Cheap Apartments for Rent in Winchester, KY from $500 (44 Rentals)

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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Atrium Townhomes
1 to 2 Bedroom Apartments

Atrium Townhomes

626 W Lexington AveWinchester, KY 40391
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Chatham Townhomes
1 to 2 Bedroom Apartments

Chatham Townhomes

135 Frontier WayWinchester, KY 40391

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

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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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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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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The Southern Spirit: Your Guide to Finding the Perfect Area of Lexington to Rent

Discover Lexington's unique balance of lively downtown growth, university energy, and friendly Southern spirit. A local guide to neighborhoods, dining, and outdoor life.

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Showing Results 1-44, Page 1 of 1

Winchester, KY Local Guide

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 $790. Summit Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $800. Here is today’s list of the most affordable Winchester apartments for rent:

Apartment ListingModel NameBed/BathPriced From
The Dawn Run ApartmentsStudio XLStudio,1BA$790
Summit Apartments1 Bedroom1BR,1BA$800
Raintree ApartmentsWillow - A11BR,1BA$894
Flats at 2875 - Newly-Renovated Single-Story!Newly-Renovated Studio Apartments!Studio,1BA$950
Prime Hamburg ApartmentsElite 1 BR1BR,1BA$975
MAA VillageHarrison1BR,1BA$983
Stoney Brooke ApartmentsAshland - Renovated1BR,1BA$989
Reserve at HamburgKeeneland1BR,1BA$1,120
Bourbon Hills1 bedroom1BR,1BA$1,125
Legacy Lake ApartmentsOne Bedroom One Bath1BR,1BA$1,160

Best Value Apartments for Rent in Winchester, KY and Nearby

As of May 29, 2026 the best value apartment in the Winchester area is the $1.40 price per square foot New Cottage/Two Car Garage Model at Legacy Lake Apartments in the starting from $2,100. The second greatest value Winchester apartment is the 3 Bedroom 2.5 Bath Model at The Pines starting at $1,650 with a $1.17 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 ListingModel NameBed/BathPrice Per Sq.Ft.
Legacy Lake ApartmentsNew Cottage/Two Car Garage3BR,2BA$1.40
The Pines3 Bedroom 2.5 Bath3BR,2.5BA$1.17
The Resort At Lake CrossingMajestic3BR,2BA$1.41
Garden EstatesTwo Bedroom2BR,2BA$1.37
Steeplechase ApartmentsC12BR,2BA$1.28
GleneaglesTwo Bedroom2BR,2BA$1.33
Stoney Brooke ApartmentsSomerset - Renovated2BR,1BA$1.42
Summit Apartments2 BD/1.5 BA2BR,1.5BA$1.30
Prime Hamburg ApartmentsElite 1 BR1BR,1BA$1.31
The Dawn Run ApartmentsStudio XLStudio ,1BA$1.32

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.

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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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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Winchester, KY

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Remember the 3 Rules of Real Estate:
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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 $790.

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

The lowest price for a Cheap One Bedroom Winchester Apartment is $800 at Summit 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 $1,000 at Summit Apartments.

What is the most affordable Winchester Three Bedroom Apartment?

The best deal on a cheap Winchester Three Bedroom Apartment rental is at Gleneagles and starts from $1,372.

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.

Helpful Local Expert Guides

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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.

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The Ultimate Lexington Student Housing Guide - Top Neighborhoods for Renting Near Major Universities

Written by: Catrina Cowart

I'm Catrina, your ApartmentHomeLiving.

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The Southern Spirit: Your Guide to Finding the Perfect Neighborhood to Rent in Lexington

Written by: Catrina Cowart

Hi, I’m Catrina, your ApartmentHomeLiving.com Local Expert for Lexington, Kentucky. Our team at ApartmentHomeLiving.

Articles, How-To's, and Tips

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.