Price cut: $900 (10/7)
Homes for Sale Under $500K in Winchester KY
109 results
- 206 Jett Dr, Winchester, KY 40391
- 3 bds
- 2 ba
- 1,635 sqft
ENSOR REAL ESTATE, LLC. Listing provided by Imagine MLS68 days on Zillow
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- Price cut: $25,000 (10/13)
- 55 Hillcrest Dr, Winchester, KY 40391
- 5 bds
- 2 ba
- 2,214 sqft
RE/MAX ELITE LEXINGTON. Listing provided by Imagine MLSFull walk-out basement
- 308 Market St, Winchester, KY 40391
- 2 bds
- 2 ba
- 828 sqft
QUICK SHOP MHC, Anthony D'andera. Listing provided by My State MLSConnected airy feel
- 309 Gallahadion Ct, Winchester, KY 40391
- 3 bds
- 3 ba
- 1,945 sqft
RE/MAX CREATIVE, WINCHESTER. Listing provided by Imagine MLSModern style
- Three bedroom
- 520 College St, Winchester, KY 40391
- 3 bds
- 1 ba
- 1,272 sqft
MCCALLIE REAL ESTATE. Listing provided by Imagine MLSComfortable living
- 225 Evergreen Dr, Winchester, KY 40391
- 3 bds
- 2 ba
- 1,855 sqft
UNITED REAL ESTATE BLUEGRASS. Listing provided by Imagine MLSGas fireplace
- 204 Jett Dr, Winchester, KY 40391
- 3 bds
- 2 ba
- 1,558 sqft
ENSOR REAL ESTATE, LLC. Listing provided by Imagine MLSGreat floor plan
- Price cut: $3,000 (10/18)
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- Private patio or deck
- 563 Constitution Dr, Winchester, KY 40391
- 2 bds
- 2 ba
- 924 sqft
KENTUCKY RESIDENTIAL REAL ESTATE, LLC. Listing provided by Imagine MLSAll new flooring
- Private patio
- 7100 Donaldson Rd, Mount Sterling, KY 40353
- 2 bds
- 1 ba
- 728 sqft
MURPHY REALTY GROUP. Listing provided by Imagine MLSNewly stained deck
- 122 Calloway St, Winchester, KY 40391
- 2 bds
- 1 ba
- 876 sqft
DREAM MAKER REALTY, LLC. Listing provided by Imagine MLS295 days on Zillow
- 335 Newcastle Ln, Winchester, KY 40391
- 3 bds
- 3 ba
- 1,904 sqft
FREEDOM REALTY & PROPERTY MANAGEMENT. Listing provided by Imagine MLSBrand-new roof
- 209 E Washington St, Winchester, KY 40391
- 3 bds
- 1 ba
- 1,249 sqft
RE/MAX CREATIVE, WINCHESTER. Listing provided by Imagine MLS3D Tour 
- Dedicated laundry room
- Spacious dining area
- 175 Magnolia St, Lexington, KY 40391
- 3 bds
- 1 ba
- 1,046 sqft
WOODS REALTY GROUP. Listing provided by Imagine MLSNewly renovated
- 546 Constitution Dr, Winchester, KY 40391
- 2 bds
- 2 ba
- 924 sqft
DREAM MAKER REALTY, LLC. Listing provided by Imagine MLSPrice increase: $5,000 (10/23)
- Top-of-the-line stainless steel appliances
- Private patio
- Private patio or deck
- Two additional bedrooms
- 300 days on Zillow
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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search, Inc. Real estate listings held by brokerage firms other than Zillow, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about each listing includes the name of the listing broker. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Metro Search, Inc.
