2 Bedroom Apartments for Rent in Winchester, KY (50 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
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1135 Dale Dr.
2 Bedroom Apartments

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391

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

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Showing Results 1-50, Page 1 of 1

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 $1,831. Colts Run in the Athens Historic District neighborhood has the second largest 2 Bedroom, which is sized at 1,302 square feet and currently listed start at $1,689. 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$1,831
Colts RunJonabell - 2 Bedroom, 2 Bath (1,302 sqft.)1,302 Sq Ft$1,689
Garden EstatesTwo Bedroom Large1,216 Sq Ft$1,573
Parkside Heights Apartments2B/2B1,211 Sq Ft$1,599
Latitude 37 Apartments2 bedrooms1,193 Sq Ft$1,705
1809 at WinchesterB4 Secretariat plus garage - 2 Bedroom, 2 Bathroom1,185 Sq Ft$1,845
Brighton 30502.1/2.1G1,160 Sq Ft$1,451
The BLVD at HaysBlvd 21,160 Sq Ft$1,727
The AveryTwo bedroom with garage1,132 Sq Ft$1,790
Steeplechase ApartmentsC11,050 Sq Ft$1,407

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of July 31, 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 2 Bedrooms Model at Eastland Hills Apartments starting at $950 in the Liberty Area neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $1,585. 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 Apartments2 Bedrooms$950
Williams Estates ApartmentsTwo Bedroom$1,039
Gleneagles ApartmentsTwo Bedroom$1,193
SPECIALS: The Reserve & Enclave at FairholmeThe Reserve$1,280
Brighton 30502.0$1,364
Steeplechase ApartmentsC1$1,407
Raintree ApartmentsMagnolia - B1$1,496
Colts RunGainesway - 2 Bedroom, 2 Bath (1,145 sqft.)$1,509
Garden EstatesTwo Bedroom Large$1,588

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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

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

The average rent for a 2 Bedroom Apartment in Winchester is $1,585.

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 $1,831 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 1,069 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 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.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.