2 Bedroom Apartments for Rent in Winchester, KY (59 Rentals)

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property at 24 White Cir

$900

Total Monthly Price

Total Monthly Price

Base Rent
$900
Total Monthly Price
$900

2 Bedroom, 1 Bath Townhome for Rent

Available Now

24 White Cir

WinchesterKY40391
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3474 Stamper Dr
2 Bedroom Apartments

3474 Stamper Dr

3474 Stamper DrWinchester, KY 40391

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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11 Hughes Ave
2 Bedroom Apartments

11 Hughes Ave

11 Hughes AveWinchester, KY 40391
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Brown Proctor
2 Bedroom Apartments

Brown Proctor

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

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391
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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
Pet Friendly
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Williams Estates Apartments
$1,079 - $1,414
Total Monthly Price

Total Monthly Price

Base Rent
$1,064 - $1,389
Required Monthly Fees
$25
Total Monthly Price
$1,089 - $1,414
2 Bedroom Apartments Available Now

Williams Estates Apartments

2005 John Stuart DrMount Sterling, KY 40353
Corporate Housing
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Lexington's Best Affordable Neighborhoods

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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 1,345 square feet priced from $1,631. Parkside Heights in the Athens Historic District neighborhood has the second largest 2 Bedroom, which is sized at 1,211 square feet and currently listed start at $1,599. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Hamburg FarmsB3 Burton - 2 Bedroom, 1.5 Bathroom1,345 Sq Ft$1,631
Parkside Heights2B 2B1,211 Sq Ft$1,599
Legacy Lake ApartmentsTwo Bedroom Two Bath1,200 Sq Ft$1,360
Brighton 30502.1/2.1G1,160 Sq Ft$1,479
1809 at WinchesterB3 Audible - 2 Bedroom, 2 Bathroom1,152 Sq Ft$1,617
Springs At Hamburg2 BR Designer Overlook1,152 Sq Ft$1,676
Colts RunGainesway - 2 Bedroom, 2 Bath (1,145 sqft.)1,145 Sq Ft$1,649
The AveryTwo bedroom with garage1,132 Sq Ft$1,790
The Retreat at Hamburg Place ApartmentsB11,105 Sq Ft$1,652
The Resort At Lake CrossingTranquility1,069 Sq Ft$1,398

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of March 14, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, KY is the 2x1 SM Model starting from $920 at The Dawn Run Apartments in the Eastland Parkway neighborhood. The second most affordable Winchester 2 Bedroom is the 2BR/1.0BA Model at The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok! starting at $1,049 . The average price for all 2 Bedroom apartments in Winchester is currently $1,566. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
The Dawn Run Apartments2x1 SM$920
The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok!2BR/1.0BA$1,049
Prime Hamburg ApartmentsElite 2 BR$1,085
Williams Estates ApartmentsTwo Bedroom$1,104
Cove Lake Village ApartmentsTwo Bedroom$1,145
GleneaglesTwo Bedroom$1,196
Steeplechase ApartmentsB1$1,201
Colts RunCalumet - 2 Bedroom, 2 Bath (950 sqft.)$1,219
Raintree ApartmentsMagnolia - B1$1,280
Stoney Brooke ApartmentsSomerset - Renovated$1,298

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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 The Dawn Run Apartments listed at $920.

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

The average rent for a 2 Bedroom Apartment in Winchester is $1,566.

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

Today's apartment with the most square footage in Winchester is a 1,345 square feet unit starting from $1,631 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 932 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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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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Maximizing Your Refund: Essential Tax Tips for Renters

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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.

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

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.