2 Bedroom Apartments for Rent in Winchester, KY (52 Rentals)

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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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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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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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1135 Dale Dr.
2 Bedroom Apartments

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391
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3474 Stamper Dr
2 Bedroom Apartments

3474 Stamper Dr

3474 Stamper DrWinchester, KY 40391

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Showing Results 1-50, Page 1 of 2

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 Colts Run in the Athens Historic District neighborhood and is 1,302 square feet priced from $1,629. Hamburg Farms in the Liberty Area neighborhood has the second largest 2 Bedroom, which is sized at 1,275 square feet and currently listed start at $1,620. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Colts RunJonabell - 2 Bedroom, 2 Bath (1,302 sqft.)1,302 Sq Ft$1,629
Hamburg FarmsB2 Stansbury - 2 Bedroom, 2.5 Bathroom1,275 Sq Ft$1,620
Garden EstatesTwo Bedroom Large1,216 Sq Ft$1,545
Parkside Heights Apartments2B/2B1,211 Sq Ft$1,599
Latitude 37 Apartments2 bedroom w/ garage1,193 Sq Ft$1,876
1809 at WinchesterB4 Secretariat plus garage - 2 Bedroom, 2 Bathroom1,185 Sq Ft$1,845
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,727
Brighton 30502.1/2.1G1,160 Sq Ft$1,451
Springs At Hamburg2 BR Designer Overlook1,152 Sq Ft$1,639
The AveryTwo bedroom with garage1,132 Sq Ft$1,790

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of September 15, 2025 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 Elite 2 BR Model at Eastland Hills Apartments starting at $1,020 in the Liberty Area neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $1,531. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
The Dawn Run Apartments2x1 SM$920
Eastland Hills ApartmentsElite 2 BR$1,020
Williams Estates ApartmentsTwo Bedroom$1,054
Stoney Brooke ApartmentsSomerset - Renovated$1,163
Gleneagles ApartmentsTwo Bedroom$1,193
Colts RunCalumet - 2 Bedroom, 2 Bath (950 sqft.)$1,279
SPECIALS: The Reserve & Enclave at FairholmeThe Reserve$1,299
MAA VillageDunaway$1,318
Steeplechase ApartmentsC1$1,375
Garden EstatesTwo Bedroom$1,399

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Winchester, KY

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Getting Around Winchester, KY

Walk Score®

46 / 100

Car-Dependent

Most errands require a car

Bike Score®

33 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

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 $1,531.

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

Today's apartment with the most square footage in Winchester is a 1,302 square feet unit starting from $1,629 at Colts Run.

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

The average size for a 2 Bedroom rental in Winchester is currently 961 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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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 Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

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

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.