Price Reduced
$255,000
3 bd · 3 ba · 2,260 sqft
209 Boone Avenue, Winchester, KY
Todd Hyatt · Lois Ann Disponett Real Est
Homes Under $500K in Winchester, KY
Hide MapHomes Under $500K in Winchester, KY
24 of 90 Listings
Price Reduced$255,000
3 bd · 3 ba · 2,260 sqft
209 Boone Avenue, Winchester, KY
Todd Hyatt · Lois Ann Disponett Real Est
Price Reduced$155,900
1 bd · 2 ba · 1,056 sqft
101 Alabama Street, Winchester, KY
A. Rebecca Woods · Woods Realty Group
58$484,900
4 bd · 3 ba · 2,381 sqft
410 Fairholme Way, Winchester, KY
Morgan Withrow · The Brokerage
New6$462,738
3 bd · 2 ba · 1,806 sqft
230 Evergreen Drive, Winchester, KY
Rex Hall · United Real Estate Bluegrass
New6$457,900
4 bd · 3 ba · 1,986 sqft
200 Evergreen Drive, Winchester, KY
Rex Hall · United Real Estate Bluegrass
New6$469,925
3 bd · 2 ba · 1,855 sqft
225 Evergreen Drive, Winchester, KY
Rex Hall · United Real Estate Bluegrass
54$250,000
3 bd · 2 ba · 1,893 sqft
13 Euclid Avenue, Winchester, KY
Robin S Jones · Keller Williams Legacy Group
New34$434,000
3 bd · 2 ba · 1,928 sqft
285 Rose Drive, Winchester, KY
Tracey Goebel · Tom Goebel & Company
New38$424,500
5 bd · 4 ba · 3,674 sqft
323 Skylark Drive, Winchester, KY
Tracey Goebel · Tom Goebel & Company
Price Reduced$325,000
4 bd · 2 ba · 3,261 sqft
443 S Maple Street, Winchester, KY
Terra Long · Keller Williams Commonwealth
46$325,000
5 bd · 3 ba · 3,378 sqft
25 W Hickman Street, Winchester, KY
Christina Bucher · Keller Williams Legacy Group
Price Reduced21$99,500
2 bd · 2 ba · 924 sqft
563 Constitution Drive, Winchester, KY
Jason Townsend · Kentucky Residential Real Estate, LLC
45$279,900
3 bd · 3 ba · 2,779 sqft
121 Bay Hill Drive, Winchester, KY
Kimberly C Dice · eXp Realty, LLC
60$255,000
3 bd · 1 ba · 1,135 sqft
26 Holiday Road, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
29$221,000
3 bd · 2 ba · 1,665 sqft
106 Quail Ridge Road, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
23$199,500
3 bd · 1 ba · 1,193 sqft
214 Center Drive, Winchester, KY
Lukas Owens · The Brokerage
30$299,900
5 bd · 4 ba · 4,456 sqft
410 W Lexington Avenue, Winchester, KY
Tracy M Ison · Bluegrass Home Group
26$265,000
3 bd · 2 ba · 1,715 sqft
122 Sunset Heights, Winchester, KY
James Woodrum · RE/MAX Creative, Winchester
29$289,900
3 bd · 2 ba · 1,254 sqft
47 Cherokee Court, Winchester, KY
Holly L Goeing · The Agency
Price Reduced36$309,900
4 bd · 3 ba · 1,963 sqft
444 Wellington Way, Winchester, KY
Michael R Hilario · The Agency
Price Reduced12$249,000
4 bd · 2 ba · 1,996 sqft
59 Hillcrest Drive, Winchester, KY
Dylan Langdon · The Agency
70$220,000
3 bd · 1 ba · 1,140 sqft
15 Maryland Avenue, Winchester, KY
Rachael Benezet · Bluegrass Properties Group
71$265,000
5 bd · 4 ba · 1,714 sqft
109 5th Street, Winchester, KY
Ernesto Martinez · Guide Realty, Inc.
43$367,700
4 bd · 2 ba · 2,352 sqft
107 S Burns Avenue, Winchester, KY
Lauren Lewis · Christies International Real Estate Bluegrass
Homes Under $500K in Winchester, KY: 90 active listings as of .
Imagine MLS (Bluegrass REALTORS)Source: HJN community data
August 2026 · This period is still settling
Selling at 98.2% of asking price
Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026