Apartments for Rent in Winchester, KY (109 Rentals)

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property at 74 Holiday Rd
$985

Total Monthly Price

Base Rent$985
Total Monthly Price$985
2 Bedroom, 1 Bath Townhome for Rent
Available Now

74 Holiday Rd

WinchesterKY40391
  • Smoke Free

Horses, Hoops, and a Short Commute: Renting Near Lexington's Top Employers

Finding the right neighborhood near your Lexington workplace doesn't have to be complicated. Our local expert breaks down the best areas to rent near Toyota, UK, Lexmark, and more.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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The Avery
$1,474 - $2,354

Total Monthly Price

Base Rent$1,474 - $2,354
Total Monthly Price$1,474 - $2,354
1 to 3 Bedroom Apartments Available Now

The Avery

6600 Man O War BlvdLexington, KY 40509
Pet Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour

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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Lexington's Best Affordable Neighborhoods

Learn about Lexington and the best places to live with original content written by our Local Expert Catrina Cowart

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Williams Estates Apartments
Rent Specials
$1,104 - $1,429

Total Monthly Price

Base Rent$1,104 - $1,429
Total Monthly Price$1,104 - $1,429
1 to 2 Bedroom Apartments Available Now

Williams Estates Apartments

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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Winchester, KY Local Guide

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

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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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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Winchester, KY

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Remember the 3 Rules of Real Estate:
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Frequently Asked Questions about Winchester

What is the current pricing and availability for apartments for rent in Winchester, KY?

As of today, September 04, 2026, there are currently 109 available Winchester apartments priced from $625 to $4,230, with an average monthly rent of $1,571.

How much are Studio apartments in Winchester?

There are currently 11 Studio Apartments in Winchester with rent ranges from $625 to $1,440 with an average price of $898.

What is the current price range for One Bedroom Winchester Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winchester ranges from $799 to $2,777 with an average monthly rent of $1,353.

What does renting a Two Bedroom Apartment in Winchester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $949 to $2,869. Today's average rental price for Two Bedrooms here is $1,603.

How expensive are Winchester Three Bedroom Apartments?

There are currently 29 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $1,020 to $4,230 - averaging $1,941 for the location.

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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Horses, Hoops, and a Short Commute: Renting Near Lexington's Top Employers

Written by: Catrina Cowart

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

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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.

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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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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.

Articles, How-To's, and Tips

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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.