Price Reduced
$325,000
4 bd · 2 ba · 3,261 sqft
443 S Maple Street, Winchester, KY
Terra Long · Keller Williams Commonwealth
Homes for Sale in Winchester, KY
Hide MapHomes for Sale in Winchester, KY
24 of 110 Listings
Price Reduced$325,000
4 bd · 2 ba · 3,261 sqft
443 S Maple Street, Winchester, KY
Terra Long · Keller Williams Commonwealth
NewOpen house Sun, Oct 18 · 2:00 PM46$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
NewOpen house Fri, Oct 16 · 5:00 PM45$279,900
3 bd · 3 ba · 2,779 sqft
121 Bay Hill Drive, Winchester, KY
Kimberly C Dice · eXp Realty, LLC
New29$221,000
3 bd · 2 ba · 1,665 sqft
106 Quail Ridge Road, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
New60$255,000
3 bd · 1 ba · 1,135 sqft
26 Holiday Road, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
23$199,500
3 bd · 1 ba · 1,193 sqft
214 Center Drive, Winchester, KY
Lukas Owens · The Brokerage
90$4,895,000
3 bd · 4 ba · 5,800 sqft
5825 Combs Ferry Road, Winchester, KY
Mike J Morrison · Bluegrass Sotheby's International Realty
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
82$2,299,000
5 bd · 4 ba · 8,389 sqft
5039 Combs Ferry Road, Winchester, KY
K Meredith Lane · Bluegrass Sotheby's International Realty
29$289,900
3 bd · 2 ba · 1,254 sqft
47 Cherokee Court, Winchester, KY
Holly L Goeing · The Agency
36$314,900
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
37$639,000
3 bd · 1 ba · 1,962 sqft
9930 Mount Sterling Road, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC
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
22$200,000
3 bd · 1 ba · 1,453 sqft
213 E Broadway Street, Winchester, KY
Nik Markovich · GSP Homes
65$769,900
3 bd · 3 ba · 2,200 sqft
330 Spencer Lane, Winchester, KY
Libby VanMeter · Marshall Lane Real Estate - Lexington
Price Reduced47$439,000
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
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