
47 Imperial Valley Dr
SpringfieldIL62702
2016 Salu St
AltonIL62002
525 W Cook St
SpringfieldIL62704
820 Eighth St
CarrolltonIL62016
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.
1028 W Iles Ave
SpringfieldIL62704
2022 Austin Dr
SpringfieldIL62704
14 Amos Valley Dr
SpringfieldIL62702
821 Alby St
AltonIL62002
27 Amos Valley Dr
SpringfieldIL62702
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.
16 Sonoma Dr
SpringfieldIL62702
31 Imperial Valley Dr
SpringfieldIL62702
Showing Results 1-17, Page 1 of 1
Winchester, IL Local Guide
Sunrise in field by Claire Y. Martin is licensed under CC BY 2.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $1,145 | $900 | $1,395 |
| Winchester 3 Bedroom Homes for Rent | $1,631 | $1,000 | $2,950 |
| Winchester 4 Bedroom Homes for Rent | $3,031 | $2,700 | $3,500 |
| Winchester 5 Bedroom Homes for Rent | $2,700 | $2,700 | $2,700 |
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, IL Local Guide
- Nearby Cities
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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. Whispering Pines Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $600. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Jacksonville Affordable Housing | 1 Bedroom 50% | 1BR,1BA | $485 |
| Whispering Pines Apartments | 1 Bed, 1 Bath - Essential | 1BR,1BA | $600 |
| The Hickox Collection | The Hickox | Studio,1BA | $665 |
| Cobblestone Apartments | Cobblestone 1BD | 1BR,1BA | $750 |
| Laborer's Home Development IV, For Age 62+ | 1 BR | 1BR,1BA | $830 |
Best Value Apartments for Rent in Winchester, IL and Nearby
As of July 22, 2026 the best value apartment in the Winchester area is the $1.09 price per square foot 3 Bedroom Model at Ash Grove in the starting from $1,450. The second greatest value Winchester apartment is the Townhome Model at Ravenwood Townhomes starting at $895 with a $0.90 price per square foot . 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. |
|---|---|---|---|
| Ash Grove | 3 Bedroom | 3BR,2BA | $1.09 |
| Ravenwood Townhomes | Townhome | 2BR,1.5BA | $0.90 |
| The Boulevard Townhomes | Townhouse | 2BR,1.5BA | $1.04 |
| 3TEN Apartments | 2 Bed 1 Bath | 2BR,1BA | $1.05 |
| New Eastlawn Apartments | Two Bedroom | 2BR,1BA | $1.03 |
| Cobblestone Apartments | Cobblestone 2BD | 2BR,1BA | $1.06 |
| 731 South Grand Ave W | 1/1 | 1BR,1BA | $1.31 |
| Pine Ridge Apartments | One Bedroom | 1BR,1BA | $1.17 |
| Smart Choice Park | 1 Bedroom Unit-Standard | 1BR,1BA | $1.32 |
| Jacksonville Affordable Housing | 1 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.
Read Article
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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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, IL Rentals by Map
See the most popular apartments and homes in Winchester, IL
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 42 Apartments for Rent in Winchester, IL with pricing that ranges from $347 to $3,400. There are also 34 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $800 to $3,500.
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 $800 to $3,500 with an average monthly rent of $1,911.
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
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.
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.