2 Bedroom Apartments for Rent in Winchester, KY (57 Rentals)

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property at 74 Holiday Rd
$985

Total Monthly Price

Base Rent$985
Total Monthly Price$985
2 Bedroom, 1 Bath Townhome for Rent
Available Now

74 Holiday Rd

WinchesterKY40391
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265 S Highland St
2 Bedroom Apartments

265 S Highland St

265 S Highland StWinchester, KY 40391

Horses, Hoops, and a Short Commute: Renting Near Lexington's Top Employers

Finding the right neighborhood near your Lexington workplace doesn't have to be complicated. Our local expert breaks down the best areas to rent near Toyota, UK, Lexmark, and more.

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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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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
Senior Living

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

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1135 Dale Dr.
2 Bedroom Apartments

1135 Dale Dr.

1135 Dale DrWinchester, KY 40391
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The Avery
$1,790 - $1,959

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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The Southern Spirit: Your Guide to Finding the Perfect Area of Lexington to Rent

Discover Lexington's unique balance of lively downtown growth, university energy, and friendly Southern spirit. A local guide to neighborhoods, dining, and outdoor life.

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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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Williams Estates Apartments
Rent Specials
$1,094 - $1,429

Total Monthly Price

Base Rent$1,104 - $1,429
Total Monthly Price$1,104 - $1,429
2 Bedroom Apartments Available Now

Williams Estates Apartments

2005 John Stuart DrMount Sterling, KY 40353
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Hamburg Farms
Rent Specials
$1,452 - $2,177

Total Monthly Price

Base Rent$1,452 - $2,177
Total Monthly Price$1,452 - $2,177
2 Bedroom Apartments Available Now

Hamburg Farms

2498 Aristocracy CirLexington, KY 40509
Corporate Housing
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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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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 $1,709. 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 $1,759. 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$1,709
Colts RunJonabell - 2 Bedroom, 2 Bath (1,302 sqft.)1,302 Sq Ft$1,759
Garden EstatesTwo Bedroom Large1,216 Sq Ft$1,570
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,807
Parkside Heights2B 2B1,211 Sq Ft$1,651
Springs At Hamburg2 BR Grand Overlook1,185 Sq Ft$1,802
1809 at WinchesterB4 Secretariat - 2 Bedroom, 2 Bathroom1,185 Sq Ft$1,683
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,779
Latitude 37 Apartments2 bedroom w/ garage1,157 Sq Ft$1,734
The AveryTwo bedroom with garage1,132 Sq Ft$1,790

Cheapest Available Winchester 2 Bedroom Apartments

As of September 13, 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 2 Beds, 1 Baths Model at 265 S Highland St starting at $955 in the Clark County neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $1,582. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
The Dawn Run Apartments2x1 SM$920
265 S Highland St2 Beds, 1 Baths$955
Polo Club Park - Senior/Affordable Housing2bd$1,040
The Lofts at Winchester2BR/1.0BA$1,049
Prime Hamburg ApartmentsElite 2BR - 1BTH$1,110
Williams Estates ApartmentsTwo Bedroom$1,119
Stoney Brooke ApartmentsSomerset - Renovated$1,134
Raintree ApartmentsMagnolia - B2$1,151
GleneaglesTwo Bedroom$1,193
The Pops2 Bedroom 1 Bathroom$1,295

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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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 $1,582.

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 $1,709 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 913 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.

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