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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
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
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
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
70
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
621 Boone Avenue Property Photo 1
101
Listing Provided By: Coldwell Banker McMahan
$1,200,000
621 Boone Avenue 
Winchester, KY 40391
  • Beds5
  • Baths 6 Total 6 Total
  • SqFt5,4985.5k
  • Built1965
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
420 Alexis Way Property Photo 1
77
McCormick Realty Inc. Logo
Listing Provided By: McCormick Realty Inc.
$950,000
420 Alexis Way 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,7702.8k
  • Built2022
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
422 Alexis Way Property Photo 1
5
National Real Estate Appalachia Logo
Listing Provided By: National Real Estate Appalachia
$760,000
422 Alexis Way 
Winchester, KY 40391
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt3,0533.1k
  • Built2024
240 Duclair Drive Property Photo 1
8
Bluegrass Properties Group Logo
Listing Provided By: Bluegrass Properties Group
$725,000
240 Duclair Drive 
Winchester, KY 40391
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt2,8502.9k
  • Built2024
1039 Cole Road Property Photo 1
105
NEW
Freedom Realty & Property Management Logo
Listing Provided By: Freedom Realty & Property Management
$719,000
1039 Cole Road 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,5572.6k
  • Built1977
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
414 Alexis Way Property Photo 1
9
National Real Estate Appalachia Logo
Listing Provided By: National Real Estate Appalachia
$625,000
414 Alexis Way 
Winchester, KY 40391
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt2,6432.6k
  • Built2024
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
31 West Hickman Street Property Photo 1
30
Block + Lot Real Estate Logo
Listing Provided By: Block + Lot Real Estate
$599,000
31 West Hickman Street 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt5,3285.3k
  • Built1814
4 Moundale Avenue Property Photo 1
74
United Real Estate Bluegrass Logo
Listing Provided By: United Real Estate Bluegrass
$589,900
4 Moundale Avenue 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,9412.9k
  • Built1945
31 Bonnie Brook Lane Property Photo 1
44
Listing Provided By: Coldwell Banker McMahan
$575,000
31 Bonnie Brook Lane 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt4,0914.1k
  • Built1958
196 Casa Landa Way Property Photo 1
48
Keller Williams Commonwealth Logo
Listing Provided By: Keller Williams Commonwealth
$559,500
196 Casa Landa Way 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt3,5013.5k
  • Built1996
485 Mccullough Lane Property Photo 1
78
Torrey Smith Realty Co, LLC Logo
Listing Provided By: Torrey Smith Realty Co, LLC
$544,500
485 McCullough Lane 
Winchester, KY 40391
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,1202.1k
  • Built1950
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
104 Bella Shae Way Property Photo 1
12
National Real Estate Appalachia Logo
Listing Provided By: National Real Estate Appalachia
$516,000
104 Bella Shae Way 
Winchester, KY 40391
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,2002.2k
  • Built2024
163 Hawthorne Drive Property Photo 1
35
The Agency Logo
Listing Provided By: The Agency
$509,900
163 Hawthorne Drive 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,8302.8k
  • Built2018
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
304 Debbia Drive Property Photo 1
43
RE/MAX Creative, Winchester Logo
Listing Provided By: RE/MAX Creative, Winchester
$470,000
304 Debbia Drive 
Winchester, KY 40391
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt3,0613.1k
  • Built1981
127 Hibiscus Lane Property Photo 1
44
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
105 Monet Boulevard Property Photo 1
38
NEW
Keller Williams Commonwealth Logo
Listing Provided By: Keller Williams Commonwealth
$429,900
105 Monet Boulevard 
Winchester, KY 40391
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,2402.2k
  • Built1995
580 Mcclure Road Property Photo 1
43
Keller Williams Commonwealth Logo
Listing Provided By: Keller Williams Commonwealth
$425,000
580 McClure Road 
Winchester, KY 40391
  • Beds4
  • Baths 2 Total 2 Total
  • SqFt2,5002.5k
  • Built2023