20 total properties
Did you mean the neighborhood Winchester?
View 142 Clubhouse Drive Winchester, KY MLS# 26008332
$650,000
6

Beds

4.0

Baths

4,351

Sq.Ft.

142 Clubhouse Drive

Winchester, KY

Bluegrass
View 722 Colby Road # #2 Winchester, KY MLS# 26008236
$600,000
Studio

Beds

0.0

Baths

722 Colby Road # #2

Winchester, KY

Bluegrass
View 905 Pretty Run Road Winchester, KY MLS# 26008251
$600,000
3

Beds

3.1

Baths

3,391

Sq.Ft.

905 Pretty Run Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1480 Irvine Road Winchester, KY MLS# 26007244
$719,900
3

Beds

3.1

Baths

3,388

Sq.Ft.

1480 Irvine Road

Winchester, KY

Bluegrass
View 186 Chardonnay Court Winchester, KY MLS# 26006869
$749,999
4

Beds

2.1

Baths

7,058

Sq.Ft.

186 Chardonnay Court

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 1775 Irvine Road Winchester, KY MLS# 26006681
$695,000
3

Beds

4.0

Baths

4,008

Sq.Ft.

1775 Irvine Road

Winchester, KY

Bluegrass
View 556 Earlymeade Drive Winchester, KY MLS# 26006630
$559,000
4

Beds

4.1

Baths

4,185

Sq.Ft.

556 Earlymeade Drive

Winchester, KY

Bluegrass
View 6595 Mt Sterling Road Winchester, KY MLS# 26005579
$609,900
5

Beds

4.0

Baths

4,515

Sq.Ft.

6595 Mt Sterling Road

Winchester, KY

Bluegrass
View 1025 Colby Road Winchester, KY MLS# 26005455
$575,000
Studio

Beds

0.0

Baths

1025 Colby Road

Winchester, KY

Bluegrass
View 218 S Maple Street Winchester, KY MLS# 26004697
$750,000
6,110

Sq.Ft.

218 S Maple Street

Winchester, KY

Bluegrass
View 7919 Mt Sterling Road Winchester, KY MLS# 26004302
$645,000
4

Beds

3.1

Baths

3,431

Sq.Ft.

7919 Mt Sterling Road

Winchester, KY

Bluegrass
View 600 Boone Avenue Winchester, KY MLS# 25018239
$569,999
4

Beds

3.2

Baths

4,374

Sq.Ft.

600 Boone Avenue

Winchester, KY

Bluegrass
View 104 Bella Shae Way Winchester, KY MLS# 26000264
  • New Construction
1 of 10
$591,650
3

Beds

2.1

Baths

2,200

Sq.Ft.

104 Bella Shae Way

Winchester, KY

Bluegrass
View 101 S Burns Avenue # 1,2,3,4 Winchester, KY MLS# 25505825
$600,000
8

Beds

4.0

Baths

5,046

Sq.Ft.

101 S Burns Avenue # 1,2,3,4

Winchester, KY

Bluegrass
View 106 Bella Shae Way Winchester, KY MLS# 24025577
  • New Construction
1 of 3
$645,000
4

Beds

2.1

Baths

2,526

Sq.Ft.

106 Bella Shae Way

Winchester, KY

Bluegrass
View 113 Bella Shae Way Winchester, KY MLS# 24025580
  • New Construction
1 of 3
$670,000
3

Beds

2.0

Baths

2,261

Sq.Ft.

113 Bella Shae Way

Winchester, KY

Bluegrass
View 414 Alexis Way Winchester, KY MLS# 24025581
  • New Construction
1 of 22
$665,000
3

Beds

2.1

Baths

2,643

Sq.Ft.

414 Alexis Way

Winchester, KY

Bluegrass
View 415 Alexis Way Winchester, KY MLS# 24025582
  • New Construction
1 of 3
$700,000
3

Beds

2.0

Baths

2,400

Sq.Ft.

415 Alexis Way

Winchester, KY

Bluegrass
View 422 Alexis Way Winchester, KY MLS# 24025583
  • New Construction
1 of 4
$635,000
4

Beds

2.1

Baths

2,537

Sq.Ft.

422 Alexis Way

Winchester, KY

Bluegrass
View 424 Alexis Way Winchester, KY MLS# 24025584
  • New Construction
1 of 4
$625,000
3

Beds

2.1

Baths

2,405

Sq.Ft.

424 Alexis Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

303

Estimated median home price

$269,000
Winchester KY Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Kentucky real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, KY.

Homes for Sale by Price in Winchester, KY

PriceCount
$0 - 100K36
$100K - 200K70
$200K - 300K72
$300K - 400K39
$400K - 500K23
$500K - 600K12
$600K - 700K10
$700K - 800K15
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family173
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 4/29/2026)

Information deemed reliable but not guaranteed.

Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 4/30/2026.