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2090 Pretty Run Road Property Photo 1
11
Kentucky Prime Realty, LLC Logo
Listing Provided By: Kentucky Prime Realty, LLC
$5,795,000
2090 Pretty Run Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built0
5325 Lexington Road Property Photo 1
3
United Real Estate Lexington KY Logo
Listing Provided By: United Real Estate Lexington KY
$3,750,000
5325 Lexington Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
5045 Van Meter Road Property Photo 1
129
Bluegrass Sotheby's International Realty Logo
Listing Provided By: Bluegrass Sotheby's International Realty
$3,599,000
5045 Van Meter Road 
Winchester, KY 40391
  • Beds6
  • Baths 6 Total 6 Total
  • SqFt7,4707.5k
  • Built2004
4664 Lexington Road Property Photo 1
118
NEW
Kirkpatrick & Company Logo
Listing Provided By: Kirkpatrick & Company
$3,500,000
4664 Lexington Road 
Winchester, KY 40391
  • Beds8
  • Baths 8 Total 8 Total
  • SqFt12,70212.7k
  • Built1997
4664 Lexington Road Property Photo 1
118
NEW
Kirkpatrick & Company Logo
Listing Provided By: Kirkpatrick & Company
$3,500,000
4664 Lexington Road 
Winchester, KY 40391
  • Beds8
  • Baths 8 Total 8 Total
  • SqFt13,52113.5k
  • Built1997
1395 Two Mile Road Property Photo 1
1
Tom Goebel & Company Logo
Listing Provided By: Tom Goebel & Company
$2,500,000
1395 Two Mile Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
100 Moundale Property Photo 1
48
Block + Lot Real Estate Logo
Listing Provided By: Block + Lot Real Estate
$2,199,000
100 Moundale 
Winchester, KY 40391
  • Beds9
  • Baths 6 Total 6 Total
  • SqFt11,23011.2k
  • Built1904
6450 Bybee Road Property Photo 1
56
United Real Estate Bluegrass Logo
Listing Provided By: United Real Estate Bluegrass
$1,650,000
6450 Bybee Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
6085 Combs Ferry Road Property Photo 1
6
United Real Estate Bluegrass Logo
Listing Provided By: United Real Estate Bluegrass
$1,397,400
6085 Combs Ferry Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
6085 Combs Ferry Road Property Photo 1
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United Real Estate Bluegrass Logo
Listing Provided By: United Real Estate Bluegrass
$1,200,000
6085 Combs Ferry Road 
Winchester, KY 40391
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt4,2264.2k
  • Built2020
3475 Old Boonesboro Road Property Photo 1
Tom Goebel & Company Logo
Listing Provided By: Tom Goebel & Company
$1,060,000
3475 Old Boonesboro Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
511 Boone Avenue Property Photo 1
53
Block + Lot Real Estate Logo
Listing Provided By: Block + Lot Real Estate
$975,000
511 Boone Avenue 
Winchester, KY 40391
  • Beds4
  • Baths 5 Total 5 Total
  • SqFt4,6984.7k
  • Built1885
423 Alexis Way Property Photo 1
Keller Williams Legacy Group Logo
Listing Provided By: Keller Williams Legacy Group
$947,190
423 Alexis Way 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,3582.4k
  • Built2024
1800 Athens-boonesboro Road Property Photo 1
25
Keller Williams Legacy Group Logo
Listing Provided By: Keller Williams Legacy Group
$896,640
1800 Athens-Boonesboro Road 
Winchester, KY 40391
  • Beds4
  • Baths 2 Total 2 Total
  • SqFt3,3723.4k
  • Built1792
1275 Old Log Lick Road Property Photo 1
24
Bluegrass Properties Group Logo
Listing Provided By: Bluegrass Properties Group
$800,000
1275 Old Log Lick Road 
Winchester, KY 40391
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt1,3921.4k
  • Built1982
1995 Gay Evans Road Property Photo 1
96
Lifstyl Real Estate Logo
Listing Provided By: Lifstyl Real Estate
$789,000
1995 Gay Evans Road 
Winchester, KY 40391
  • Beds4
  • Baths 4 Total 4 Total
  • SqFt3,2723.3k
  • Built1998
31 Bonnie Brook Lane Property Photo 1
44
Listing Provided By: Coldwell Banker McMahan
$650,000
31 Bonnie Brook Lane 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt4,0914.1k
  • Built1958
9953 Ironworks Road Property Photo 1
56
Keller Williams Commonwealth Logo
Listing Provided By: Keller Williams Commonwealth
$649,900
9953 Ironworks Road 
Winchester, KY 40391
  • Beds6
  • Baths 3 Total 3 Total
  • SqFt3,8003.8k
  • Built2003
31 West Hickman Street Property Photo 1
30
Block + Lot Real Estate Logo
Listing Provided By: Block + Lot Real Estate
$649,000
31 West Hickman Street 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt5,3285.3k
  • Built1814
427 Alexis Way Property Photo 1
21
JPAR Aspire Logo
Listing Provided By: JPAR Aspire
$635,000
427 Alexis Way 
Winchester, KY 40391
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt2,1992.2k
  • Built2024
6130 Van Meter Road Property Photo 1
13
RE/MAX Elite Lexington Logo
Listing Provided By: RE/MAX Elite Lexington
$629,000
6130 Van Meter Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
1395 Two Mile Road Property Photo 1
1
Tom Goebel & Company Logo
Listing Provided By: Tom Goebel & Company
$603,750
1395 Two Mile Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
6595 Mt Sterling Road Property Photo 1
60
Ro&Co Real Estate Logo
Listing Provided By: Ro&Co Real Estate
$599,900
6595 Mt Sterling Road 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt4,5154.5k
  • Built2010
414 Alexis Way Property Photo 1
6
JPAR Aspire Logo
Listing Provided By: JPAR Aspire
$595,000
414 Alexis Way 
Winchester, KY 40391
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt2,6432.6k
  • Built2024
485 Mccullough Lane Property Photo 1
78
Torrey Smith Realty Co, LLC Logo
Listing Provided By: Torrey Smith Realty Co, LLC
$579,500
485 McCullough Lane 
Winchester, KY 40391
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,1202.1k
  • Built1950
281 Rose Drive Property Photo 1
54
NEW
McConnell Real Estate, Inc. Logo
Listing Provided By: McConnell Real Estate, Inc.
$565,000
281 Rose Drive 
Winchester, KY 40391
  • Beds4
  • Baths 4 Total 4 Total
  • SqFt5,4405.4k
  • Built2002
1395 Two Mile Road Property Photo 1
1
Tom Goebel & Company Logo
Listing Provided By: Tom Goebel & Company
$519,500
1395 Two Mile Road 
Winchester, KY 40391
  • Beds0
  • Baths 0 Total 0 Total
  • SqFt00.0k
  • Built
146 Hawthorne Drive Property Photo 1
38
Keller Williams Commonwealth Logo
Listing Provided By: Keller Williams Commonwealth
$515,000
146 Hawthorne Drive 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt2,7112.7k
  • Built2021
42 Mockingbird Valley Road Property Photo 1
98
Freedom Realty & Property Management Logo
Listing Provided By: Freedom Realty & Property Management
$499,900
42 Mockingbird Valley Road 
Winchester, KY 40391
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt3,1483.1k
  • Built1960
1026 Crowe Ridge Road Property Photo 1
17
Herald Real Estate Logo
Listing Provided By: Herald Real Estate
$495,000
1026 Crowe Ridge Road 
Winchester, KY 40391
  • Beds3
  • Baths 1 Total 1 Total
  • SqFt1,2001.2k
  • Built9999
106 Bella Shae Way Way Property Photo 1
8
JPAR Aspire Logo
Listing Provided By: JPAR Aspire
$480,000
106 Bella Shae Way Way 
Winchester, KY 40391
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,2002.2k
  • Built2024
312 Briarwood Lane Property Photo 1
45
Listing Provided By: Coldwell Banker McMahan
$475,000
312 Briarwood Lane 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt4,1084.1k
  • Built2003
127 Hibiscus Lane Property Photo 1
45
Freedom Realty & Property Management Logo
Listing Provided By: Freedom Realty & Property Management
$469,900
127 Hibiscus Lane 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,8002.8k
  • Built2024
1159 Cabin Creek Road Property Photo 1
45
Listing Provided By: Coldwell Banker McMahan
$469,000
1159 Cabin Creek Road 
Winchester, KY 40391
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt2,2442.2k
  • Built2007
336 Runnymeade Drive Property Photo 1
41
Keller Williams Legacy Group Logo
Listing Provided By: Keller Williams Legacy Group
$459,900
336 Runnymeade Drive 
Winchester, KY 40391
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt2,7842.8k
  • Built2000
4353 Old Boonesboro Road Property Photo 1
69
Kassie & Associates Logo
Listing Provided By: Kassie & Associates
$441,000
4353 Old Boonesboro Road 
Winchester, KY 40391
  • Beds5
  • Baths 3 Total 3 Total
  • SqFt2,9523.0k
  • Built1990