Cheap Apartments for Rent in Winchester, KY from $500 (39 Rentals)

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

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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

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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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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Williams Estates Apartments
$1,099 - $1,424
Total Monthly Price

Total Monthly Price

Base Rent
$1,099 - $1,424
Total Monthly Price
$1,099 - $1,424
1 to 2 Bedroom Apartments Available Jul 17

Williams Estates Apartments

2005 John Stuart DrMount Sterling, KY 40353
Corporate Housing
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  • Utilities Included

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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Showing Results 1-39, 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. Studio 28 in the Clark County neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $814. 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
Studio 280BR/1.0BAStudio,1BA$814
Richwood Bend - Affordable HousingOne bedroom1BR,1BA$883
Flats at 2875Newly-Renovated Studio Apartments!Studio,1BA$950
Prime Hamburg ApartmentsElite 1 BR1BR,1BA$975
EAGLE CREEK TOWNHOMESThe Aspen1BR,1BA$975
Sunrise SuitesSuiteStudio,1BA$995
Raintree ApartmentsWillow - A11BR,1BA$1,023
Stoney Brooke ApartmentsAshland - Renovated1BR,1BA$1,091
The BLVD at HaysBlvd 11BR,1BA$1,109

Best Value Apartments for Rent in Winchester, KY and Nearby

As of July 14, 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$1.32
Parkside Heights1B 1B1BR,1BA$1.54
Garden EstatesOne Bedroom1BR,1BA$1.46
The Pops2 Bedroom 1 Bathroom2BR,1BA$1.49
GleneaglesTwo Bedroom2BR,2BA$1.33
Prime Hamburg ApartmentsElite 1 BR1BR,1BA$1.31
Richwood Bend - Affordable HousingOne bedroom1BR,1BA$1.20
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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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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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 $830 at The Dawn Run 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 Richwood Bend - Affordable Housing and starts from $1,270.

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

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

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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.

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For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.