Price Reduced12$249,000
4 bd · 2 ba · 1,996 sqft
59 Hillcrest Drive, Winchester, KY
Dylan Langdon · The Agency
Homes for Sale in Winchester, KY
Hide MapHomes for Sale in Winchester, KY
24 of 112 Listings
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.
32$367,700
4 bd · 2 ba · 2,352 sqft
107 S Burns Avenue, Winchester, KY
Lauren Lewis · Christies International Real Estate Bluegrass
22$200,000
3 bd · 1 ba · 1,453 sqft
213 E Broadway Street, Winchester, KY
Nik Markovich · GSP Homes
33$335,000
3 bd · 2 ba · 1,836 sqft
2550 Kiddville Road, Winchester, KY
Monique Gamble · The Real Estate Co - W Liberty
45$299,900
3 bd · 2 ba · 1,444 sqft
8 Monroe Avenue, Winchester, KY
Robyn R Bradley · Woods Realty Group
65$769,900
3 bd · 3 ba · 2,200 sqft
330 Spencer Lane, Winchester, KY
Libby VanMeter · Marshall Lane Real Estate - Lexington
Price Reduced47$445,500
3 bd · 3 ba · 2,961 sqft
42 Mockingbird Valley Road, Winchester, KY
Markus Cross · McCallie Real Estate
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
109$1,125,000
3 bd · 4 ba · 3,672 sqft
2100 Irvine Road 40391, Winchester, KY
Lucy Martin Jenkins · United Real Estate Bluegrass
Open house Wed, Oct 14 · 12:00 PM34$225,000
3 bd · 1 ba · 2,244 sqft
326 W Lexington Avenue, Winchester, KY
Jonathan Noel · Noel Auctioneers and Real Estate Advisors
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 Reduced21$99,500
2 bd · 2 ba · 924 sqft
563 Constitution Drive, Winchester, KY
Jason Townsend · Kentucky Residential Real Estate, LLC
Price Reduced29$220,000
3 bd · 2 ba · 1,737 sqft
600 College Street, Winchester, KY
Ally Robertson · The Brokerage
54$375,000
4 bd · 2 ba · 1,828 sqft
609 W Barlow Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
90$5,495,000
3 bd · 4 ba · 5,800 sqft
5825 Combs Ferry Road, Winchester, KY
Mike J Morrison · Bluegrass Sotheby's International Realty
48$304,900
3 bd · 3 ba · 1,904 sqft
335 Newcastle Lane, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
94$675,000
4 bd · 4 ba · 2,659 sqft
1477 Sewell Shop Road, Winchester, KY
Jason Townsend · Kentucky Residential Real Estate, LLC
22$243,500
3 bd · 3 ba · 1,856 sqft
102 Quail Ridge Road, Winchester, KY
Tracey Goebel · Tom Goebel & Company
46$475,000
3 bd · 2 ba · 2,174 sqft
625 Pine Ridge Road, Winchester, KY
Tonya Morrow · KY Local
Price Reduced37$249,000
3 bd · 2 ba · 1,386 sqft
33 Bon-Haven Avenue, Winchester, KY
Erika Beatty · Plum Tree Realty
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