Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Reload
 

Winchester, KY Real Estate and Homes for Sale

$749,900
Active
Data Source Icon

2509 Mount Sterling Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 4 Baths
  • 4,346 sqft
$275,000
Active
Data Source Icon

304 Newcastle Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,787 sqft
$40,000
Active
Data Source Icon

16 Virginia Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,842 sqft
$279,900
Active
Data Source Icon

136 Sturbridge Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,604 sqft
$429,000
Pending
Data Source Icon

1661 Waterworks Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,793 sqft
$414,800
Active
Data Source Icon

608 Colby Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,803 sqft
$125,000
Active
Data Source Icon

25 Oliver Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 900 sqft
$355,000
Active
Data Source Icon

119 Gibson Way

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,325 sqft
$350,000
Active
Data Source Icon

6888 Bybee Road

Winchester, KY 40391

  • Single Family
  • 1 Bed
  • 1 Bath
  • 800 sqft
$235,000
Pending
Data Source Icon

5127 Combs Ferry Road

Winchester, KY 40391

  • Single Family
$310,000
Active
Data Source Icon

872 Stratton Lane

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,285 sqft
$289,900
Pending
Data Source Icon

198 Hilltop Drive

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,752 sqft
$545,000
Active
Data Source Icon

665 Lillies Ferry Road

Winchester, KY 40391

  • Single Family
$155,000
Active
Data Source Icon

220 E Washington Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,097 sqft
$230,000
Active
Data Source Icon

122 Spruce Court

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,210 sqft
$420,000
Active
Data Source Icon

19 Fontaine Boulevard

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,235 sqft
$289,000
Pending
Data Source Icon

110 Buckingham Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,240 sqft
$289,000
Active
Data Source Icon

214 S Burns Avenue

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,170 sqft
$249,900
Pending
Data Source Icon

312 Buffalo Trace

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,284 sqft
$329,900
Active
Data Source Icon

8 Monroe Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,444 sqft
$329,900
Active
Data Source Icon

335 Newcastle Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,904 sqft
$152,500
Active
Data Source Icon

65 Fitch Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,680 sqft
$385,000
Active
Data Source Icon

309 Gallahadion Court

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,945 sqft
$180,000
Pending
Data Source Icon

371 E Washington Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,198 sqft
$1,349,000
Active
Data Source Icon

1200 Craig Crossing

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,350 sqft
$349,500
Pending
Data Source Icon

221 W Hickman Street

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,800 sqft
$235,000
Pending
Data Source Icon

120 Windsor Drive

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 1 Bath
  • 1,609 sqft
$464,000
Active
Data Source Icon

105 Monet Boulevard

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,296 sqft
$265,000
Active
Data Source Icon

119 Sunset Heights

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,324 sqft
$229,500
Active
Data Source Icon

2 Western Avenue

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 1 Bath
  • 1,454 sqft
$249,900
Pending
Data Source Icon

17 Holiday Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,161 sqft
$239,000
Active
Data Source Icon

30 Virginia Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,050 sqft
$549,900
Active
Data Source Icon

600 Boone Avenue

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 5 Baths
  • 4,173 sqft
$354,900
Active
Data Source Icon

107 Gibson Way

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,266 sqft
$249,500
Active
Data Source Icon

377 Crescent Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,533 sqft
$499,000
Pending
Data Source Icon

182 Chardonnay Court

Winchester, KY 40392

  • Single Family
  • 5 Beds
  • 3 Baths
  • 3,097 sqft
$899,000
Active
Data Source Icon

330 Spencer Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,200 sqft
$449,900
Pending
Data Source Icon

207 Hibiscus Lane

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,126 sqft
$274,900
Active
Data Source Icon

955 Right Angle Road

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 1 Bath
  • 849 sqft
$160,000
Pending
Data Source Icon

107 Patio Street

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 1 Bath
  • 864 sqft
$939,000
Active
Data Source Icon

200 Old Log Lick Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 4,019 sqft
$339,900
Active
Data Source Icon

23 Windridge Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,858 sqft
$235,000
Active
Data Source Icon

13 Long Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,297 sqft
$233,000
Active
Data Source Icon

14 Cook Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,261 sqft
$390,000
Pending
Data Source Icon

178 Hawthorne Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,156 sqft
$99,500
Active
Data Source Icon

563 Constitution Drive

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 2 Baths
  • 924 sqft
$275,000
Active
Data Source Icon

20 Jackson Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,650 sqft
$320,000
Pending
Data Source Icon

4100 Crowe Ridge Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,100 sqft
$109,900
Pending
Data Source Icon

310 W Hickman Street

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,391 sqft
$315,000
Pending
Data Source Icon

305 Abbeywood Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,899 sqft
$400,000
Pending
Data Source Icon

233 Schollsville Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,347 sqft
$339,900
Active
Data Source Icon

410 W Lexington Avenue

Winchester, KY 40391

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,456 sqft
$234,900
Pending
Data Source Icon

528 Estes Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,904 sqft
$360,000
Active
Data Source Icon

3359 Trapp-Goffs Corner Road

Winchester, KY 40391

  • Single Family
  • 1 Bed
  • 2 Baths
  • 2,179 sqft
$294,900
Active
Data Source Icon

162 French Avenue

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 1 Bath
  • 2,327 sqft
$249,900
Pending
Data Source Icon

12 Pocahontas Trail

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,064 sqft
$795,000
Active
Data Source Icon

6356 Van Meter Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 3,336 sqft
$299,900
Pending
Data Source Icon

3622 Stamper Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,821 sqft
$229,900
Pending
Data Source Icon

217 Short Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,042 sqft
$595,000
Pending
Data Source Icon

7919 Mt Sterling Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,431 sqft
$785,000
Active
Data Source Icon

7300 Old Boonesboro Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,311 sqft
$235,500
Active
Data Source Icon

125 Kittison Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,100 sqft
$225,000
Pending
Data Source Icon

86 Brink Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,136 sqft
$269,000
Pending
Data Source Icon

20 Bon Haven Avenue

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,850 sqft
$268,900
Pending
Data Source Icon

311 Geronimo Court

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,510 sqft
$277,500
Active
Data Source Icon

116 Sturbridge Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,260 sqft
$1,650,000
Active
Data Source Icon

4578 Combs Ferry Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,860 sqft
$199,900
Active
Data Source Icon

225 Buffalo Trace

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 915 sqft
$609,900
Pending
Data Source Icon

6595 Mt Sterling Road

Winchester, KY 40391

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,515 sqft
$1,695,000
Active
Data Source Icon

3166 Colby Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 4,518 sqft
$225,000
Pending
Data Source Icon

516 Hidden Hills Way

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,134 sqft
$315,000
Pending
Data Source Icon

13 Lakeview Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,932 sqft
$255,000
Active
Data Source Icon

316 Maryland Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,809 sqft
$274,500
Active
Data Source Icon

137 Eastridge Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,420 sqft
$200,000
Pending
Data Source Icon

128 Bay Hill Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,289 sqft
$99,900
Active
Data Source Icon

2799 Pine Ridge Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 675 sqft
$484,900
Active
Data Source Icon

414 Fairholme Way

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,418 sqft
$465,000
Active
Data Source Icon

287 Logan Lick Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,680 sqft
$395,000
Pending
Data Source Icon

18 Casa Landa Way

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,883 sqft
$294,900
Active
Data Source Icon

209 Boone Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,260 sqft
$219,900
Pending
Data Source Icon

339 S Main Street

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,848 sqft
$225,000
Pending
Data Source Icon

450 Jameson Way

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,458 sqft
$294,900
Pending
Data Source Icon

147 Sunset Heights

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,128 sqft
$539,900
Pending
Data Source Icon

146 Hawthorne Drive

Winchester, KY 40391

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,711 sqft
$269,900
Pending
Data Source Icon

205 Providence Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,644 sqft
$210,000
Pending
Data Source Icon

301 Snowden Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,386 sqft
$350,000
Pending
Data Source Icon

274 Greenway Drive

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,208 sqft
$635,000
Pending
Data Source Icon

5865 Van Meter Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,765 sqft
$349,000
Pending
Data Source Icon

405 Tremont Lane

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,274 sqft
$558,900
Active
Data Source Icon

108 Bella Shae Way

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,280 sqft
$499,900
Active
Data Source Icon

16 Manor Drive

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 5,646 sqft
$350,000
Active
Data Source Icon

27 Hampton Avenue

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,835 sqft
$427,000
Active
Data Source Icon

20 Edgewood Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,288 sqft
$199,900
Pending
Data Source Icon

265 Cunningham Lane

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,140 sqft
$274,900
Pending
Data Source Icon

403 Pueblo Court

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,311 sqft
$445,500
Active
Data Source Icon

42 Mockingbird Valley Road

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,961 sqft
$350,000
Active
Data Source Icon

38 N Burns Avenue

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,310 sqft
$230,000
Pending
Data Source Icon

108 Spruce Court

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,106 sqft
$160,900
Active
Data Source Icon

22 Magnolia Street

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 1 Bath
  • 842 sqft
$2,750,000
Active
Data Source Icon

4664 Lexington Road

Winchester, KY 40391

  • Single Family
  • 8 Beds
  • 8 Baths
  • 13,433 sqft

Nearby Cities to Winchester

Postal Codes Near Winchester

© 2026 Bluegrass REALTORS® Multiple Listing Service. All Rights Reserved.
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the Bluegrass REALTORS® Multiple Listing Service. Real estate listings held by IDX Brokerage firms other than Rector Hayden Realtors are marked with the IDX logo or the IDX thumbnail logo, and detailed information about them includes the name of the listing IDX Brokers. Information deemed reliable but not guaranteed.