Price Reduced25$219,900
3 bd · 2 ba · 1,904 sqft
528 Estes Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Homes Under $300K in Winchester, KY
Hide MapHomes Under $300K in Winchester, KY
24 of 55 Listings
Price Reduced25$219,900
3 bd · 2 ba · 1,904 sqft
528 Estes Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
New38$299,900
3 bd · 2 ba · 1,648 sqft
314 Botts Court, Winchester, KY
Edgar Saborit · Lifstyl Real Estate
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
54$250,000
3 bd · 2 ba · 1,893 sqft
13 Euclid Avenue, Winchester, KY
Robin S Jones · 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 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.
22$200,000
3 bd · 1 ba · 1,453 sqft
213 E Broadway Street, Winchester, KY
Nik Markovich · GSP Homes
Price Reduced18$169,000
3 bd · 1 ba · 1,046 sqft
175 Magnolia Street, Winchester, KY
A. Rebecca Woods · Woods Realty Group
23$204,900
3 bd · 1 ba · 1,128 sqft
38 MacKay Avenue, Winchester, KY
Nena Honaker · Tom Goebel & Company
Price Reduced46$229,000
3 bd · 1 ba · 1,050 sqft
30 Virginia Avenue, Winchester, KY
Brenda H Sipes · WEICHERT REALTORS - ABG Properties
26$215,000
3 bd · 1 ba · 1,134 sqft
14 Shelley Drive, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
Price Reduced29$220,000
3 bd · 2 ba · 1,737 sqft
600 College Street, Winchester, KY
Ally Robertson · The Brokerage
Price Reduced22$239,000
3 bd · 3 ba · 1,856 sqft
102 Quail Ridge Road, Winchester, KY
Tracey Goebel · Tom Goebel & Company
Price Reduced43$296,000
4 bd · 2 ba · 1,953 sqft
6 French Avenue, Winchester, KY
A. Rebecca Woods · Woods Realty Group
Homes Under $300K in Winchester, KY: 55 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