2 Bedroom Apartments for Rent in Winchester, KY (59 Rentals)

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265 S Highland St
2 Bedroom Apartments

265 S Highland St

265 S Highland StWinchester, KY 40391
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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

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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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
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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 - $1,949
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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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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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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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 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 1,345 square feet priced from $1,637. 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 $1,749. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Hamburg FarmsB3 Burton - 2 Bedroom, 1.5 Bathroom1,345 Sq Ft$1,637
Colts RunJonabell - 2 Bedroom, 2 Bath (1,302 sqft.)1,302 Sq Ft$1,749
Garden EstatesTwo Bedroom Large1,216 Sq Ft$1,630
Waterstone at Hamburg Apartments2BR 2BA (1214 SF)1,214 Sq Ft$1,812
Parkside Heights2B 2B1,211 Sq Ft$1,736
Springs At Hamburg2 BR Grand Overlook Garage1,185 Sq Ft$2,118
The BLVD at HaysBlvd 2G-With Garage1,160 Sq Ft$1,779
The AveryTwo bedroom with garage1,132 Sq Ft$1,790
1809 at WinchesterB2 Solomini plus garage - 2 Bedroom, 2 Bathroom1,088 Sq Ft$1,671
Brighton 30502.0 - 2.11,069 Sq Ft$1,509

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of July 29, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, KY is the 2 Beds, 1 Baths Model starting from $955 at 265 S Highland St in the Clark County neighborhood. The second most affordable Winchester 2 Bedroom is the Two Bedroom Model at Richwood Bend - Affordable Housing starting at $1,050 in the Boone Creek neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $1,638. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
265 S Highland St2 Beds, 1 Baths$955
Richwood Bend - Affordable HousingTwo Bedroom$1,050
Prime Hamburg ApartmentsElite 2 BR$1,110
GleneaglesTwo Bedroom$1,193
Stoney Brooke ApartmentsSomerset - Renovated$1,229
Flats at 2875Newly Renovated 2 Bed, 1 Bath Apartments$1,345
Bourbon Hills2 bedroom$1,350
Colts RunCalumet - 2 Bedroom, 2 Bath (950 sqft.)$1,369
The Pops2 Bedroom 1 Bathroom$1,375
Raintree ApartmentsMagnolia - B1$1,421

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 265 S Highland St listed at $955.

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

The average rent for a 2 Bedroom Apartment in Winchester is $1,638.

What is the largest available 2 Bedroom Winchester Apartment for rent?

Today's apartment with the most square footage in Winchester is a 1,345 square feet unit starting from $1,637 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 1,031 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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