
Cheap Homes for Rent in Winchester, KY from $600 (9 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.


1586 Martha Ct

325 Clearwater Way

453 Race St

60 Holiday Rd

231 W Main St

2822 Hanna Pl

208 Wedgefield Pl

733 Gatehouse Pl
Lexington's Best Affordable Neighborhoods
Learn about Lexington and the best places to live with original content written by our Local Expert Catrina Cowart
Winchester, KY Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $1,256 | $850 | $1,650 |
Winchester 3 Bedroom Homes for Rent | $1,776 | $899 | $2,800 |
Winchester 4 Bedroom Homes for Rent | $2,258 | $1,650 | $3,700 |
Winchester 5 Bedroom Homes for Rent | $3,499 | $3,499 | $3,499 |
Browse Top Homes for Rent 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 Studio unit found at The Dawn Run Apartments in the Eastland Parkway neighborhood priced from $690. Raintree Apartments in the Liberty Area neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $833. Here is today’s list of the most affordable Winchester apartments for rent:
Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
The Dawn Run Apartments | Studio MD | Studio,1BA | $690 |
Raintree Apartments | Willow - A1 | 1BR,1BA | $833 |
Stoney Brooke Apartments | Ashland - Renovated | 1BR,1BA | $888 |
Best Value Apartments for Rent in Winchester, KY and Nearby
As of April 13, 2025 the best value apartment in the Winchester area is the $1.41 price per square foot 3 bedrooms townhouse Model at Latitude 37 Apartments in the in the Athens Historic District neighborhood starting from $2,346. The second greatest value Winchester apartment is the 3 Bedroom 2.5 Bath Model at The Pines starting at $1,500 with a $1.07 price per square foot in the Boone Creek 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. |
---|---|---|---|
Latitude 37 Apartments | 3 bedrooms townhouse | 3BR,2BA | $1.41 |
The Pines | 3 Bedroom 2.5 Bath | 3BR,2.5BA | $1.07 |
Richwood Bend - Affordable Housing | Three Bedroom | 3BR,2BA | $1.09 |
SPECIALS: The Reserve & Enclave at Fairholme | The Enclave | 2BR,2.5BA | $1.36 |
Stoney Brooke Apartments | Lexington - Renovated | 2BR,2BA | $1.32 |
Williams Estates Apartments | Two Bedroom | 2BR,1BA | $1.04 |
127 W Hickman St, Unit 5 | 127 W Hickman St | 1BR,1BA | $1.05 |
Parkside Heights Apartments | 1B/1B | 1BR,1BA | $1.37 |
Garden Estates | One Bedroom | 1BR,1BA | $1.42 |
Legacy Lake Apartments | One Bedroom One Bath | 1BR,1BA | $1.28 |
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 65 Apartments for Rent in Winchester, KY with pricing that ranges from $709 to $3,197. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $675 to $3,700.
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 $675 to $3,700 with an average monthly rent of $1,892.
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.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.