2 Bedroom Apartments for Rent in Winchester, KY (51 Rentals)

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3474 Stamper Dr
2 Bedroom Apartments

3474 Stamper Dr

3474 Stamper DrWinchester, KY 40391

Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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11 Hughes Ave
2 Bedroom Apartments

11 Hughes Ave

11 Hughes AveWinchester, 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
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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

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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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
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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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Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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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 $1,817. Garden Estates in the Athens Historic District neighborhood has the second largest 2 Bedroom, which is sized at 1,216 square feet and currently listed start at $1,593. 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$1,817
Garden EstatesTwo Bedroom Large1,216 Sq Ft$1,593
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,785
Parkside Heights2B 2B1,211 Sq Ft$1,755
Latitude 37 Apartments2 bedroom w/ garage1,193 Sq Ft$1,756
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,779
The AveryTwo bedroom with garage1,132 Sq Ft$1,790
The Retreat at Hamburg Place ApartmentsB11,105 Sq Ft$1,656
Steeplechase ApartmentsC11,050 Sq Ft$1,373
Stoney Brooke ApartmentsLexington - Renovated986 Sq Ft$1,364

Cheapest Available Winchester 2 Bedroom Apartments

As of June 12, 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 Elite 2 BR Model at Prime Hamburg Apartments starting at $1,110 in the Liberty Area neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $1,645. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
The Dawn Run Apartments2x1 SM$920
Prime Hamburg ApartmentsElite 2 BR$1,110
GleneaglesTwo Bedroom$1,193
Raintree ApartmentsMagnolia - B1$1,205
Stoney Brooke ApartmentsSomerset - Renovated$1,286
Flats at 2875Newly Renovated 2 Bed, 1 Bath Apartments$1,345
Steeplechase ApartmentsC1$1,373
Garden EstatesTwo Bedroom$1,513
The BLVD at HaysBlvd 2.2$1,559
Hamburg FarmsB3 Burton - 2 Bedroom, 1.5 Bathroom$1,631

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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 $1,645.

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 $1,817 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 1,078 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.

Helpful Local Expert Guides

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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 Lexington Student Housing Guide - Top Neighborhoods for Renting Near Major Universities

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The Southern Spirit: Your Guide to Finding the Perfect Neighborhood to Rent in Lexington

Written by: Catrina Cowart

Hi, I’m Catrina, your ApartmentHomeLiving.com Local Expert for Lexington, Kentucky. Our team at ApartmentHomeLiving.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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