2 Bedroom Apartments for Rent in Winchester, KY (57 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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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
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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

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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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

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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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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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 $1,886. Brighton 3050 has the second largest 2 Bedroom, which is sized at 1,362 square feet and currently listed start at $1,564. 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$1,886
Brighton 3050Loft 21,362 Sq Ft$1,564
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,901
Parkside Heights2B 2B1,211 Sq Ft$1,499
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$1,640
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,727
Springs At Hamburg2 BR Designer Overlook1,152 Sq Ft$1,610
The AveryTwo bedroom with garage1,132 Sq Ft$1,790

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of December 09, 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 BD/1.5 BA Model at Summit Apartments starting at $1,029 . The average price for all 2 Bedroom apartments in Winchester is currently $1,544. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
The Dawn Run Apartments2x1 SM$920
Summit Apartments2 BD/1.5 BA$1,029
Stoney Brooke ApartmentsSomerset - Renovated$1,067
Williams Estates ApartmentsTwo Bedroom$1,074
Eastland Hills ApartmentsElite 2 BR$1,085
Gleneagles ApartmentsTwo Bedroom$1,193
Brighton 30502.0$1,262
Raintree ApartmentsMagnolia - B2$1,273
Steeplechase ApartmentsC1$1,302
Reserve at HamburgDerby$1,434

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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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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Remember the 3 Rules of Real Estate:
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Explore Winchester, KY Rentals by Map

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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 $1,544.

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 $1,886 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

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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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!