Cheap Apartments for Rent in Winchester, KY from $500 (13 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.

Eastland Hills

The Dawn Run Apartments

Raintree Apartments

Polo Club Park - Senior/Affordable Housing

Richwood Bend - Affordable Housing

Stoney Brooke Apartments

1590 Martha Ct
Lexington's Best Affordable Neighborhoods
Learn about Lexington and the best places to live with original content written by our Local Expert Catrina Cowart

1586 Martha Ct

325 Clearwater Way

453 Race St
Winchester, KY Local Guide

How much does it cost to rent an apartment in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester Studio Apartments | $1,127 | $790 | $2,500 |
Winchester 1 Bedroom Apartments | $1,291 | $709 | $2,289 |
Winchester 2 Bedroom Apartments | $1,532 | $799 | $2,745 |
Winchester 3 Bedroom Apartments | $1,967 | $1,020 | $3,197 |
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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 |
Steeplechase Apartments | A2 | 1BR,1BA | $949 |
Gleneagles Apartments | One Bedroom | 1BR,1BA | $995 |
Best Value Apartments for Rent in Winchester, KY and Nearby
As of April 12, 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 Three Bedroom Model at Richwood Bend - Affordable Housing starting at $1,250 with a $1.09 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. |
---|---|---|---|
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 |
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 |
Brighton 3050 | 1.2 | 1BR,1BA | $1.46 |
Stoney Brooke Apartments | Ashland - Renovated | 1BR,1BA | $1.31 |
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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
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at The Dawn Run Apartments listed at $690.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $798 at Raintree 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 $900 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 Richwood Bend - Affordable Housing and starts from $1,250.
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
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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.

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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.