![Property at 221 S Highland St #3, Winchester, KY, 40391, 2 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/d5056877-8afc-4cc8-ba78-cb19277443f0/islphoto/genIsl.0_1.webp)
221 S Highland St #3, Winchester, KY, 40391
![Property at 27 E Washington St Unit 16, Winchester, KY, 40391, 0 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/389d14dc-e42f-4a67-9f06-e2cfe60d447d/islphoto/genIsl.0_1.webp)
27 E Washington St Unit 16, Winchester, KY, 40391![Property at 200 Hubbard Rd Unit 605, Winchester, KY, 40391, 0 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/b7ed3923-c325-45df-b487-727795af4ffa/islphoto/genIsl.0_1.webp)
200 Hubbard Rd Unit 605, Winchester, KY, 40391![Property at 401 N Maple St Unit 03, Winchester, KY, 40391, 0 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/94d8e8f1-fb2e-41fc-b321-d19b013db3b8/islphoto/genIsl.0_1.webp)
401 N Maple St Unit 03, Winchester, KY, 40391
![Property at Crosskeys - 1021 Cross Keys Rd, Lexington, KY, 40504, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/2d4b0920-7d10-43fa-afeb-c0d7dd6f249b/islphoto/genIsl.0_1.webp)
Crosskeys - 1021 Cross Keys Rd, Lexington, KY, 40504![Property at Matador North - 1053 Winburn Dr, Lexington, KY, 40511, 0 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/72591939-6a41-441a-bd7c-374959529c59/islphoto/genIsl.0_3.webp)
Matador North - 1053 Winburn Dr, Lexington, KY, 40511![Property at Lansdowne Grove - 3489 Lansdowne Dr, Lexington, KY, 40517, 0 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/56e52034-ea9a-4950-a5ef-28cabce72855/islphoto/genIsl.0_3.webp)
Lansdowne Grove - 3489 Lansdowne Dr, Lexington, KY, 40517![Property at 165 Donabrook Ct, Lexington, KY, 40517, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/eb729d2e-196d-4644-b4f5-7407a7aa8150/islphoto/genIsl.0_6.webp)
165 Donabrook Ct, Lexington, KY, 40517![Property at Eastland Hills Apartments - 1740 Jennifer Rd, Lexington, KY, 40505, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/a39e09f6-9ce2-46dc-9bdf-35fd2f68edf9/islphoto/genIsl.0_6.webp)
Eastland Hills Apartments - 1740 Jennifer Rd, Lexington, KY, 40505![Property at 1685 Alexandria Dr, Lexington, KY, 40504, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/bc170dc5-4b2d-4a66-ba89-aaf6604c30cd/islphoto/genIsl.0_1.webp)
1685 Alexandria Dr, Lexington, KY, 40504![Property at VELO - Waller Avenue - 353 Waller Ave, Lexington, KY, 40504, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/e5212078-eeea-4d03-bb03-9863bb08a532/islphoto/genIsl.0_3.webp)
VELO - Waller Avenue - 353 Waller Ave, Lexington, KY, 40504![Property at Heritage Hills - 1 Bedroom 1 Bath - New Ownership - 1708 Jennifer Rd, Lexington, KY, 40505, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/fe2c38ba-3047-4567-bbbc-d1c9449c1d24/islphoto/genIsl.0_3.webp)
Heritage Hills - 1 Bedroom 1 Bath - New Ownership - 1708 Jennifer Rd, Lexington, KY, 40505![Property at Pebblecreek Crossing - 418 Big Hill Ave, Richmond, KY, 40475, 1-2 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/4fb6023c-e808-425c-b9f2-89b490ad396a/islphoto/genIsl.0_6.webp)
Pebblecreek Crossing - 418 Big Hill Ave, Richmond, KY, 40475![Property at Rivers at Bluegrass - 2504 Larkin Rd, Lexington, KY, 40503, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/8d1d2f6b-ac02-4808-aaec-f616f2a4b998/islphoto/genIsl.0_6.webp)
Rivers at Bluegrass - 2504 Larkin Rd, Lexington, KY, 40503![Property at Flats at Devonport - 1349 Devonport Dr, Lexington, KY, 40504, 1 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/9d96983a-56c6-41c5-9f36-93244a74b953/islphoto/genIsl.0_7.webp)
Flats at Devonport - 1349 Devonport Dr, Lexington, KY, 40504![Property at Park Place - 535 Mahaffey Dr, Richmond, KY, 40475, 1-2 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/a1063410-fae3-49df-9cd5-e3502105eac7/islphoto/genIsl.0_5.webp)
Park Place - 535 Mahaffey Dr, Richmond, KY, 40475![Property at Reserves of Madison - 450 N Keeneland Dr, Richmond, KY, 40475, 1-2 bed, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/8d3cadfc-f915-4870-999b-c2d48cac4480/islphoto/genIsl.0_5.webp)
Reserves of Madison - 450 N Keeneland Dr, Richmond, KY, 40475More to explore in Winchester, KY
- Property Types
- Bedrooms
- Amenities
- Price
Rentals near Winchester, KY
Apartments for rent near Winchester, KY
Popular rental markets in Kentucky
- Rentals
- Apartments
About us
Find us
Subsidiaries
United States
CanadaCopyright: © 2025 Redfin. All rights reserved.
Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.
Do not sell or share my personal information.
REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.
California DRE #01521930
Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures
New Mexico Real Estate Licenses
TREC: Info About Brokerage Services, Consumer Protection Notice
Rocket Mortgage is an affiliated business of Redfin. All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.
Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).
If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.
REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.