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
 

Real Estate and Properties 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
$599,000
Active
Data Source Icon

8586 Wades Mill Road

Mt Sterling, KY 40353

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,528 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
$199,900
Active
Data Source Icon

18 N Main Street

Winchester, KY 40391

  • Commercial
  • 4,300 sqft
$155,000
Active
Data Source Icon

220 E Washington Street

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,097 sqft
$400,000
Active
Data Source Icon

4095 Basin Springs Road

Winchester, KY 40391

  • Vacant Land
$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
$339,900
Active
Data Source Icon

410 W Lexington Avenue

Winchester, KY 40391

  • Commercial
  • 4,456 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
$250,000
Active
Data Source Icon

3150 Waterworks Road

Winchester, KY 40391

  • Commercial
  • 2,591 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
$154,900
Active
Data Source Icon

750 Craig Crossing

Winchester, KY 40391

  • Vacant Land
$499,000
Pending
Data Source Icon

182 Chardonnay Court

Winchester, KY 40392

  • Single Family
  • 5 Beds
  • 3 Baths
  • 3,097 sqft
$14
Active
Data Source Icon

1946 Bypass Road

Winchester, KY 40391

  • Commercial
  • 62,525 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
$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
$199,000
Active
Data Source Icon

104 Bay Hill Drive

Winchester, KY 40391

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,200 sqft
$595,000
Pending
Data Source Icon

7919 Mt Sterling Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,431 sqft
$280,000
Active
Data Source Icon

133 Bay Hill Drive

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,276 sqft
$1,400
Active
Data Source Icon

1129 W LEXINGTON Avenue

Winchester, KY 40391

  • Commercial
  • 1,155 sqft
$785,000
Active
Data Source Icon

7300 Old Boonesboro Road

Winchester, KY 40391

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,311 sqft
$1,599,900
Active
Data Source Icon

599 BLT Way

Winchester, KY 40391

  • Commercial
  • 20,252 sqft
$235,500
Active
Data Source Icon

125 Kittison Drive

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,100 sqft
$389,900
Active
Data Source Icon

23 Wheeler Avenue

Winchester, KY 40391

  • Multi-Family
  • 8 Beds
  • 5 Baths
  • 4,687 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
$219,500
Pending
Data Source Icon

525 Colby Ridge Boulevard

Winchester, KY 40391

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,197 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
$399,000
Active
Data Source Icon

0 Fairholme Way

Winchester, KY 40391

  • Vacant Land
$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
$882,000
Active
Data Source Icon

Lot 1 - 7 Plantations Drive

Winchester, KY 40391

  • Vacant Land
$78,500
Active
Data Source Icon

Lot 4 Plantations Drive

Winchester, KY 40391

  • Vacant Land
$78,500
Active
Data Source Icon

Lot 3 Plantations Drive

Winchester, KY 40391

  • Vacant Land
$14,100,000
Active
Data Source Icon

2395 Paris Road

Winchester, KY 40391

  • Vacant Land
$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
$20
Active
Data Source Icon

2 Carol Road

Winchester, KY 40391

  • Commercial
  • 2,175 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
© 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.