2 Bedroom Apartments for Rent in Winchester, KY (58 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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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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3474 Stamper Dr
2 Bedroom Apartments

3474 Stamper Dr

3474 Stamper DrWinchester, KY 40391
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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

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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1135 Dale Dr.
2 Bedroom Apartments

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391

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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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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Showing Results 1-50, Page 1 of 2

Winchester, KY Local Guide

Largest Available Winchester 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 $1,589. 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$1,589
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,781
Parkside Heights2B 2B1,211 Sq Ft$1,605
Legacy Lake ApartmentsTwo Bedroom Two Bath1,200 Sq Ft$1,360
Latitude 37 Apartments2 bedrooms1,193 Sq Ft$1,705
1809 at WinchesterB4 Secretariat - 2 Bedroom, 2 Bathroom1,185 Sq Ft$1,636
The Retreat at Hamburg Place ApartmentsB21,176 Sq Ft$1,639
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,827
The Avery2 Bedroom1,132 Sq Ft$1,790

Cheapest Available Winchester 2 Bedroom Apartments

As of January 02, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, KY is the Two Bedroom Model starting from $995 at Williams Estates Apartments . 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 $999 . The average price for all 2 Bedroom apartments in Winchester is currently $1,578. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Williams Estates ApartmentsTwo Bedroom$995
The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok!2BR/1.0BA$999
Summit Apartments2 Bedroom$1,000
Richwood Bend - Affordable HousingTwo Bedroom$1,033
Eastland Hills ApartmentsElite 2 BR$1,085
Stoney Brooke ApartmentsLexington - Renovated$1,103
GleneaglesTwo Bedroom$1,196
MAA VillageDunaway$1,303
Steeplechase ApartmentsB1$1,307
Raintree ApartmentsMagnolia - B1$1,318

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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Quick Rent Budget Calculator

How much rent can you afford?

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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Winchester, KY

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Explore Winchester, KY Rentals by Map

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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 Williams Estates Apartments listed at $995.

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

The average rent for a 2 Bedroom Apartment in Winchester is $1,578.

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 1,080 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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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.