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Cheap Apartments for Rent in Winchester, KY from $500 (15 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
401 N Maple St
WinchesterKY40391
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.
7 Calloway St
WinchesterKY40391
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$800 - $1,3001 to 3 Bedroom Apartments Available Now
Summit Apartments
260 Oxford DrWinchester, KY 40391
134 Central Ave
WinchesterKY40391
221 S Highland St
WinchesterKY40391
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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108 Yorktowne Ct
WinchesterKY40391
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$625 - $1,020Studio to 3 Bedroom Apartments Available Now
The Dawn Run Apartments
1800 Augusta CtLexington, KY 40505
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Rent Specials
$850 - $1,0851 to 2 Bedroom Apartments Available Now
Eastland Hills Apartments
1740-1760 Jennifer RdLexington, KY 40505
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$865 - $1,0301 to 2 Bedroom Apartments Contact Us For Availability
Polo Club Park - Senior/Affordable Housing
6411 Polo Club LnLexington, KY 40509
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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$870 - $1,2501 to 3 Bedroom Apartments Contact Us For Availability
Richwood Bend - Affordable Housing
100 Codell DrLexington, KY 40509
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$898 - $2,2481 to 2 Bedroom Apartments Available Sep 3
MAA Village
151 S Locust Hill DrLexington, KY 40517
205 Clay St
Mount SterlingKY40353
Showing Results 1-15, Page 1 of 1
Winchester, KY Local Guide
Aerial view of Winchester by Flickr User: kenlund is licensed under CC BY 2.0
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Studio Apartments | $1,031 | $625 | $1,477 |
| Winchester 1 Bedroom Apartments | $1,275 | $799 | $2,197 |
| Winchester 2 Bedroom Apartments | $1,567 | $850 | $2,692 |
| Winchester 3 Bedroom Apartments | $1,981 | $1,020 | $3,725 |
Browse Top Apartments in Winchester
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Winchester, KY Local Guide
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Cheapest Available Winchester Apartments for Rent and Nearby
The cheapest available apartment rental in Winchester, KY is a 1 Bed unit found at Eastland Hills Apartments in the Liberty Area neighborhood priced from $850. The Dawn Run Apartments in the Eastland Parkway neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $920. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Eastland Hills Apartments | Elite 1 BR | 1BR,1BA | $850 |
| The Dawn Run Apartments | 2x1 SM | 2BR,1BA | $920 |
| Raintree Apartments | Willow - A1 | 1BR,1BA | $943 |
| Cove Lake Village Apartments | One Bedroom | 1BR,1BA | $945 |
| Steeplechase Apartments | A2 | 1BR,1BA | $967 |
Best Value Apartments for Rent in Winchester, KY and Nearby
As of August 29, 2025 the best value apartment in the Winchester area is the $1.07 price per square foot 3 Bedroom 2.5 Bath Model at The Pines in the in the Boone Creek neighborhood starting from $1,500. The second greatest value Winchester apartment is the B3 Burton - 2 Bedroom, 1.5 Bathroom Model at Hamburg Farms starting at $1,715 with a $1.28 price per square foot in the Liberty Area 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. |
|---|---|---|---|
| The Pines | 3 Bedroom 2.5 Bath | 3BR,2.5BA | $1.07 |
| Hamburg Farms | B3 Burton - 2 Bedroom, 1.5 Bathroom | 2BR,1.5BA | $1.28 |
| SPECIALS: The Reserve & Enclave at Fairholme | The Enclave | 2BR,2.5BA | $1.36 |
| 127 W Hickman St, Unit #5 | 127 W Hickman St | 1BR,1BA | $1.00 |
| Williams Estates Apartments | Two Bedroom | 2BR,1BA | $1.09 |
| Colts Run | Calumet - 2 Bedroom, 2 Bath (950 sqft.) | 2BR,2BA | $1.38 |
| Parkside Heights Apartments | 1B/1B | 1BR,1BA | $1.37 |
| The Dawn Run Apartments | 2x1 | 2BR,1BA | $1.20 |
| Eastland Hills Apartments | Elite 1 BR | 1BR,1BA | $1.14 |
| 192 Wabash Ave | 192 Wabash Ave | Studio ,1BA | $1.08 |
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Best Local Schools in Winchester, KY
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Getting Around Winchester, KY
Walk Score®
46 / 100
Car-Dependent
Most errands require a car
Bike Score®
33 / 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
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $850 at Eastland Hills Apartments.
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 $920 at The Dawn Run Apartments.
What is the most affordable Winchester Three Bedroom Apartment?
The best deal on a cheap Winchester Three Bedroom Apartment rental is at Gleneagles Apartments and starts from $1,372.
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.
A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Lexington
Written by: Catrina Cowart
Hi, I'm Catrina, your ApartmentHomeLiving.com Local Expert for Lexington, Kentucky, and I'm happy to talk to you about some of the neighborhoods that I've found to be particularly charming in this small city.
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.
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.
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.