Affordable Homes For Sale in Winchester, KY

220 homes

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0.47 ACRES
$110,000
139 Jacob Ct,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.5 ACRES
$110,000
260 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.32 ACRES
$110,000
250 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.34 ACRES
$110,000
230 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.38 ACRES
$110,000
200 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.35 ACRES
$110,000
150 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
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3D VIEW
0.29 ACRES
$110,000
160 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
3D VIEW
0.38 ACRES
$110,000
120 Duclair Dr,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
$124,000
2 Beds
2 Baths
1,360 sqft
404 Mount Vernon Dr,
Winchester, KY 40391
Dream Maker Realty, LLC, Imagine MLS
$124,500
2 Beds
1 Bath
876 sqft
122 Calloway St,
Winchester, KY 40391
Dream Maker Realty, LLC, Imagine MLS
0.5 ACRES
$135,000
2 Beds
1 Bath
807 sqft
3208 Ford Hampton Rd,
Winchester, KY 40391
eXp Realty, LLC, Imagine MLS
$139,900
3 Beds
1.5 Baths
1,680 sqft
65 Fitch Ave,
Winchester, KY 40391
Ensor Real Estate, LLC, Imagine MLS
2.77 ACRES
$150,000
3385 Colby Rd,
Winchester, KY 40391
Steven D Adams Real Estate Services, LLC, Imagine MLS
7.44 ACRES
$150,000
1 Bed
1 Bath
384 sqft
2915 College Hill Rd,
Waco, KY 40385
Keller Williams Commonwealth, Imagine MLS
3D VIEW
2.11 ACRES
$150,000
125 Knox Ct,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
3D VIEW
2.16 ACRES
$150,000
120 Knox Ct,
Winchester, KY 40391
Bluegrass Properties Group, Imagine MLS
4.21 ACRES
$150,000
1030 Craig Crossing Rd,
Winchester, KY 40391
Coldwell Banker McMahan, Imagine MLS
2.53 ACRES
$154,900
750 Craig Xing #7,
Winchester, KY 40391
Coldwell Banker McMahan, Imagine MLS
$155,900
1 Bed
2 Baths
1,056 sqft
101 Alabama St,
Winchester, KY 40391
Woods Realty Group, Imagine MLS
3D VIEW
$159,000
3 Beds
1 Bath
1,249 sqft
209 E Washington St,
Winchester, KY 40391
RE/MAX Creative, Winchester, Imagine MLS
AUCTION
0.56 ACRES
$160,000
3 Beds
1 Bath
1,173 sqft
24 Spring St,
Winchester, KY 40391
EXIT Town & Country Realtors, Imagine MLS
$169,000
3 Beds
1 Bath
1,046 sqft
175 Magnolia St,
Lexington, KY 40391
Woods Realty Group, Imagine MLS
6.59 ACRES
$175,000
990 Craig Crossing Rd,
Winchester, KY 40391
Coldwell Banker McMahan, Imagine MLS
FOR SALE BY OWNER
0.34 ACRES
$175,900
6 Beds
2 Baths
3,008 sqft
290 S Main St,
Winchester, KY 40391
$179,900
3 Beds
2 Baths
1,299 sqft
16 Bon Haven Ave,
Winchester, KY 40391
Dustin Hepburn, Rebuilt Brokerage, My State MLS
8.35 ACRES
$195,000
6699 Boonesboro Rd,
Winchester, KY 40391
RE/MAX Elite Realty, Imagine MLS
$197,000
3 Beds
1 Bath
1,193 sqft
214 Center Dr,
Winchester, KY 40391
The Brokerage, Imagine MLS
$199,000
2 Beds
1 Bath
1,154 sqft
606 College St,
Winchester, KY 40391
Marshall Lane Real Estate
$199,900
3 Beds
1 Bath
1,272 sqft
520 College St,
Winchester, KY 40391
McCallie Real Estate, Imagine MLS
$200,000
3 Beds
1 Bath
1,453 sqft
213 E Broadway St,
Winchester, KY 40391
GSP Homes, Imagine MLS
$204,900
3 Beds
1 Bath
1,128 sqft
38 Mackay Ave,
Winchester, KY 40391
Tom Goebel & Company, Imagine MLS
$205,000
3 Beds
2 Baths
1,319 sqft
3 Nunnelly Ct,
Winchester, KY 40391
Black Mountain Realty, Imagine MLS
3D VIEW
$209,000
3 Beds
2 Baths
1,261 sqft
14 Cook Ave,
Winchester, KY 40391
United Real Estate Bluegrass, Imagine MLS
NEW - 1 DAY AGO
$209,000
3 Beds
1 Bath
1,075 sqft
117 Colonial Park Dr,
Winchester, KY 40391
Four Seasons Realty, Imagine MLS
3D VIEW
$215,000
3 Beds
1 Bath
1,134 sqft
14 Shelley Dr,
Winchester, KY 40391
RE/MAX Creative, Winchester, Imagine MLS
$219,500
3 Beds
2 Baths
1,130 sqft
527 Hidden Hills Way,
Winchester, KY 40391
The Agency, Imagine MLS
$219,900
3 Beds
2 Baths
1,904 sqft
528 Estes Dr,
Winchester, KY 40391
Freedom Realty & Property Management, Imagine MLS
$219,900
3 Beds
1 Bath
1,100 sqft
125 Kittison Dr,
Winchester, KY 40391
Coldwell Banker McMahan, Imagine MLS
3D VIEW
23.83 ACRES
$219,900
3686 Crowe Ridge Rd,
Winchester, KY 40391
Freedom Realty & Property Management, Imagine MLS
$220,000
3 Beds
2 Baths
1,737 sqft
600 College St,
Winchester, KY 40391
The Brokerage, Imagine MLS

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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.

Affordable Homes For Sale in Winchester, KY

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