2 Bedroom Apartments for Rent in Winchester, KY (60 Rentals)

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3474 Stamper Dr
2 Bedroom Apartments

3474 Stamper Dr

3474 Stamper DrWinchester, KY 40391
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11 Hughes Ave
2 Bedroom Apartments

11 Hughes Ave

11 Hughes AveWinchester, KY 40391

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

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Atrium Townhomes
2 Bedroom Apartments

Atrium Townhomes

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

Chatham Townhomes

135 Frontier WayWinchester, KY 40391
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7 North Main
2 Bedroom Apartments

7 North Main

7 N Main StWinchester, KY 40391
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Brown Proctor
2 Bedroom Apartments

Brown Proctor

108 S Main StWinchester, KY 40391
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1135 Dale Dr.
2 Bedroom Apartments

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391

The Art of the Rental Viewing: What to look for during a property tour

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The Avery
Rent Specials
$1,790 - $1,949
Total Monthly Price

Total Monthly Price

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

The Avery

6600 Man O War BlvdLexington, KY 40509
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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

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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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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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Winchester, KY Local Guide

Largest Available Winchester and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winchester, KY is found at Hamburg Farms in the Liberty Area neighborhood and is 1,650 square feet priced from $1,817. Waterstone at Hamburg Apartments in the Athens Historic District neighborhood has the second largest 2 Bedroom, which is sized at 1,214 square feet and currently listed start at $1,793. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Hamburg FarmsB4 Stanton - 2 Bedroom, 3 Bathroom1,650 Sq Ft$1,817
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,793
Parkside Heights2B 2B1,211 Sq Ft$1,965
Legacy Lake ApartmentsTwo Bedroom Two Bath1,200 Sq Ft$1,360
Latitude 37 Apartments2 bedroom w/ garage1,193 Sq Ft$1,756
The Retreat at Hamburg Place ApartmentsB2 | Renovated1,176 Sq Ft$1,804
Brighton 30502.1/2.1G1,160 Sq Ft$1,494
1809 at WinchesterB3 Audible - 2 Bedroom, 2 Bathroom1,152 Sq Ft$1,649
Garden EstatesTwo Bedroom1,135 Sq Ft$1,675
The AveryTwo bedroom with garage1,132 Sq Ft$1,790

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of April 28, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, KY is the 2 Bed 1 Bath W/D HK Model starting from $900 at Summit Apartments . The second most affordable Winchester 2 Bedroom is the Two Bedroom Model at Williams Estates Apartments starting at $1,104 . The average price for all 2 Bedroom apartments in Winchester is currently $1,594. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Summit Apartments2 Bed 1 Bath W/D HK$900
Williams Estates ApartmentsTwo Bedroom$1,104
Prime Hamburg ApartmentsElite 2 BR$1,110
Stoney Brooke ApartmentsSomerset - Renovated$1,119
Steeplechase ApartmentsB1$1,180
GleneaglesTwo Bedroom$1,193
Raintree ApartmentsMagnolia - B1$1,203
Bourbon Hills2 bedroom$1,325
Flats at 2875 - Newly-Renovated Single-Story!Newly Renovated 2 Bed, 1 Bath Apartments$1,345
Legacy Lake ApartmentsTwo Bedroom Two Bath$1,360

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

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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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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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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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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Frequently Asked Questions about 2 Bedroom Winchester Apartments

What is the Cheapest apartment in Winchester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winchester is at Summit Apartments listed at $900.

How much is the average rent for a 2 Bedroom Winchester Apartment?

The average rent for a 2 Bedroom Apartment in Winchester is $1,594.

What is the largest available 2 Bedroom Winchester Apartment for rent?

Today's apartment with the most square footage in Winchester is a 1,650 square feet unit starting from $1,817 at Hamburg Farms.

What is the average size for Winchester 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winchester is currently 997 sq ft.

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.

Articles, How-To's, and Tips

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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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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.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.